Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities.
This communication describes the facile synthesis of five novel berberine dimers and their strong affinities toward double-stranded DNA. These berberine dimers were synthesized in 37-84% yields from the reaction of berberrubine with dihaloalkanes of varying lengths, and fully characterized by HRMS and 1H NMR. Compared with the monomeric parent berberine, these dimers showed greatly enhanced binding affinities up to approximately 100-fold, with two double helical oligodeoxynucleotides, d(AAGAATTCTT)2 and d(TAAGAATTCTTA)2, which was investigated by means of fluorescence spectrometry.
Chen
Wen-Hua
WH
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, PR China. cescwh@zsu.edu.cn
Pang
Ji-Yan
JY
Qin
Yong
Y
Peng
Qian
Q
Cai
Zongwei
Z
Jiang
Zhi-Hong
ZH
D001483:Base Sequence; D001599:Berberine / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D004247:DNA / Q000378:metabolism*; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D013050:Spectrometry, Fluorescence
D001599:Berberine; D004247:DNA