title: Photochemical Generation of Benzyl Cations That Selectively Cross-Link Guanine and Cytosine in DNA.
abstract: UV irradiation of several aryl boronates efficiently produced bifunctional benzyl cations that selectively form guanine-cytosine cross-links in DNA. Photoinduced homolysis of the C-Br bond took place with the aryl boronate bromides 3a and 4a, generating free radicals that were oxidized to benzyl cations via electron transfer. However, photoirradiation of the quaternary ammonium salts 3b and 4b led to heterolysis of C-N bond, directly producing benzyl cations. The electron-donating group in the aromatic ring greatly enhanced cross-linking efficiency.
authors.affiliation: Department of Chemistry and Biochemistry and Milwaukee Institute of Drug Discovery, University of Wisconsin Milwaukee , 3210 North Cramer Street, Milwaukee, Wisconsin 53211, United States.
authors.forename: Yibin
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of California Riverside , 501 Big Springs Road, Riverside, California 92521-0403, United States.
authors.forename: Shuo
authors.initials: S
authors.lastname: Liu
authors.affiliation: Department of Chemistry and Biochemistry and Milwaukee Institute of Drug Discovery, University of Wisconsin Milwaukee , 3210 North Cramer Street, Milwaukee, Wisconsin 53211, United States.
authors.forename: Zechao
authors.initials: Z
authors.lastname: Lin
authors.affiliation: Department of Chemistry and Biochemistry and Milwaukee Institute of Drug Discovery, University of Wisconsin Milwaukee , 3210 North Cramer Street, Milwaukee, Wisconsin 53211, United States.
authors.forename: Yukai
authors.initials: Y
authors.lastname: Fan
authors.affiliation: Department of Chemistry, University of California Riverside , 501 Big Springs Road, Riverside, California 92521-0403, United States.
authors.forename: Yinsheng
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Department of Chemistry and Biochemistry and Milwaukee Institute of Drug Discovery, University of Wisconsin Milwaukee , 3210 North Cramer Street, Milwaukee, Wisconsin 53211, United States.
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Peng
mesh_terms: D001483:Base Sequence; D001555:Benzene Derivatives / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D002412:Cations; D003432:Cross-Linking Reagents / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000737:chemistry; D003596:Cytosine / Q000737:chemistry*; D004247:DNA / Q000737:chemistry; D018736:DNA Adducts / Q000737:chemistry; D006147:Guanine / Q000737:chemistry*; D006898:Hydroxylamines / Q000737:chemistry; D010084:Oxidation-Reduction; D055668:Photochemical Processes
chemical_list: D001555:Benzene Derivatives; D001897:Boronic Acids; D002412:Cations; D003432:Cross-Linking Reagents; D003497:Cyclic N-Oxides; D018736:DNA Adducts; D006898:Hydroxylamines; D006147:Guanine; D003596:Cytosine; D004247:DNA; C005214:methoxyamine; C003959:TEMPO