百里香酚和香芹酚与DNA的结合：药物 - DNA相互作用模型

Thymol and carvacrol binding to DNA: model for drug-DNA interaction.

作者信息

Nafisi Sh, Hajiakhoondi A, Yektadoost A

机构信息

Department of Chemistry, Azad University, Tehran Central Branch, South Felestine Street, Below the Felestine Square, Tehran 14169 63316, Iran.

出版信息

Biopolymers. 2004 Aug 5;74(5):345-51. doi: 10.1002/bip.20080.

DOI:10.1002/bip.20080

PMID:15222014

Abstract

Thymol and carvacrol can bind to major and minor grooves of B-DNA. The aim of this study was to examine the interaction of calf thymus DNA with thymol and carvacrol in aqueous solution and physiological pH with thymol/DNA and carvacrol/DNA (phosphate) molar ratios of 1/20, 1/10, 1/5, and 1/1. Fourier transform infrared and UV-visible difference spectroscopy were used to determine the thymol and carvacrol binding mode, binding constant, sequence selectivity, DNA secondary structure, and structural variations of thymol/DNA and carvacrol/DNA complexes in aqueous solution. Spectroscopic evidence showed that the thymol and carvacrol interaction occurred mainly through H-bonding of the thymol and carvacrol OH group to the guanine N7, cytosine N3, and backbone phosphate group with overall binding constant of K(thymol-DNA) = 2.43 x 10(3) M(-1), K(carvacrol-DNA) = 1.55 x 10(3) M(-1). In thymol and carvacrol-DNA complexes, DNA remains in the B-family structure.

摘要

百里香酚和香芹酚能够与B型DNA的大沟和小沟结合。本研究的目的是在水溶液和生理pH条件下，考察小牛胸腺DNA与百里香酚和香芹酚在百里香酚/DNA和香芹酚/DNA（磷酸盐）摩尔比为1/20、1/10、1/5和1/1时的相互作用。采用傅里叶变换红外光谱和紫外可见差示光谱法来确定百里香酚和香芹酚的结合模式、结合常数、序列选择性、DNA二级结构以及水溶液中百里香酚/DNA和香芹酚/DNA复合物的结构变化。光谱学证据表明，百里香酚和香芹酚的相互作用主要通过百里香酚和香芹酚的羟基与鸟嘌呤N7、胞嘧啶N3以及主链磷酸基团形成氢键，其总结合常数为K（百里香酚-DNA）= 2.43×10³ M⁻¹，K（香芹酚-DNA）= 1.55×10³ M⁻¹。在百里香酚和香芹酚-DNA复合物中，DNA保持B族结构。