Elucidation of the Binding Mechanism of Coumarin Derivatives with Human Serum Albumin

PLoS ONE

Volumn 8, Issue 5, 2013, Pages

  Garg, Archit ^a   Mark Manidhar, Darla ^b   Gokara, Mahesh ^a   Malleda, Chandramouli ^a   Suresh Reddy, Cirandur ^b   Subramanyam, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b SRI VENKATESWARA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYANO 3 (7 HYDROXY 4 METHYL 2 OXO 2H CHROMEN 8 YL) N METHYLPROP 2 ENAMIDE; 2 CYANO N (2 HYDROXYETHYL) 3 (7 HYDROXY 4 METHYL 2 OXO 2H CHROMEN 8 YL)PROP 2 ENAMIDE; COUMARIN DERIVATIVE; ETHYL 2 CYANO 3 (7 HYDROXY 4 METHYL 2 OXO 2H CHROMEN 8 YL)PROP 2 ENOATE; HUMAN SERUM ALBUMIN; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL PARAMETERS; CIRCULAR DICHROISM; CONCENTRATION RESPONSE; CONFORMATIONAL TRANSITION; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG STRUCTURE; FLUORESCENCE SPECTROSCOPY; FREE ENERGY; HUMAN; HYDROGEN BOND; HYDROPHOBICITY; LIGAND BINDING; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PH; PROTEIN SECONDARY STRUCTURE; PROTEIN STABILITY; PROTEIN UNFOLDING;

BINDING SITES; BUFFERS; CIRCULAR DICHROISM; HUMANS; HYDROGEN-ION CONCENTRATION; HYMECROMONE; KINETICS; MOLECULAR DOCKING SIMULATION; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; THERMODYNAMICS; TIME FACTORS;

HERPES;

EID: 84878409115     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0063805     Document Type: Article

References (63)

1. Bourinbaiar AS, Nagorny R, (1993) Human immunodeficiency virus type 1 infection of choriocarcinoma-derived trophoblasts. Acta Virol 37: 21-28.
2. Hoult JR, Forder RA, de las Heras B, Lobo IB, Paya M, (1994) Inhibitory activity of a series of coumarins on leukocyte eicosanoid generation. Agents Actions 42: 44-49.
3. de Julian-Ortiz JV, Galvez J, Munoz-Collado C, Garcia-Domenech R, Gimeno-Cardona C, (1999) Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds. J Med Chem 42: 3308-3314.
4. Farinola N, Piller N, (2005) Pharmacogenomics: its role in re-establishing coumarin as treatment for lymphedema. Lymphat Res Biol 3: 81-86.
5. Bye A, King HK, (1970) The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius. Biochem J 117: 237-245.
6. Lowenthal J, Birnbaum H, (1969) Vitamin K and coumarin anticoagulants: dependence of anticoagulant effect on inhibition of vitamin K transport. Science 164: 181-183.
7. Singh R, Singh B, Singh S, Kumar N, Kumar S, et al. (2010) Umbelliferone- An antioxidant isolated from Acacia nilotica (L.) Willd. Ex. Del. Food Chem 120: 825-830.
8. Muller WE, Wollert U, (1979) Human serum albumin as a 'silent receptor' for drugs and endogenous substances. Pharmacology 19: 59-67.
9. Ahmad B, Parveen S, Khan RH, (2006) Effect of albumin conformation on the binding of ciprofloxacin to human serum albumin: a novel approach directly assigning binding site. Biomacromolecules 7: 1350-1356.
10. Karnaukhova E, (2007) Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. Biochem Pharmacol 73: 901-910.
11. Sinha SS, Mitra RK, Pal SK, (2008) Temperature-dependent simultaneous ligand binding in human serum albumin. J Phys Chem B 112: 4884-4891.
12. Maiti TK, Ghosh KS, Samanta A, Dasgupta S, (2008) The interaction of silibinin with human serum albumin: A spectroscopic investigation. J Photochem Photobiol A 194: 297-307.
13. Charbonneau D, Beauregard M, Tajmir-Riahi HA, (2009) Structural analysis of human serum albumin complexes with cationic lipids. J Phys Chem B 113: 1777-1784.
14. Yue YY, Chen XG, Qin J, Yao XJ, (2009) Characterization of the mangiferin-human serum albumin complex by spectroscopic and molecular modeling approaches. J Pharm Biomed Anal 49: 753-759.
15. Varshney A, Sen P, Ahmad E, Rehan M, Subbarao N, et al. (2010) Ligand binding strategies of human serum albumin: how can the cargo be utilized? Chirality 22: 77-87.
16. Cheng Z, (2012) Interaction of ergosterol with bovine serum albumin and human serum albumin by spectroscopic analysis. Mol Biol Rep 39: 9493-9508.
17. Carter DC, Ho JX, (1994) Structure of serum albumin. Adv Protein Chem 45: 153-203.
18. Peters T (1996) All about albumin: biochemistry, genetics, and medical applications. San Diego: Academic Press. xx, 432 p., 432 p. of plates p.
19. He XM, Carter DC, (1992) Atomic structure and chemistry of human serum albumin. Nature 358: 209-215.
20. Curry S, Mandelkow H, Brick P, Franks N, (1998) Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat Struct Biol 5: 827-835.
21. Curry S, Brick P, Franks NP, (1999) Fatty acid binding to human serum albumin: new insights from crystallographic studies. Biochim Biophys Acta 1441: 131-140.
22. Sugio S, Kashima A, Mochizuki S, Noda M, Kobayashi K, (1999) Crystal structure of human serum albumin at 2.5 A resolution. Protein Eng 12: 439-446.
23. Bhattacharya AA, Grune T, Curry S, (2000) Crystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin. J Mol Biol 303: 721-732.
24. Petitpas I, Grune T, Bhattacharya AA, Curry S, (2001) Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids. J Mol Biol 314: 955-960.
25. Ghuman J, Zunszain PA, Petitpas I, Bhattacharya AA, Otagiri M, et al. (2005) Structural basis of the drug-binding specificity of human serum albumin. J Mol Biol 353: 38-52.
26. N'Soukpoe-Kossi CN, Sedaghat-Herati R, Ragi C, Hotchandani S, Tajmir-Riahi HA, (2007) Retinol and retinoic acid bind human serum albumin: stability and structural features. Int J Biol Macromol 40: 484-490.
27. Krishnakumar SS, Panda D, (2002) Spatial relationship between the prodan site, Trp-214, and Cys-34 residues in human serum albumin and loss of structure through incremental unfolding. Biochemistry 41: 7443-7452.
28. Il'ichev YV, Perry JL, Ruker F, Dockal M, Simon JD, (2002) Interaction of ochratoxin A with human serum albumin. Binding sites localized by competitive interactions with the native protein and its recombinant fragments. Chem Biol Interact 141: 275-293.
29. Kubarych CJ, Adams MM, Anslyn EV, (2010) Serum albumins as differential receptors for the discrimination of fatty acids and oils. Organic Letters 12: 4780-4783.
30. Subramanyam R, Gollapudi A, Bonigala P, Chinnaboina M, Amooru DG, (2009) Betulinic acid binding to human serum albumin: a study of protein conformation and binding affinity. J Photochem Photobiol B 94: 8-12.
31. Subramanyam R, Goud M, Sudhamalla B, Reddeem E, Gollapudi A, et al. (2009) Novel binding studies of human serum albumin with trans-feruloyl maslinic acid. J Photochem Photobiol B 95: 81-88.
32. Gokara M, Sudhamalla B, Amooru DG, Subramanyam R, (2010) Molecular interaction studies of trimethoxy flavone with human serum albumin. PLoS One 5: e8834.
33. Neelam S, Gokara M, Sudhamalla B, Amooru DG, Subramanyam R, (2010) Interaction studies of coumaroyltyramine with human serum albumin and its biological importance. J Phys Chem B 114: 3005-3012.
34. Sudhamalla B, Gokara M, Ahalawat N, Amooru DG, Subramanyam R, (2010) Molecular dynamics simulation and binding studies of beta-sitosterol with human serum albumin and its biological relevance. J Phys Chem B 114: 9054-9062.
35. Malleda C, Ahalawat N, Gokara M, Subramanyam R, (2012) Molecular dynamics simulation studies of betulinic acid with human serum albumin. J Mol Model 18: 2589-2597.
36. Manidhar DM, Uma Maheswara Rao K, Bakthavatchala Reddy N, Syamasundar C, Suresh Reddy C, (2012) Synthesis of New 8-Formyl-4-methyl-7-hydroxy Coumarin Derivatives. J Korean Chem Soc 6: 459-463.
37. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, et al. (2009) AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 30: 2785-2791.
38. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, et al. (1998) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19: 1639-1662.
39. Jones G, Willett P, Glen RC, (1995) Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation. J Mol Biol 245: 43-53.
40. Jones G, Willett P, Glen RC, Leach AR, Taylor R, (1997) Development and validation of a genetic algorithm for flexible docking. J Mol Biol 267: 727-748.
41. Allouche AR, (2011) Gabedit-a graphical user interface for computational chemistry softwares. J Comput Chem 32: 174-182.
42. Karplus M, McCammon JA, (2002) Molecular dynamics simulations of biomolecules. Nat Struct Biol 9: 646-652.
43. Brunger AT, Brooks CL, 3rd, Karplus M (1985) Active site dynamics of ribonuclease. Proc Natl Acad Sci U S A 82: 8458-8462.
44. Frauenfelder H, Hartmann H, Karplus M, Kuntz ID Jr, Kuriyan J, et al. (1987) Thermal expansion of a protein. Biochemistry 26: 254-261.
45. Case DA, Karplus M, (1979) Dynamics of ligand binding to heme proteins. J Mol Biol 132: 343-368.
46. Nilsson L, Clore GM, Gronenborn AM, Brunger AT, Karplus M, (1986) Structure refinement of oligonucleotides by molecular dynamics with nuclear Overhauser effect interproton distance restraints: application to 5′ d(C-G-T-A-C-G)2. J Mol Biol 188: 455-475.
47. Brunger AT, Kuriyan J, Karplus M, (1987) Crystallographic R factor refinement by molecular dynamics. Science 235: 458-460.
48. Lindahl E, Hess B, van der Spoel D, (2001) GROMACS 3.0: a package for molecular simulation and trajectory analysis. J Mol Model7: 306-317.
49. Berendsen HJC, Vanderspoel D, Vandrunen R, (1995) Gromacs- a Message-Passing Parallel Molecular-Dynamics Implementation. Comput Phys Commun. 91: 43-56.
50. Scott WRP, Hunenberger PH, Tironi IG, Mark AE, Billeter SR, et al. (1999) The GROMOS biomolecular simulation program package. J Phys Chem A 103: 3596-3607.
51. Schuler LD, Daura X, Van Gunsteren WF, (2001) An improved GROMOS96 force field for aliphatic hydrocarbons in the condensed phase. J Comput Chem. 22: 1205-1218.
52. Schuttelkopf AW, van Aalten DM, (2004) PRODRG: a tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr D Biol Crystallogr 60: 1355-1363.
53. Lehrer SS, (1971) Solute perturbation of protein fluorescence. The quenching of the tryptophyl fluorescence of model compounds and of lysozyme by iodide ion. Biochemistry 10: 3254-3263.
54. Lakowicz JR (1999) Principles of fluorescence spectroscopy. New York: Kluwer Academic/Plenum. xxiii, 698 p. p.
55. Sulkowska A, (2002) Interaction of drugs with bovine and human serum albumin. J Mol Struct 614: 227-232.
56. Kandagal PB, Kalanur SS, Manjunatha DH, Seetharamappa J, (2008) Mechanism of interaction between human serum albumin and N-alkyl phenothiazines studied using spectroscopic methods. J Pharm Biomed Anal 47: 260-267.
57. Agudelo D, Bourassa P, Bruneau J, Berube G, Asselin E, et al. (2012) Probing the binding sites of antibiotic drugs doxorubicin and N-(trifluoroacetyl) doxorubicin with human and bovine serum albumins. PLoS One 7: e43814.
58. Shobini, Mishra AK, Sandhya K, Chandra N, (2001) Interaction of coumarin derivatives with human serum albumin: investigation by fluorescence spectroscopic technique and modeling studies. Spectrochim Acta A Mol Biomol Spectrosc 57A: 1133-1147.
59. Liang L, Tajmir-Riahi HA, Subirade M, (2008) Interaction of beta-lactoglobulin with resveratrol and its biological implications. Biomacromolecules 9: 50-56.
60. Zunszain PA, Ghuman J, Komatsu T, Tsuchida E, Curry S, (2003) Crystal structural analysis of human serum albumin complexed with hemin and fatty acid. BMC Struct Biol 3: 6.
61. Zunszain PA, Ghuman J, McDonagh AF, Curry S, (2008) Crystallographic analysis of human serum albumin complexed with 4Z,15E-bilirubin-IXalpha. J Mol Biol 381: 394-406.
62. Pils B, Copley RR, Schultz J, (2005) Variation in structural location and amino acid conservation of functional sites in protein domain families. BMC Bioinformatics 6: 210.
63. Kiselev MA, Gryzunov Iu A, Dobretsov GE, Komarova MN, (2001) Size of a human serum albumin molecule in solution. Biofizika 46: 423-427.