Conjugation of citric acid and gallic acid with serum albumins: Acid binding sites and protein conformation

Del Giudice, 2017, Time-dependent pH scanning of acid-induce unfolding of human serum albumin reveals stabilization of native from of palmitic acid binding, J. Phys. Chem. B, 121, 4388, 10.1021/acs.jpcb.7b01342 Kanse, 2017, A review on citric acid production and its applications, Int. J. Curr. Adv. Res., 6, 5880 Hiruna, 2012, Experimental FTIR and theoretical studies of gallic acid–acetonitrile clusters, Spectrochim. Acta A, 86, 93, 10.1016/j.saa.2011.10.009 Yang, 2014, Interactive association of drugs binding to human serum albumin, Int. J. Mol. Sci., 15, 3580, 10.3390/ijms15033580 Ghuman, 2005, Structural basis of the drug-binding specificity of human serum albumin, J. Mol. Biol., 353, 38, 10.1016/j.jmb.2005.07.075 Kratochwil, 2002, Predicting plasma protein binding of drugs: a new approach, Biochem. Pharmacol., 64, 1355, 10.1016/S0006-2952(02)01074-2 Ahmed Ouameur, 2006, An overview of drug binding to human serum albumin: protein folding and unfolding, Cell Biochem. Biophys., 45, 203, 10.1385/CBB:45:2:203 Elsadek, 2012, Impact of albumin on drug-delivery-new application on the horizon, J. Control. Release, 157, 4, 10.1016/j.jconrel.2011.09.069 Kratz, 2012, Clinical impact of serum proteins on drug delivery, J. Control. Release, 161, 429, 10.1016/j.jconrel.2011.11.028 Kratz, 2008, Albumin as a drug carrier: design of prodrugs, drug conjugates and nanoparticles, J. Control. Release, 132, 171, 10.1016/j.jconrel.2008.05.010 Tajmir-Riahi, 2017 Akdogan, 2012, Evidence for water-tuned structural differences in proteins: an approach emphasizing variations in local hydrophilicity, PLoS One, 7, 1, 10.1371/journal.pone.0045681 Painter, 1998, Synthesis and interaction with human serum albumin of the first 3,18-disub-stituted derivative of bilirubin, J. Chem. Soc. Perkin Trans., 18, 3041, 10.1039/a803429j Zhong, 2004, The interaction of human serum albumin with a novel antidiabetic agent-SU-118, J. Pharm. Sci., 93, 1039, 10.1002/jps.20005 Dousseau, 1989, On the spectral subtraction of water from the FT-IR spectra of aqueous solutions of proteins, Appl. Spectrosc., 43, 538, 10.1366/0003702894202814 Byler, 1986, Examination of the secondary structure of proteins by deconvoluted FTIR spectra, Biopolymers, 25, 469, 10.1002/bip.360250307 Beauchemin, 2007, Polyamine analogues bind human serum albumin, Biomacromolecules, 8, 3177, 10.1021/bm700697a Sugio, 1999, Crystal structure of human serum albumin at 2.5 a ° resolution, Protein Eng., 12, 439, 10.1093/protein/12.6.439 Arnold, 2006, A web-based environment for protein structure homology modeling, Bioinformatics, 22, 195, 10.1093/bioinformatics/bti770 Rost, 1999, Twilight zone of protein sequence alignment, Protein Eng., 12, 85, 10.1093/protein/12.2.85 Bourassa, 2011, Folic acid complexes with human and bovine serum albumins, Food Chem., 129, 1148, 10.1016/j.foodchem.2011.05.094 Ross, 1981, Thermodynamics of protein association reactions: forces contributing to stability, Biochemistry, 20, 3096, 10.1021/bi00514a017 Bose, 2016, Interaction of tea polyphenols with serum albumins: a fluorescence spectroscopic analysis, J. Lumin., 169, 220, 10.1016/j.jlumin.2015.09.018 Bekale, 2015, Effect of polymer molecular weight on chitosan-protein interaction, Colloids Surf. B Biointerfaces, 125, 309, 10.1016/j.colsurfb.2014.11.037 Bekale, 2014, Microscopic and thermodynamic analysis of PEG-lactoglobulin interaction, RSC Adv., 4, 31084, 10.1039/C4RA03303E Chandra, 2011, Dendrimer–doxorubicin conjugate for enhanced therapeutic effects for cancer, J. Mater. Chem., 21, 5729, 10.1039/c0jm04198j Krimm, 1986, Vibrational spectroscopy and conformation of peptides, polypeptides, and proteins, Adv. Protein Chem., 38, 181, 10.1016/S0065-3233(08)60528-8 Tian, 2005, Binding of the scutellarin to albumin using tryptophan fluorescence quenching, CD and FT-IR spectra, Am. J. Immunol., 1, 21, 10.3844/ajisp.2005.21.23 Grdadolnik, 2003, Saturation effects in FTIR spectroscopy: intensity of amide I and amide II bands in protein spectra, Acta Chim. Slov., 50, 777 Gokara, 2014, Differential interactions and structural stability of chitosan oligomers with human serum albumin and α-1-glycoprotein, J. Biomol. Struct. Dyn., 33, 196, 10.1080/07391102.2013.868321 Yeggoni, 2014, Binding and molecular dynamics studies of 7- hydroxycoumarin derivatives with human serum albumin and its pharmacological importance, Mol. Pharm., 11, 1117, 10.1021/mp500051f Nerusu, 2017, Unraveling the stability of plasma proteins upon interaction of synthesized androstenedione and its derivatives—a biophysical and computational approach, ACS Omega, 2, 6514, 10.1021/acsomega.7b00577 Chanphai, 2018, Conjugation of testo and testo-Pt(II) with serum proteins: loading efficacy and protein conformation, Int. J. Biol. Macromol., 118, 1112, 10.1016/j.ijbiomac.2018.06.186