title: DNA interstrand cross-linking by a mycotoxic diepoxide.
abstract: The diepoxide mycotoxin (2R, 3R, 8R, 9R)-4,6-decadiyne-2,3:8,9-diepoxy-1,10-diol (repandiol) was both isolated from the mushroom Hydnum repandum and synthesized de novo. Repandiol was found to form interstrand cross-links within a restriction fragment of DNA, linking deoxyguanosines on opposite strands primarily within the 5'-GNC and 5'-GNNC sequences preferred by diepoxyoctane. However, repandiol was a significantly less efficient cross-linker than either of the diepoxyalkanes (diepoxyoctane and diepoxybutane) to which it was compared.
authors.affiliation: Department of Chemistry, Colby College, 5757 Mayflower Hill Drive, Maine Waterville, ME 04901, USA. jtmillar@colby.edu
authors.forename: J T
authors.initials: JT
authors.lastname: Millard
authors.forename: J L
authors.initials: JL
authors.lastname: Katz
authors.forename: J
authors.initials: J
authors.lastname: Goda
authors.forename: E D
authors.initials: ED
authors.lastname: Frederick
authors.forename: S E
authors.initials: SE
authors.lastname: Pierce
authors.forename: T J
authors.initials: TJ
authors.lastname: Speed
authors.forename: D M
authors.initials: DM
authors.lastname: Thamattoor
mesh_terms: D000480:Alkynes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001483:Base Sequence; D003432:Cross-Linking Reagents / Q000737:chemistry / Q000494:pharmacology*; D003603:Cytotoxins / Q000737:chemistry / Q000494:pharmacology*; D004247:DNA / Q000737:chemistry* / Q000187:drug effects; D004852:Epoxy Compounds / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008969:Molecular Sequence Data; D010880:Piperidines / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000480:Alkynes; D003432:Cross-Linking Reagents; D003603:Cytotoxins; D004852:Epoxy Compounds; D010880:Piperidines; C080187:repandiol; C032727:piperidine; D004247:DNA