Spacer length and attaching position-dependent binding of synthesized protoberberine dimers to double-stranded DNA.
Six jatrorrhizine homodimers and berberine-jatrorrhizine heterodimers have been synthesized in moderate to good yields from the reaction of jatrorrhizine with alpha,omega-dibromoalkanes and 9-O-(omega-bromoalkyl)berberines, respectively. Their binding activities toward calf thymus (CT) DNA and three double-stranded oligodeoxynucleotides, d(AAGAATTCTT)(2), d(TAAGAATTCTTA)(2), and d(TTAAGAATTCTTAA)(2), were investigated by means of spectrofluorimetric and spectrophotometric titrations. The results indicate that these dimers exhibit enhanced DNA-binding affinities due to the cooperative interaction of the two protoberberine subunits. A comparative study of the DNA-binding behaviors of berberine homodimers, jatrorrhizine homodimers, and berberine-jatrorrhizine heterodimers suggests that spacer length and attaching position are of great importance in modulating their DNA-binding affinities.
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China.
Yu-Hua
YH
Long
Li-Ping
LP
Bai
Yong
Y
Qin
Ji-Yan
JY
Pang
Wen-Hua
WH
Chen
Zongwei
Z
Cai
Zun-Le
ZL
Xu
Zhi-Hong
ZH
Jiang
D001599:Berberine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001600:Berberine Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D019281:Dimerization
D001600:Berberine Alkaloids; C055785:jatrorrhizine; D001599:Berberine; C009090:protoberberine; D004247:DNA