DNA cleavage by the photolysis of cyclopentadienyl metal complexes: mechanistic studies and sequence selectivity of strand scission by CpW(CO)3CH3.
Mohler-DL; Downs-JR; Hurley-Predecki-AL; Sallman-JR; Gannett-PM; Shi-XL
J Org Chem 2005 Nov; 70(23):9093-9102
The photolysis of CpW(CO)3Me has been shown to produce methyl radicals and to cleave DNA in a single-stranded manner, and preliminary evidence implicated a carbon-centered radical in this process. In this work, the mechanism of strand scission in this reaction was determined to occur by hydrogen atom abstraction from the 4'- and 5'-positions of the deoxyribose moiety of the backbone of DNA. Additionally, in a side reaction that does not lead to frank strand scission, all four bases of DNA are methylated under these conditions; however, none of these base or backbone modifications lead to the formation of abasic sites.
Methyl-compounds; Genetics; Analytical-chemistry; Analytical-processes
Research Tools and Approaches: Cancer Research Methods
Journal of Organic Chemistry