Interchain cross-linking of DNA mediated by the principal adduct of acrolein

I. D. Kozekov, L. V. Nechev, A. Sanchez, C. M. Harris, R. S. Lloyd, T. M. Harris

Research output: Contribution to journalArticlepeer-review

62 Scopus citations


A DNA duplex containing the primary acrolein adduct, 3-(2-deoxy-β-D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8- hydroxypyrimido[1,2-a]purin-10(3H)-one (2), of deoxyguanosine in a 5′-CpG sequence context spontaneously but reversibly formed an interchain cross-link with the exocyclic amino group of deoxyguanosine in the opposing chain. The linkage was sufficiently stable that the cross-linked duplex could be isolated by HPLC and characterized by MALDI-TOF mass spectrometry. Enzymatic degradation gave bis-nucleoside 6, which was independently prepared by direct reaction of 2 with dGuo.

Original languageEnglish (US)
Pages (from-to)1482-1485
Number of pages4
JournalChemical Research in Toxicology
Issue number11
StatePublished - 2001
Externally publishedYes

ASJC Scopus subject areas

  • Toxicology


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