DNA interstrand cross-linking by a mycotoxic diepoxide.
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.
Millard
J T
JT
Department of Chemistry, Colby College, 5757 Mayflower Hill Drive, Maine Waterville, ME 04901, USA. jtmillar@colby.edu
Katz
J L
JL
Goda
J
J
Frederick
E D
ED
Pierce
S E
SE
Speed
T J
TJ
Thamattoor
D M
DM
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
D000480:Alkynes; D003432:Cross-Linking Reagents; D003603:Cytotoxins; D004852:Epoxy Compounds; D010880:Piperidines; C080187:repandiol; C032727:piperidine; D004247:DNA