Characterization of hydroxycinnamic acid derivatives binding to bovine serum albumin

被引:54
作者
Jin, Xiao-Ling [1 ]
Wei, Xia [1 ]
Qi, Feng-Ming [1 ]
Yu, Sha-Sha [1 ]
Zhou, Bo [1 ]
Bai, Shi [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
SPIN-LATTICE-RELAXATION; TRANSFER DIFFERENCE NMR; CINNAMIC ACID; ANTIOXIDANT ACTIVITY; LIGAND-BINDING; PHENOLIC-ACIDS; CAFFEIC ACID; IN-VITRO; SPECTROSCOPY; POLYPHENOLS;
D O I
10.1039/c2ob25237f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydroxycinnamic acid derivatives (HCAs) are a group of naturally occurring polyphenolic compounds which possess various pharmacological activities. In this work, the interactions of bovine serum albumin (BSA) with six HCA derivatives, including chlorogenic acid (CHA), caffeic acid (CFA), m-coumaric acid (m-CA), p-coumaric acid (p-CA), ferulic acid (FA) and sinapic acid (SA) have been investigated by NMR spectroscopic techniques in combination with fluorescence and molecular modeling methods. Competitive STD NMR experiments using warfarin sodium and L-tryptophan as site-selective probes indicated that HCAs bind to site I in the subdomain IIA of BSA. From the analysis of the STD NMR-derived binding epitopes and molecular docking models, it was deduced that CHA, CFA, m-CA and p-CA show similar binding modes and orientation, in which the phenyl ring is in close contact with protein surface, whereas carboxyl group points out of the protein. However, FA and SA showed slightly different binding modes, due to the steric hindrance of methoxy-substituents on the phenyl ring. Relaxation experiments provided detailed information about the relationship between the affinity and structure of HCAs. The binding affinity was the strongest for CHA and ranked in the order CHA > CFA > m-CA >= p-CA > FA > SA, which agreed well with the results from fluorescence experiments. Based on our experimental results, we also conclude that HCAs bind to BSA mainly by hydrophobic interaction and hydrogen bonding. This study therefore provides valuable information for elucidating the mechanisms of BSA-HCAs interaction.
引用
收藏
页码:3424 / 3431
页数:8
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