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Cisplatin

February 29, 2024

"Cisplatine" redirects here. For the Brazilian province that existed from 1821 to 1828, see Cisplatina. For the conflict in that province, see Cisplatine War.

Cisplatin is a chemical compound with formula cis-[Pt(NH3)2Cl2]. It is a coordination complex of platinum that is used as a chemotherapy medication used to treat a number of cancers.[3] These include testicular cancer, ovarian cancer, cervical cancer, bladder cancer, head and neck cancer, esophageal cancer, lung cancer, mesothelioma, brain tumors and neuroblastoma.[3] It is given by injection into a vein.[3]

Cisplatin
Clinical data
Trade namesPlatinol, others
Other namesCisplatinum, platamin, neoplatin, cismaplat, cis-diamminedichloroplatinum(II) (CDDP)
AHFS/Drugs.comMonograph
MedlinePlusa684036
License data
Pregnancy
category
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability100% (IV)
Protein binding> 95%
Elimination half-life30–100 hours
ExcretionRenal
Identifiers
CAS Number
  • 15663-27-1 Y
PubChem CID
  • 2767
DrugBank
  • DB00515 Y
ChemSpider
  • 76401 N
UNII
  • Q20Q21Q62J
KEGG
  • D00275 Y
ChEBI
  • CHEBI:27899 Y
ChEMBL
  • ChEMBL2068237 N
PDB ligand
  • CPT (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID50275807
ECHA InfoCard100.036.106
Chemical and physical data
Formula[Pt(NH3)2Cl2]
Molar mass300.05 g·mol−1
3D model (JSmol)
  • Interactive image
  • [NH3+]-[Pt-2](Cl)(Cl)[NH3+]
  • InChI=1S/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+2/p-2 Y
  • Key:LXZZYRPGZAFOLE-UHFFFAOYSA-L Y
 NY (what is this?)  (verify)

Common side effects include bone marrow suppression, hearing problems including severe hearing loss, kidney damage, and vomiting.[3][4][5] Other serious side effects include numbness, trouble walking, allergic reactions, electrolyte problems, and heart disease.[3] Use during pregnancy can cause harm to the developing fetus.[1][3] Cisplatin is in the platinum-based antineoplastic family of medications.[3] It works in part by binding to DNA and inhibiting its replication.[3]

Cisplatin was discovered in 1845 and licensed for medical use in 1978 and 1979.[6][3] It is on the World Health Organization's List of Essential Medicines.[7][8]

Medical use edit

Cisplatin is administered intravenously as short-term infusion in normal saline for treatment of solid and haematological malignancies. It is used to treat various types of cancers, including sarcomas, some carcinomas (e.g., small cell lung cancer, squamous cell carcinoma of the head and neck and ovarian cancer), lymphomas, bladder cancer, cervical cancer,[9] and germ cell tumors.

The introduction of cisplatin as a standard treatment for testicular cancer improved remission rates from 5-10% before 1974 to 75-85% by 1984.[10]

Side effects edit

Cisplatin has a number of side effects that can limit its use:

  • Nephrotoxicity (kidney damage) is the primary dose-limiting side effect and is of major clinical concern. Cisplatin selectively accumulates into the proximal tubule via basolateral-to-apical transport, where it disrupts mitochondrial energetics and endoplasmic reticulum Ca2+ homeostasis and stimulates reactive oxygen species and pro-inflammatory cytokines.[11] Multiple mitigation strategies are being explored clinically and pre-clinically, including hydration regimens, amifostine, transporter inhibitors, antioxidants, anti-inflammatories, and epoxyeicosatrienoic acids and their analogues.[11][12]
  • Neurotoxicity (nerve damage) can be anticipated by performing nerve conduction studies before and after treatment. Common neurological side effects of cisplatin include visual perception and hearing disorder, which can occur soon after treatment begins.[13] While triggering apoptosis through interfering with DNA replication remains the primary mechanism of cisplatin, this has not been found to contribute to neurological side effects. Recent studies have shown that cisplatin noncompetitively inhibits an archetypal, membrane-bound mechanosensitive sodium-hydrogen ion transporter known as NHE-1.[13] It is primarily found on cells of the peripheral nervous system, which are aggregated in large numbers near the ocular and aural stimuli-receiving centers. This noncompetitive interaction has been linked to hydroelectrolytic imbalances and cytoskeleton alterations, both of which have been confirmed in vitro and in vivo. However, NHE-1 inhibition has been found to be both dose-dependent (half-inhibition = 30 μg/mL) and reversible.[13] Cisplatin can increase levels of sphingosine-1-phosphate in the central nervous system, contributing to the development of post-chemotherapy cognitive impairment.[14][15]
  • Nausea and vomiting: cisplatin is one of the most emetogenic chemotherapy agents, but this symptom is managed with prophylactic antiemetics (ondansetron, granisetron, etc.) in combination with corticosteroids. Aprepitant combined with ondansetron and dexamethasone has been shown to be better for highly emetogenic chemotherapy than just ondansetron and dexamethasone.
  • Ototoxicity and hearing loss associated with cisplatin can be severe and is considered to be a dose-limiting side effect.[5] Audiometric analysis may be necessary to assess the severity of ototoxicity. Other drugs (such as the aminoglycoside antibiotic class) may also cause ototoxicity, and the administration of this class of antibiotics in patients receiving cisplatin is generally avoided. The ototoxicity of both the aminoglycosides and cisplatin may be related to their ability to bind to melanin in the stria vascularis of the inner ear or the generation of reactive oxygen species. In September 2022, the U.S. Food and Drug Administration (FDA) approved sodium thiosulfate under the brand name Pedmark to lessen the risk of ototoxicity and hearing loss in people receiving cisplatin.[16][17][18] There is ongoing investigation of acetylcysteine injections as a preventative measure.[5][19]
  • Electrolyte disturbance: Cisplatin can cause hypomagnesaemia, hypokalaemia and hypocalcaemia. The hypocalcaemia seems to occur in those with low serum magnesium secondary to cisplatin, so it is not primarily due to the cisplatin.
  • Hemolytic anemia can be developed after several courses of cisplatin. It is suggested that an antibody reacting with a cisplatin-red-cell membrane is responsible for hemolysis.[20]

Pharmacology edit

Cisplatin interferes with DNA replication, which kills the fastest proliferating cells, which in theory are cancerous. Following administration, one chloride ion is slowly displaced by water to give the aquo complex cis-[PtCl(NH3)2(H2O)]+, in a process termed aquation. Dissociation of the chloride is favored inside the cell because the intracellular chloride concentration is only 3–20% of the approximately 100 mM chloride concentration in the extracellular fluid.[21][22]

The water molecule in cis-[PtCl(NH3)2(H2O)]+ is itself easily displaced by the N-heterocyclic bases on DNA. Guanine preferentially binds. A model compound has been prepared and crystals were examined by X-ray crystallography[23]

Subsequent to formation of [PtCl(guanine-DNA)(NH3)2]+, crosslinking can occur via displacement of the other chloride, typically by another guanine.[24] Cisplatin crosslinks DNA in several different ways, interfering with cell division by mitosis. The damaged DNA elicits DNA repair mechanisms, which in turn activate apoptosis when repair proves impossible. In 2008, researchers were able to show that the apoptosis induced by cisplatin on human colon cancer cells depends on the mitochondrial serine-protease Omi/Htra2.[25] Since this was only demonstrated for colon carcinoma cells, it remains an open question whether the Omi/Htra2 protein participates in the cisplatin-induced apoptosis in carcinomas from other tissues.[25]

Most notable among the changes in DNA are the 1,2-intrastrand cross-links with purine bases. These include 1,2-intrastrand d(GpG) adducts, which form nearly 90% of the adducts, and the less common 1,2-intrastrand d(ApG) adducts. Coordination chemists have obtained crystals of the products of reacting cisplain with small models of DNA. Here is a POVray plot of the platinum binding to a small model of DNA.[26]

 
A POVray plot of the atomic coordinates for the cis Pt(NH3)2 and short fragment of DNA which was reported by Stephen J. Lippard in Science 1985

1,3-intrastrand d(GpXpG) adducts occur but are readily excised by the nucleotide excision repair (NER). Other adducts include inter-strand crosslinks and nonfunctional adducts that have been postulated to contribute to cisplatin's activity. Interaction with cellular proteins, particularly HMG domain proteins, has also been advanced as a mechanism of interfering with mitosis, although this is probably not its primary method of action.[27]

Cisplatin resistance edit

Cisplatin combination chemotherapy is the cornerstone of treatment of many cancers. Initial platinum responsiveness is high, but the majority of cancer patients will eventually relapse with cisplatin-resistant disease. Many mechanisms of cisplatin resistance have been proposed, including changes in cellular uptake and efflux of the drug, increased detoxification of the drug, inhibition of apoptosis , increased DNA repair or changes in metabolism.[28][29] Oxaliplatin is active in highly cisplatin-resistant cancer cells in the laboratory; however, there is little evidence for its activity in the clinical treatment of patients with cisplatin-resistant cancer.[29] The drug paclitaxel may be useful in the treatment of cisplatin-resistant cancer; the mechanism for this activity is as yet unknown.[30]

Transplatin edit

Transplatin, the trans-stereoisomer of cisplatin, has formula trans-[PtCl2(NH3)2] and does not exhibit a comparably useful pharmacological effect. Two mechanisms have been suggested to explain the reduced anticancer effect of transplatin. Firstly, the trans arrangement of the chloro ligands is thought to confer transplatin with greater chemical reactivity, causing transplatin to become deactivated before it reaches the DNA, where cisplatin exerts its pharmacological action. Secondly, the stereo-conformation of transplatin is such that it is unable to form the characteristic 1,2-intrastrand d(GpG) adducts formed by cisplatin in abundance.[31]

Molecular structure edit

Cisplatin is the square planar coordination complex cis-[Pt(NH3)2Cl2].[32]: 286–8 [33]: 689  The prefix cis indicates the cis isomer in which two similar ligands are in adjacent positions.[32][33]: 550  The systematic chemical name of this molecule is cis–diamminedichloroplatinum,[32]: 286  where ammine with two m's indicates an ammonia (NH3) ligand, as opposed to an organic amine with one m.[32]: 284 

  •  
    Solution structure of cisplatin (highlighted) interstrand GG adducts with double-stranded DNA. (PDB: 1DDP)
  •  
    2.60Å resolution crystal structure of cisplatin (highlighted) intrastrand GG adducts with double-stranded DNA. Note: the hydrogens on amine ligands are not shown. (PDB: 1AIO)

History edit

The compound cis-[Pt(NH3)2Cl2] was first described by Italian chemist Michele Peyrone in 1845, and known for a long time as Peyrone's salt.[34][35] The structure was deduced by Alfred Werner in 1893.[24] In 1965, Barnett Rosenberg, Van Camp et al. of Michigan State University discovered that electrolysis of platinum electrodes generated a soluble platinum complex which inhibited binary fission in Escherichia coli (E. coli) bacteria. Although bacterial cell growth continued, cell division was arrested, the bacteria growing as filaments up to 300 times their normal length.[36] The octahedral Pt(IV) complex cis-[PtCl4(NH3)2], but not the trans isomer, was found to be effective at forcing filamentous growth of E. coli cells. The square planar Pt(II) complex, cis-[PtCl2(NH3)2] turned out to be even more effective at forcing filamentous growth.[37][38] This finding led to the observation that cis-[PtCl2(NH3)2] was indeed highly effective at regressing the mass of sarcomas in rats.[39] Confirmation of this discovery, and extension of testing to other tumour cell lines launched the medicinal applications of cisplatin. Cisplatin was approved for use in testicular and ovarian cancers by the U.S. Food and Drug Administration on 19 December 1978.[24][40][41] and in the UK (and in several other European countries) in 1979.[42] Cisplatin was the first to be developed.[43] In 1983 pediatric oncologist Roger Packer began incorporating cisplatin into adjuvant chemotherapy for the treatment of childhood medulloblastoma.[44] The new protocol that he developed led to a marked increase in disease-free survival rates for patients with medulloblastoma, up to around 85%.[45] The Packer Protocol has since become a standard treatment for medulloblastoma. Likewise, cisplatin has been found to be particularly effective against testicular cancer, where its use improved the cure rate from 10% to 85%.[10]

Recently, some researchers have investigated at the preclinical level new forms of cisplatin prodrugs in combination with nanomaterials in order to localize the release of the drug in the target.[46][47]

Synthesis edit

Syntheses of cisplatin start from potassium tetrachloroplatinate. Several procedures are available. One obstacle is the facile formation of Magnus's green salt (MGS), which has the same empirical formula as cisplatin. The traditional way to avoid MGS involves the conversion of K2PtCl4 to K2PtI4, as originally described by Dhara.[48][49] Reaction with ammonia forms PtI2(NH3)2 which is isolated as a yellow compound. When silver nitrate in water is added insoluble silver iodide precipitates and [Pt(OH2)2(NH3)2](NO3)2 remains in solution. Addition of potassium chloride will form the final product which precipitates[49] In the triiodo intermediate the addition of the second ammonia ligand is governed by the trans effect.[49]

 

A one-pot synthesis of cisplatin from K2PtCl4 has been developed. It relies on the slow release of ammonia from ammonium acetate.[50]

Research edit

Cisplatin has been studied with Auger therapy to increase the therapeutic effects of cisplatin, without increasing normal tissue toxicities.[51] However, due to significant side effects, the search for structurally novel Pt(II) and Pd(II) compounds exhibiting antineoplastic activity is extremely important and aims to develop more effective and less toxic drugs.[52] Metal complexes comprising cisplatin-like molecules ([PtCl(NH3)2] or [Pt(NH3)Cl2]) linked by variable length alkandiamine chains have attracted great interest in the last few years as next-generation alternatives drugs in cancer chemotherapy.[53][54][55]

References edit

  1. ^ a b c d "Cisplatin Use During Pregnancy". Drugs.com. 12 September 2019. Retrieved 25 February 2020.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ a b c d e f g h i "Cisplatin". The American Society of Health-System Pharmacists. from the original on 21 December 2016. Retrieved 8 December 2016.
  4. ^ Oun R, Moussa YE, Wheate NJ (May 2018). "The side effects of platinum-based chemotherapy drugs: a review for chemists". Dalton Transactions. 47 (19): 6645–6653. doi:10.1039/c8dt00838h. PMID 29632935.
  5. ^ a b c Callejo A, Sedó-Cabezón L, Juan ID, Llorens J (July 2015). "Cisplatin-Induced Ototoxicity: Effects, Mechanisms and Protection Strategies". Toxics. 3 (3): 268–293. doi:10.3390/toxics3030268. PMC 5606684. PMID 29051464.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 513. ISBN 9783527607495. from the original on 20 December 2016.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  9. ^ "Cisplatin". National Cancer Institute. 2 March 2007. from the original on 8 October 2014. Retrieved 13 November 2014.
  10. ^ a b Einhorn LH (November 1990). "Treatment of testicular cancer: a new and improved model". Journal of Clinical Oncology. 8 (11): 1777–81. doi:10.1200/JCO.1990.8.11.1777. PMID 1700077.
  11. ^ a b Miller RP, Tadagavadi RK, Ramesh G, Reeves WB (October 2010). "Mechanisms of Cisplatin Nephrotoxicity". Toxins. 2 (11): 2490–2518. doi:10.3390/toxins2112490. PMC 3153174. PMID 22069563.
  12. ^ Singh N, Vik A, Lybrand DB, Morisseau C, Hammock BD (November 2021). "New Alkoxy- Analogues of Epoxyeicosatrienoic Acids Attenuate Cisplatin Nephrotoxicity In Vitro via Reduction of Mitochondrial Dysfunction, Oxidative Stress, Mitogen-Activated Protein Kinase Signaling, and Caspase Activation". Chemical Research in Toxicology. 34 (12): 2579–2591. doi:10.1021/acs.chemrestox.1c00347. PMC 8853703. PMID 34817988.
  13. ^ a b c Milosavljevic N, Duranton C, Djerbi N, Puech PH, Gounon P, Lagadic-Gossmann D, et al. (October 2010). "Nongenomic effects of cisplatin: acute inhibition of mechanosensitive transporters and channels without actin remodeling". Cancer Research. 70 (19): 7514–22. doi:10.1158/0008-5472.CAN-10-1253. PMID 20841472.
  14. ^ Squillace S, Niehoff ML, Doyle TM, Green M, Esposito E, Cuzzocrea S, Arnatt CK, Spiegel S, Farr SA, Salvemini D (September 2022). "Sphingosine-1-phosphate receptor 1 activation in the central nervous system drives cisplatin-induced cognitive impairment". The Journal of Clinical Investigation. 132 (17). doi:10.1172/JCI157738. PMC 9433103. PMID 36047496.
  15. ^ "Unlocking the Mystery of "Chemo Brain"". Neuroscience News. 2 September 2022.
  16. ^ Orgel E, Villaluna D, Krailo MD, Esbenshade A, Sung L, Freyer DR (May 2022). "Sodium thiosulfate for prevention of cisplatin-induced hearing loss: updated survival from ACCL0431". The Lancet. Oncology. 23 (5): 570–572. doi:10.1016/S1470-2045(22)00155-3. PMC 9635495. PMID 35489339.
  17. ^ Winstead E (6 October 2022). "Sodium Thiosulfate Reduces Hearing Loss in Kids with Cancer". National Cancer Institute. Retrieved 9 March 2023.
  18. ^ "FDA approves sodium thiosulfate to reduce the risk of ototoxicity associated with cisplatin in pediatric patients with localized, non-metastatic solid tumors". Food and Drug Administration. 20 September 2022. Retrieved 9 March 2023.
  19. ^ Sarafraz Z, Ahmadi A, Daneshi A (June 2018). "Transtympanic Injections of N-acetylcysteine and Dexamethasone for Prevention of Cisplatin-Induced Ototoxicity: Double Blind Randomized Clinical Trial". The International Tinnitus Journal. 22 (1): 40–45. doi:10.5935/0946-5448.20180007. PMID 29993216.
  20. ^ Levi JA, Aroney RS, Dalley DN (June 1981). "Haemolytic anaemia after cisplatin treatment". British Medical Journal. 282 (6281): 2003–4. doi:10.1136/bmj.282.6281.2003. PMC 1505958. PMID 6788166.
  21. ^ Wang D, Lippard SJ (April 2005). "Cellular processing of platinum anticancer drugs". Nature Reviews. Drug Discovery. 4 (4): 307–320. doi:10.1038/nrd1691. PMID 15789122. S2CID 31357727.
  22. ^ Johnstone TC, Suntharalingam K, Lippard SJ (March 2016). "The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs". Chemical Reviews. 116 (5): 3436–3486. doi:10.1021/acs.chemrev.5b00597. PMC 4792284. PMID 26865551.
  23. ^ Orbell JD, Solorzano C, Marzilli LG, Kistenmacher TJ (October 1982). "Preparation and structure of cis-chlorodiammine (N2, N2-dimethyl-9-methylguanine) platinum (II) hexafluorophosphate. A model for the intermediate in the proposed crosslinking mode of action of platinum (II) antitumor agents". Inorganic Chemistry. 21 (10): 3806–3810. doi:10.1021/ic00140a041.
  24. ^ a b c Trzaska S (20 June 2005). "Cisplatin". Chemical & Engineering News. 83 (25): 52. doi:10.1021/cen-v083n025.p052.
  25. ^ a b Pruefer FG, Lizarraga F, Maldonado V, Melendez-Zajgla J (June 2008). "Participation of Omi Htra2 serine-protease activity in the apoptosis induced by cisplatin on SW480 colon cancer cells". Journal of Chemotherapy. 20 (3): 348–354. doi:10.1179/joc.2008.20.3.348. PMID 18606591. S2CID 11052459.
  26. ^ Sherman SE, Gibson D, Wang AH, Lippard SJ (October 1985). "X-ray structure of the major adduct of the anticancer drug cisplatin with DNA: cis-[Pt(NH3)2(d(pGpG))]". Science. 230 (4724): 412–7. Bibcode:1985Sci...230..412S. doi:10.1126/science.4048939. PMID 4048939.
  27. ^ Hu J, Lieb JD, Sancar A, Adar S (October 2016). "Cisplatin DNA damage and repair maps of the human genome at single-nucleotide resolution". PNAS. 113 (41): 11507–11512. Bibcode:2016PNAS..11311507H. doi:10.1073/pnas.1614430113. PMC 5068337. PMID 27688757. S2CID 11052459.
  28. ^ Cruz-Bermúdez A, Laza-Briviesca R, Vicente-Blanco RJ, García-Grande A, Coronado MJ, Laine-Menéndez S, et al. (May 2019). "Cisplatin resistance involves a metabolic reprogramming through ROS and PGC-1α in NSCLC which can be overcome by OXPHOS inhibition". Free Radical Biology & Medicine. 135: 167–181. doi:10.1016/j.freeradbiomed.2019.03.009. hdl:10486/688357. PMID 30880247.
  29. ^ a b Stordal B, Davey M (November 2007). "Understanding cisplatin resistance using cellular models" (PDF). IUBMB Life. 59 (11): 696–699. doi:10.1080/15216540701636287. PMID 17885832. S2CID 30879019.
  30. ^ Stordal B, Pavlakis N, Davey R (December 2007). "A systematic review of platinum and taxane resistance from bench to clinic: an inverse relationship" (PDF). Cancer Treatment Reviews. 33 (8): 688–703. doi:10.1016/j.ctrv.2007.07.013. hdl:2123/4068. PMID 17881133.
  31. ^ Coluccia M, Natile G (January 2007). "Trans-platinum complexes in cancer therapy". Anti-Cancer Agents in Medicinal Chemistry. 7 (1): 111–123. doi:10.2174/187152007779314080. PMID 17266508.
  32. ^ a b c d Miessler GL, Tarr DA (1999). Inorganic Chemistry (2nd ed.). Prentice Hall. ISBN 978-0-13-841891-5.
  33. ^ a b Housecroft CE, Sharpe AG (2005). Inorganic Chemistry (2nd ed.). Pearson Prentice Hall. ISBN 978-0-130-39913-7.
  34. ^ Kauffman GB, Pentimalli R, Hall MD (2010). "Michele Peyrone (1813–1883), Discoverer of Cisplatin". Platinum Metals Review. 54 (4): 250–256. doi:10.1595/147106710X534326. Retrieved 3 October 2022. This biographical article aims to present, for the first time in the English language, a summary of his life and the achievements that he made during his scientific career.
  35. ^ Peyrone M (1844). "Ueber die Einwirkung des Ammoniaks auf Platinchlorür" [On the action of ammonia on platinum chloride]. Ann. Chem. Pharm. 51 (1): 1–29. doi:10.1002/jlac.18440510102.
  36. ^ Rosenberg B, Vancamp L, Krigas T (February 1965). "Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode". Nature. 205 (4972): 698–9. Bibcode:1965Natur.205..698R. doi:10.1038/205698a0. PMID 14287410. S2CID 9543916.
  37. ^ Rosenberg B, Van Camp L, Grimley EB, Thomson AJ (March 1967). "The inhibition of growth or cell division in Escherichia coli by different ionic species of platinum(IV) complexes". The Journal of Biological Chemistry. 242 (6): 1347–52. doi:10.1016/S0021-9258(18)96186-7. PMID 5337590.
  38. ^ Christie DA, Tansey EM (2007). Christie DA, Tansey EM, Thomson AJ (eds.). The Discovery, Use and Impact of Platinum Salts as Chemotherapy Agent for Cancer. Wellcome Trust Witnesses to Twentieth Century Medicine. Vol. 30. pp. 6–15. ISBN 978-0-85484-112-7.
  39. ^ Rosenberg B, VanCamp L, Trosko JE, Mansour VH (April 1969). "Platinum compounds: a new class of potent antitumour agents". Nature. 222 (5191): 385–6. Bibcode:1969Natur.222..385R. doi:10.1038/222385a0. PMID 5782119. S2CID 32398470.
  40. ^ Carpenter DP (2010). Reputation and power: organizational image and pharmaceutical regulation at the FDA. Princeton, NJ: Princeton University Press. ISBN 978-0-691-14180-0.
  41. ^ . FDA Oncology Tools. Food and Drug Administration, Center for Drug Evaluation and Research. 19 December 1978. Archived from the original on 8 February 2008. Retrieved 15 July 2009.
  42. ^ Wiltshaw E (1979). "Cisplatin in the treatment of cancer". Platinum Metals Review. 23 (3): 90–8. doi:10.1595/003214079X2339098. S2CID 267470502.
  43. ^ Kelland L (2007). "The resurgence of platinum-based cancer chemotherapy". Nature Reviews Cancer. 7 (8): 573–584. doi:10.1038/nrc2167. PMID 17625587. S2CID 205468214.
  44. ^ Packer RJ, Sutton LN, Elterman R, Lange B, Goldwein J, Nicholson HS, et al. (November 1994). "Outcome for children with medulloblastoma treated with radiation and cisplatin, CCNU, and vincristine chemotherapy". Journal of Neurosurgery. 81 (5): 690–8. doi:10.3171/jns.1994.81.5.0690. PMID 7931615.
  45. ^ Packer RJ, Sutton LN, Goldwein JW, Perilongo G, Bunin G, Ryan J, et al. (March 1991). "Improved survival with the use of adjuvant chemotherapy in the treatment of medulloblastoma". Journal of Neurosurgery. 74 (3): 433–40. doi:10.3171/jns.1991.74.3.0433. PMID 1847194.
  46. ^ Dhar S, Daniel WL, Giljohann DA, Mirkin CA, Lippard SJ (October 2009). "Polyvalent oligonucleotide gold nanoparticle conjugates as delivery vehicles for platinum(IV) warheads". Journal of the American Chemical Society. 131 (41): 14652–3. doi:10.1021/ja9071282. PMC 2761975. PMID 19778015.
  47. ^ Santi M, Mapanao AK, Cassano D, Vlamidis Y, Cappello V, Voliani V (April 2020). "Endogenously-Activated Ultrasmall-in-Nano Therapeutics: Assessment on 3D Head and Neck Squamous Cell Carcinomas". Cancers. 12 (5): 1063. doi:10.3390/cancers12051063. PMC 7281743. PMID 32344838.
  48. ^ Dhara SC (1970). "Cisplatin". Indian J. Chem. 8: 123–134.
  49. ^ a b c Alderden RA, Hall MD, Hambley TW (2006). "The Discovery and Development of Cisplatin". J. Chem. Educ. 83 (5): 728. Bibcode:2006JChEd..83..728A. doi:10.1021/ed083p728. S2CID 29546931.
  50. ^ Kukushikin VY, Oskarsson Å, Elding LI, Farrell N (2007). "Facile Synthesis of Isomerically Pure cis -Dichlorodiammineplatinum(II), Cisplatin". Facile Synthesis of Isomerically Pure cis -Dichlorodiammineplatinum(II), Cisplatin. Inorganic Syntheses. Vol. 32. pp. 141–144. doi:10.1002/9780470132630.ch23. ISBN 9780470132630.
  51. ^ Ku A, Facca VJ, Cai Z, Reilly RM (October 2019). "Auger electrons for cancer therapy - a review". EJNMMI Radiopharmacy and Chemistry. 4 (1): 27. doi:10.1186/s41181-019-0075-2. PMC 6800417. PMID 31659527.
  52. ^ Fiuza SM, Amado AM, Oliveira PJ, Sardão VA, De Carvalho LB, Marques MP (2006). "Pt(II) vs Pd(II) Polyamine Complexes as New Anticancer Drugs: A Structure- Activity Study". Letters in Drug Design & Discovery. 3 (3): 149–151. doi:10.2174/157018006776286989. hdl:10316/45139.
  53. ^ Teixeira LJ, Seabra M, Reis E, da Cruz MT, de Lima MC, Pereira E, et al. (May 2004). "Cytotoxic activity of metal complexes of biogenic polyamines: polynuclear platinum(II) chelates". Journal of Medicinal Chemistry. 47 (11): 2917–2925. doi:10.1021/jm0311238. hdl:10316/10605. PMID 15139770.
  54. ^ Vinci D, Chateigner D (1 December 2022). "Synthesis and structural characterization of a new dinuclear platinum(III) complex, [Pt 2 Cl 4 (NH 3 ) 2 {μ-HN=C(O)Bu t } 2 ]". Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials. 78 (6): 835–841. doi:10.1107/S2052520622009660. ISSN 2052-5206. PMC 9728019.
  55. ^ Omondi RO, Ojwach SO, Jaganyi D (November 2020). "Review of comparative studies of cytotoxic activities of Pt(II), Pd(II), Ru(II)/(III) and Au(III) complexes, their kinetics of ligand substitution reactions and DNA/BSA interactions". Inorganica Chimica Acta. 512: 119883. doi:10.1016/j.ica.2020.119883. S2CID 225575546.

Further reading edit

  • Riddell IA, Lippard SJ (2018). "Cisplatin and Oxaliplatin: Our Current Understanding of Their Actions". In Sigel A, Sigel H, Freisinger E, Sigel RK (eds.). Metallo-Drugs: Development and Action of Anticancer Agents. Metal Ions in Life Sciences. Vol. 18. Berlin: de Gruyter GmbH. pp. 1–42. doi:10.1515/9783110470734-007. ISBN 978-3-11-046984-4. PMID 29394020.

External links edit

  • "Cisplatin". Drug Information Portal. U.S. National Library of Medicine.
  • IARC Monograph: "Cisplatin"

February 29, 2024
cisplatin, redirects, here, brazilian, province, that, existed, from, 1821, 1828, conflict, that, province, chemical, compound, with, formula, 2cl2, coordination, complex, platinum, that, used, chemotherapy, medication, used, treat, number, cancers, these, inc. Cisplatine redirects here For the Brazilian province that existed from 1821 to 1828 see Cisplatina For the conflict in that province see Cisplatine War Cisplatin is a chemical compound with formula cis Pt NH3 2Cl2 It is a coordination complex of platinum that is used as a chemotherapy medication used to treat a number of cancers 3 These include testicular cancer ovarian cancer cervical cancer bladder cancer head and neck cancer esophageal cancer lung cancer mesothelioma brain tumors and neuroblastoma 3 It is given by injection into a vein 3 CisplatinClinical dataTrade namesPlatinol othersOther namesCisplatinum platamin neoplatin cismaplat cis diamminedichloroplatinum II CDDP AHFS Drugs comMonographMedlinePlusa684036License dataUS DailyMed CisplatinPregnancycategoryAU D 1 Contraindicated 1 Routes ofadministrationIntravenousATC codeL01XA01 WHO Legal statusLegal statusAU S4 Prescription only CA only UK POM Prescription only US WARNING 2 Rx onlyPharmacokinetic dataBioavailability100 IV Protein binding gt 95 Elimination half life30 100 hoursExcretionRenalIdentifiersIUPAC name SP 4 2 diamminedichloridoplatinum II CAS Number15663 27 1 YPubChem CID2767DrugBankDB00515 YChemSpider76401 NUNIIQ20Q21Q62JKEGGD00275 YChEBICHEBI 27899 YChEMBLChEMBL2068237 NPDB ligandCPT PDBe RCSB PDB CompTox Dashboard EPA DTXSID50275807ECHA InfoCard100 036 106Chemical and physical dataFormula Pt NH3 2Cl2 Molar mass300 05 g mol 13D model JSmol Interactive imageSMILES NH3 Pt 2 Cl Cl NH3 InChI InChI 1S 2ClH 2H3N Pt h2 1H 2 1H3 q 2 p 2 YKey LXZZYRPGZAFOLE UHFFFAOYSA L Y N Y what is this verify Common side effects include bone marrow suppression hearing problems including severe hearing loss kidney damage and vomiting 3 4 5 Other serious side effects include numbness trouble walking allergic reactions electrolyte problems and heart disease 3 Use during pregnancy can cause harm to the developing fetus 1 3 Cisplatin is in the platinum based antineoplastic family of medications 3 It works in part by binding to DNA and inhibiting its replication 3 Cisplatin was discovered in 1845 and licensed for medical use in 1978 and 1979 6 3 It is on the World Health Organization s List of Essential Medicines 7 8 Contents 1 Medical use 2 Side effects 3 Pharmacology 3 1 Cisplatin resistance 3 2 Transplatin 4 Molecular structure 5 History 6 Synthesis 7 Research 8 References 9 Further reading 10 External linksMedical use editCisplatin is administered intravenously as short term infusion in normal saline for treatment of solid and haematological malignancies It is used to treat various types of cancers including sarcomas some carcinomas e g small cell lung cancer squamous cell carcinoma of the head and neck and ovarian cancer lymphomas bladder cancer cervical cancer 9 and germ cell tumors The introduction of cisplatin as a standard treatment for testicular cancer improved remission rates from 5 10 before 1974 to 75 85 by 1984 10 Side effects editCisplatin has a number of side effects that can limit its use Nephrotoxicity kidney damage is the primary dose limiting side effect and is of major clinical concern Cisplatin selectively accumulates into the proximal tubule via basolateral to apical transport where it disrupts mitochondrial energetics and endoplasmic reticulum Ca2 homeostasis and stimulates reactive oxygen species and pro inflammatory cytokines 11 Multiple mitigation strategies are being explored clinically and pre clinically including hydration regimens amifostine transporter inhibitors antioxidants anti inflammatories and epoxyeicosatrienoic acids and their analogues 11 12 Neurotoxicity nerve damage can be anticipated by performing nerve conduction studies before and after treatment Common neurological side effects of cisplatin include visual perception and hearing disorder which can occur soon after treatment begins 13 While triggering apoptosis through interfering with DNA replication remains the primary mechanism of cisplatin this has not been found to contribute to neurological side effects Recent studies have shown that cisplatin noncompetitively inhibits an archetypal membrane bound mechanosensitive sodium hydrogen ion transporter known as NHE 1 13 It is primarily found on cells of the peripheral nervous system which are aggregated in large numbers near the ocular and aural stimuli receiving centers This noncompetitive interaction has been linked to hydroelectrolytic imbalances and cytoskeleton alterations both of which have been confirmed in vitro and in vivo However NHE 1 inhibition has been found to be both dose dependent half inhibition 30 mg mL and reversible 13 Cisplatin can increase levels of sphingosine 1 phosphate in the central nervous system contributing to the development of post chemotherapy cognitive impairment 14 15 Nausea and vomiting cisplatin is one of the most emetogenic chemotherapy agents but this symptom is managed with prophylactic antiemetics ondansetron granisetron etc in combination with corticosteroids Aprepitant combined with ondansetron and dexamethasone has been shown to be better for highly emetogenic chemotherapy than just ondansetron and dexamethasone Ototoxicity and hearing loss associated with cisplatin can be severe and is considered to be a dose limiting side effect 5 Audiometric analysis may be necessary to assess the severity of ototoxicity Other drugs such as the aminoglycoside antibiotic class may also cause ototoxicity and the administration of this class of antibiotics in patients receiving cisplatin is generally avoided The ototoxicity of both the aminoglycosides and cisplatin may be related to their ability to bind to melanin in the stria vascularis of the inner ear or the generation of reactive oxygen species In September 2022 the U S Food and Drug Administration FDA approved sodium thiosulfate under the brand name Pedmark to lessen the risk of ototoxicity and hearing loss in people receiving cisplatin 16 17 18 There is ongoing investigation of acetylcysteine injections as a preventative measure 5 19 Electrolyte disturbance Cisplatin can cause hypomagnesaemia hypokalaemia and hypocalcaemia The hypocalcaemia seems to occur in those with low serum magnesium secondary to cisplatin so it is not primarily due to the cisplatin Hemolytic anemia can be developed after several courses of cisplatin It is suggested that an antibody reacting with a cisplatin red cell membrane is responsible for hemolysis 20 Pharmacology editCisplatin interferes with DNA replication which kills the fastest proliferating cells which in theory are cancerous Following administration one chloride ion is slowly displaced by water to give the aquo complex cis PtCl NH3 2 H2O in a process termed aquation Dissociation of the chloride is favored inside the cell because the intracellular chloride concentration is only 3 20 of the approximately 100 mM chloride concentration in the extracellular fluid 21 22 The water molecule in cis PtCl NH3 2 H2O is itself easily displaced by the N heterocyclic bases on DNA Guanine preferentially binds A model compound has been prepared and crystals were examined by X ray crystallography 23 Subsequent to formation of PtCl guanine DNA NH3 2 crosslinking can occur via displacement of the other chloride typically by another guanine 24 Cisplatin crosslinks DNA in several different ways interfering with cell division by mitosis The damaged DNA elicits DNA repair mechanisms which in turn activate apoptosis when repair proves impossible In 2008 researchers were able to show that the apoptosis induced by cisplatin on human colon cancer cells depends on the mitochondrial serine protease Omi Htra2 25 Since this was only demonstrated for colon carcinoma cells it remains an open question whether the Omi Htra2 protein participates in the cisplatin induced apoptosis in carcinomas from other tissues 25 Most notable among the changes in DNA are the 1 2 intrastrand cross links with purine bases These include 1 2 intrastrand d GpG adducts which form nearly 90 of the adducts and the less common 1 2 intrastrand d ApG adducts Coordination chemists have obtained crystals of the products of reacting cisplain with small models of DNA Here is a POVray plot of the platinum binding to a small model of DNA 26 nbsp A POVray plot of the atomic coordinates for the cis Pt NH3 2 and short fragment of DNA which was reported by Stephen J Lippard in Science 19851 3 intrastrand d GpXpG adducts occur but are readily excised by the nucleotide excision repair NER Other adducts include inter strand crosslinks and nonfunctional adducts that have been postulated to contribute to cisplatin s activity Interaction with cellular proteins particularly HMG domain proteins has also been advanced as a mechanism of interfering with mitosis although this is probably not its primary method of action 27 Cisplatin resistance edit Cisplatin combination chemotherapy is the cornerstone of treatment of many cancers Initial platinum responsiveness is high but the majority of cancer patients will eventually relapse with cisplatin resistant disease Many mechanisms of cisplatin resistance have been proposed including changes in cellular uptake and efflux of the drug increased detoxification of the drug inhibition of apoptosis increased DNA repair or changes in metabolism 28 29 Oxaliplatin is active in highly cisplatin resistant cancer cells in the laboratory however there is little evidence for its activity in the clinical treatment of patients with cisplatin resistant cancer 29 The drug paclitaxel may be useful in the treatment of cisplatin resistant cancer the mechanism for this activity is as yet unknown 30 Transplatin edit Transplatin the trans stereoisomer of cisplatin has formula trans PtCl2 NH3 2 and does not exhibit a comparably useful pharmacological effect Two mechanisms have been suggested to explain the reduced anticancer effect of transplatin Firstly the trans arrangement of the chloro ligands is thought to confer transplatin with greater chemical reactivity causing transplatin to become deactivated before it reaches the DNA where cisplatin exerts its pharmacological action Secondly the stereo conformation of transplatin is such that it is unable to form the characteristic 1 2 intrastrand d GpG adducts formed by cisplatin in abundance 31 Molecular structure editCisplatin is the square planar coordination complex cis Pt NH3 2Cl2 32 286 8 33 689 The prefix cis indicates the cis isomer in which two similar ligands are in adjacent positions 32 33 550 The systematic chemical name of this molecule is cis diamminedichloroplatinum 32 286 where ammine with two m s indicates an ammonia NH3 ligand as opposed to an organic amine with one m 32 284 nbsp Solution structure of cisplatin highlighted interstrand GG adducts with double stranded DNA PDB 1DDP nbsp 2 60A resolution crystal structure of cisplatin highlighted intrastrand GG adducts with double stranded DNA Note the hydrogens on amine ligands are not shown PDB 1AIO History editThe compound cis Pt NH3 2Cl2 was first described by Italian chemist Michele Peyrone in 1845 and known for a long time as Peyrone s salt 34 35 The structure was deduced by Alfred Werner in 1893 24 In 1965 Barnett Rosenberg Van Camp et al of Michigan State University discovered that electrolysis of platinum electrodes generated a soluble platinum complex which inhibited binary fission in Escherichia coli E coli bacteria Although bacterial cell growth continued cell division was arrested the bacteria growing as filaments up to 300 times their normal length 36 The octahedral Pt IV complex cis PtCl4 NH3 2 but not the trans isomer was found to be effective at forcing filamentous growth of E coli cells The square planar Pt II complex cis PtCl2 NH3 2 turned out to be even more effective at forcing filamentous growth 37 38 This finding led to the observation that cis PtCl2 NH3 2 was indeed highly effective at regressing the mass of sarcomas in rats 39 Confirmation of this discovery and extension of testing to other tumour cell lines launched the medicinal applications of cisplatin Cisplatin was approved for use in testicular and ovarian cancers by the U S Food and Drug Administration on 19 December 1978 24 40 41 and in the UK and in several other European countries in 1979 42 Cisplatin was the first to be developed 43 In 1983 pediatric oncologist Roger Packer began incorporating cisplatin into adjuvant chemotherapy for the treatment of childhood medulloblastoma 44 The new protocol that he developed led to a marked increase in disease free survival rates for patients with medulloblastoma up to around 85 45 The Packer Protocol has since become a standard treatment for medulloblastoma Likewise cisplatin has been found to be particularly effective against testicular cancer where its use improved the cure rate from 10 to 85 10 Recently some researchers have investigated at the preclinical level new forms of cisplatin prodrugs in combination with nanomaterials in order to localize the release of the drug in the target 46 47 Synthesis editSyntheses of cisplatin start from potassium tetrachloroplatinate Several procedures are available One obstacle is the facile formation of Magnus s green salt MGS which has the same empirical formula as cisplatin The traditional way to avoid MGS involves the conversion of K2PtCl4 to K2PtI4 as originally described by Dhara 48 49 Reaction with ammonia forms PtI2 NH3 2 which is isolated as a yellow compound When silver nitrate in water is added insoluble silver iodide precipitates and Pt OH2 2 NH3 2 NO3 2 remains in solution Addition of potassium chloride will form the final product which precipitates 49 In the triiodo intermediate the addition of the second ammonia ligand is governed by the trans effect 49 nbsp A one pot synthesis of cisplatin from K2PtCl4 has been developed It relies on the slow release of ammonia from ammonium acetate 50 Research editCisplatin has been studied with Auger therapy to increase the therapeutic effects of cisplatin without increasing normal tissue toxicities 51 However due to significant side effects the search for structurally novel Pt II and Pd II compounds exhibiting antineoplastic activity is extremely important and aims to develop more effective and less toxic drugs 52 Metal complexes comprising cisplatin like molecules PtCl NH3 2 or Pt NH3 Cl2 linked by variable length alkandiamine chains have attracted great interest in the last few years as next generation alternatives drugs in cancer chemotherapy 53 54 55 References edit a b c d Cisplatin Use During Pregnancy Drugs com 12 September 2019 Retrieved 25 February 2020 FDA sourced list of all drugs with black box warnings Use Download Full Results and View Query links nctr crs fda gov FDA Retrieved 22 October 2023 a b c d e f g h i Cisplatin The American Society of Health System Pharmacists Archived from the original on 21 December 2016 Retrieved 8 December 2016 Oun R Moussa YE Wheate NJ May 2018 The side effects of platinum based chemotherapy drugs a review for chemists Dalton Transactions 47 19 6645 6653 doi 10 1039 c8dt00838h PMID 29632935 a b c Callejo A Sedo Cabezon L Juan ID Llorens J July 2015 Cisplatin Induced Ototoxicity Effects Mechanisms and Protection Strategies Toxics 3 3 268 293 doi 10 3390 toxics3030268 PMC 5606684 PMID 29051464 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 513 ISBN 9783527607495 Archived from the original on 20 December 2016 World Health Organization 2019 World Health Organization model list of essential medicines 21st list 2019 Geneva World Health Organization hdl 10665 325771 WHO MVP EMP IAU 2019 06 License CC BY NC SA 3 0 IGO World Health Organization 2021 World Health Organization model list of essential medicines 22nd list 2021 Geneva World Health Organization hdl 10665 345533 WHO MHP HPS EML 2021 02 Cisplatin National Cancer Institute 2 March 2007 Archived from the original on 8 October 2014 Retrieved 13 November 2014 a b Einhorn LH November 1990 Treatment of testicular cancer a new and improved model Journal of Clinical Oncology 8 11 1777 81 doi 10 1200 JCO 1990 8 11 1777 PMID 1700077 a b Miller RP Tadagavadi RK Ramesh G Reeves WB October 2010 Mechanisms of Cisplatin Nephrotoxicity Toxins 2 11 2490 2518 doi 10 3390 toxins2112490 PMC 3153174 PMID 22069563 Singh N Vik A Lybrand DB Morisseau C Hammock BD November 2021 New Alkoxy Analogues of Epoxyeicosatrienoic Acids Attenuate Cisplatin Nephrotoxicity In Vitro via Reduction of Mitochondrial Dysfunction Oxidative Stress Mitogen Activated Protein Kinase Signaling and Caspase Activation Chemical Research in Toxicology 34 12 2579 2591 doi 10 1021 acs chemrestox 1c00347 PMC 8853703 PMID 34817988 a b c Milosavljevic N Duranton C Djerbi N Puech PH Gounon P Lagadic Gossmann D et al October 2010 Nongenomic effects of cisplatin acute inhibition of mechanosensitive transporters and channels without actin remodeling Cancer Research 70 19 7514 22 doi 10 1158 0008 5472 CAN 10 1253 PMID 20841472 Squillace S Niehoff ML Doyle TM Green M Esposito E Cuzzocrea S Arnatt CK Spiegel S Farr SA Salvemini D September 2022 Sphingosine 1 phosphate receptor 1 activation in the central nervous system drives cisplatin induced cognitive impairment The Journal of Clinical Investigation 132 17 doi 10 1172 JCI157738 PMC 9433103 PMID 36047496 Unlocking the Mystery of Chemo Brain Neuroscience News 2 September 2022 Orgel E Villaluna D Krailo MD Esbenshade A Sung L Freyer DR May 2022 Sodium thiosulfate for prevention of cisplatin induced hearing loss updated survival from ACCL0431 The Lancet Oncology 23 5 570 572 doi 10 1016 S1470 2045 22 00155 3 PMC 9635495 PMID 35489339 Winstead E 6 October 2022 Sodium Thiosulfate Reduces Hearing Loss in Kids with Cancer National Cancer Institute Retrieved 9 March 2023 FDA approves sodium thiosulfate to reduce the risk of ototoxicity associated with cisplatin in pediatric patients with localized non metastatic solid tumors Food and Drug Administration 20 September 2022 Retrieved 9 March 2023 Sarafraz Z Ahmadi A Daneshi A June 2018 Transtympanic Injections of N acetylcysteine and Dexamethasone for Prevention of Cisplatin Induced Ototoxicity Double Blind Randomized Clinical Trial The International Tinnitus Journal 22 1 40 45 doi 10 5935 0946 5448 20180007 PMID 29993216 Levi JA Aroney RS Dalley DN June 1981 Haemolytic anaemia after cisplatin treatment British Medical Journal 282 6281 2003 4 doi 10 1136 bmj 282 6281 2003 PMC 1505958 PMID 6788166 Wang D Lippard SJ April 2005 Cellular processing of platinum anticancer drugs Nature Reviews Drug Discovery 4 4 307 320 doi 10 1038 nrd1691 PMID 15789122 S2CID 31357727 Johnstone TC Suntharalingam K Lippard SJ March 2016 The Next Generation of Platinum Drugs Targeted Pt II Agents Nanoparticle Delivery and Pt IV Prodrugs Chemical Reviews 116 5 3436 3486 doi 10 1021 acs chemrev 5b00597 PMC 4792284 PMID 26865551 Orbell JD Solorzano C Marzilli LG Kistenmacher TJ October 1982 Preparation and structure of cis chlorodiammine N2 N2 dimethyl 9 methylguanine platinum II hexafluorophosphate A model for the intermediate in the proposed crosslinking mode of action of platinum II antitumor agents Inorganic Chemistry 21 10 3806 3810 doi 10 1021 ic00140a041 a b c Trzaska S 20 June 2005 Cisplatin Chemical amp Engineering News 83 25 52 doi 10 1021 cen v083n025 p052 a b Pruefer FG Lizarraga F Maldonado V Melendez Zajgla J June 2008 Participation of Omi Htra2 serine protease activity in the apoptosis induced by cisplatin on SW480 colon cancer cells Journal of Chemotherapy 20 3 348 354 doi 10 1179 joc 2008 20 3 348 PMID 18606591 S2CID 11052459 Sherman SE Gibson D Wang AH Lippard SJ October 1985 X ray structure of the major adduct of the anticancer drug cisplatin with DNA cis Pt NH3 2 d pGpG Science 230 4724 412 7 Bibcode 1985Sci 230 412S doi 10 1126 science 4048939 PMID 4048939 Hu J Lieb JD Sancar A Adar S October 2016 Cisplatin DNA damage and repair maps of the human genome at single nucleotide resolution PNAS 113 41 11507 11512 Bibcode 2016PNAS 11311507H doi 10 1073 pnas 1614430113 PMC 5068337 PMID 27688757 S2CID 11052459 Cruz Bermudez A Laza Briviesca R Vicente Blanco RJ Garcia Grande A Coronado MJ Laine Menendez S et al May 2019 Cisplatin resistance involves a metabolic reprogramming through ROS and PGC 1a in NSCLC which can be overcome by OXPHOS inhibition Free Radical Biology amp Medicine 135 167 181 doi 10 1016 j freeradbiomed 2019 03 009 hdl 10486 688357 PMID 30880247 a b Stordal B Davey M November 2007 Understanding cisplatin resistance using cellular models PDF IUBMB Life 59 11 696 699 doi 10 1080 15216540701636287 PMID 17885832 S2CID 30879019 Stordal B Pavlakis N Davey R December 2007 A systematic review of platinum and taxane resistance from bench to clinic an inverse relationship PDF Cancer Treatment Reviews 33 8 688 703 doi 10 1016 j ctrv 2007 07 013 hdl 2123 4068 PMID 17881133 Coluccia M Natile G January 2007 Trans platinum complexes in cancer therapy Anti Cancer Agents in Medicinal Chemistry 7 1 111 123 doi 10 2174 187152007779314080 PMID 17266508 a b c d Miessler GL Tarr DA 1999 Inorganic Chemistry 2nd ed Prentice Hall ISBN 978 0 13 841891 5 a b Housecroft CE Sharpe AG 2005 Inorganic Chemistry 2nd ed Pearson Prentice Hall ISBN 978 0 130 39913 7 Kauffman GB Pentimalli R Hall MD 2010 Michele Peyrone 1813 1883 Discoverer of Cisplatin Platinum Metals Review 54 4 250 256 doi 10 1595 147106710X534326 Retrieved 3 October 2022 This biographical article aims to present for the first time in the English language a summary of his life and the achievements that he made during his scientific career Peyrone M 1844 Ueber die Einwirkung des Ammoniaks auf Platinchlorur On the action of ammonia on platinum chloride Ann Chem Pharm 51 1 1 29 doi 10 1002 jlac 18440510102 Rosenberg B Vancamp L Krigas T February 1965 Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode Nature 205 4972 698 9 Bibcode 1965Natur 205 698R doi 10 1038 205698a0 PMID 14287410 S2CID 9543916 Rosenberg B Van Camp L Grimley EB Thomson AJ March 1967 The inhibition of growth or cell division in Escherichia coli by different ionic species of platinum IV complexes The Journal of Biological Chemistry 242 6 1347 52 doi 10 1016 S0021 9258 18 96186 7 PMID 5337590 Christie DA Tansey EM 2007 Christie DA Tansey EM Thomson AJ eds The Discovery Use and Impact of Platinum Salts as Chemotherapy Agent for Cancer Wellcome Trust Witnesses to Twentieth Century Medicine Vol 30 pp 6 15 ISBN 978 0 85484 112 7 Rosenberg B VanCamp L Trosko JE Mansour VH April 1969 Platinum compounds a new class of potent antitumour agents Nature 222 5191 385 6 Bibcode 1969Natur 222 385R doi 10 1038 222385a0 PMID 5782119 S2CID 32398470 Carpenter DP 2010 Reputation and power organizational image and pharmaceutical regulation at the FDA Princeton NJ Princeton University Press ISBN 978 0 691 14180 0 Approval Summary for cisplatin for Metastatic ovarian tumors FDA Oncology Tools Food and Drug Administration Center for Drug Evaluation and Research 19 December 1978 Archived from the original on 8 February 2008 Retrieved 15 July 2009 Wiltshaw E 1979 Cisplatin in the treatment of cancer Platinum Metals Review 23 3 90 8 doi 10 1595 003214079X2339098 S2CID 267470502 Kelland L 2007 The resurgence of platinum based cancer chemotherapy Nature Reviews Cancer 7 8 573 584 doi 10 1038 nrc2167 PMID 17625587 S2CID 205468214 Packer RJ Sutton LN Elterman R Lange B Goldwein J Nicholson HS et al November 1994 Outcome for children with medulloblastoma treated with radiation and cisplatin CCNU and vincristine chemotherapy Journal of Neurosurgery 81 5 690 8 doi 10 3171 jns 1994 81 5 0690 PMID 7931615 Packer RJ Sutton LN Goldwein JW Perilongo G Bunin G Ryan J et al March 1991 Improved survival with the use of adjuvant chemotherapy in the treatment of medulloblastoma Journal of Neurosurgery 74 3 433 40 doi 10 3171 jns 1991 74 3 0433 PMID 1847194 Dhar S Daniel WL Giljohann DA Mirkin CA Lippard SJ October 2009 Polyvalent oligonucleotide gold nanoparticle conjugates as delivery vehicles for platinum IV warheads Journal of the American Chemical Society 131 41 14652 3 doi 10 1021 ja9071282 PMC 2761975 PMID 19778015 Santi M Mapanao AK Cassano D Vlamidis Y Cappello V Voliani V April 2020 Endogenously Activated Ultrasmall in Nano Therapeutics Assessment on 3D Head and Neck Squamous Cell Carcinomas Cancers 12 5 1063 doi 10 3390 cancers12051063 PMC 7281743 PMID 32344838 Dhara SC 1970 Cisplatin Indian J Chem 8 123 134 a b c Alderden RA Hall MD Hambley TW 2006 The Discovery and Development of Cisplatin J Chem Educ 83 5 728 Bibcode 2006JChEd 83 728A doi 10 1021 ed083p728 S2CID 29546931 Kukushikin VY Oskarsson A Elding LI Farrell N 2007 Facile Synthesis of Isomerically Pure cis Dichlorodiammineplatinum II Cisplatin Facile Synthesis of Isomerically Pure cis Dichlorodiammineplatinum II Cisplatin Inorganic Syntheses Vol 32 pp 141 144 doi 10 1002 9780470132630 ch23 ISBN 9780470132630 Ku A Facca VJ Cai Z Reilly RM October 2019 Auger electrons for cancer therapy a review EJNMMI Radiopharmacy and Chemistry 4 1 27 doi 10 1186 s41181 019 0075 2 PMC 6800417 PMID 31659527 Fiuza SM Amado AM Oliveira PJ Sardao VA De Carvalho LB Marques MP 2006 Pt II vs Pd II Polyamine Complexes as New Anticancer Drugs A Structure Activity Study Letters in Drug Design amp Discovery 3 3 149 151 doi 10 2174 157018006776286989 hdl 10316 45139 Teixeira LJ Seabra M Reis E da Cruz MT de Lima MC Pereira E et al May 2004 Cytotoxic activity of metal complexes of biogenic polyamines polynuclear platinum II chelates Journal of Medicinal Chemistry 47 11 2917 2925 doi 10 1021 jm0311238 hdl 10316 10605 PMID 15139770 Vinci D Chateigner D 1 December 2022 Synthesis and structural characterization of a new dinuclear platinum III complex Pt 2 Cl 4 NH 3 2 m HN C O Bu t 2 Acta Crystallographica Section B Structural Science Crystal Engineering and Materials 78 6 835 841 doi 10 1107 S2052520622009660 ISSN 2052 5206 PMC 9728019 Omondi RO Ojwach SO Jaganyi D November 2020 Review of comparative studies of cytotoxic activities of Pt II Pd II Ru II III and Au III complexes their kinetics of ligand substitution reactions and DNA BSA interactions Inorganica Chimica Acta 512 119883 doi 10 1016 j ica 2020 119883 S2CID 225575546 Further reading editRiddell IA Lippard SJ 2018 Cisplatin and Oxaliplatin Our Current Understanding of Their Actions In Sigel A Sigel H Freisinger E Sigel RK eds Metallo Drugs Development and Action of Anticancer Agents Metal Ions in Life Sciences Vol 18 Berlin de Gruyter GmbH pp 1 42 doi 10 1515 9783110470734 007 ISBN 978 3 11 046984 4 PMID 29394020 External links edit Cisplatin Drug Information Portal U S National Library of Medicine IARC Monograph Cisplatin Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Cisplatin amp oldid 1210798639, wikipedia, wiki, book, books, library,

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