Fatty acid binding to serum albumin: Molecular simulation approaches

Biochimica et Biophysica Acta - General Subjects

Volumn 1830, Issue 12, 2013, Pages 5427-5434

  Fujiwara, Shin Ichi ^a   Amisaki, Takashi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

Docking; Fatty acid; Free energy; Human serum albumin; Molecular dynamics; Simulation

Indexed keywords

EID: 84885361968     PISSN: 03044165     EISSN: 18728006     Source Type: Journal    
DOI: 10.1016/j.bbagen.2013.03.032     Document Type: Review

References (154)

1. U. Kragh-Hansen, V.T.G. Chuang, and M. Otagiri Practical aspects of the ligand-binding and enzymatic properties of human serum albumin Biol. Pharm. Bull. 25 2002 695 704 (Pubitemid 40036701)
2. M. Otagiri A molecular functional study on the interactions of drugs with plasma proteins Drug Metab. Pharmacokinet. 20 2005 309 323
3. G. Fanali, A. di Masi, V. Trezza, M. Marino, M. Fasano, and P. Ascenzi Human serum albumin: from bench to bedside Mol. Aspects Med. 33 2012 209 290
4. S. Mandal, M. Hossain, P.S. Devi, G.S. Kumar, and K. Chaudhuri Interaction of carbon nanoparticles to serum albumin: elucidation of the extent of perturbation of serum albumin conformations and thermodynamical parameters J. Hazard. Mater. 248-249C 2013 238 245
5. C. Han, S. Fang, H. Cao, Y. Lu, Y. Ma, D. Wei, X. Xie, X. Liu, X. Li, D. Fei, and C. Zhao Molecular interaction of PCB153 to human serum albumin: insights from spectroscopic and molecular modeling studies J. Hazard. Mater. 248-249C 2013 313 321
6. X.M. He, and D.C. Carter Atomic structure and chemistry of human serum albumin Nature 358 1992 209 215
7. S. Curry, H. Mandelkow, P. Brick, and N. Franks Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites Nat. Struct. Biol. 5 1998 827 835 (Pubitemid 28402087)
8. S. Sugio, A. Kashima, S. Mochizuki, M. Noda, and K. Kobayashi Crystal structure of human serum albumin at 2.5 angstrom resolution Protein Eng. 12 1999 439 446 (Pubitemid 29322441)
9. A.A. Bhattacharya, S. Curry, and N.P. Franks Binding of the general anesthetics propofol and halothane to human serum albumin. High resolution crystal structures J. Biol. Chem. 275 2000 38731 38738 (Pubitemid 32009208)
10. A.A. Bhattacharya, T. Grüne, and S. Curry Crystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin J. Mol. Biol. 303 2000 721 732
11. I. Petitpas, T. Grüne, A.A. Bhattacharya, and S. Curry Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids J. Mol. Biol. 314 2001 955 960 (Pubitemid 34073060)
12. I. Petitpas, A.A. Bhattacharya, S. Twine, M. East, and S. Curry Crystal structure analysis of warfarin binding to human serum albumin: anatomy of drug site I J. Biol. Chem. 276 2001 22804 22809
13. M. Wardell, Z. Wang, J.X. Ho, J. Robert, F. Ruker, J. Ruble, and D.C. Carter The atomic structure of human methemalbumin at 1.9 A Biochem. Biophys. Res. Commun. 291 2002 813 819 (Pubitemid 34694348)
14. I. Petitpas, C.E. Petersen, C.E. Ha, A.A. Bhattacharya, P.A. Zunszain, J. Ghuman, N.V. Bhagavan, and S. Curry Structural basis of albumin-thyroxine interactions and familial dysalbuminemic hyperthyroxinemia Proc. Natl. Acad. Sci. U. S. A. 100 2003 6440 6445 (Pubitemid 36666600)
15. P.A. Zunszain, J. Ghuman, T. Komatsu, E. Tsuchida, and S. Curry Crystal structural analysis of human serum albumin complexed with hemin and fatty acid BMC Struct. Biol. 3 2003 6
16. S. Lejon, I.M. Frick, L. Bjorck, M. Wikstrom, and S. Svensson Crystal structure and biological implications of a bacterial albumin binding module in complex with human serum albumin J. Biol. Chem. 279 2004 42924 42928 (Pubitemid 39372183)
17. J. Ghuman, P.A. Zunszain, I. Petitpas, A.A. Bhattacharya, M. Otagiri, and S. Curry Structural basis of the drug-binding specificity of human serum albumin J. Mol. Biol. 353 2005 38 52 (Pubitemid 41338838)
18. F. Yang, C. Bian, L. Zhu, G. Zhao, Z. Huang, and M. Huang Effect of human serum albumin on drug metabolism: structural evidence of esterase activity of human serum albumin J. Struct. Biol. 157 2007 348 355 (Pubitemid 46109335)
19. S. Lejon, J.F. Cramer, and P. Nordberg Structural basis for the binding of naproxen to human serum albumin in the presence of fatty acids and the GA module Acta Crystallogr. F 64 2008 64 69 (Pubitemid 351348062)
20. L. Zhu, F. Yang, L. Chen, E.J. Meehan, and M. Huang A new drug binding subsite on human serum albumin and drug-drug interaction studied by X-ray crystallography J. Struct. Biol. 162 2008 40 49
21. P.A. Zunszain, J. Ghuman, A.F. McDonagh, and S. Curry Crystallographic analysis of human serum albumin complexed with 4Z,15E-bilirubin-IXα J. Mol. Biol. 381 2008 394 406
22. S. Guo, X. Shi, F. Yang, L. Chen, E.J. Meehan, C. Bian, and M. Huang Structural basis of transport of lysophospholipids by human serum albumin Biochem. J. 423 2009 23 30
23. 2 as a product and ligand of human serum albumin: formation of an unusual covalent adduct at His146 J. Am. Chem. Soc. 132 2010 824 832
24. K.L. Hein, U. Kragh-Hansen, J.P. Morth, M.D. Jeppesen, D. Otzen, J.V. Moller, and P. Nissen Crystallographic analysis reveals a unique lidocaine binding site on human serum albumin J. Struct. Biol. 171 2010 353 360
25. D. Buttar, N. Colclough, S. Gerhardt, P.A. MacFaul, S.D. Phillips, A. Plowright, P. Whittamore, K. Tam, K. Maskos, S. Steinbacher, and H. Steuber A combined spectroscopic and crystallographic approach to probing drug-human serum albumin interactions Bioorg. Med. Chem. 18 2010 7486 7496
26. A.J. Ryan, J. Ghuman, P.A. Zunszain, C.W. Chung, and S. Curry Structural basis of binding of fluorescent, site-specific dansylated amino acids to human serum albumin J. Struct. Biol. 174 2011 84 91
27. A.J. Ryan, C.W. Chung, and S. Curry Crystallographic analysis reveals the structural basis of the high-affinity binding of iophenoxic acid to human serum albumin BMC Struct. Biol. 11 2011 18
28. Y. He, T. Ning, T. Xie, Q. Qiu, L. Zhang, Y. Sun, D. Jiang, K. Fu, F. Yin, W. Zhang, L. Shen, H. Wang, J. Li, Q. Lin, H. Li, Y. Zhu, and D. Yang Large-scale production of functional human serum albumin from transgenic rice seeds Proc. Natl. Acad. Sci. U. S. A. 108 2011 19078 19083
29. Y. Wang, Z. Luo, X. Shi, H. Wang, L. Nie, and M. Huang A fluorescent fatty acid probe, DAUDA, selectively displaces two myristates bound in human serum albumin Protein Sci. 20 2011 2095 2101
30. Z. Luo, X. Shi, Q. Hu, B. Zhao, and M. Huang Structural evidence of perfluorooctane sulfonate transport by human serum albumin Chem. Res. Toxicol. 25 2012 990 992
31. T. Oltersdorf, S.W. Elmore, A.R. Shoemaker, R.C. Armstrong, D.J. Augeri, B.A. Belli, M. Bruncko, T.L. Deckwerth, J. Dinges, P.J. Hajduk, M.K. Joseph, S. Kitada, S.J. Korsmeyer, A.R. Kunzer, A. Letai, C. Li, M.J. Mitten, D.G. Nettesheim, S. Ng, P.M. Nimmer, J.M. O'Connor, A. Oleksijew, A.M. Petros, J.C. Reed, W. Shen, S.K. Tahir, C.B. Thompson, K.J. Tomaselli, B. Wang, M.D. Wendt, H. Zhang, S.W. Fesik, and S.H. Rosenberg An inhibitor of Bcl-2 family proteins induces regression of solid tumours Nature 435 2005 677 681 (Pubitemid 40825512)
32. A. Almogren, P.B. Furtado, Z. Sun, S.J. Perkins, and M.A. Kerr Purification, properties and extended solution structure of the complex formed between human immunoglobulin A1 and human serum albumin by scattering and ultracentrifugation J. Mol. Biol. 356 2006 413 431 (Pubitemid 43099980)
33. T. Hansson, C. Oostenbrink, and W. van Gunsteren Molecular dynamics simulations Curr. Opin. Struct. Biol. 12 2002 190 196 (Pubitemid 34327478)
34. J.L. Klepeis, K. Lindorff-Larsen, R.O. Dror, and D.E. Shaw Long-timescale molecular dynamics simulations of protein structure and function Curr. Opin. Struct. Biol. 19 2009 120 127
35. J.D. Durrant, and J.A. McCammon Molecular dynamics simulations and drug discovery BMC Biol. 9 2011 71
36. G.J. van der Vusse Albumin as fatty acid transporter Drug Metab. Pharmacokinet. 24 2009 300 307
37. 14-labeled unesterified fatty acids in normal human subjects J. Clin. Invest. 37 1958 1504 1515
38. R. Brodersen, S. Andersen, H. Vorum, S.U. Nielsen, and A.O. Pedersen Multiple fatty acid binding to albumin in human blood plasma Eur. J. Biochem. 189 1990 343 349 (Pubitemid 20146018)
39. R. Bahr, A.T. Hostmark, E.A. Newsholme, O. Gronnerod, and O.M. Sejersted Effect of exercise on recovery changes in plasma levels of FFA, glycerol, glucose and catecholamines Acta Physiol. Scand. 143 1991 105 115
40. 13C nuclear magnetic resonance study J. Clin. Invest. 87 1991 1431 1441
41. G. Paolisso, P.A. Tataranni, J.E. Foley, C. Bogardus, B.V. Howard, and E. Ravussin A high concentration of fasting plasma non-esterified fatty acids is a risk factor for the development of NIDDM Diabetologia 38 1995 1213 1217
42. V.A. Kurien, and M.F. Oliver Free fatty acids during acute myocardial infarction Prog. Cardiovasc. Dis. 13 1971 361 373
43. D.S. Goodman The interaction of human serum albumin with long-chain fatty acid anions J. Am. Chem. Soc. 80 1958 3892 3898
44. A.A. Spector, K. John, and J.E. Fletcher Binding of long-chain fatty acids to bovine serum albumin J. Lipid Res. 10 1969 56 67
45. J.D. Ashbrook, A.A. Spector, E.C. Santos, and J.E. Fletcher Long chain fatty acid binding to human plasma albumin J. Biol. Chem. 250 1975 2333 2338
46. A.O. Pedersen, and R. Brodersen Myristic acid binding to human serum albumin investigated by dialytic exchange rate J. Biol. Chem. 263 1988 10236 10239
47. G.V. Richieri, A. Anel, and A.M. Kleinfeld Interactions of long-chain fatty acids and albumin: determination of free fatty acid levels using the fluorescent probe ADIFAB Biochemistry 32 1993 7574 7580 (Pubitemid 23232334)
48. S. Curry, P. Brick, and N.P. Franks Fatty acid binding to human serum albumin: new insights from crystallographic studies Biochim. Biophys. Acta 1441 1999 131 140 (Pubitemid 29537733)
49. J.R. Simard, P.A. Zunszain, C.E. Ha, J.S. Yang, N.V. Bhagavan, I. Petitpas, S. Curry, and J.A. Hamilton Locating high-affinity fatty acid-binding sites on albumin by X-ray crystallography and NMR spectroscopy Proc. Natl. Acad. Sci. U. S. A. 102 2005 17958 17963 (Pubitemid 41798484)
50. J.R. Simard, P.A. Zunszain, J.A. Hamilton, and S. Curry Location of high and low affinity fatty acid binding sites on human serum albumin revealed by NMR drug-competition analysis J. Mol. Biol. 361 2006 336 351 (Pubitemid 44092787)
51. U. Kragh-Hansen, H. Watanabe, K. Nakajou, Y. Iwao, and M. Otagiri Chain length-dependent binding of fatty acid anions to human serum albumin studied by site-directed mutagenesis J. Mol. Biol. 363 2006 702 712 (Pubitemid 44486220)
52. P. Ascenzi, and M. Fasano Allostery in a monomeric protein: the case of human serum albumin Biophys. Chem. 148 2010 16 22
53. G. Sudlow, D.J. Birkett, and D.N. Wade The characterization of two specific drug binding sites on human serum albumin Mol. Pharmacol. 11 1975 824 832
54. S. Curry Lessons from the crystallographic analysis of small molecule binding to human serum albumin Drug Metab. Pharmacokinet. 24 2009 342 357
55. G. Fanali, R. Fesce, C. Agrati, P. Ascenzi, and M. Fasano Allosteric modulation of myristate and Mn(III) heme binding to human serum albumin. Optical and NMR spectroscopy characterization FEBS J. 272 2005 4672 4683 (Pubitemid 41366990)
56. K. Maruyama, S. Awazu, H. Nishigori, and M. Iwatsuru Effects of fatty acid on the specific drug-binding sites of human serum albumin Chem. Pharm. Bull. 34 1986 3394 3402 (Pubitemid 17172405)
57. P. Claudepierre, S. Urien, O. Chassany, and J.P. Tillement Analysis of free fatty acid effect on methotrexate binding to albumin Biochem. Pharmacol. 47 1994 415 417 (Pubitemid 24050901)
58. A.M.L. Zaton, J.M. Ferrer, J.C.R. Degordoa, and M.A. Marquinez Binding of coumarins to site I of human serum albumin. Effect of the fatty acids Chem. Biol. Interact. 97 1995 169 174
59. H. Vorum, and B. Honore Influence of fatty acids on the binding of warfarin and phenprocoumon to human serum albumin with relation to anticoagulant therapy J. Pharm. Pharmacol. 48 1996 870 875 (Pubitemid 26335272)
60. N. Takamura, S. Shinozawa, T. Maruyama, A. Suenaga, and M. Otagiri Effects of fatty acids on serum binding between furosemide and valproic acid Biol. Pharm. Bull. 21 1998 174 176 (Pubitemid 28120150)
61. V.T.G. Chuang, and M. Otagiri How do fatty acids cause allosteric binding of drugs to human serum albumin? Pharm. Res. 19 2002 1458 1464 (Pubitemid 35266549)
62. P. Ascenzi, A. Bocedi, S. Notari, G. Fanali, R. Fesce, and M. Fasano Allosteric modulation of drug binding to human serum albumin Mini Rev. Med. Chem. 6 2006 483 489
63. M.A. Quevedo, S.R. Ribone, G.N. Moroni, and M.C. Briñón Binding to human serum albumin of zidovudine (AZT) and novel AZT derivatives. Experimental and theoretical analyses Bioorg. Med. Chem. 16 2008 2779 2790 (Pubitemid 351418222)
64. B. Bojko, A. Sulkowska, M. Maciazek, J. Rownicka, F. Njau, and W.W. Sulkowski Changes of serum albumin affinity for aspirin induced by fatty acid Int. J. Biol. Macromol. 42 2008 314 323
65. G.J. Amirtharaj, S.K. Natarajan, A. Mukhopadhya, U.G. Zachariah, S.K. Hegde, G. Kurian, K.A. Balasubramanian, and A. Ramachandran Fatty acids influence binding of cobalt to serum albumin in patients with fatty liver Biochim. Biophys. Acta 1782 2008 349 354
66. 1H NMR relaxometric and circular dichroism study J. Biol. Inorg. Chem. 14 2009 209 217
67. A. Bolli, M. Marino, G. Rimbach, G. Fanali, M. Fasano, and P. Ascenzi Flavonoid binding to human serum albumin Biochem. Biophys. Res. Commun. 398 2010 444 449
68. 1H NMR relaxometric study J. Inorg. Biochem. 117 2012 198 203
69. K.R. Grymonpré, B.A. Staggemeier, P.L. Dubin, and K.W. Mattison Identification by integrated computer modeling and light scattering studies of an electrostatic serum albumin-hyaluronic acid binding site Biomacromolecules 2 2001 422 429 (Pubitemid 32707521)
70. Y.F. Song, and M.R. Gunner Using multiconformation continuum electrostatics to compare chloride binding motifs in α-amylase, human serum albumin, and Omp32 J. Mol. Biol. 387 2009 840 856
71. Y. Li, W. He, Y. Dong, F. Sheng, and Z. Hu Human serum albumin interaction with formononetin studied using fluorescence anisotropy, FT-IR spectroscopy, and molecular modeling methods Bioorg. Med. Chem. 14 2006 1431 1436 (Pubitemid 43120279)
72. G. Fanali, A. Bocedi, P. Ascenzi, and M. Fasano Modulation of heme and myristate binding to human serum albumin by anti-HIV drugs. An optical and NMR spectroscopic study FEBS J. 274 2007 4491 4502 (Pubitemid 47301710)
73. J. Tang, N. Lian, C. Bi, and W. Li Analysis of eupatilin-human serum albumin interactions by means of spectroscopic and computational modelling J. Pharm. Pharmacol. 59 2007 637 643 (Pubitemid 47051106)
74. F. Cui, X. Kong, L. Qin, G. Zhang, Q. Liu, B. Lei, and X. Yao Specific interaction of 4'-O-(a-l-Cladinosyl) daunorubicin with human serum albumin: the binding site II on HSA molecular using spectroscopy and modeling J. Photochem. Photobiol. B 95 2009 162 169
75. F. Cui, Y. Yan, Q. Zhang, J. Du, X. Yao, G. Qu, and Y. Lu Characterization of the interaction between 2'-deoxyuridine and human serum albumin Carbohydr. Res. 344 2009 642 647
76. Z. Liu, X. Zheng, X. Yang, E. Wang, and J. Wang Affinity and specificity of levamlodipine-human serum albumin interactions: insights into its carrier function Biophys. J. 96 2009 3917 3925
77. G. Fanali, V. Rampoldi, A. di Masi, A. Bolli, L. Lopiano, P. Ascenzi, and M. Fasano Binding of anti-Parkinson's disease drugs to human serum albumin is allosterically modulated IUBMB Life 62 2010 371 376
78. H. Liu, W. Bao, H. Ding, J. Jang, and G. Zou Binding modes of flavones to human serum albumin: insights from experimental and computational studies J. Phys. Chem. B 114 2010 12938 12947
79. F. Ding, W. Liu, X. Zhang, L. Zhang, and Y. Sun Fluorescence and circular dichroism studies of conjugates between metsulfuron-methyl and human serum albumin Colloids Surf. B 76 2010 441 448
80. B. Sudhamalla, M. Gokara, N. Ahalawat, D.G. Amooru, and R. Subramanyam Molecular dynamics simulation and binding studies of β-sitosterol with human serum albumin and its biological relevance J. Phys. Chem. B 114 2010 9054 9062
81. F. Ding, L. Wei, J.X. Diao, and Y. Sun Characterization of Alizarin Red S binding sites and structural changes on human serum albumin: a biophysical study J. Hazard. Mater. 186 2011 352 359
82. Z. Omidvar, K. Parivar, H. Sanee, Z. Amiri-Tehranizadeh, A. Baratian, M.R. Saberi, A. Asoodeh, and J. Chamani Investigations with spectroscopy, zeta potential and molecular modeling of the non-cooperative behaviour between cyclophosphamide hydrochloride and aspirin upon interaction with human serum albumin: binary and ternary systems from multi-drug therapy J. Biomol. Struct. Dyn. 29 2011 181 206
83. G. Fanali, Y. Cao, P. Ascenzi, V. Trezza, T. Rubino, D. Parolaro, and M. Fasano Binding of â-9-tetrahydrocannabinol and diazepam to human serum albumin IUBMB Life 63 2011 446 451
84. C. Calderon, E. Abuin, E. Lissi, and R. Montecinos Effect of human serum albumin on the kinetics of 4-methylumbelliferyl-beta-D-N-N'-N'' triacetylchitotrioside hydrolysis catalyzed by hen egg white lysozyme Protein J. 30 2011 367 373
85. P. Ascenzi, A. Bolli, A. di Masi, G.R. Tundo, G. Fanali, M. Coletta, and M. Fasano Isoniazid and rifampicin inhibit allosterically heme binding to albumin and peroxynitrite isomerization by heme-albumin J. Biol. Inorg. Chem. 16 2011 97 108
86. H. Vahedian-Movahed, M.R. Saberi, and J. Chamani Comparison of binding interactions of lomefloxacin to serum albumin and serum transferrin by resonance light scattering and fluorescence quenching methods J. Biomol. Struct. Dyn. 28 2011 483 502
87. M.J. Kimzey, H.N. Yassine, B.M. Riepel, G. Tsaprailis, T.J. Monks, and S.S. Lau New site(s) of methylglyoxal-modified human serum albumin, identified by multiple reaction monitoring, alter warfarin binding and prostaglandin metabolism Chem. Biol. Interact. 192 2011 122 128
88. Y. Sun, B. Su, Q. Xu, and R. Liu Insights into the binding of 2-aminobenzothiazole with human serum albumin (HSA): spectroscopic investigation and molecular modeling studies Appl. Spectrosc. 66 2012 791 797
89. M.R. Housaindokht, Z. Rouhbakhsh Zaeri, M. Bahrololoom, J. Chamani, and M.R. Bozorgmehr Investigation of the behavior of HSA upon binding to amlodipine and propranolol: spectroscopic and molecular modeling approaches Spectrochim. Acta A 85 2012 79 84
90. F. Samari, M. Shamsipur, B. Hemmateenejad, T. Khayamian, and S. Gharaghani Investigation of the interaction between amodiaquine and human serum albumin by fluorescence spectroscopy and molecular modeling Eur. J. Med. Chem. 54 2012 255 263
91. F. Ding, L. Zhang, J.X. Diao, X.N. Li, L. Ma, and Y. Sun Human serum albumin stability and toxicity of anthraquinone dye alizarin complexone: an albumin-dye model Ecotoxicol. Environ. Saf. 79 2012 238 246
92. T. Zohoorian-Abootorabi, H. Sanee, H. Iranfar, M.R. Saberi, and J. Chamani Separate and simultaneous binding effects through a non-cooperative behavior between cyclophosphamide hydrochloride and fluoxymesterone upon interaction with human serum albumin: multi-spectroscopic and molecular modeling approaches Spectrochim. Acta A 88 2012 177 191
93. O.K. Abou-Zied Revealing the ionization ability of binding site I of human serum albumin using 2-(2'-hydroxyphenyl)benzoxazole as a pH sensitive probe Phys. Chem. Chem. Phys. 14 2012 2832 2839
94. A. Hosainzadeh, M. Gharanfoli, M. Saberi, and J. Chamani Probing the interaction of human serum albumin with bilirubin in the presence of aspirin by multi-spectroscopic, molecular modeling and zeta potential techniques: insight on binary and ternary systems J. Biomol. Struct. Dyn. 29 2012 1013 1050
95. M.I. Sabela, N.J. Gumede, L. Escuder-Gilabert, Y. Martin-Biosca, K. Bisetty, M.J. Medina-Hernandez, and S. Sagrado Connecting simulated, bioanalytical, and molecular docking data on the stereoselective binding of (+/-)-catechin to human serum albumin Anal. Bioanal. Chem. 402 2012 1899 1909
96. X.L. Han, F.F. Tian, Y.S. Ge, F.L. Jiang, L. Lai, D.W. Li, Q.L. Yu, J. Wang, C. Lin, and Y. Liu Spectroscopic, structural and thermodynamic properties of chlorpyrifos bound to serum albumin: a comparative study between BSA and HSA J. Photochem. Photobiol. B 109 2012 1 11
97. J. Zhu, L. Wu, Q. Zhang, X. Chen, and X. Liu Investigation the interaction of daphnin with human serum albumin using optical spectroscopy and molecular modeling methods Spectrochim. Acta A 95 2012 252 257
98. R. Huo, C. Li, F. Cui, G. Zhang, Q. Liu, and X. Yao Spectroscopic and molecular modeling studies of the interaction between 4'-O-(α-l- oleandrosyl)daunorubicin and human serum albumin and its analytical application J. Fluoresc. 22 2012 111 119
99. Y. Yue, J. Liu, M. Yao, X. Yao, J. Fan, and H. Ji The investigation of the binding behavior between ethyl maltol and human serum albumin by multi-spectroscopic methods and molecular docking Spectrochim. Acta A 96 2012 316 323
100. S. Jana, S. Dalapati, S. Ghosh, and N. Guchhait Study of microheterogeneous environment of protein human serum albumin by an extrinsic fluorescent reporter: a spectroscopic study in combination with molecular docking and molecular dynamics simulation J. Photochem. Photobiol. B 112 2012 48 58
101. A. Sengupta, W.D. Sasikala, A. Mukherjee, and P. Hazra Comparative study of flavins binding with human serum albumin: a fluorometric, thermodynamic, and molecular dynamics approach Chemphyschem 13 2012 2142 2153
102. 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
103. I.P. Caruso, W. Vilegas, M.A. Fossey, and M.L. Cornelio Exploring the binding mechanism of Guaijaverin to human serum albumin: fluorescence spectroscopy and computational approach Spectrochim. Acta A 97C 2012 449 455
104. B. Hemmateenejad, M. Shamsipur, F. Samari, T. Khayamian, M. Ebrahimi, and Z. Rezaei Combined fluorescence spectroscopy and molecular modeling studies on the interaction between harmalol and human serum albumin J. Pharm. Biomed. Anal. 67-68 2012 201 208
105. F. Ding, J.X. Diao, and Y. Sun Bioevaluation of human serum albumin-hesperidin bioconjugate: insight into protein vector function and conformation J. Agric. Food Chem. 60 2012 7218 7228
106. H.H. Sun, J. Zhang, Y.Z. Zhang, L.Y. Yang, L.L. Yuan, and Y. Liu Interaction of human serum albumin with 10-hydroxycamptothecin: spectroscopic and molecular modeling studies Mol. Biol. Rep. 39 2012 5115 5123
107. M. Banerjee, U. Pal, A. Subudhhi, A. Chakrabarti, and S. Basu Interaction of merocyanine 540 with serum albumins: photophysical and binding studies J. Photochem. Photobiol. B 108 2012 23 33
108. J. Sochacka, and W. Baran The investigation of the binding of 6-mercaptopurine to site I on human serum albumin Protein J. 31 2012 689 702
109. F. Ding, X.N. Li, J.X. Diao, Y. Sun, and L. Zhang Chiral recognition of metalaxyl enantiomers by human serum albumin: evidence from molecular modeling and photophysical approach Chirality 24 2012 471 480
110. L.S. Yu, Y.J. Hong, L. Li, Y.X. Jin, M.Y. Zheng, H.L. Jiang, and S. Zeng Enantioselective drug-protein interaction between mexiletine and plasma protein J. Pharm. Pharmacol. 64 2012 792 801
111. F. Deng, C. Dong, and Y. Liu Characterization of the interaction between nitrofurazone and human serum albumin by spectroscopic and molecular modeling methods Mol. Biosyst. 8 2012 1446 1451
112. X.M. Zhou, W.J. Lu, L. Su, Z.J. Shan, and X.G. Chen Binding of phthalate plasticizers to human serum albumin in vitro: a multispectroscopic approach and molecular modeling J. Agric. Food Chem. 60 2012 1135 1145
113. Y. Sun, Z. Ji, X. Liang, G. Li, S. Yang, S. Wei, Y. Zhao, X. Hu, and J. Fan Studies on the binding of rhaponticin with human serum albumin by molecular spectroscopy, modeling and equilibrium dialysis Spectrochim. Acta A 87 2012 171 178
114. T. Chatterjee, A. Pal, S. Dey, B.K. Chatterjee, and P. Chakrabarti Interaction of virstatin with human serum albumin: spectroscopic analysis and molecular modeling PLoS One 7 2012 e37468
115. S. Tabassum, W.M. Al-Asbahy, M. Afzal, and F. Arjmand Synthesis, characterization and interaction studies of copper based drug with human serum albumin (HSA): spectroscopic and molecular docking investigations J. Photochem. Photobiol. B 114 2012 132 139
116. D. De, H. Kaur, and A. Datta Unusual binding of a potential biomarker with human serum albumin Chem. Asian J. 8 2013 728 735
117. C. Dong, S. Ma, and Y. Liu Studies of the interaction between demeclocycline and human serum albumin by multi-spectroscopic and molecular docking methods Spectrochim. Acta A 103 2013 179 186
118. N. Zaidi, E. Ahmad, M. Rehan, G. Rabbani, M.R. Ajmal, Y. Zaidi, N. Subbarao, and R.H. Khan Biophysical insight into furosemide binding to human serum albumin: a study to unveil its impaired albumin binding in uremia J. Phys. Chem. B 117 2013 2595 2604
119. O.K. Abou-Zied, N. Al-Lawatia, M. Elstner, and T.B. Steinbrecher Binding of hydroxyquinoline probes to human serum albumin: combining molecular modeling and forster's resonance energy transfer spectroscopy to understand flexible ligand binding J. Phys. Chem. B 117 2013 1062 1074
120. N. Fani, A.K. Bordbar, and Y. Ghayeb A combined spectroscopic, docking and molecular dynamics simulation approach to probing binding of a Schiff base complex to human serum albumin Spectrochim. Acta A 103 2013 11 17
121. H. Pu, H. Jiang, and R. Chen Combined multispectroscopic and molecular docking investigation on the interaction between strictosamide and human serum albumin Luminescence 2013 10.1002/bio.2480 (in press)
122. S.K. Ghorai, S.K. Samanta, M. Mukherjee, P. Saha Sardar, and S. Ghosh Tuning of "antenna effect" of Eu(III) in ternary systems in aqueous medium through binding with protein Inorg. Chem. 52 2013 1476 1487
123. S. Aggarwal, A.K. Tiwari, P. Srivastava, N. Chadha, V. Kumar, G. Singh, and A.K. Mishra Investigation for the interaction of tyramine-based anthraquinone analogue with human serum albumin by optical spectroscopic technique Chem. Biol. Drug Des. 81 2013 343 348
124. M. Domínguez-García, C. Ortega-Zúñiga, and E. Meléndez New tungstenocenes containing 3-hydroxy-4-pyrone ligands: antiproliferative activity on HT-29 and MCF-7 cell lines and binding to human serum albumin studied by fluorescence spectroscopy and molecular modeling methods J. Biol. Inorg. Chem. 18 2013 195 209
125. Z. Moosavi-Movahedi, H. Bahrami, M. Zahedi, K. Mahnam, J. Chamani, S. Safarian, A.A. Saboury, and A.A. Moosavi-Movahedi A theoretical elucidation of bilirubin interaction with HSA's lysines: first electrostatic binding site in IIA subdomain Biophys. Chem. 125 2007 375 387 (Pubitemid 46123772)
126. N. Díaz, D. Suárez, T.L. Sordo, and K.M. Merz Jr. Molecular dynamics study of the IIA binding site in human serum albumin: influence of the protonation state of Lys195 and Lys199 J. Med. Chem. 44 2001 250 260 (Pubitemid 32096670)
127. 2 + binding to N-terminal of human serum albumin (HSA) J. Mol. Struct. 711 2004 73 81 (Pubitemid 40247353)
128. R. Artali, G. Bombieri, L. Calabi, and A. Del Pra A molecular dynamics study of human serum albumin binding sites Farmaco 60 2005 485 495 (Pubitemid 40943387)
129. S. Fujiwara, and T. Amisaki Molecular dynamics study of conformational changes in human serum albumin by binding of fatty acids Proteins 64 2006 730 739 (Pubitemid 44100738)
130. R. Artali, A. Del Pra, E. Foresti, I.G. Lesci, N. Roveri, and P. Sabatino Adsorption of human serum albumin on the chrysotile surface: a molecular dynamics and spectroscopic investigation J. R. Soc. Interface 5 2008 273 283
131. J.W. Shen, T. Wu, Q. Wang, and Y. Kang Induced stepwise conformational change of human serum albumin on carbon nanotube surfaces Biomaterials 29 2008 3847 3855
132. H.J. Hsu, S.Y. Sheu, and R.Y. Tsay Preferred orientation of albumin adsorption on a hydrophilic surface from molecular simulation Colloids Surf. B 67 2008 183 191
133. J. Giri, M.S. Diallo, A.J. Simpson, Y. Liu, W.A. Goddard, R. Kumar, and G.C. Woods Interactions of poly(amidoamine) dendrimers with human serum albumin: binding constants and mechanisms ACS Nano 5 2011 3456 3468
134. H.W. Fang, M.C. Hsieh, H.T. Huang, C.Y. Tsai, and M.H. Chang Conformational and adsorptive characteristics of albumin affect interfacial protein boundary lubrication: from experimental to molecular dynamics simulation approaches Colloids Surf. B 68 2009 171 177
135. R. Nasiri, H. Bahrami, M. Zahedi, A.A. Moosavi-Movahedi, and N. Sattarahmady A theoretical elucidation of glucose interaction with HSA's domains J. Biomol. Struct. Dyn. 28 2010 211 226
136. J. Li, X. Zhu, C. Yang, and R. Shi Characterization of the binding of angiotensin II receptor blockers to human serum albumin using docking and molecular dynamics simulation J. Mol. Model. 16 2010 789 798
137. C. Malleda, N. Ahalawat, M. Gokara, and R. Subramanyam Molecular dynamics simulation studies of betulinic acid with human serum albumin J. Mol. Model. 18 2012 2589 2597
138. K. Aidas, J.M. Olsen, J. Kongsted, and H. Ågren Photoabsorption of acridine yellow and proflavin bound to human serum albumin studied by means of quantum mechanics/molecular dynamics J. Phys. Chem. B 117 2013 2069 2080
139. O. Deeb, M.C. Rosales-Hernandez, C. Gomez-Castro, R. Garduno-Juarez, and J. Correa-Basurto Exploration of human serum albumin binding sites by docking and molecular dynamics flexible ligand-protein interactions Biopolymers 93 2010 161 170
140. H.A. Alvarez, A.N. McCarthy, and J.R. Grigera A molecular dynamics approach to ligand-receptor interaction in the aspirin-human serum albumin complex J. Biophys. 2012 2012 642745
141. T.R. Guizado, S.R. Louro, and C. Anteneodo Dynamics of heme complexed with human serum albumin: a theoretical approach Eur. Biophys. J. 41 2012 1033 1042
142. G. Paris, S. Kraszewski, C. Ramseyer, and M. Enescu About the structural role of disulfide bridges in serum albumins: evidence from protein simulated unfolding Biopolymers 97 2012 889 898
143. N.A. Kratochwil, W. Huber, F. Muller, M. Kansy, and P.R. Gerber Predicting plasma protein binding of drugs: a new approach Biochem. Pharmacol. 64 2002 1355 1374 (Pubitemid 35248253)
144. E. Gianolio, G.B. Giovenzana, D. Longo, I. Longo, I. Menegotto, and S. Aime Relaxometric and modelling studies of the binding of a lipophilic Gd-AAZTA complex to fatted and defatted human serum albumin Chemistry 13 2007 5785 5797 (Pubitemid 47117400)
145. S. Fujiwara, and T. Amisaki Identification of high affinity fatty acid binding sites on human serum albumin by MM-PBSA method Biophys. J. 94 2008 95 103
146. M. Salvalaglio, I. Muscionico, and C. Cavallotti Determination of energies and sites of binding of PFOA and PFOS to human serum albumin J. Phys. Chem. B 114 2010 14860 14874
147. S. Fujiwara, and T. Amisaki Steric and allosteric effects of fatty acids on the binding of warfarin to human serum albumin revealed by molecular dynamics and free energy calculations Chem. Pharm. Bull. 59 2011 860 867
148. B. Rizzuti, M. Pantusa, and R. Guzzi The role of Lys525 on the head-group anchoring of fatty acids in the highest affinity binding site of albumin Spectroscopy 24 2010 159 163
149. K. Paal, and A. Shkarupin Paclitaxel binding to the fatty acid-induced conformation of human serum albumin - automated docking studies Bioorg. Med. Chem. 15 2007 7568 7575 (Pubitemid 47575928)
150. D.E. Shaw, M.M. Deneroff, R.O. Dror, J.S. Kuskin, R.H. Larson, J.K. Salmon, C. Young, B. Batson, K.J. Bowers, J.C. Chao, M.P. Eastwood, J. Gagliardo, J.P. Grossman, C.R. Ho, D.J. Ierardi, I. Kolossvary, J.L. Klepeis, T. Layman, C. McLeavey, M.A. Moraes, R. Mueller, E.C. Priest, Y.B. Shan, J. Spengler, M. Theobald, B. Towles, and S.C. Wang Anton, a special-purpose machine for molecular dynamics simulation Commun. ACM 51 2008 91 97
151. T. Seto, H. Isogai, M. Ozaki, and S. Nosaka Noble gas binding to human serum albumin using docking simulation: nonimmobilizers and anesthetics bind to different sites Anesth. Analg. 107 2008 1223 1228
152. F. Ding, W. Liu, L. Zhang, B. Yin, and Y. Sun Sulfometuron-methyl binding to human serum albumin: evidence that sulfometuron-methyl binds at the Sudlow's site I J. Mol. Struct. 968 2010 59 66
153. S.W. Sarsam, D.R. Nutt, K. Strohfeldt, and K.A. Watson Titanocene anticancer complexes and their binding mode of action to human serum albumin: a computational study Metallomics 3 2011 152 161
154. W. Humphrey, A. Dalke, and K. Schulten VMD: visual molecular dynamics J. Mol. Graph. 14 1996 33 38 (Pubitemid 26152973)