title: Binding of a chromen-4-one Schiff's base with bovine serum albumin: capping with β-cyclodextrin influences the binding.
abstract: This work deals with the synthesis of 6-methyl-3-[(4'-methylphenyl)imino]methyl-4H-chromen-4-one (MMPIMC), its binding to β-cyclodextrin, and the influence of the cyclodextrin complexation on the compound's binding to bovine serum albumin (BSA). The 1:2 stoichiometry for the complexation of MMPIMC with β-cyclodextrin is determined with the binding constant of 1.90 × 10(4) M(-2). The structure of host-guest complex plays a role in protein binding of MMPIMC. One- and two-dimensional NMR spectra are used to determine the mode of binding of the guest to β-cyclodextrin cavity and the structure of the inclusion complex is proposed. The binding of MMPIMC with BSA in the absence and the presence of β-cyclodextrin is studied. The binding strengths of MMPIMC-BSA (1.73 × 10(5) M(-1)) and β-cyclodextrin-complexed MMPIMC-BSA (9.0 × 10(4) M(-1)) show difference in magnitude. The Förster Resonance Energy Transfer efficiency and the proximity of the donor and acceptor molecules, are modulated by β-cyclodextrin. Molecular modeling is used to optimize the sites and mode of binding of MMPIMC with bovine serum albumin.
authors.affiliation: a Department of Chemistry, School of Science and Humanities , Karunya University , Karunya Nagar, Coimbatore 641 114 , Tamil Nadu , India.
authors.forename: Sowrirajan
authors.initials: S
authors.lastname: Chandrasekaran
authors.forename: Natesan
authors.initials: N
authors.lastname: Sudha
authors.forename: D
authors.initials: D
authors.lastname: Premnath
authors.forename: Israel V M V
authors.initials: IV
authors.lastname: Enoch
mesh_terms: D000818:Animals; D002417:Cattle; D002867:Chromones / Q000737:chemistry*; D002942:Circular Dichroism; D031541:Fluorescence Resonance Energy Transfer; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011485:Protein Binding; D011487:Protein Conformation; D012545:Schiff Bases / Q000737:chemistry*; D012710:Serum Albumin, Bovine / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: C000606743:6-methyl-3-((4'-methylphenyl)imino)methyl-4H-chromen-4-one; D002867:Chromones; D012545:Schiff Bases; D047392:beta-Cyclodextrins; D012710:Serum Albumin, Bovine; C031215:betadex
keywords: COSY; FRET; ROESY; bovine serum albumin; chromen-4-one Schiff’s base; β-cyclodextrin