Journal of the American Chemical Society p. 1690 - 1697 (1994)
Update date:2022-08-17
Topics:
Chatterjee, Moneesh
Rokita, Steven E.
Oligonucleotide-naphthoquinone conjugates were prepared and examined for use as inducible, site-directed alkylating agents of DNA. Reaction was found to be sequence specific and under control of either biomimetic reduction or near-UV irradiation. Both conditions induced the formation of a transient and highly electrophilic intermediate consistent with a quinone methide. Enzymatic reduction of 5-((mesyloxy)methyl)- and 5-(bromomethyl)naphthoquinone derivatives produced cross-linking between a target and probe sequence, but the equivalent 5-(acetoxymethyl), 5-(hydroxymethyl) and 5-methyl analogues were predictably inactive. Conversely, irradiation of the 5-methylnaphthoquinone derivative produced cross-linking through a mechanism of photochemical enolization that was not available to the 6-methyl, 3-methyl, or unsubstituted analogues. Hydroxyl radical footprinting of the modified DNA demonstrated that guanine and cytosine were targets of alkylation.
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