As their name suggests, taxanes were first derived from natural sources, but some have been semisynthesized. Paclitaxel was originally derived from the Pacific yew tree.[4][5] Taxanes are difficult to synthesize because of their numerous chiral centres—taxol has 11 of these.
Recently, the presence of taxanes in the shells and leaves of Corylus avellana (the common hazel plant) has been reported.[6][7]
Mechanism of action
The principal mechanism of action of the taxane class of drugs is the disruption of microtubule function. Microtubules are essential to cell division, and taxanes stabilize GDP-bound tubulin in the microtubule, thereby inhibiting the process of cell division as depolymerization is prevented. Thus, in essence, taxanes are mitotic inhibitors. In contrast to the taxanes, the vinca alkaloids prevent mitotic spindle formation through inhibition of tubulinpolymerization. Both taxanes and vinca alkaloids are, therefore, named spindle poisons or mitosis poisons, but they act in different ways. Taxanes are also thought to be radiosensitizing.
Substances
Chemical structure of hongdoushan A
Hongdoushans A–C are oxygenated taxane diterpenes, isolated from the wood of Taxus wallichiana. Hongdoushan A (C29H44O7), hongdoushan B (C27H40O7), and hongdoushan C (C27H42O6) are reported to have anticancer activity in vitro.[8]Taxuspines A–D have been isolated from Taxus.[9][10][11][12]
Taxuspine A
Taxuspine B
Names
Taxanes are usually treated as synonymous with taxoids. The name "taxol" began as a common noun (analogous with other terms in which a genus name root was suffixed with -ol or -in), but it was later capitalized as a trade name, and the international nonproprietary name of the compound is paclitaxel.
^Hagiwara, H.; Sunada, Y. (2004). "Mechanism of taxane neurotoxicity". Breast Cancer (Tokyo, Japan). 11 (1): 82–85. doi:10.1007/BF02968008. PMID 14718798. S2CID 22096988.
^Rowinsky, MD, Eric K. (February 1997). "The Development and Clinical Utility of the Taxane Class of Antimicrotubule Chemotherapy Agents". Annual Review of Medicine. 48 (1): 353–374. doi:10.1146/annurev.med.48.1.353. PMID 9046968.
^Hacker, Miles (2009). "Adverse Drug Reactions". Pharmacology. pp. 327–352. doi:10.1016/B978-0-12-369521-5.00013-0. ISBN9780123695215.
^Weaver, Beth A.; Bement, William (2014). "How Taxol/paclitaxel kills cancer cells". Molecular Biology of the Cell. 25 (18): 2677–2681. doi:10.1091/mbc.e14-04-0916. ISSN 1059-1524. PMC4161504. PMID 25213191.
^Ottaggio, Laura; Bestoso, Federica; Armirotti, Andrea; Balbi, Alessandro; Damonte, Gianluca; Mazzei, Mauro; Sancandi, Monica; Miele, Mariangela (2008). "Taxanes from Shells and Leaves of Corylus avellana". Journal of Natural Products. 71 (1): 58–60. doi:10.1021/np0704046. PMID 18163585.
^Hoffman, Angela M; Shahidi, Fereidoon (January 2009). "Paclitaxel and other taxanes in hazel". Journal of Functional Foods. 1 (1): 33–37. doi:10.1016/j.jff.2008.09.004.
^Banskota AH, Usia T, Tezuka Y, Kouda K, Nguyen NT, Kadota S (2002). "Three new C-14 oxygenated taxanes from the wood of Taxus yunnanensis". J Nat Prod. 65 (11): 1700–2. doi:10.1021/np020235j. PMID 12444707.
taxane, class, diterpenes, they, were, originally, identified, from, plants, genus, taxus, yews, feature, taxadiene, core, paclitaxel, taxol, docetaxel, taxotere, widely, used, chemotherapy, agents, cabazitaxel, approved, treat, hormone, refractory, prostate, . Taxanes are a class of diterpenes They were originally identified from plants of the genus Taxus yews and feature a taxadiene core Paclitaxel Taxol and docetaxel Taxotere are widely used as chemotherapy agents 2 3 Cabazitaxel was FDA approved to treat hormone refractory prostate cancer Taxane NamesIUPAC name Taxane 1 Systematic IUPAC name 4R 4aR 6S 9R 10S 12aS 4 9 12a 13 13 Pentamethyltetradecahydro 6 10 methanobenzo 10 annuleneIdentifiersCAS Number 1605 68 13D model JSmol Interactive imageChemSpider 7827751PubChem CID 9548828InChI InChI 1S C20H36 c1 14 7 6 11 20 5 12 10 17 15 2 8 9 16 13 18 14 20 19 17 3 4 h14 18H 6 13H2 1 5H3 t14 15 16 17 18 20 m1 s1Key DKPFODGZWDEEBT QFIAKTPHSA NInChI 1S C20H36 c1 14 7 6 11 20 5 12 10 17 15 2 8 9 16 13 18 14 20 19 17 3 4 h14 18H 6 13H2 1 5H3 t14 15 16 17 18 20 m1 s1Key DKPFODGZWDEEBT QFIAKTPHSA NSMILES C C H 1CCC C 2 C H 1C C H 3CC C H C H C3 C C CC2 C CPropertiesChemical formula C 20H 36Molar mass 276 508 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Baccatin III left Paclitaxel right 10 Deacetylbaccatin left Docetaxel right Taxanes present difficulties in formulation as medicines because they are poorly soluble in water Contents 1 Production 2 Mechanism of action 3 Substances 4 Names 5 See also 6 References 7 External linksProduction EditAs their name suggests taxanes were first derived from natural sources but some have been semisynthesized Paclitaxel was originally derived from the Pacific yew tree 4 5 Taxanes are difficult to synthesize because of their numerous chiral centres taxol has 11 of these Recently the presence of taxanes in the shells and leaves of Corylus avellana the common hazel plant has been reported 6 7 Mechanism of action EditThe principal mechanism of action of the taxane class of drugs is the disruption of microtubule function Microtubules are essential to cell division and taxanes stabilize GDP bound tubulin in the microtubule thereby inhibiting the process of cell division as depolymerization is prevented Thus in essence taxanes are mitotic inhibitors In contrast to the taxanes the vinca alkaloids prevent mitotic spindle formation through inhibition of tubulin polymerization Both taxanes and vinca alkaloids are therefore named spindle poisons or mitosis poisons but they act in different ways Taxanes are also thought to be radiosensitizing Substances Edit Chemical structure of hongdoushan AHongdoushans A C are oxygenated taxane diterpenes isolated from the wood of Taxus wallichiana Hongdoushan A C29H44O7 hongdoushan B C27H40O7 and hongdoushan C C27H42O6 are reported to have anticancer activity in vitro 8 Taxuspines A D have been isolated from Taxus 9 10 11 12 Taxuspine A Taxuspine BNames EditTaxanes are usually treated as synonymous with taxoids The name taxol began as a common noun analogous with other terms in which a genus name root was suffixed with ol or in but it was later capitalized as a trade name and the international nonproprietary name of the compound is paclitaxel See also EditAbeotaxane Docetaxel Taxine TaxuyunnanineReferences Edit International Union of Pure and Applied Chemistry 2014 Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 The Royal Society of Chemistry p 1540 doi 10 1039 9781849733069 ISBN 978 0 85404 182 4 Hagiwara H Sunada Y 2004 Mechanism of taxane neurotoxicity Breast Cancer Tokyo Japan 11 1 82 85 doi 10 1007 BF02968008 PMID 14718798 S2CID 22096988 Rowinsky MD Eric K February 1997 The Development and Clinical Utility of the Taxane Class of Antimicrotubule Chemotherapy Agents Annual Review of Medicine 48 1 353 374 doi 10 1146 annurev med 48 1 353 PMID 9046968 Hacker Miles 2009 Adverse Drug Reactions Pharmacology pp 327 352 doi 10 1016 B978 0 12 369521 5 00013 0 ISBN 9780123695215 Weaver Beth A Bement William 2014 How Taxol paclitaxel kills cancer cells Molecular Biology of the Cell 25 18 2677 2681 doi 10 1091 mbc e14 04 0916 ISSN 1059 1524 PMC 4161504 PMID 25213191 Ottaggio Laura Bestoso Federica Armirotti Andrea Balbi Alessandro Damonte Gianluca Mazzei Mauro Sancandi Monica Miele Mariangela 2008 Taxanes from Shells and Leaves of Corylus avellana Journal of Natural Products 71 1 58 60 doi 10 1021 np0704046 PMID 18163585 Hoffman Angela M Shahidi Fereidoon January 2009 Paclitaxel and other taxanes in hazel Journal of Functional Foods 1 1 33 37 doi 10 1016 j jff 2008 09 004 Banskota AH Usia T Tezuka Y Kouda K Nguyen NT Kadota S 2002 Three new C 14 oxygenated taxanes from the wood of Taxus yunnanensis J Nat Prod 65 11 1700 2 doi 10 1021 np020235j PMID 12444707 CID 10417482 from PubChem CID 5321744 from PubChem CID 100991639 from PubChem CID 5321746 from PubChemExternal links Edit Media related to taxanes at Wikimedia Commons Retrieved from https en wikipedia org w index php title Taxane amp oldid 1153688471, wikipedia, wiki, book, books, library,
