title: Multispectroscopic and docking studies on the binding of chlorogenic acid isomers to human serum albumin: Effects of esteryl position on affinity.
abstract: Structural differences among various dietary polyphenols affect their absorption, metabolism, and bioactivities. In this work, chlorogenic acid (CA) and its two positional isomers, neochlorogenic acid (NCA) and cryptochlorogenic acid (CCA), were investigated for their binding reactions with human serum albumin (HSA) using fluorescence, ultraviolet-visible, Fourier transform infrared and circular dichroism spectroscopies, as well as molecular docking. All three isomers were bound to HSA at Sudlow's site I and affected the protein secondary structure. CCA presented the strongest ability of hydrogen-bond formation, and both CA and NCA generated more electrostatic interactions with HSA. The albumin-binding capacity of these compounds decreased in the order CCA>NCA>CA. The compound with 4-esteryl structure showed higher binding affinity and larger conformational changes to HSA than that with 3- or 5-esteryl structures. These comparative studies on structure-affinity relationship contributed to the structural modification and design of phenolic food additives or new polyphenol-like drugs.
authors.affiliation: College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, PR China.
authors.forename: Bin
authors.initials: B
authors.lastname: Tang
authors.affiliation: College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, PR China.
authors.forename: Yanmei
authors.initials: Y
authors.lastname: Huang
authors.affiliation: College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, PR China.
authors.forename: Xiangling
authors.initials: X
authors.lastname: Ma
authors.affiliation: College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, PR China; Technology Center, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650204, Yunnan, PR China.
authors.forename: Xiaoxiang
authors.initials: X
authors.lastname: Liao
authors.affiliation: College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, PR China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Wang
authors.affiliation: College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, PR China.
authors.forename: Xinnuo
authors.initials: X
authors.lastname: Xiong
authors.affiliation: College of Chemical Engineering, Sichuan University, Chengdu 610065, Sichuan, PR China. Electronic address: lihuilab@sina.com.
authors.forename: Hui
authors.initials: H
authors.lastname: Li
mesh_terms: D002726:Chlorogenic Acid / Q000737:chemistry* / Q000378:metabolism*; D002942:Circular Dichroism / Q000379:methods*; D006801:Humans; D007536:Isomerism; D062105:Molecular Docking Simulation / Q000379:methods*; D011485:Protein Binding; D017433:Protein Structure, Secondary; D012709:Serum Albumin / Q000737:chemistry* / Q000378:metabolism*; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods
chemical_list: D012709:Serum Albumin; D002726:Chlorogenic Acid
keywords: Affinity; Chlorogenic acid; Chlorogenic acid (PubChem CID: 1794427); Cryptochlorogenic acid (PubChem CID: 9798666); Food additive; Human serum albumin; Ibuprofen (PubChem CID: 3672); Neochlorogenic acid (PubChem CID: 5280633); Phenylbutazone (PubChem CID: 4781); Polyphenol; Spectroscopy; Structure