Investigation of the interaction between salvianolic acid C and xanthine oxidase: Insights from experimental studies merging with molecular docking methods

Bioorganic Chemistry - Tập 88 - Trang 102981 - 2019
Hongjin Tang1, Dongsheng Zhao2
1College of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu 241000, PR China
2College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, PR China

Tài liệu tham khảo

Abeles, 2007, Update on gout: pathophysiology and potential treatments, Curr. Pain. Headache Rep., 11, 440, 10.1007/s11916-007-0231-3 Enroth, 2000, Crystal structures of bovine milk xanthine dehydrogenase and xanthine oxidase: structure-based mechanism of conversion, Proc. Natl. Acad. Sci., 97, 10723, 10.1073/pnas.97.20.10723 Harrison, 2002, Structure and function of xanthine oxidoreductase: where are we now?, Free Radical Biol. Med., 33, 774, 10.1016/S0891-5849(02)00956-5 Kumar, 2014, Synthesis and xanthine oxidase inhibitory activity of 5,6-dihydropyrazolo/pyrazolo[1,5-c] quinazoline derivatives, Bioorg. Chem., 57, 57, 10.1016/j.bioorg.2014.08.007 Cheng, 2011, Antioxidant xanthone derivatives induce cell cycle arrest and apoptosis and enhance cell death induced by cisplatin in NTUB1 cells associated with ROS, Eur. J. Med. Chem., 46, 1222, 10.1016/j.ejmech.2011.01.043 Khanna, 2012, Isocytosine-based inhibitors of xanthine oxidase: design, synthesis, SAR, PK and in vivo efficacy in rat model of hyperuricemia, Bioorg. Med. Chem. Lett., 22, 7543, 10.1016/j.bmcl.2012.10.029 B-Rao, 2012, Identification of novel isocytosine derivatives as xanthine oxidase inhibitors from a set of virtual screening hits, Bioorg. Med. Chem., 20, 2930, 10.1016/j.bmc.2012.03.019 Wang, 2010, Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors, Eur. J Med. Chem., 45, 2663, 10.1016/j.ejmech.2010.02.013 Li, 2017, Synthesis and bioevaluation of 1-phenyl-pyrazole-4-carboxylic acid derivatives as potent xanthine oxidoreductase inhibitors, Eur. J. Med. Chem., 140, 20, 10.1016/j.ejmech.2017.08.047 Tang, 2016, Molecular modelling studies of 3,5-dipyridyl-1,2,4-triazole derivatives as xanthine oxidoreductase inhibitors using 3D-QSAR, Topomer CoMFA, molecular docking and molecular dynamic simulations, J. Taiwan Inst. Chem. E, 68, 64, 10.1016/j.jtice.2016.09.018 Matsumoto, 2010, FYX-051: a novel and potent hybrid-type inhibitor of xanthine oxidoreductase, J. Pharmacol. Exp. Ther., 336, 95, 10.1124/jpet.110.174540 Ishibuchi, 2001, Synthesis and structure-activity relationships of 1-phenylpyrazoles as xanthine oxidase inhibitors, Bioorg. Med. Chem. Lett., 11, 879, 10.1016/S0960-894X(01)00093-2 Guan, 2014, Synthesis and bioevaluation of 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acids as potent xanthine oxidase inhibitors, Eur. J. Med. Chem., 85, 508, 10.1016/j.ejmech.2014.08.014 Chen, 2015, Synthesis and evaluation of 1-hydroxy/methoxy-4-methyl-2-phenyl-1H-imidazole-carboxylic acid derivatives as non-purine xanthine oxidase inhibitors, Eur. J. Med. Chem., 103, 343, 10.1016/j.ejmech.2015.08.056 Morrison, 2014, Natural products as starting points for the synthesis of complex and diverse compounds, Nat. Prod. Rep., 31, 6, 10.1039/C3NP70063A Dias, 2012, A historical overview of natural products in drug discovery, Metabolites, 2, 303, 10.3390/metabo2020303 Ouyang, 2014, Plant natural products: from traditional compounds to new emerging drugs in cancer therapy, Cell Proliferat., 47, 506, 10.1111/cpr.12143 Tsai, 2014, Neolignans as xanthine oxidase inhibitors from Hyptis rhomboids, Phytochemistry, 101, 121, 10.1016/j.phytochem.2014.01.016 Liu, 2015, Xanthine oxidase inhibitors isolated from Piper nudibaccatum, Phytochem. Lett., 12, 133, 10.1016/j.phytol.2015.03.005 Nepali, 2011, A rational approach for the design and synthesis of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles as a new class of potential non-purine xanthine oxidase inhibitors, Bioorg. Med. Chem., 19, 1950, 10.1016/j.bmc.2011.01.058 Darwish, 2010, Spectroscopic investigations of pentobarbital interaction with human serum albumin, J. Mol. Struct., 963, 122, 10.1016/j.molstruc.2009.10.023 Zhang, 2012, Multispectroscopic studies on the interaction of maltol, a food additive, with bovine serum albumin, Food Chem., 133, 264, 10.1016/j.foodchem.2012.01.014 Ghasemi, 2015, Conformational stability, spectroscopic and computational studies, hikes' occupied molecular orbital, lowest unoccupied molecular orbital, natural bond orbital analysis and thermodynamic parameters of anticancer drug on nanotube-A review, Cell Mol. Biol., 61, 74 Zou, 2019, Norepinephrine inhibits Alzheimer's amyloid-beta peptide aggregation and destabilizes amyloid-beta protofibrils: a molecular dynamics simulation study, ACS Chem. Neurosci., 10, 1585, 10.1021/acschemneuro.8b00537 Tang, 2016, Synthesis and evaluation of xanthine oxidase inhibitory and antioxidant activities of 2-arylbenzo[b]furan derivatives based on salvianolic acid C, Eur. J. Med. Chem., 124, 637, 10.1016/j.ejmech.2016.08.019 Xiong, 2016, Mushroom (Agaricus bisporus) polyphenoloxidase inhibited by apigenin: multi-spectroscopic analyses and computational docking simulation, Food Chem., 203, 430, 10.1016/j.foodchem.2016.02.045 Wang, 2014, Inhibitory effect of morin on tyrosinase: insights from spectroscopic and molecular docking studies, Food. Chem., 163, 226, 10.1016/j.foodchem.2014.04.106 Peng, 2014, Evaluation of the biointeraction of colorant flavazin with human serum albumin: Insights from multiple spectroscopic studies, in silico docking and molecular dynamics simulation, Food Funct., 5, 1203, 10.1039/C3FO60712G Shahabadi, 2011, Multispectroscopic studies on the interaction of 2-tert-butylhydroquinone (TBHQ), a food additive, with bovine serum albumin, Food Chem., 124, 1063, 10.1016/j.foodchem.2010.07.079 Zhang, 2016, Galangin competitively inhibits xanthine oxidase by a ping-pong mechanism, Food Res. Int., 89, 152, 10.1016/j.foodres.2016.07.021 Li, 2018, Investigation of the interaction between benzaldehyde thiosemicarbazone compounds and xanthine oxidase, J Mol. Struct., 1159, 23, 10.1016/j.molstruc.2018.01.020 Fu, 2014, Affinity selection-based two-dimensional chromatography coupled with high-performance liquid chromatography-mass spectrometry for discovering xanthine oxidase inhibitors from Radix Salviae Miltiorrhizae, Anal. Bioanal. Chem., 406, 4987, 10.1007/s00216-014-7902-9 Varlan, 2011, Spectral study of coumarin-3-carboxylic acid interaction with human and bovine serum albumins, Cent. Eur. J. Chem., 9, 624 Ross, 1981, Thermodynamics of protein association reactions: forces contributing to stability, Biochemistry, 20, 3096, 10.1021/bi00514a017 Yan, 2013, Effect of luteolin on xanthine oxidase: inhibition kinetics and interaction mechanism merging with docking simulation, Food Chem., 141, 3766, 10.1016/j.foodchem.2013.06.092 Zhang, 2011, Mechanism and conformational studies of farrerol binding to bovine serum albumin by spectroscopic methods, Spectrochim Acta A: Mol. Biomol. Spectrosc., 82, 424, 10.1016/j.saa.2011.07.073 Gull, 2009, Spectroscopic studies on the interaction of cationic surfactants with bovine serum albumin, Colloids Surf. B, 69, 122, 10.1016/j.colsurfb.2008.11.009 Ganim, 2006, Spectral signatures of heterogeneous protein ensembles revealed by MD simulations of 2DIR spectra, Biophys. J., 91, 2636, 10.1529/biophysj.106.088070 Elkins, 2011, Rapid presumptive “fingerprinting” of body fluids and materials by ATR FT-IR spectroscopy, J. Forensic. Sci., 56, 1580, 10.1111/j.1556-4029.2011.01870.x Zhang, 2012, Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques, J. Agric. Food Chem., 60, 2721, 10.1021/jf205260g