Binding mechanism of trans-N-caffeoyltyramine and human serum albumin: Investigation by multi-spectroscopy and docking simulation

Bioorganic Chemistry

Volumn 66, Issue , 2016, Pages 102-110

  Ma, Xiaoli ^a   Yan, Jin ^a   Xu, Kailin ^a   Guo, Luiqi ^a   Li, Hui ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Human serum albumin; Interaction; Nuclear magnetic resonance; Spectroscopy; trans N Caffeoyltyramine

Indexed keywords

HUMAN SERUM ALBUMIN; TYRAMINE; CAFFEIC ACID DERIVATIVE; N-CAFFEOYLTYRAMINE; SERUM ALBUMIN;

ALBUMIN BLOOD LEVEL; ARTICLE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; FORCE; HUMAN; HYDROGEN BOND; MOLECULAR DOCKING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN INTERACTION; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; SPECTROFLUOROMETRY; STRUCTURE ACTIVITY RELATION;

BINDING SITES; CAFFEIC ACIDS; CIRCULAR DICHROISM; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP; TYRAMINE;

EID: 84964792514     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2016.04.002     Document Type: Article

References (52)

1. Z. Ye, Q. Huang, H.X. Ni, and D. Wang Cortex Lycii Radicis extracts improve insulin resistance and lipid metabolism in obese-diabetic rats Phytother. Res. 22 2008 1665 1670
2. D. Gao, Q. Li, Z. Liu, Y. Li, Z. Liu, Y. Fan, K. Li, Z. Han, and J. Li Hypoglycemic effects and mechanisms of action of Cortex Lycii Radicis on alloxan-induced diabetic mice Yakugaku Zasshi 127 2007 1715 1721
3. J.Y.W. Chan, F.C. Lam, P.C. Leung, C.T. Che, and K.P. Fung Antihyperglycemic and antioxidative effects of a herbal formulation of Radix Astragali, Radix Codonopsis and Cortex Lycii in a mouse model of type 2 diabetes mellitus Phytother. Res. 23 2009 658 665
4. J.C. Jeong, S.J. Kim, Y.K. Kim, C.H. Kwon, and K.H. Kim Lycii cortex radicis extract inhibits glioma tumor growth in vitro and in vivo through downregulation of the Akt/ERK pathway Oncol. Rep. 27 2012 1467 1474
5. J.-X. Zhang, S.-H. Guan, M. Yang, R.-H. Feng, Y. Wang, Y.-B. Zhang, X. Chen, X.-H. Chen, K.-S. Bi, and D.-A. Guo Simultaneous determination of 24 constituents in Cortex Lycii using high-performance liquid chromatography-triple quadrupole mass spectrometry J. Pharm. Biomed. Anal. 77 2013 63 70
6. D.G. Lee, Y. Park, M.-R. Kim, H.J. Jung, Y.B. Seu, K.-S. Hahm, and E.-R. Woo Anti-fungal effects of phenolic amides isolated from the root bark of Lycium chinense Biotechnol. Lett. 26 2004 1125 1130
7. E.H. Han, J.Y. Kim, H.G. Kim, J.H. Choi, J.H. Im, E.R. Woo, and H.G. Jeong Dihydro-N-caffeoyltyramine down-regulates cyclooxygenase-2 expression by inhibiting the activities of C/EBP and AP-1 transcription factors Food Chem. Toxicol. 48 2010 579 586
8. L.-W. Xie, A.G. Atanasov, D.-A. Guo, C. Malainer, J.-X. Zhang, M. Zehl, S.-H. Guan, E.H. Heiss, E. Urban, and V.M. Dirsch Activity-guided isolation of NF-κB inhibitors and PPARγ agonists from the root bark of Lycium chinense Miller J. Ethnopharmacol. 152 2014 470 477
9. A. Papadopoulou, R.J. Green, and R.A. Frazier Interaction of flavonoids with bovine serum albumin: a fluorescence quenching study J. Agric. Food Chem. 53 2005 158 163
10. A. Sułkowska Interaction of drugs with bovine and human serum albumin J. Mol. Struct. 614 2002 227 232
11. X.-N. Zhao, Y. Liu, L.-Y. Niu, and C.-P. Zhao Spectroscopic studies on the interaction of bovine serum albumin with surfactants and apigenin Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 94 2012 357 364
12. S. Martini, C. Bonechi, M. Casolaro, G. Corbini, and C. Rossi Drug-protein recognition processes investigated by NMR relaxation data. A study on corticosteroid-albumin interactions Biochem. Pharmacol. 71 2006 858 864
13. 1H STD NMR and computational docking studies Eur. J. Inorg. Chem. 2013 2013 4619 4627
14. Z.S. Ji, H.Z. Yuan, M.L. Liu, and J.M. Hu H-1-NMR study of the effect of acetonitrile on the interaction of ibuprofen with human serum albumin J. Pharm. Biomed. Anal. 30 2002 151 159
15. K. Kitamura, A.A. Omran, S. Takegami, R. Tanaka, and T. Kitade F-19 NMR spectroscopic characterization of the interaction of niflumic acid with human serum albumin Anal. Bioanal. Chem. 387 2007 2843 2848
16. S.-H. Han, H.-H. Lee, I.-S. Lee, Y.-H. Moon, and E.-R. Woo A new phenolic amide from Lycium chinense Miller Arch. Pharmacal Res. 25 2002 433 437
17. S.-Y. Lin, M.-J. Li, and Y.-S. Wei Ethanol or/and captopril-induced precipitation and secondary conformational changes of human serum albumin Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 60 2004 3107 3111
18. J. He, Q. Wang, L. Zhang, X. Lin, and H. Li Docking simulations and spectroscopy of the interactions of ellagic acid and oleuropein with human serum albumin J. Lumin. 154 2014 578 583
19. M. del Carmen Pinto, A.L. Duque, and P. Macías Fluorescence quenching study on the interaction between quercetin and lipoxygenase J. Fluoresc. 21 2011 1311 1318
20. S. Neamtu, N. Tosa, and M. Bogdan Spectroscopic investigation of tolmetin interaction with human serum albumin J. Pharm. Biomed. Anal. 85 2013 277 282
21. S. Martini, C. Bonechi, and C. Rossi Interaction of quercetin and its conjugate quercetin 3-O-β-glucopyranoside with albumin as determined by NMR relaxation data J. Nat. Prod. 71 2008 175 178
22. C. Rossi, C. Bonechi, S. Martini, M. Ricci, G. Corbini, P. Corti, and A. Donati Ligand-macromolecule complexes: affinity index determination by selective nuclear relaxation analysis Magn. Reson. Chem. 39 2001 457 462
23. Y. Wang, T. Zhang, J. Xu, and W. Du Comparison of the binding affinity of chlorogenic acid with two serum albumins Int. J. Biol. Macromol. 48 2011 81 86
24. D. Wu, Y. Zhai, J. Yan, K. Xu, Q. Wang, Y. Li, and H. Li Binding mechanism of tauroursodeoxycholic acid to human serum albumin: insights from NMR relaxation and docking simulations RSC Adv. 5 2015 11036 11042
25. C. Bonechi, S. Martini, and C. Rossi Interaction study of indigo carmine with albumin and dextran by NMR relaxation J. Mater. Sci. 46 2010 2541 2547
26. M. Skrt, E. Benedik, Č. Podlipnik, and N.P. Ulrih Interactions of different polyphenols with bovine serum albumin using fluorescence quenching and molecular docking Food Chem. 135 2012 2418 2424
27. G. Zhang, X. Chen, J. Guo, and J. Wang Spectroscopic investigation of the interaction between chrysin and bovine serum albumin J. Mol. Struct. 921 2009 346 351
28. Y.-J. Hu, Y. Liu, Z.-B. Pi, and S.-S. Qu Interaction of cromolyn sodium with human serum albumin: a fluorescence quenching study Bioorg. Med. Chem. 13 2005 6609 6614
29. M.D. Hays, D.K. Ryan, and S. Pennell A modified multisite Stern-Volmer equation for the determination of conditional stability constants and ligand concentrations of soil fulvic acid with metal ions Anal. Chem. 76 2004 848 854
30. S.S. Singh, and J. Mehta Measurement of drug-protein binding by immobilized human serum albumin-HPLC and comparison with ultrafiltration J. Chromatogr. B 834 2006 108 116
31. S.R. Feroz, S.B. Mohamad, N. Bujang, S.N. Malek, and S. Tayyab Multispectroscopic and molecular modeling approach to investigate the interaction of flavokawain B with human serum albumin J. Agric. Food Chem. 60 2012 5899 5908
32. S.-L. Zhang, H. Yao, C. Wang, and K.Y. Tam Study the interactions between human serum albumin and two antifungal drugs: fluconazole and its analogue DTP Bioorg. Med. Chem. Lett. 24 2014 4963 4968
33. H.-J. Zeng, T. Qi, R. Yang, J. You, and L.-B. Qu Spectroscopy and molecular docking study on the interaction behavior between nobiletin and pepsin J. Fluoresc. 24 2014 1031 1040
34. J. Tang, F. Luan, and X. Chen Binding analysis of glycyrrhetinic acid to human serum albumin: fluorescence spectroscopy, FTIR, and molecular modeling Bioorg. Med. Chem. 14 2006 3210 3217
35. P.D. Ross, and S. Subramanian Thermodynamics of protein association reactions: forces contributing to stability Biochemistry 20 1981 3096 3102
36. T. Hu, and Y. Liu Probing the interaction of cefodizime with human serum albumin using multi-spectroscopic and molecular docking techniques J. Pharm. Biomed. Anal. 107 2015 325 332
37. T.S. Olsson, M.A. Williams, W.R. Pitt, and J.E. Ladbury The thermodynamics of protein-ligand interaction and solvation: insights for ligand design J. Mol. Biol. 384 2008 1002 1017
38. Q. Zhang, Y. Ni, and S. Kokot Molecular spectroscopic studies on the interaction between ractopamine and bovine serum albumin J. Pharm. Biomed. Anal. 52 2010 280 288
39. C.-Q. Jiang, M.-X. Gao, and J.-X. He Study of the interaction between terazosin and serum albumin: synchronous fluorescence determination of terazosin Anal. Chim. Acta 452 2002 185 189
40. U. Mote, S. Bhattar, S. Patil, and G. Kolekar Interaction between felodipine and bovine serum albumin: fluorescence quenching study Luminescence 25 2010 1 8
41. M.S. Zaroog, and S. Tayyab Formation of molten globule-like state during acid denaturation of Aspergillus niger glucoamylase Process Biochem. 47 2012 775 784
42. N. Dash, A. Mishra, and G. Krishnamoorthy Alkyl chain dependent interactions of ligands with bovine serum albumin J. Pharm. Biomed. Anal. 77 2013 55 62
43. Z. Sattar, M.R. Saberi, and J. Chamani Determination of LMF binding site on a HSA-PPIX complex in the presence of human holo transferrin from the viewpoint of drug loading on proteins PLoS ONE 9 2014 e84045
44. L. Whitmore, and B.A. Wallace Protein secondary structure analyses from circular dichroism spectroscopy: methods and reference databases Biopolymers 89 2008 392 400
45. N. Sreerama, S.Y. Venyaminov, and R.W. Woody Estimation of the number of α-helical and β-strand segments in proteins using circular dichroism spectroscopy Protein Sci. 8 1999 370 380
46. M.M. Moghaddam, M. Pirouzi, M.R. Saberi, and J. Chamani Comparison of the binding behavior of FCCP with HSA and HTF as determined by spectroscopic and molecular modeling techniques Lumin.: J. Biol. Chem. Lumin. 29 2014 314 331
47. E. Rahnama, M. Mahmoodian-Moghaddam, S. Khorsand-Ahmadi, M.R. Saberi, and J. Chamani Binding site identification of metformin to human serum albumin and glycated human serum albumin by spectroscopic and molecular modeling techniques: a comparison study J. Biomol. Struct. Dyn. 33 2015 513 533
48. U. Katrahalli, S. Jaldappagari, and S.S. Kalanur Study of the interaction between fluoxetine hydrochloride and bovine serum albumin in the imitated physiological conditions by multi-spectroscopic methods J. Lumin. 130 2010 211 216
49. I. Matei, and M. Hillebrand Interaction of kaempferol with human serum albumin: a fluorescence and circular dichroism study J. Pharm. Biomed. Anal. 51 2010 768 773
50. G. Wu, D.H. Robertson, C.L. Brooks, and M. Vieth Detailed analysis of grid-based molecular docking: a case study of CDOCKER - a CHARMm-based MD docking algorithm J. Comput. Chem. 24 2003 1549 1562
51. M. Taufer, M. Crowley, D.J. Price, A.A. Chien, and C. Brooks Study of a highly accurate and fast protein-ligand docking method based on molecular dynamics Concurr. Comput.: Pract. Exper. 17 2005 1627 1641
52. D. Wu, J. Yan, J. Wang, Q. Wang, and H. Li Characterisation of interaction between food colourant allura red AC and human serum albumin: multispectroscopic analyses and docking simulations Food Chem. 170 2015 423 429