Binding and molecular dynamics studies of 7-hydroxycoumarin derivatives with human serum albumin and its pharmacological importance

Molecular Pharmaceutics

Volumn 11, Issue 4, 2014, Pages 1117-1131

  Yeggoni, Daniel Pushparaju ^a   Gokara, Mahesh ^a   Mark Manidhar, Darla ^b   Rachamallu, Aparna ^a   Nakka, Sailaja ^a   Reddy, Cirandur Suresh ^b   Subramanyam, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b SRI VENKATESWARA UNIVERSITY   (India)

Author keywords

7 hydroxycoumarin derivative; binding studies; circular dichroism spectroscopy; cytotoxic studies; fluorescence emission; molecular displacement; molecular docking; molecular dynamics; pharmacology

Indexed keywords

2 CYANO 3 (7 HYDROXY 2 OXO 2H CHROMEN 8 YL) N (1 PHENYLETHYL)ACRYLAMIDE; 2 CYANO N (3,5 DIMETHOXYBENZYL) 3 (7 HYDROXY 2 OXO 2 CHROMEN 8 YL)ACRYLAMIDE; ALPHA1 GLYCOPROTEIN; HUMAN SERUM ALBUMIN; IBUPROFEN; N BENZHYDRYL 2 CYANO 3 (7 HYDROXY 2 OXO 2H CHROMEN 8 YL)ACRYLAMIDE; PHENYLBUTAZONE; UMBELLIFERONE DERIVATIVE; UNCLASSIFIED DRUG; 7-HYDROXYCOUMARIN; COUMARIN DERIVATIVE; PROTEIN BINDING; SERUM ALBUMIN;

ALPHA HELIX; ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BETA SHEET; BINDING AFFINITY; CELL LINE; CIRCULAR DICHROISM; CLINICAL PHARMACOLOGY; CONCENTRATION RESPONSE; CYTOTOXICITY; FLUORESCENCE; GROWTH INHIBITION; HYDROPHOBICITY; IC 50; MACROPHAGE; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MOUSE; NONHUMAN; PH; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN INTERACTION; PROTEIN SECONDARY STRUCTURE; ANIMAL; CELL CULTURE; CHEMISTRY; HUMAN; METABOLISM; SPECTROFLUOROMETRY; THERMODYNAMICS;

ANIMALS; CELLS, CULTURED; CIRCULAR DICHROISM; COUMARINS; HUMANS; MICE; MOLECULAR DOCKING SIMULATION; MOLECULAR DYNAMICS SIMULATION; PROTEIN BINDING; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; THERMODYNAMICS; UMBELLIFERONES;

EID: 84897990201     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500051f     Document Type: Article

References (83)

1. Müller, W.; Wollert, U. Human serum albumin as a "silent receptor" for drugs and endogenous substances Pharmacology 2008, 19 (2) 59-67
2. Bailey, D. N.; Briggs, J. R. The binding of selected therapeutic drugs to human serum α-1 acid glycoprotein and to human serum albumin in vitro Ther. Drug Monit. 2004, 26 (1) 40-43
3. Yamasaki, K.; Chuang, V. T.; Maruyama, T.; Otagiri, M. Albumin-drug interaction and its clinical implication Biochim. Biophys. Acta 2013, 1830 (12) 5435-5443
4. Varshney, A.; Sen, P.; Ahmad, E.; Rehan, M.; Subbarao, N.; Khan, R. H. Ligand binding strategies of human serum albumin: how can the cargo be utilized? Chirality 2010, 22 (1) 77-87
5. He, X. M.; Carter, D. C. Atomic structure and chemistry of human serum albumin Nature 1992, 358, 209-215
6. Carter, D. C.; He, X. M.; Munson, S. H.; Twigg, P. D.; Gernert, K. M.; Broom, M. B.; Miller, T. Y. Three-dimensional structure of human serum albumin Science 1989, 244 (4909) 1195-1198
7. Trivella, D. B.; dos Reis, C. V.; Lima, L. M.; Foguel, D.; Polikarpov, I. Flavonoid interactions with human transthyretin: Combined structural and thermodynamic analysis J. Struct. Biol. 2012, 180 (1) 143-153
8. Sugio, S.; Kashima, A.; Mochizuki, S.; Noda, M.; Kobayashi, K. Crystal structure of human serum albumin at 2.5 Å resolution Protein Eng. 1999, 12 (6) 439-446
9. Roy, D.; Dutta, S.; Maity, S. S.; Ghosh, S.; Roy, A. S.; Ghosh, K. S.; Dasgupta, S. Spectroscopic and docking studies of the binding of two stereoisomeric antioxidant catechins to serum albumins J. Lumin. 2012, 132 (6) 1364-1375
10. Kragh-Hansen, U.; Chuang, V. T.; Otagiri, M. Practical aspects of the ligand-binding and enzymatic properties of human serum albumin Biol. Pharm. Bull. 2002, 25 (6) 695-704
11. Ghuman, J.; Zunszain, P. A.; Petitpas, I.; Bhattacharya, A. A.; Otagiri, M.; Curry, S. Structural basis of the drug-binding specificity of human serum albumin J. Mol. Biol. 2005, 353 (1) 38-52
12. Zsila, F. Subdomain IB is the third major drug binding region of human serum albumin: Toward the three-sites model Mol. Pharmaceutics 2013, 10 (5) 1668-1682
13. Zunszain, P. A.; Ghuman, J.; McDonagh, A. F.; Curry, S. Crystallographic analysis of human serum albumin complexed with 4Z, 15E-bilirubin-IXα J. Mol. Biol. 2008, 381 (2) 394-406
14. Sudlow, G.; Birkett, D.; Wade, D. Further characterization of specific drug binding sites on human serum albumin Mol. Pharmacol. 1976, 12 (6) 1052-1061
15. Petitpas, I.; Grüne, T.; Bhattacharya, A. A.; Curry, S. Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids J. Mol. Biol. 2001, 314 (5) 955-960
16. Curry, S.; Brick, P.; Franks, N. P. Fatty acid binding to human serum albumin: new insights from crystallographic studies Biochim. Biophys. Acta-Mol. Cell. Biol. Lett. 1999, 1441 (2) 131-140
17. Bhattacharya, A. A.; Curry, S.; Franks, N. P. Binding of the general anesthetics propofol and halothane to human serum albumin high resolution crystal structures J. Biol. Chem. 2000, 275 (49) 38731-38738
18. Mandeville, J. S.; Froehlich, E.; Tajmir-Riahi, H. A. Study of curcumin and genistein interactions with human serum albumin J. Pharm. Biomed. Anal. 2009, 49 (2) 468-474
19. Bourassa, P.; Dubeau, S.; Maharvi, G. M.; Fauq, A. H.; Thomas, T. J.; Tajmir-Riahi, H. A. Binding of antitumor tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen to human serum albumin Biochimie 2011, 93 (7) 1089-1101
20. Sudhamalla, B.; Gokara, M.; Ahalawat, N.; Amooru, D. G.; Subramanyam, R. Molecular dynamics simulation and binding studies of β-sitosterol with human serum albumin and its biological relevance J. Phys. Chem. B 2010, 114 (27) 9054-9062
21. Subramanyam, R.; Goud, M.; Sudhamalla, B.; Reddeem, E.; Gollapudi, A.; Nellaepalli, S.; Yadavalli, V.; Chinnaboina, M.; Amooru, D. G. Novel binding studies of human serum albumin with trans-feruloyl maslinic acid J. Photochem. Photobiol., B 2009, 95 (2) 81-88
22. Subramanyam, R.; Gollapudi, A.; Bonigala, P.; Chinnaboina, M.; Amooru, D. G. Betulinic acid binding to human serum albumin: A study of protein conformation and binding affinity J. Photochem. Photobiol., B 2009, 94 (1) 8-12
23. Neelam, S.; Gokara, M.; Sudhamalla, B.; Amooru, D. G.; Subramanyam, R. Interaction studies of coumaroyltyramine with human serum albumin and its biological importance J. Phys. Chem. B 2010, 114 (8) 3005-3012
24. Malleda, C.; Ahalawat, N.; Gokara, M.; Subramanyam, R. Molecular dynamics simulation studies of betulinic acid with human serum albumin J. Mol. Model. 2012, 18 (6) 2589-2597
25. Gokara, M.; Sudhamalla, B.; Amooru, D. G.; Subramanyam, R. Molecular interaction studies of trimethoxy flavone with human serum albumin PLoS One 2010, 5 (1) e8834
26. Gokara, M.; Malavath, T.; Kalangi, S. K.; Pallu, R.; Subramanyam, R. Unraveling the binding mechanism of asiatic acid with human serum albumin and its biological implications. J. Biomol. Struct. Dyn. 2013, in press
27. Huang, J. X.; Azad, M. A.; Yuriev, E.; Baker, M. A.; Nation, R. L.; Li, J.; Cooper, M. A.; Velkov, T. Molecular characterization of lipopolysaccharide binding to human α-1-acid glycoprotein J. Lipids 2012, 475153
28. Schmid, K.; Nimberg, R. B.; Kimura, A.; Yamaguchi, H.; Binette, J. The carbohydrate units of human plasma α1-Acid glycoprotein Biochim. Biophys. Acta 1977, 492 (2) 291-302
29. Dente, L.; Pizza, M.; Metspalu, A.; Cortese, R. Structure and expression of the genes coding for human alpha 1-acid glycoprotein EMBO J. 1987, 6 (8) 2289-2296
30. Allen, P. C.; Hill, E. A.; Stokes, A. M. Alpha1-acid glycoprotein. In Plasma Proteins: Analytical and Preparative Techniques; Blackwell Scientific: Oxford, U.K., 1977
31. Imamura, H.; Ismail, K. T.; Suenaga, A.; Otagiri, M. Stereoselective protein binding of alprenolol in the renal diseased state Chirality 2002, 14 (7) 599-603
32. Hochepied, T.; Berger, F. G.; Baumann, H.; Libert, C. α-1-acid glycoprotein: an acute phase protein with inflammatory and immunomodulating properties Cytokine Growth Factor Rev. 2003, 14 (1) 25-34
33. Tozer, T. N. Introduction to pharmacokinetics and pharmacodynamics: the quantitative basis of drug therapy; Wolters Kluwer Health: Philadelphia, 2006.
34. Kwong, T. C. Free drug measurements: methodology and clinical significance Clin. Chim. Acta 1985, 151 (3) 193-216
35. Lusch, A.; Kaup, M.; Marx, U.; Tauber, R.; Blanchard, V.; Berger, M. Development and analysis of alpha 1-antitrypsin neoglycoproteins-the impact of additional N glycosylation sites on serum half-life Mol. Pharmaceutics 2013, 10 (7) 2616-2629
36. Heegaard, P. M.; Miller, I.; Sorensen, N. S.; Soerensen, K. E.; Skovgaard, K. Pig α1-acid glycoprotein: Characterization and first description in any species as a negative acute phase protein PLoS One 2013, 8 (7) e68110
37. Howard, M. L.; Hill, J. J.; Galluppi, G. R.; McLean, M. A. Plasma protein binding in drug discovery and development Comb. Chem. High Throughput Screen. 2010, 13 (2) 170-187
38. Chuang, V. T.; Otagiri, M. Stereoselective binding of human serum albumin Chirality 2006, 18 (3) 159-166
39. Ojala, T. Biological screening of plant coumarins; University of Helsinki: Helsinki, 2001.
40. Finn, G. J.; Kenealy, E.; Creaven, B. S.; Egan, D. A. In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines Cancer Lett. 2002, 183 (1) 61-68
41. Egan, D. A.; O'Kennedy, R. Rapid and sensitive determination of coumarin and 7-hydroxycoumarin and its glucuronide conjugate in urine and plasma by high-performance liquid chromatography J. Chromatogr., B: Biomed. Sci. Appl. 1992, 582 (1-2) 137-143
42. Egan, D.; O'Kennedy, R.; Moran, E.; Cox, D.; Prosser, E.; Thornes, R. D. The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds Drug Metab. Dispos. Rev. 1990, 22 (5) 503-529
43. Keating, G.; O'Kennedy, R. The chemistry and occurrence of coumarins. Coumarins: biology, applications and mode of action; John Wiley & Sons, Inc.: New York, 1997; p 348.
44. Riveiro, M.; De Kimpe, N.; Moglioni, A.; Vazquez, R.; Monczor, F.; Shayo, C.; Davio, C. Coumarins: old compounds with novel promising therapeutic perspectives Curr. Med. Chem. 2010, 17 (13) 1325-1338
45. Lacy, A.; O'Kennedy, R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer Curr. Pharm. Des. 2004, 10 (30) 3797-3811
46. Kontogiorgis, C.; Hadjipavlou-Litina, D. Biological evaluation of several coumarin derivatives designed as possible anti-inflammatory/antioxidant agents J. Enzyme Inhib. Med. Chem. 2003, 18 (1) 63-69
47. Campos-Toimil, M.; Orallo, F.; Santana, L.; Uriarte, E. Synthesis and vasorelaxant activity of new coumarin and furocoumarin derivatives Bioorg. Med. Chem. Lett. 2002, 12 (5) 783-786
48. Gormley, N. A.; Orphanides, G.; Meyer, A.; Cullis, P. M.; Maxwell, A. The interaction of coumarin antibiotics with fragments of the DNA gyrase B protein Biochemistry (Moscow) 1996, 35 (15) 5083-5092
49. Kabeya, L. M.; de Marchi, A. A.; Kanashiro, A.; Lopes, N. P.; da Silva, C. H.; Pupo, M. T.; Lucisano-Valim, Y. M. Inhibition of horseradish peroxidase catalytic activity by new 3-phenylcoumarin derivatives: Synthesis and structure-activity relationships Bioorg. Med. Chem. 2007, 15 (3) 1516-1524
50. Chilin, A.; Battistutta, R.; Bortolato, A.; Cozza, G.; Zanatta, S.; Poletto, G.; Mazzorana, M.; Zagotto, G.; Uriarte, E.; Guiotto, A.; Pinna, L. A.; Meggio, F.; Moro, S. Coumarin as attractive casein kinase 2 (CK2) inhibitor scaffold: an integrate approach to elucidate the putative binding motif and explain structure-activity relationships J. Med. Chem. 2008, 51 (4) 752-759
51. Garg, A.; Manidhar, D. M.; Gokara, M.; Malleda, C.; Reddy, C. S.; Subramanyam, R. Elucidation of the binding mechanism of coumarin derivatives with human serum albumin PLoS One 2013, 8 (5) e63805
52. Pechmann, H.; Duisberg, C. Synthesis of coumarins by condensation of phenols with beta keto ester in presence of Lewis acid catalysts Berichte 1893, 2119, 16
53. MicMihael, B.; Cadogan, J.; Hamish, M. N.; Andrew, D. M. P.; Peter Roddam, V.; Carol, S.; Helen, R. S. R.S. Synthesis of fused furans by gas phase pyrolysis of 2-allyoxyaryl propenoic ester J. Chem. Soc., Perkin Trans. 1997, 1, 2483-2493
54. Wang, K.; Nguyen, K.; Huang, Y.; Dömling, A. Cyanoacetamide multicomponent reaction (I): parallel synthesis of cyanoacetamides J. Comb. Chem. 2009, 11 (5) 920-927
55. McCluskey, A.; Robinson, P. J.; Hill, T.; Scott, J. L.; Edwards, J. K. Green chemistry approaches to the Knoevenagel condensation: comparison of ethanol, water and solvent free (dry grind) approaches Tetrahedron Lett. 2002, 43 (17) 3117-3120
56. Darla, M. M.; Krishna, B. S.; Rao, K. U.; Reddy, N. B.; Srivash, M. K.; Adeppa, K.; Sundar, C. S.; Reddy, C. S.; Misra, K. Synthesis and bio-evaluation of novel 7-hydroxy coumarin derivatives via Knoevenagel reaction. Res. Chem. Intermed., 10.1007/s11164-013-1258-1.
57. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65 (1) 55-63
58. Zsila, F.; Bikádi, Z.; Simonyi, M. Probing the binding of the flavonoid, quercetin to human serum albumin by circular dichroism, electronic absorption spectroscopy and molecular modelling methods Biochem. Pharmacol. 2003, 65 (3) 447-456
59. Min, J.; Meng-Xia, X.; Dong, Z.; Yuan, L.; Xiao-Yu, L.; Xing, C. Spectroscopic studies on the interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin J. Mol. Struct. 2004, 692 (1-3) 71-80
60. Liang, L.; Tajmir-Riahi, H. A.; Subirade, M. Interaction of β-lactoglobulin with resveratrol and its biological implications Biomacromolecules 2007, 9 (1) 50-56
61. Hussein, B. H. M. Spectroscopic studies of 7,8-dihydroxy-4-methylcoumarin and its interaction with bovine serum albumin J. Lumin. 2011, 131 (5) 900-908
62. Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility J. Comput. Chem. 2009, 30 (16) 2785-2791
63. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 1998, 19 (14) 1639-1662
64. Jones, G.; Willett, P.; Glen, R. C. Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation J. Mol. Biol. 1995, 245 (1) 43-53
65. Gorelik, B.; Goldblum, A. High quality binding modes in docking ligands to proteins Proteins: Struct., Funct., Bioinf. 2008, 71 (3) 1373-1386
66. Goodford, P. J. A computational procedure for determining energetically favorable binding sites on biologically important macromolecules J. Med. Chem. 1985, 28 (7) 849-857
67. Hetényi, C.; van der Spoel, D. Blind docking of drug-sized compounds to proteins with up to a thousand residues FEBS Lett. 2006, 580 (5) 1447-1450
68. Lindahl, E.; Hess, B.; Van Der Spoel, D. GROMACS 3.0: a package for molecular simulation and trajectory analysis Mol. Model. Annu. 2001, 7 (8) 306-317
69. Berendsen, H. J. C.; van der Spoel, D.; van Drunen, R. GROMACS: A message-passing parallel molecular dynamics implementation Comput. Phys. Commun. 1995, 91 (1-3) 43-56
70. Scott, W. R.; Hünenberger, P. H.; Tironi, I. G.; Mark, A. E.; Billeter, S. R.; Fennen, J.; Torda, A. E.; Huber, T.; Krüger, P.; van Gunsteren, W. F. The GROMOS biomolecular simulation program package J. Phys. Chem. A 1999, 103 (19) 3596-3607
71. Schuler, L. D.; Daura, X.; Van Gunsteren, W. F. An improved GROMOS96 force field for aliphatic hydrocarbons in the condensed phase J. Comput. Chem. 2001, 22 (11) 1205-1218
72. Schuttelkopf, A. W.; van Aalten, D. M. PRODRG: a tool for high-throughput crystallography of protein-ligand complexes Acta Crystallogr., Sect D: Biol. Crystallogr. 2004, 60 (8) 1355-1363
73. Jana, S.; Dalapati, S.; Ghosh, S.; Guchhait, N. Potential charge transfer probe induced conformational changes of model plasma protein human serum albumin: Spectroscopic, molecular docking, and molecular dynamics simulation study Biopolymers 2012, 97 (10) 766-777
74. Sułkowska, A. Interaction of drugs with bovine and human serum albumin J. Mol. Struct. 2002, 614 (1) 227-232
75. Il'ichev, Y. V.; Perry, J. L.; Simon, J. D. Interaction of ochratoxin A with human serum albumin. Preferential binding of the dianion and pH effects J. Phys. Chem. B 2002, 106 (2) 452-459
76. Lakowicz, J. R. Principles of fluorescence spectroscopy; Springer: New York, 2009.
77. Kandagal, P. B.; Kalanur, S. S.; Manjunatha, D. H.; Seetharamappa, J. Mechanism of interaction between human serum albumin and N-alkyl phenothiazines studied using spectroscopic methods J. Pharm. Biomed. Anal. 2008, 47 (2) 260-267
78. Agudelo, D.; Bourassa, P.; Bruneau, J.; Bérubé, G.; Asselin, é.; Tajmir-Riahi, H. A. Probing the binding sites of antibiotic drugs doxorubicin and N-(trifluoroacetyl) doxorubicin with human and bovine serum albumins PLoS One 2012, 7 (8) e43814
79. Kalanur, S. S.; Seetharamappa, J.; Kalalbandi, V. K. Characterization of interaction and the effect of carbamazepine on the structure of human serum albumin J. Pharm. Biomed. Anal. 2010, 53 (3) 660-666
80. Zhang, G.; Que, Q.; Pan, J.; Guo, J. Study of the interaction between icariin and human serum albumin by fluorescence spectroscopy J. Mol. Struct. 2008, 881 (1) 132-138
81. Tayeh, N.; Rungassamy, T.; Albani, J. R. Fluorescence spectral resolution of tryptophan residues in bovine and human serum albumins J. Pharm. Biomed. Anal. 2009, 50 (2) 107-116
82. Zhang, M. F.; Xu, Z.-Q.; Ge, Y. S.; Jiang, F. L.; Liu, Y. Binding of fullerol to human serum albumin: spectroscopic and electrochemical approach J. Photochem. Photobiol., B 2012, 108, 34-43
83. Kiselev, M. A.; IuA, G.; Dobretsov, G. E.; Komarova, M. N. Size of a human serum albumin molecule in solution Biofizika 2001, 46 (3) 423