脱氢枞基苯并咪唑希夫碱和酰腙衍生物与DNA作用的比较研究

doi:10.3969/j.issn.0253-2417.2016.03.012

Abstract

Abstract: Two derivatives of dehydroabietylamine and dehydroabietic acid, i.e., dehydroabietic-1-methyl benzoimidazol Schiff base (1) and dehydroabietic-1-methyl benzoimidazol hydrazone (2) were synthesized and characterized by FT-IR, MS, elemental analysis and ¹H NMR. Their interactions with salmon sperm DNA were investigated by fluorescence spectra, viscosity analysis and circular dichronism spectra. In fluorescence spectra, different concentrations of compounds 1 and 2 were added into DNA-EB system, and with the increase of concentration, the quenching effect of fluorescence intensity of DNA-EB system was obviously occurred. The results suggested that the compounds might be inserted into the base pairs of DNA, just like EB. According to Stern-Volmer equation analysis, the interaction of compound 1 and DNA was better than that of compound 2. With the increase of concentration of compounds 1 and 2, the viscosity of DNA increased gradually, and the increase amplitude of compound 1 was greater than that of compound 2. CD spectra showed that the same concentration of different compounds could make different changes of the CD signal quantity of the DNA, and the influence of compound 1 on the conformation of DNA was greater than compound 2. The three experimental results indicated that the two compounds bound to DNA by intercalation mode. The results of agarose gel electrophoresis suggested that compounds 1 and 2 could cleave PBR322 plasmid DNA by single strand in the presence of ascorbic acid. While in the absence of ascorbic acid, only compound 1 showed the same activity. All the data showed that Schiff base had stronger DNA binding ability.

Key words: dehydroabietic acid, dehydroabietylamine, benzimidazole, schiff base, hydrazone, DNA

CLC Number:

TQ351
O629

YIN Bin, XU Wu-shuang, XIE Jing-cong, ZHANG Yu, LIU Qing-bo, LONG Jian-ying, FEI Bao-li. Comparation Study of DNA Binding Property with Dehydrobietic Benzimidazole Schiff Base and Hydrazone Derivatives[J]. Chemistry and Industry of Forest Products, 2016, 36(3): 81-87.

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Comparation Study of DNA Binding Property with Dehydrobietic Benzimidazole Schiff Base and Hydrazone Derivatives

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