DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine.
A comparative study on the intercalating binding of sanguinarine, chelerythrine, and nitidine with CT DNA, poly(dG-dC).poly(dG-dC), poly(dA-dT).poly(dA-dT), and seven sequence-designed double-stranded oligodeoxynucleotides has been performed using fluorometric and spectrophotometric techniques, aiming at providing insights into their sequence selectivity for DNA-binding. The results show that both sanguinarine and nitidine bind preferentially to DNA containing alternating GC base pairs [d(TGCGCA)(2)], while chelerythrine exhibits quite distinct sequence selectivity from sanguinarine, which shows a high specificity for DNA containing contiguous GC base pairs [5'-TGGGGA-3'/3'-ACCCCT-5'].
Bai
Li-Ping
LP
School of Chinese Medicine, Hong Kong Baptist University, Kowloon Tong.
Zhao
Zhong-Zhen
ZZ
Cai
Zongwei
Z
Jiang
Zhi-Hong
ZH
D000470:Alkaloids / Q000737:chemistry / Q000494:pharmacology*; D020029:Base Pairing; D001483:Base Sequence; D053119:Benzophenanthridines; D001665:Binding Sites; D004247:DNA / Q000737:chemistry / Q000187:drug effects* / Q000378:metabolism; D007364:Intercalating Agents / Q000737:chemistry / Q000378:metabolism; D007546:Isoquinolines; D010617:Phenanthridines / Q000737:chemistry / Q000494:pharmacology*; D011089:Polydeoxyribonucleotides / Q000737:chemistry / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D013053:Spectrophotometry
D000470:Alkaloids; D053119:Benzophenanthridines; D007364:Intercalating Agents; D007546:Isoquinolines; D010617:Phenanthridines; D011089:Polydeoxyribonucleotides; D004247:DNA; C427203:calf thymus DNA; C013615:nitidine; C005705:sanguinarine; C016299:chelerythrine