title: Spectroscopic investigation of the interaction of water-soluble azocalix[4]arenes with bovine serum albumin.
abstract: In this work, three hydrosoluble azocalix[4]arene derivatives, 5-(o-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]arene (o-MAC-Calix), 5-(m-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]arene (m-MAC-Calix) and 5-(p-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]arene (p-MAC-Calix) were synthesized. Their structures were characterized by infrared spectrum (IR), nuclear magnetic resonance spectrum (1H NMR and 13C NMR) and mass spectrum (MS). The interactions between these compounds and bovine serum albumin (BSA) were studied by fluorescence spectroscopy, UV-vis spectrophotometry and circular dichroic spectroscopy. According to experimental results, three azocalix[4]arene derivatives can efficiently bind to BSA molecules and the o-MAC-Calix displays more efficient interactions with BSA molecules than m-MAC-Calix and p-MAC-Calix. Molecular docking showed that the o-MAC-Calix was embedded in the hydrophobic cavity of helical structure of BSA molecular and the tryptophan (Trp) residue of BSA molecular had strong interaction with o-MAC-Calix. The fluorescence quenching of BSA caused by azocalix[4]arene derivatives is attributed to the static quenching process. In addition, the synchronous fluorescence spectroscopy indicates that these azocalix[4]arene derivatives are more accessible to Trp residues of BSA molecules than the tyrosine (Tyr) residues. The circular dichroic spectroscopy further verified the binding of azocalix[4]arene derivatives and BSA.
authors.affiliation: College of Chemistry, Liaoning University, Shenyang 110036, PR China. Electronic address: pingfan_bft@126.com.
authors.forename: Ping
authors.initials: P
authors.lastname: Fan
authors.affiliation: College of Chemistry, Liaoning University, Shenyang 110036, PR China.
authors.forename: Lu
authors.initials: L
authors.lastname: Wan
authors.affiliation: State Key Laboratory of Heavy Oil Processing, The Key Laboratory of Catalysis of CNPC, China University of Petroleum, Changping, Beijing 102249, PR China.
authors.forename: Yunshan
authors.initials: Y
authors.lastname: Shang
authors.affiliation: College of Chemistry, Liaoning University, Shenyang 110036, PR China.
authors.forename: Jun
authors.initials: J
authors.lastname: Wang
authors.affiliation: College of Chemistry, Liaoning University, Shenyang 110036, PR China.
authors.forename: Yulong
authors.initials: Y
authors.lastname: Liu
authors.affiliation: College of Chemistry, Liaoning University, Shenyang 110036, PR China.
authors.forename: Xiaoyu
authors.initials: X
authors.lastname: Sun
authors.affiliation: College of Chemistry, Liaoning University, Shenyang 110036, PR China.
authors.forename: Chen
authors.initials: C
authors.lastname: Chen
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D047250:Calixarenes / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D012710:Serum Albumin, Bovine / Q000737:chemistry*; D012995:Solubility; D013057:Spectrum Analysis / Q000379:methods*; D014867:Water / Q000737:chemistry
chemical_list: D001391:Azo Compounds; D010636:Phenols; C121325:calix(4)arene; D014867:Water; D047250:Calixarenes; D012710:Serum Albumin, Bovine
keywords: Azocalix[4]arene derivatives; Bovine serum albumin (BSA); Fluorescence spectroscopy; Interaction