C-9不同位阻取代小檗碱衍生物的合成及对DNA键合作用的影响

Synthesis and DNA-binding Activities of C-9 Substituted Berberines

以小檗碱为原料,合成了小檗碱C-9位不同空间位阻取代的9-乙氧基小檗碱、9-异丙氧基小檗碱,通过MS、1H NMR确认其结构。运用紫外可见吸收光谱法和荧光光谱法研究了化合物与CT DNA的结合作用。结果发现,小檗碱C-9位上的不同空间位阻会影响小檗碱衍生物与CT DNA的相互作用,随空间位阻增大结合强度减小,结合模式也发生了变化,初步证明了小檗碱类化合物可能是从环的C-8,9,10这一侧与DNA相互作用,用实验验证了Mazzini计算机模拟的结合模型。

9-Ethoxyberberine and 9-isopropanoxyberberine bearing with different sterically hindered groups were synthesized from beberrubine material. The interaction between these berberine derivatives and CT DNA were analyzed by UV-vis and fluorescence spectroscopies. The results indicated that increasing in the steric hindrance of the C-9 position of berberine derivatives leads to a decrease in the DNA-binding affinity, which may provide an evidence supporting the binding of berberine to DNA from its C5-C6-N^ ＋-C8 side.