Description and references

Family of 15-20 enediyne antitumor antibiotics produced by Micromonospora echinospora ssp. calichensis, a bacterium isolated from chalky soil or a caliche. Naming is based on TLC mobility using Greek letters with subscripts and on the halogen substitution which is indicted by the superscript. Binds to the minor groove of DNA and initiates double stranded DNA cleavage via a radical abstraction process. This type of damage is usually lethal as it is not repairable by the cell. Isoln: W. M. Maiese et al., J. Antibiot. 42, 558 (1989). Structure elucidation: M. D. Lee et al., J. Am. Chem. Soc. 109, 3464, 3466 (1987); and NMR studies: eidem, ibid. 114, 985 (1992). DNA cleavage behavior: N. Zein et al., Science 240, 1198 (1988); S. Walker et al., Proc. Natl. Acad. Sci. USA 89, 4608 (1992); M. Chatterjee et al., J. Am. Chem. Soc. 118, 1938 (1996). Series of articles on total synthesis of γ₁^I: ibid. 115, 7593-7635 (1993). Book on calicheamicins and related compounds: Enediyne Antibiotics As Antitumor Agents, D. B. Borders, T. W. Doyle, Eds. (Marcel Dekker, Inc., New York, 1995) 478 pp.

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