Delineating noncovalent interactions between the azinomycins and double-stranded DNA: importance of the naphthalene substitution pattern on interstrand cross-linking efficiency.
[reaction: see text] Using a series of synthetic azinomycin analogues, it is shown that the efficiency of in vitro DNA interstrand cross-linking is markedly reduced when either the C-5' methyl group or both the C-5' methyl and C-3' methoxy groups are deleted from the naphthalene ring.
Landreau
Cyrille A S
CA
Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, U.K., School of Chemistry, University of St. Andrews, Purdie Building, St. Andrews, Fife KY16 9ST, UK.
LePla
Rachel C
RC
Shipman
Michael
M
Slawin
Alexandra M Z
AM
Hartley
John A
JA
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D053961:Azabicyclo Compounds; D003432:Cross-Linking Reagents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D004247:DNA / Q000737:chemistry / Q000187:drug effects*; D004151:Dipeptides; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D036341:Intercellular Signaling Peptides and Proteins; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000494:pharmacology; D010455:Peptides; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D053961:Azabicyclo Compounds; D003432:Cross-Linking Reagents; D004151:Dipeptides; D006020:Glycopeptides; D036341:Intercellular Signaling Peptides and Proteins; D009281:Naphthalenes; D010455:Peptides; C051055:azinomycin B; C051054:azinomycin A; C031721:naphthalene; D004247:DNA