Open AccessPhoto-induced DNA cleavage reaction characteristics of propargylic sulfones possessing an anthraquinone chromophore
Author(s) -
Kenichi Haruna,
Atsushi Ishii,
Kazuhito Tanabe,
WeiMin Dai,
Hiroshi Hatta,
Satoshi Nishimoto
Publication year - 2003
Publication title -
nucleic acids symposium series
Language(s) - English
Resource type - Journals
eISSN - 1746-8272
pISSN - 0261-3166
DOI - 10.1093/nass/3.1.81
Subject(s) - cleavage (geology) , dna , chemistry , guanine , alkylation , intercalation (chemistry) , anthraquinone , stereochemistry , cleave , base pair , biochemistry , organic chemistry , nucleotide , biology , catalysis , paleontology , fracture (geology) , gene
Propargylic sulfones (PS) are known as pH dependent DNA cleaver. DNA cleavage by PS was considered to proceed by alkylation of G base to allenic sulfones formed from PS in basic condition. We designed PS posessing naphthalene and anthraquinone (AQ) unit and investigated DNA cleavage characteristics. Although these compounds showed high intercalating abilities, this high intercalating ability did not lead to DNA cleaving activity. This result indicates that spatial arrangement of activated allene against guanine base is very important in DNA cleavage by PS. In addition, UV-irradiation to PS possessing AQ unit leads to efficient DNA cleavage at 5'-G of GG sequence. This cleavage pattern exhibited typical cleavage of one-electron oxidation of B-form DNA. Therefore, this result suggests that PS possessing AQ unit cleave DNA by both the alkylation mechanism and the photooxidaization mechanism.
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