Photochemical cycloaromatization reactions of ortho-dialkynylarenes: A new class of DNA photocleaving agents

Raymond Lee Funk, E. R R Young, R. M. Williams, M. F. Flanagan, T. L. Cecil

Research output: Contribution to journalArticlepeer-review

93 Scopus citations

Abstract

We are intrigued by the possibility of consolidating the functional elements of the enediyne anticancer antibiotics, thereby simplifying the task of synthesizing potential chemotherapeutic agents which operate by DNA cleavage pathways. Thus, it was envisaged that certain polycyclic ortho-dialkynylarenes would intercalate into DNA and, moreover, the planar π systems might be further exploited by facilitating photochemical, as opposed to thermal, cycloaromatization/cleavage reactions. We report herein on the viability of this photochemical transformation and the resultant new class of DNA photocleaving agents, whose binding and photoactive domains are consolidated, and which generate two reactive sites for subsequent ribose hydrogen atom abstraction(s).

Original languageEnglish (US)
Pages (from-to)3291-3292
Number of pages2
JournalJournal of the American Chemical Society
Volume118
Issue number13
DOIs
StatePublished - Apr 3 1996

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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