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Plicamycin

January 01, 1970

Plicamycin (INN, also known as mithramycin; trade name Mithracin) is an antineoplastic antibiotic produced by Streptomyces plicatus. It is an RNA synthesis inhibitor.[1] The manufacturer discontinued production in 2000. Several different structures are currently reported in different places all with the same chromomycin core, but with different stereochemistry in the glycoside chain, a 1999 study has re-investigated the compound and proposed a revised structure.[2]

Plicamycin
Clinical data
Other namesAureolic acid; Mithracin; Antibiotic LA 7017; Mithramycin A; Mitramycin; Plicatomycin
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
Identifiers
  • (1S)-5-deoxy-1-C-((2S,3S)-7-{[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl)-1-O-methyl-D-xylulose
CAS Number
  • 18378-89-7 Y
PubChem CID
  • 5284610
DrugBank
  • DB06810 Y
ChemSpider
  • 4447655 Y
UNII
  • NIJ123W41V
KEGG
  • D00468 N
ChEMBL
  • ChEMBL509846 N
CompTox Dashboard (EPA)
  • DTXSID6023492
ECHA InfoCard100.162.065
Chemical and physical data
FormulaC52H76O24
Molar mass1085.156 g·mol−1
3D model (JSmol)
  • Interactive image
  • CO[C@H](C(=O)[C@@H](O)[C@@H](C)O)C1Cc2cc3cc(O[C@H]4C[C@@H](O[C@H]5C[C@@H](O)[C@H](O)[C@@H](C)O5)[C@@H](O)[C@@H](C)O4)c(C)c(O)c3c(O)c2C(=O)[C@H]1O[C@H]1C[C@@H](O[C@H]2C[C@@H](O[C@H]3C[C@](C)(O)[C@H](O)[C@@H](C)O3)[C@H](O)[C@@H](C)O2)[C@H](O)[C@@H](C)O1
  • InChI=1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27?,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43+,44-,45-,49+,50+,51-,52+/m1/s1 Y
  • Key:CFCUWKMKBJTWLW-GWRQQDNDSA-N Y
 NY (what is this?)  (verify)

Uses edit

Plicamycin has been used in the treatment of testicular cancer,[3][4] Paget's disease of bone,[5][6] and, rarely, the management of hypercalcemia.

Plicamycin has been tested in chronic myeloid leukemia.[7]

Plicamycin is currently used in multiple areas of research, including cancer cell apoptosis[8] and as a metastasis inhibitor.[9]

One elucidated pathway shows it interacts by cross-binding chromatin GC-rich promoter motifs, thereby inhibiting gene transcription.[10]

References edit

  1. ^ "Mithramycin A". Fermentek.
  2. ^ Wohlert SE, Künzel E, Machinek R, Méndez C, Salas JA, Rohr J (January 1999). "The structure of mithramycin reinvestigated". Journal of Natural Products. 62 (1): 119–121. doi:10.1021/np980355k. PMID 9917296.
  3. ^ Kennedy BJ, Torkelson JL (May 1995). "Long-term follow-up of stage III testicular carcinoma treated with mithramycin (plicamycin)". Medical and Pediatric Oncology. 24 (5): 327–328. doi:10.1002/mpo.2950240511. PMID 7700186.
  4. ^ Brown JH, Kennedy BJ (January 1965). "Mithramycin in the Treatment of Disseminated Testicular Neoplasms". The New England Journal of Medicine. 272 (3): 111–118. doi:10.1056/NEJM196501212720301. PMID 14224214.
  5. ^ Hall TJ, Schaeublin M, Chambers TJ (September 1993). "The majority of osteoclasts require mRNA and protein synthesis for bone resorption in vitro". Biochemical and Biophysical Research Communications. 195 (3): 1245–1253. doi:10.1006/bbrc.1993.2178. PMID 8216256.
  6. ^ Remsing LL, Bahadori HR, Carbone GM, McGuffie EM, Catapano CV, Rohr J (July 2003). "Inhibition of c-src transcription by mithramycin: structure-activity relationships of biosynthetically produced mithramycin analogues using the c-src promoter as target". Biochemistry. 42 (27): 8313–8324. doi:10.1021/bi034091z. PMID 12846580.
  7. ^ Dutcher JP, Coletti D, Paietta E, Wiernik PH (May 1997). "A pilot study of alpha-interferon and plicamycin for accelerated phase of chronic myeloid leukemia". Leukemia Research. 21 (5): 375–380. doi:10.1016/S0145-2126(96)00108-7. PMID 9225062.
  8. ^ Lee TJ, Jung EM, Lee JT, Kim S, Park JW, Choi KS, Kwon TK (November 2006). "Mithramycin A sensitizes cancer cells to TRAIL-mediated apoptosis by down-regulation of XIAP gene promoter through Sp1 sites". Molecular Cancer Therapeutics. 5 (11): 2737–2746. doi:10.1158/1535-7163.MCT-06-0426. PMID 17121920.
  9. ^ Lin RK, Hsu CH, Wang YC (November 2007). "Mithramycin A inhibits DNA methyltransferase and metastasis potential of lung cancer cells". Anti-Cancer Drugs. 18 (10): 1157–1164. doi:10.1097/CAD.0b013e3282a215e9. PMID 17893516.
  10. ^ Majee S, Chakrabarti A (May 1999). "Membrane interaction of an antitumor antibiotic, mithramycin, with anionic phospholipid vesicles". Biochemical Pharmacology. 57 (9): 981–987. doi:10.1016/S0006-2952(98)00374-8. PMID 10796068.

External links edit

January 01, 1970
plicamycin, also, known, mithramycin, trade, name, mithracin, antineoplastic, antibiotic, produced, streptomyces, plicatus, synthesis, inhibitor, manufacturer, discontinued, production, 2000, several, different, structures, currently, reported, different, plac. Plicamycin INN also known as mithramycin trade name Mithracin is an antineoplastic antibiotic produced by Streptomyces plicatus It is an RNA synthesis inhibitor 1 The manufacturer discontinued production in 2000 Several different structures are currently reported in different places all with the same chromomycin core but with different stereochemistry in the glycoside chain a 1999 study has re investigated the compound and proposed a revised structure 2 PlicamycinClinical dataOther namesAureolic acid Mithracin Antibiotic LA 7017 Mithramycin A Mitramycin PlicatomycinAHFS Drugs comMicromedex Detailed Consumer InformationRoutes ofadministrationIntravenousATC codeL01DC02 WHO Legal statusLegal statusUS only discontinuedIdentifiersIUPAC name 1S 5 deoxy 1 C 2S 3S 7 2 6 dideoxy 3 O 2 6 dideoxy b D arabino hexopyranosyl b D arabino hexopyranosyl oxy 3 2 6 dideoxy 3 C methyl b D ribo hexopyranosyl 1 3 2 6 dideoxy b D arabino hexopyranosyl 1 3 2 6 dideoxy b D arabino hexopyranosyl oxy 5 10 dihydroxy 6 methyl 4 oxo 1 2 3 4 tetrahydroanthracen 2 yl 1 O methyl D xyluloseCAS Number18378 89 7 YPubChem CID5284610DrugBankDB06810 YChemSpider4447655 YUNIINIJ123W41VKEGGD00468 NChEMBLChEMBL509846 NCompTox Dashboard EPA DTXSID6023492ECHA InfoCard100 162 065Chemical and physical dataFormulaC 52H 76O 24Molar mass1085 156 g mol 13D model JSmol Interactive imageSMILES CO C H C O C H O C H C O C1Cc2cc3cc O C H 4C C H O C H 5C C H O C H O C H C O5 C H O C H C O4 c C c O c3c O c2C O C H 1O C H 1C C H O C H 2C C H O C H 3C C C O C H O C H C O3 C H O C H C O2 C H O C H C O1InChI InChI 1S C52H76O24 c1 18 29 72 34 14 30 43 58 21 4 68 34 73 33 13 28 54 42 57 20 3 67 33 12 26 10 25 11 27 49 66 9 48 63 41 56 19 2 53 50 47 62 39 25 46 61 38 26 40 18 55 76 36 16 31 44 59 23 6 70 36 74 35 15 32 45 60 22 5 69 35 75 37 17 52 8 65 51 64 24 7 71 37 h10 12 19 24 27 28 30 37 41 45 49 51 53 61 64 65H 11 13 17H2 1 9H3 t19 20 21 22 23 24 27 28 30 31 32 33 34 35 36 37 41 42 43 44 45 49 50 51 52 m1 s1 YKey CFCUWKMKBJTWLW GWRQQDNDSA N Y N Y what is this verify Uses editPlicamycin has been used in the treatment of testicular cancer 3 4 Paget s disease of bone 5 6 and rarely the management of hypercalcemia Plicamycin has been tested in chronic myeloid leukemia 7 Plicamycin is currently used in multiple areas of research including cancer cell apoptosis 8 and as a metastasis inhibitor 9 One elucidated pathway shows it interacts by cross binding chromatin GC rich promoter motifs thereby inhibiting gene transcription 10 References edit Mithramycin A Fermentek Wohlert SE Kunzel E Machinek R Mendez C Salas JA Rohr J January 1999 The structure of mithramycin reinvestigated Journal of Natural Products 62 1 119 121 doi 10 1021 np980355k PMID 9917296 Kennedy BJ Torkelson JL May 1995 Long term follow up of stage III testicular carcinoma treated with mithramycin plicamycin Medical and Pediatric Oncology 24 5 327 328 doi 10 1002 mpo 2950240511 PMID 7700186 Brown JH Kennedy BJ January 1965 Mithramycin in the Treatment of Disseminated Testicular Neoplasms The New England Journal of Medicine 272 3 111 118 doi 10 1056 NEJM196501212720301 PMID 14224214 Hall TJ Schaeublin M Chambers TJ September 1993 The majority of osteoclasts require mRNA and protein synthesis for bone resorption in vitro Biochemical and Biophysical Research Communications 195 3 1245 1253 doi 10 1006 bbrc 1993 2178 PMID 8216256 Remsing LL Bahadori HR Carbone GM McGuffie EM Catapano CV Rohr J July 2003 Inhibition of c src transcription by mithramycin structure activity relationships of biosynthetically produced mithramycin analogues using the c src promoter as target Biochemistry 42 27 8313 8324 doi 10 1021 bi034091z PMID 12846580 Dutcher JP Coletti D Paietta E Wiernik PH May 1997 A pilot study of alpha interferon and plicamycin for accelerated phase of chronic myeloid leukemia Leukemia Research 21 5 375 380 doi 10 1016 S0145 2126 96 00108 7 PMID 9225062 Lee TJ Jung EM Lee JT Kim S Park JW Choi KS Kwon TK November 2006 Mithramycin A sensitizes cancer cells to TRAIL mediated apoptosis by down regulation of XIAP gene promoter through Sp1 sites Molecular Cancer Therapeutics 5 11 2737 2746 doi 10 1158 1535 7163 MCT 06 0426 PMID 17121920 Lin RK Hsu CH Wang YC November 2007 Mithramycin A inhibits DNA methyltransferase and metastasis potential of lung cancer cells Anti Cancer Drugs 18 10 1157 1164 doi 10 1097 CAD 0b013e3282a215e9 PMID 17893516 Majee S Chakrabarti A May 1999 Membrane interaction of an antitumor antibiotic mithramycin with anionic phospholipid vesicles Biochemical Pharmacology 57 9 981 987 doi 10 1016 S0006 2952 98 00374 8 PMID 10796068 External links editMithramycin A from Center for Pharmaceutical Research and Innovation Retrieved from https en wikipedia org w index php title Plicamycin amp oldid 1164443438, wikipedia, wiki, book, books, library,

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