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Vinca alkaloid

February 15, 2024

Vinca alkaloids are a set of anti-mitotic and anti-microtubule alkaloid agents originally derived from the periwinkle plant Catharanthus roseus (basionym Vinca rosea) and other vinca plants. They block beta-tubulin polymerization in a dividing cell.

Chemical structure of the vinca alkaloid vincristine

Sources edit

The Madagascan periwinkle Catharanthus roseus L. is the source for a number of important natural products,[1] including catharanthine and vindoline[2] and the vinca alkaloids it produces from them: leurosine and the chemotherapy agents vinblastine[3] and vincristine,[4] all of which can be obtained from the plant.[5][6][7][8] The newer semi-synthetic chemotherapeutic agent vinorelbine is used in the treatment of non-small-cell lung cancer[7][9] and is not known to occur naturally. However, it can be prepared either from vindoline and catharanthine[7][10] or from leurosine,[11] in both cases by synthesis of anhydrovinblastine, which "can be considered as the key intermediate for the synthesis of vinorelbine."[7] The leurosine pathway uses the Nugent–RajanBabu reagent in a highly chemoselective de-oxygenation of leurosine.[12][11] Anhydrovinblastine is then reacted sequentially with N-bromosuccinimide and trifluoroacetic acid followed by silver tetrafluoroborate to yield vinorelbine.[10]

 

Applications edit

Vinca alkaloids are used in chemotherapy for cancer. They are a class of cell cycle–specific cytotoxic drugs that work by inhibiting the ability of cancer cells to divide: Acting upon tubulin, they prevent it from forming into microtubules, a necessary component for cellular division.[13] The vinca alkaloids thus prevent microtubule polymerization, as opposed to the mechanism of action of taxanes.

Vinca alkaloids are now produced synthetically and used as drugs in cancer therapy and as immunosuppressive drugs. These compounds include vinblastine, vincristine, vindesine, and vinorelbine. Additional researched vinca alkaloids include vincaminol, vineridine, and vinburnine.

Vinpocetine is a semi-synthetic derivative of vincamine (sometimes described as "a synthetic ethyl ester of apovincamine").[14]

Minor vinca alkaloids include minovincine, methoxyminovincine, minovincinine, vincadifformine, desoxyvincaminol, and vincamajine.[15][16][17]

References edit

  1. ^ van der Heijden, Robert; Jacobs, Denise I.; Snoeijer, Wim; Hallard, Didier; Verpoorte, Robert (2004). "The Catharanthus alkaloids: Pharmacognosy and biotechnology". Current Medicinal Chemistry. 11 (5): 607–628. doi:10.2174/0929867043455846. PMID 15032608.
  2. ^ Hirata, K.; Miyamoto, K.; Miura, Y. (1994). "Catharanthus roseus L. (Periwinkle): Production of Vindoline and Catharanthine in Multiple Shoot Cultures". In Bajaj, Y. P. S. (ed.). Biotechnology in Agriculture and Forestry 26. Medicinal and Aromatic Plants. Vol. VI. Springer-Verlag. pp. 46–55. ISBN 9783540563914.
  3. ^ Sears, Justin E.; Boger, Dale L. (2015). "Total Synthesis of Vinblastine, Related Natural Products, and Key Analogues and Development of Inspired Methodology Suitable for the Systematic Study of Their Structure-Function Properties". Accounts of Chemical Research. 48 (3): 653–662. doi:10.1021/ar500400w. PMC 4363169. PMID 25586069.
  4. ^ Kuboyama, Takeshi; Yokoshima, Satoshi; Tokuyama, Hidetoshi; Fukuyama, Tohru (2004). "Stereocontrolled total synthesis of (+)-vincristine". Proceedings of the National Academy of Sciences of the United States of America. 101 (33): 11966–11970. Bibcode:2004PNAS..10111966K. doi:10.1073/pnas.0401323101. PMC 514417. PMID 15141084.
  5. ^ Gansäuer, Andreas; Justicia, José; Fan, Chun-An; Worgull, Dennis; Piestert, Frederik (2007). "Reductive C—C bond formation after epoxide opening via electron transfer". In Krische, Michael J. (ed.). Metal Catalyzed Reductive C—C Bond Formation: A Departure from Preformed Organometallic Reagents. Topics in Current Chemistry. Vol. 279. Springer Science & Business Media. pp. 25–52. doi:10.1007/128_2007_130. ISBN 9783540728795.
  6. ^ Cooper, Raymond; Deakin, Jeffrey John (2016). "Africa's gift to the world". Botanical Miracles: Chemistry of Plants That Changed the World. CRC Press. pp. 46–51. ISBN 9781498704304.
  7. ^ a b c d Keglevich, Péter; Hazai, Laszlo; Kalaus, György; Szántay, Csaba (2012). "Modifications on the basic skeletons of vinblastine and vincristine". Molecules. 17 (5): 5893–5914. doi:10.3390/molecules17055893. PMC 6268133. PMID 22609781.
  8. ^ Raviña, Enrique (2011). "Vinca alkaloids". The evolution of drug discovery: From traditional medicines to modern drugs. John Wiley & Sons. pp. 157–159. ISBN 9783527326693.
  9. ^ Faller, Bryan A.; Pandi, Trailokya N. (2011). "Safety and efficacy of vinorelbine in the treatment of non-small cell lung cancer". Clinical Medicine Insights: Oncology. 5: 131–144. doi:10.4137/CMO.S5074. PMC 3117629. PMID 21695100.
  10. ^ a b Ngo, Quoc Anh; Roussi, Fanny; Cormier, Anthony; Thoret, Sylviane; Knossow, Marcel; Guénard, Daniel; Guéritte, Françoise (2009). "Synthesis and biological evaluation of Vinca alkaloids and phomopsin hybrids". Journal of Medicinal Chemistry. 52 (1): 134–142. doi:10.1021/jm801064y. PMID 19072542.
  11. ^ a b Hardouin, Christophe; Doris, Eric; Rousseau, Bernard; Mioskowski, Charles (2002). "Concise synthesis of anhydrovinblastine from leurosine". Organic Letters. 4 (7): 1151–1153. doi:10.1021/ol025560c. PMID 11922805.
  12. ^ Morcillo, Sara P.; Miguel, Delia; Campaña, Araceli G.; Cienfuegos, Luis Álvarez de; Justicia, José; Cuerva, Juan M. (2014). "Recent applications of Cp2TiCl in natural product synthesis". Organic Chemistry Frontiers. 1 (1): 15–33. doi:10.1039/c3qo00024a. hdl:10481/47295.
  13. ^ Takimoto, C. H.; Calvo, E. (2008). . In Pazdur, R.; Wagman, L. D.; Camphausen, K. A.; Hoskins, W. J. (eds.). Cancer Management: A Multidisciplinary Approach (11th ed.). ISBN 978-1-891483-62-2. Archived from the original on 2009-05-15. Retrieved 2011-05-26.
  14. ^ Lörincz C, Szász K, Kisfaludy L (1976). "The synthesis of ethyl apovincaminate". Arzneimittel-Forschung. 26 (10a): 1907. PMID 1037211.
  15. ^ Plat, M; Fellion, E; Le Men, J; Janot, M (1962). "4 new alkaloids of Vinca minor L.: minovincine, methoxyminovincine, minovincinine and (-) vincadifformine, alkaloids of periwinkles". Ann. Pharm. Fr. (in French). 20: 899–906. PMID 13943964.
  16. ^ Smeyers, Yves G.; Smeyers, Nadine J.; Randez, Juan J.; Hernandez-Laguna, A.; Galvez-Ruano, E. (1991). "A structural and pharmacological study of alkaloids of Vinca Minor". Molecular Engineering. 1 (2): 153–160. doi:10.1007/BF00420051. S2CID 93210480.
  17. ^ Janot, M. M.; Le Men, J; Fan, C (1958). "The alkaloids of the periwinkles (Vinca): Relation between, vincamedine and vincamajine". Comptes Rendus Hebdomadaires des Séances de l'Académie des Sciences. 247 (25): 2375–7. PMID 13619121.

External links edit

  • Chemotherapeutic vinca alkaloids

February 15, 2024
vinca, alkaloid, anti, mitotic, anti, microtubule, alkaloid, agents, originally, derived, from, periwinkle, plant, catharanthus, roseus, basionym, vinca, rosea, other, vinca, plants, they, block, beta, tubulin, polymerization, dividing, cell, chemical, structu. Vinca alkaloids are a set of anti mitotic and anti microtubule alkaloid agents originally derived from the periwinkle plant Catharanthus roseus basionym Vinca rosea and other vinca plants They block beta tubulin polymerization in a dividing cell Chemical structure of the vinca alkaloid vincristine Contents 1 Sources 2 Applications 3 References 4 External linksSources editThe Madagascan periwinkle Catharanthus roseus L is the source for a number of important natural products 1 including catharanthine and vindoline 2 and the vinca alkaloids it produces from them leurosine and the chemotherapy agents vinblastine 3 and vincristine 4 all of which can be obtained from the plant 5 6 7 8 The newer semi synthetic chemotherapeutic agent vinorelbine is used in the treatment of non small cell lung cancer 7 9 and is not known to occur naturally However it can be prepared either from vindoline and catharanthine 7 10 or from leurosine 11 in both cases by synthesis of anhydrovinblastine which can be considered as the key intermediate for the synthesis of vinorelbine 7 The leurosine pathway uses the Nugent RajanBabu reagent in a highly chemoselective de oxygenation of leurosine 12 11 Anhydrovinblastine is then reacted sequentially with N bromosuccinimide and trifluoroacetic acid followed by silver tetrafluoroborate to yield vinorelbine 10 nbsp Applications editVinca alkaloids are used in chemotherapy for cancer They are a class of cell cycle specific cytotoxic drugs that work by inhibiting the ability of cancer cells to divide Acting upon tubulin they prevent it from forming into microtubules a necessary component for cellular division 13 The vinca alkaloids thus prevent microtubule polymerization as opposed to the mechanism of action of taxanes Vinca alkaloids are now produced synthetically and used as drugs in cancer therapy and as immunosuppressive drugs These compounds include vinblastine vincristine vindesine and vinorelbine Additional researched vinca alkaloids include vincaminol vineridine and vinburnine Vinpocetine is a semi synthetic derivative of vincamine sometimes described as a synthetic ethyl ester of apovincamine 14 Minor vinca alkaloids include minovincine methoxyminovincine minovincinine vincadifformine desoxyvincaminol and vincamajine 15 16 17 References edit van der Heijden Robert Jacobs Denise I Snoeijer Wim Hallard Didier Verpoorte Robert 2004 The Catharanthus alkaloids Pharmacognosy and biotechnology Current Medicinal Chemistry 11 5 607 628 doi 10 2174 0929867043455846 PMID 15032608 Hirata K Miyamoto K Miura Y 1994 Catharanthus roseus L Periwinkle Production of Vindoline and Catharanthine in Multiple Shoot Cultures In Bajaj Y P S ed Biotechnology in Agriculture and Forestry 26 Medicinal and Aromatic Plants Vol VI Springer Verlag pp 46 55 ISBN 9783540563914 Sears Justin E Boger Dale L 2015 Total Synthesis of Vinblastine Related Natural Products and Key Analogues and Development of Inspired Methodology Suitable for the Systematic Study of Their Structure Function Properties Accounts of Chemical Research 48 3 653 662 doi 10 1021 ar500400w PMC 4363169 PMID 25586069 Kuboyama Takeshi Yokoshima Satoshi Tokuyama Hidetoshi Fukuyama Tohru 2004 Stereocontrolled total synthesis of vincristine Proceedings of the National Academy of Sciences of the United States of America 101 33 11966 11970 Bibcode 2004PNAS 10111966K doi 10 1073 pnas 0401323101 PMC 514417 PMID 15141084 Gansauer Andreas Justicia Jose Fan Chun An Worgull Dennis Piestert Frederik 2007 Reductive C C bond formation after epoxide opening via electron transfer In Krische Michael J ed Metal Catalyzed Reductive C C Bond Formation A Departure from Preformed Organometallic Reagents Topics in Current Chemistry Vol 279 Springer Science amp Business Media pp 25 52 doi 10 1007 128 2007 130 ISBN 9783540728795 Cooper Raymond Deakin Jeffrey John 2016 Africa s gift to the world Botanical Miracles Chemistry of Plants That Changed the World CRC Press pp 46 51 ISBN 9781498704304 a b c d Keglevich Peter Hazai Laszlo Kalaus Gyorgy Szantay Csaba 2012 Modifications on the basic skeletons of vinblastine and vincristine Molecules 17 5 5893 5914 doi 10 3390 molecules17055893 PMC 6268133 PMID 22609781 Ravina Enrique 2011 Vinca alkaloids The evolution of drug discovery From traditional medicines to modern drugs John Wiley amp Sons pp 157 159 ISBN 9783527326693 Faller Bryan A Pandi Trailokya N 2011 Safety and efficacy of vinorelbine in the treatment of non small cell lung cancer Clinical Medicine Insights Oncology 5 131 144 doi 10 4137 CMO S5074 PMC 3117629 PMID 21695100 a b Ngo Quoc Anh Roussi Fanny Cormier Anthony Thoret Sylviane Knossow Marcel Guenard Daniel Gueritte Francoise 2009 Synthesis and biological evaluation of Vinca alkaloids and phomopsin hybrids Journal of Medicinal Chemistry 52 1 134 142 doi 10 1021 jm801064y PMID 19072542 a b Hardouin Christophe Doris Eric Rousseau Bernard Mioskowski Charles 2002 Concise synthesis of anhydrovinblastine from leurosine Organic Letters 4 7 1151 1153 doi 10 1021 ol025560c PMID 11922805 Morcillo Sara P Miguel Delia Campana Araceli G Cienfuegos Luis Alvarez de Justicia Jose Cuerva Juan M 2014 Recent applications of Cp2TiCl in natural product synthesis Organic Chemistry Frontiers 1 1 15 33 doi 10 1039 c3qo00024a hdl 10481 47295 Takimoto C H Calvo E 2008 Chapter 3 Principles of Oncologic Pharmacotherapy In Pazdur R Wagman L D Camphausen K A Hoskins W J eds Cancer Management A Multidisciplinary Approach 11th ed ISBN 978 1 891483 62 2 Archived from the original on 2009 05 15 Retrieved 2011 05 26 Lorincz C Szasz K Kisfaludy L 1976 The synthesis of ethyl apovincaminate Arzneimittel Forschung 26 10a 1907 PMID 1037211 Plat M Fellion E Le Men J Janot M 1962 4 new alkaloids of Vinca minor L minovincine methoxyminovincine minovincinine and vincadifformine alkaloids of periwinkles Ann Pharm Fr in French 20 899 906 PMID 13943964 Smeyers Yves G Smeyers Nadine J Randez Juan J Hernandez Laguna A Galvez Ruano E 1991 A structural and pharmacological study of alkaloids of Vinca Minor Molecular Engineering 1 2 153 160 doi 10 1007 BF00420051 S2CID 93210480 Janot M M Le Men J Fan C 1958 The alkaloids of the periwinkles Vinca Relation between vincamedine and vincamajine Comptes Rendus Hebdomadaires des Seances de l Academie des Sciences 247 25 2375 7 PMID 13619121 External links editChemotherapeutic vinca alkaloids Retrieved from https en wikipedia org w index php title Vinca alkaloid amp oldid 1170652860, wikipedia, wiki, book, books, library,

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