Enediynes are organic compounds containing two triple bonds and one double bond. The term is usually used to describe a class of bacterial natural products characterized by either nine- and ten-membered rings in which the double bond lies between the two triple bonds. Many of these compounds are capable of undergoing Bergman cyclization. The resulting diradical, a 1,4-dehydrobenzene derivative, is capable of abstracting hydrogen atoms from the sugar backbone of DNA which results in strand scission. This high reactivity with DNA makes the substances toxic. They are being researched as antitumor agents. Several of the naturally occurring enediynes have entered clinical trials against cancer and in Japan neocarzinostatin is used clinically.
Three classes of enediynes exist:
The enediyne group in those compounds is often called a warhead.
- K. C. Nicolaou; A. L. Smith; E. W. Yue (1993). "Chemistry and biology of natural and designed enediynes". PNAS. 90 (13): 5881–5888. Bibcode:1993PNAS...90.5881N. doi:10.1073/pnas.90.13.5881. PMC . PMID 8327459.
- S. Walker; R. Landovitz; W.D. Ding; G.A. Ellestad; D. Kahne (1992). "Cleavage behavior of calicheamicin gamma 1 and calicheamicin T". Proc Natl Acad Sci USA. 89 (10): 4608–12. Bibcode:1992PNAS...89.4608W. doi:10.1073/pnas.89.10.4608. PMC . PMID 1584797.
- Jones, G. B.; Fouad, F. S. (1 January 2004). "Designed Enediyne Antitumor Agents". Frontiers in Medicinal Chemistry - Online. 1 (1): 189–214. doi:10.2174/1567204043396640.
- Jones, G.; Fouad, F. (1 December 2002). "Designed Enediyne Antitumor Agents". Current Pharmaceutical Design. 8 (27): 2415–2440. doi:10.2174/1381612023392810.