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Camptothecin (Molecule of the Month for June 2012)



Camptothecin is a cytotoxic quinoline alkaloid which inhibits the DNA enzyme topoisomerase I (topo I). It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs. It was isolated from the bark and stem of Camptotheca acuminata (Camptotheca, Happy tree), a tree native to China used as a cancer treatment in Traditional Chinese Medicine.

Camptothecin showed remarkable anticancer activity in preliminary clinical trials but also low solubility and (high) adverse drug reaction. Because of these disadvantages synthetic and medicinal chemists have developed numerous syntheses of Camptothecin and various derivatives to increase the benefits of the chemical, with good results. Two Camptothecin analogues have been approved and are used in cancer chemotherapy today, topotecan and irinotecan.

Camptothecin binds to the topo I and DNA complex (the covalent complex) resulting in a ternary complex, and thereby stabilizing it. This prevents DNA re-ligation and therefore causes DNA damage which results in apoptosis. Camptothecin binds both to the enzyme and DNA with hydrogen bonds.

Formal Chemical Name (IUPAC)
(S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b] quinoline-3,14-(4H,12H)-dione

References

http://en.wikipedia.org/wiki/Camptothecin

Picture of Camptothecin 3D model

click on the picture of  Camptothecin above to interact
with the 3D model of the
Camptothecin structure
(this will open a new browser window)

Picture of Camptothecin

C20H16N2O4



Update by Karl Harrison
(Molecule of the Month for June 2012 )

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