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Enediynes are a class of bacterial natural products characterized by either nine- and ten-membered rings containing two triple bonds separated by a double bond.[1] 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.[2] 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[3] [4] and in Japan neocarzinostatin is used clinically.

Three classes of enediynes exist:

The enediyne group in those compounds is often called a warhead.