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C1-C5 Photochemical Cyclization of Enediynes Igor V. Alabugin* and Serguei V. Kovalenko
 

Summary: C1-C5 Photochemical Cyclization of Enediynes
Igor V. Alabugin* and Serguei V. Kovalenko
Department of Chemistry and Biochemistry, Florida State UniVersity, Tallahassee, Florida 32306-4390
Received April 22, 2002
The high biological activity of the naturally occurring enediyne
antibiotics such as calicheamicin, esperamicin, dynemicin, and
neocarzinostatin1 is associated with formation of a reactive 1,4-
dehydrobenzene diradical through a thermal cyclization of the
enediyne moiety (the Bergman cyclization).2 The simultaneous
formation of two radical centers is important because it leads to
the abstraction of two hydrogen atoms, one from the sugar backbone
of each strand of a double-stranded DNA. The double hydrogen-
atom (H-atom) abstraction results in double-strand cleavage of DNA
and, ultimately, the self-programmed cell death (apoptosis).
Unfortunately, the high reactivity of natural enediynes renders
them extremely toxic. This explains recent efforts devoted to the
development of the photochemical version of the Bergman cycliza-
tion3,4 as an attractive strategy for designing less toxic enediyne
drugs. The appeal of the photochemical activation is that it allows
time- and space-resolved drug activation with the drug being

  

Source: Alabugin, Igor - Department of Chemistry and Biochemistry, Florida State University

 

Collections: Chemistry; Biology and Medicine