Combretastatin A-4

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Combretastatin A-4
Combretastatin A4.svg
Names
IUPAC name
2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenol
Other names
Combretastatin A4
CA-4
Identifiers
117048-59-6 N
ChEMBL ChEMBL67 YesY
ChemSpider 4508364 YesY
Jmol 3D model Interactive image
PubChem 5351344
Properties
C18H20O5
Molar mass 316.34 g/mol
Melting point 116 °C (241 °F; 389 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Combretastatin A-4 is a combretastatin and a stilbenoid. It can be isolated from Combretum caffrum, the Eastern Cape South African bushwillow tree or in Combretum leprosum, the mofumbo, a species found in Brazil.[2][3]

Function[edit]

Tubulin represents a potent target in cancer chemotherapy, given its role in cell division. Combretastatin is a naturally occurring well known tubulin polymerization inhibitor. Combretastatin A-4 comes in two isomers, only one of which inhibits polymerization.[3][4]

Derivatives[edit]

Combretastatin A-4 is the active component of combretastatin A-4 phosphate, a prodrug designed to damage the vasculature (blood vessels) of cancer tumors causing central necrosis. A large number of synthetic derivatives have been reported, including beta-lactam based compounds.[5]

See also[edit]

  • Ombrabulin, a combretastatin A-4 derivative in clinical trials for treatment of cancer

References[edit]

  1. ^ Pettit, G. R.; Sheo Bux Singh Boyd; M. R. Hamel, E. (1995), "Antineoplastic Agents. 291. Isolation and Synthesis of Combretastatins A-4, A-5, and A-6", Journal of Medicinal Chemistry, 38: 1666–1672, doi:10.1021/jm00010a011 
  2. ^ Determination of Combretastatin A-4 in Combretum leprosum. SCN Queiroz, MR Assalin, S Nobre, IS Melo, RM Moraes, VL Ferracini and AL Cerdeira, Planta Med, 2010, volume 76, pages 53, doi:10.1055/s-0030-1251815
  3. ^ a b Gill, Rupinder; Kaur, Ramandeep; Kaur, Gurneet; Rawal, Ravindra; Shah, Anamik; Bariwal, Jitender. "A Comprehensive Review on Combretastatin Analogues as Tubulin Binding Agents". Current Organic Chemistry. 18 (19): 2462–2512. doi:10.2174/138527281819141028114428. 
  4. ^ "Colourful chemotherapy". The Economist. July 11, 2015. ISSN 0013-0613. Retrieved 2016-06-19. 
  5. ^ O'Boyle, N; Miriam Carr; Lisa M. Greene; Orla Bergin; Seema M. Nathwani; Thomas McCabe; David G. Lloyd; Daniela M Zisterer; Mary J. Meegan (2010). "Synthesis and evaluation of azetidinone analogues of combretastatin A-4 as tubulin targeting agents.". Journal of Medicinal Chemistry. 53 (24): 8569–8584. doi:10.1021/jm101115u. PMID 21080725.