Chinese Journal of Organic Chemistry >
Syntheses, Spectral Properties of Novel Carbazole Derivatives and Evaluations of Its Ct-DNA Interaction
Received date: 2013-09-23
Revised date: 2013-11-18
Online published: 2013-12-06
Supported by
Project supported by the National Natural Science Foundation of China (No. 21102095), the Liaoning Provincial Natural Science Foundation (No. 201102209), the Program of Liaoning Excellent Talents in University (No. LJQ2012090), the Liaoning Provincial Postdoctoral Converging Project (No. 2011921013), and the Undergraduates Innovative Entrepreneurship Training Project of Liaoning Province (No. 201210163012).
A series of carbazole derivatives were synthesized via reactions of C—N bond formation catalyzed by CuBr·SMe2, nitration, reduction as well as Pd-catalyzed C—N crossing coupling, respectively. Their UV-Vis and fluorescence spectra in different solvents were investigated, as well as the evaluation of the interaction between compound 2 hydrochloride and Ct-DNA. The results showed that all compounds exhibited distinct solvatochromism effects and among them, compound 4 was the most obvious one. Upon binding with DNA, the fluorescence of compound 2 hydrochloride turned on, instead of quenching, and the minor groove of DNA is the most possible position for the molecule to bind with. The calculated binding constant is around 104 L·mol-1, showing a moderate binding affinity.
Key words： carbazole; C—N cross coupling; solvatochromism; spectral properties; Ct-DNA
Jian Yong , Li Gang , Yang Peng , Deng Tuo , Zhou Xue , Xu Haiyan . Syntheses, Spectral Properties of Novel Carbazole Derivatives and Evaluations of Its Ct-DNA Interaction[J]. Chinese Journal of Organic Chemistry, 2014 , 34(4) : 809 -816 . DOI: 10.6023/cjoc201309030
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