Differential interactions and structural stability of chitosan oligomers with human serum albumin and α-1-glycoprotein

Journal of Biomolecular Structure and Dynamics

Volumn 33, Issue 1, 2015, Pages 196-210

  Gokara, Mahesh ^a   Kimavath, Geetha Bai ^a   Podile, Appa Rao ^a   Subramanyam, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

chitooligomers; drug binding; fluorescence quenching; human serum albumin; molecular dynamics simulation; glycoprotein

Indexed keywords

ALPHA1 GLYCOPROTEIN; CHITOSAN; DIMER; HUMAN SERUM ALBUMIN; MONOMER; OLIGOMER; OROSOMUCOID; PROTEIN BINDING; SERUM ALBUMIN;

ARTICLE; BINDING AFFINITY; CIRCULAR DICHROISM; COMPLEX FORMATION; FLUORESCENCE SPECTROSCOPY; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR DOCKING; MOLECULAR DYNAMICS; POLYMERIZATION; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN SECONDARY STRUCTURE; PROTEIN STABILITY; PROTEIN UNFOLDING; THERMODYNAMICS; ALGORITHM; BINDING COMPETITION; BINDING SITE; CHEMISTRY; CONFORMATION; DIMERIZATION; HUMAN; METABOLISM; PROTEIN TERTIARY STRUCTURE; SPECTROFLUOROMETRY;

ALGORITHMS; BINDING SITES; BINDING, COMPETITIVE; CHITOSAN; DIMERIZATION; HUMANS; HYDROGEN BONDING; MOLECULAR CONFORMATION; MOLECULAR DOCKING SIMULATION; MOLECULAR DYNAMICS SIMULATION; OROSOMUCOID; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; THERMODYNAMICS;

EID: 84908566946     PISSN: 07391102     EISSN: 15380254     Source Type: Journal    
DOI: 10.1080/07391102.2013.868321     Document Type: Article

References (69)

1. Agudelo, D., Bourassa, P., Bruneau, J., Bérubé, G., Asselin, É., & Tajmir-Riahi, H.-A. (2012). Probing the binding sites of antibiotic drugs doxorubicin and N-(trifluoroacetyl) doxorubicin with human and bovine serum albumins. PLoS ONE, 7, e43814.
2. Ahmad, B., Parveen, S., & Khan, R. H. (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.
3. Bailey, D. N., & Briggs, J. R. (2004). The binding of selected therapeutic drugs to human serum α-1 acid glycoprotein and to human serum albumin in vitro. Therapeutic Drug Monitoring, 26, 40-43.
4. Beaven, G. H., D'Albis, A., & Gratzer, W. B. (1973). The interaction of bilirubin with human serum albumin. European Journal of Biochemistry, 33, 500-509.
5. Belpaire, F. M., & Bogaert, M. G. (1989). Pharmacokinetic and pharmacodynamic consequences of altered binding of drugs to alpha 1-acid glycoprotein. Progress in Clinical and Biological Research, 300, 337-350.
6. Berendsen, H., Postma, J., Van Gunsteren, W., & Hermans, J. (1981). Interaction models for water in relation to protein hydration. Intermolecular Forces, 11, 331-342.
7. Berendsen, H. J., van der Spoel, D., & van Drunen, R. (1995). GROMACS: A message-passing parallel molecular dynamics implementation. Computer Physics Communications, 91, 43-56.
8. Bhattacharya, A. A., Grune, T., & Curry, S. (2000). Crystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin. Journal of Molecular Biology, 303, 721-732.
9. Bories, P. N., Feger, J., Benbernou, N., Rouzeau, J.-D., Agneray, J., & Durand, G. (1990). Prevalence of tri- and tetraantennary glycans of humanα 1-acid glycoprotein in release of macrophage inhibitor of interleukin-1 activity. Inflammation, 14, 315-323.
10. Bourassa, P., Dubeau, S., Maharvi, G. M., Fauq, A. H., Thomas, T. J., & Tajmir-Riahi, H. A. (2011). Binding of antitumor tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen to human serum albumin. Biochimie, 93, 1089-1101.
11. Bourassa, P., Hasni, I., & Tajmir-Riahi, H. A. (2011). Folic acid complexes with human and bovine serum albumins. Food Chemistry, 129, 1148-1155.
12. Carter, D. C., He, X.-M., Munson, S. H., Twigg, P. D., Gernert, K. M., Broom, M. B., & Miller, T. Y. (1989). Three-dimensional structure of human serum albumin. Science, 244, 1195-1198.
13. Curry, S., Brick, P., & Franks, N. (1999). Fatty acid binding to human serum albumin: New insights from crystallographic studies. Biochimica et Biophysica Acta (BBA)/Molecular and Cell Biology of Lipids, 1441, 131-140.
14. Eftink, M., & Ghiron, C. (1976). Exposure of tryptophanyl residues in proteins. Quantitative determination by fluorescence quenching studies. Biochemistry, 15, 672-680.
15. Gallaher, D. D., Gallaher, C. M., Mahrt, G. J., Carr, T. P., Hollingshead, C. H., Hesslink, R., Jr, & Wise, J. (2002). A glucomannan and chitosan fiber supplement decreases plasma cholesterol and increases cholesterol excretion in overweight normocholesterolemic humans. Journal of the American College of Nutrition, 21, 428-433.
16. Gambacorti-Passerini, C., Zucchetti, M., Russo, D., Frapolli, R., Verga, M., Bungaro, S., ... Pogliani, E. (2003). α1 acid glycoprotein binds to imatinib (STI571) and substantially alters its pharmacokinetics in chronic myeloid leukemia patients. Clinical Cancer Research, 9, 625-632.
17. Garg, A., Mark Manidhar, D., Gokara, M., Malleda, C., Suresh Reddy, C., & Subramanyam, R. (2013). Elucidation of the binding mechanism of coumarin derivatives with human serum albumin. PLoS ONE, 8, e63805.
18. Gokara, M., Sudhamalla, B., Amooru, D. G., & Subramanyam, R. (2010). Molecular interaction studies of trimethoxy flavone with human serum albumin. PLoS ONE, 5, e8834.
19. Gokara, M., Malavath, T., Kalangi, S. K., Pallu, R., & Subramanyam, R. (2013). Unraveling the binding mechanism of asiatic acid with human serum albumin and its biological implications. Journal of Biomolecular Structure and Dynamics, 1-13.
20. He, X. M., & Carter, D. C. (1992). Atomic structure and chemistry of human serum albumin. Nature, 358, 209-215.
21. Hochepied, T., Berger, F. G., Baumann, H., & Libert, C. (2003). α1-Acid glycoprotein: An acute phase protein with inflammatory and immunomodulating properties. Cytokine and Growth Factor Reviews, 14, 25-34.
22. Howling, G. I., Dettmar, P. W., Goddard, P. A., Hampson, F. C., Dornish, M., & Wood, E. J. (2001). The effect of chitin and chitosan on the proliferation of human skin fibroblasts and keratinocytes in vitro. Biomaterials, 22, 2959-2966.
23. Hushcha, T. O., Luik, A. I., & Naboka, Y. N. (2000). Conformation changes of albumin in its interaction with physiologically active compounds as studied by quasi-elastic light scattering spectroscopy and ultrasonic method. Talanta, 53, 29-34.
24. Israili, Z., & Dayton, P. (2001). Human alpha-1-glycoprotein and its interactions with drugs. Drug Metabolism Reviews, 33, 161-235.
25. Kalanur, S. S., Seetharamappa, J., & Kalalbandi, V. K. A. (2010). Characterization of interaction and the effect of carbamazepine on the structure of human serum albumin. Journal of Pharmaceutical and Biomedical Analysis, 53, 660-666.
26. Kanakis, C. D., Tarantilis, P. A., Tajmir-Riahi, H. A., & Polissiou, M. G. (2007). Crocetin, dimethylcrocetin, and safranal bind human serum albumin: Stability and antioxidative properties. Journal of Agricultural and Food Chemistry, 55, 970-977.
27. Kiselev, M. A., Gryzunov Iu, A., Dobretsov, G. E., & Komarova, M. N. (2001). Size of a human serum albumin molecule in solution. Biofizika, 46, 423-427.
28. Knorr, D. (1982). Functional properties of chitin and chitosan. Journal of Food Science, 47, 593-595.
29. Lakowicz, J. R. (2006). Principles of fluorescence spectroscopy. Berlin: Springer.
30. Lehrer, S. (1971). Solute perturbation of protein fluorescence. Quenching of the tryptophyl fluorescence of model compounds and of lysozyme by iodide ion. Biochemistry, 10, 3254-3263.
31. Li, X. K., & Xia, W. S. (2011). Effects of concentration, degree of deacetylation and molecular weight on emulsifying properties of chitosan. International Journal of Biological Macromolecules, 48, 768-772.
32. Malleda, C., Ahalawat, N., Gokara, M., & Subramanyam, R. (2012). Molecular dynamics simulation studies of betulinic acid with human serum albumin. Journal of Molecular Modeling, 18, 2589-2597.
33. Mandeville, J.-S., Froehlich, E., & Tajmir-Riahi, H. (2009). Study of curcumin and genistein interactions with human serum albumin. Journal of Pharmaceutical and Biomedical Analysis, 49, 468-474.
34. Matei, I., & Hillebrand, M. (2010). Interaction of kaempferol with human serum albumin: A fluorescence and circular dichroism study. Journal of Pharmaceutical and Biomedical Analysis, 51, 768-773.
35. Meijer, D. F., & Sluijs, P. (1987). The influence of binding to albumin and α1-acid glycoprotein on the clearance of drugs by the liver. Pharmaceutisch Weekblad, 9, 65-74.
36. Min, J., Meng-Xia, X., Dong, Z., Yuan, L., Xiao-Yu, L., & Xing, C. (2004). Spectroscopic studies on the interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin. Journal of Molecular Structure, 692, 71-80.
37. Neelam, S., Gokara, M., Sudhamalla, B., Amooru, D. G., & Subramanyam, R. (2010). Interaction studies of coumaroyltyramine with human serum albumin and its biological importance. The Journal of Physical Chemistry B, 114, 3005-3012.
38. No, H. K., & Meyers, S. P. (1995). Preparation and characterization of chitin and chitosan - A review. Journal of Aquatic Food Product Technology, 4, 27-52.
39. No, H. K., Park, N. Y., Lee, S. H., & Meyers, S. P. (2002). Antibacterial activity of chitosans and chitosan oligomers with different molecular weights. International Journal of Food Microbiology, 74, 65-72.
40. Omwancha, W. S., Mallipeddi, R., Valle, B. L., & Neau, S. H. (2013). Chitosan as a pore former in coated beads for colon specific drug delivery of 5-ASA. International Journal of Pharmaceutics, 441, 343-351.
41. Otagiri, M. (2005). A molecular functional study on the interactions of drugs with plasma proteins. Drug Metabolism and Pharmacokinetics, 20, 309-323.
42. Park, P. J., Je, J. Y., & Kim, S. K. (2004). Free radical scavenging activities of differently deacetylated chitosans using an ESR spectrometer. Carbohydrate Polymers, 55, 17-22.
43. Park, J. H., Saravanakumar, G., Kim, K., & Kwon, I. C. (2010). Targeted delivery of low molecular drugs using chitosan and its derivatives. Advanced Drug Delivery Reviews, 62, 28-41.
44. Peters, Jr T. (1995). All about albumin: Biochemistry, genetics and medical applications. San Diego, CA: Academic Press.
45. Piafsky, K. (1980). Disease-induced changes in the plasma binding of basic drugs. Clinical Pharmacokinetics, 5, 246-262.
46. Pos, O., Oostendorp, R. A., Van Der Stelt, M. E., Scheper, R. J., & Van Dijk, W. (1990). Con A-nonreactive human α1-acid glycoprotein (AGP) is more effective in modulation of lymphocyte proliferation than Con A-reactive AGP serum variants. Inflammation, 14, 133-141.
47. Pu, H., Jiang, H., & Chen, R. (2013). Combined multispectroscopic and molecular docking investigation on the interaction between strictosamide and human serum albumin. Luminescence, 28, 482-489.
48. Qian, Y., Zhou, X., Chen, J., & Zhang, Y. (2012). Binding of bezafibrate to human serum albumin: Insight into the non-covalent interaction of an emerging contaminant with biomacromolecules. Molecules, 17, 6821-6831.
49. Schuttelkopf, A. W., & van Aalten, D. M. (2004). PRODRG: A tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallographica Section D: Biological Crystallography, 60, 1355-1363.
50. Simard, J. R., Zunszain, P. A., Hamilton, J. A., & Curry, S. (2006). Location of high and low affinity fatty acid binding sites on human serum albumin revealed by NMR drug-competition analysis. Journal of Molecular Biology, 361, 336-351.
51. Subramanyam, R., Gollapudi, A., Bonigala, P., Chinnaboina, M., & Amooru, D. G. (2009a). Betulinic acid binding to human serum albumin: A study of protein conformation and binding affinity. Journal of Photochemistry and Photobiology B: Biology, 94, 8-12.
52. Subramanyam, R., Goud, M., Sudhamalla, B., Reddeem, E., Gollapudi, A., Nellaepalli, S., ... Amooru, D. G. (2009b). Novel binding studies of human serum albumin with trans-feruloyl maslinic acid. Journal of Photochemistry and Photobiology B: Biology, 95, 81-88.
53. Sudhamalla, B., Gokara, M., Ahalawat, N., Amooru, D. G., & Subramanyam, R. (2010). Molecular dynamics simulation and binding studies of β-sitosterol with human serum albumin and its biological relevance. The Journal of Physical Chemistry B, 114, 9054-9062.
54. Sudlow, G., Birkett, D. J., & Wade, D. N. (1975). The characterization of two specific drug binding sites on human serum albumin. Molecular Pharmacology, 11, 824-832.
55. Sugio, S., Kashima, A., Mochizuki, S., Noda, M., & Kobayashi, K. (1999). Crystal structure of human serum albumin at 2.5 Å resolution. Protein Engineering Design and Selection, 12, 439-446.
56. Sułkowska, A. (2002). Interaction of drugs with bovine and human serum albumin. Journal of Molecular Structure, 614, 227-232.
57. Tabachnick, M. (1964). Thyroxine-protein interactions I. Binding of thyroxine to human serum albumin and modified albumins. Journal of Biological Chemistry, 239, 1242-1249.
58. Tayeh, N., Rungassamy, T., & Albani, J. R. (2009). Fluorescence spectral resolution of tryptophan residues in bovine and human serum albumins. Journal of Pharmaceutical and Biomedical Analysis, 50, 107-116.
59. Tillement, J.-P., Houin, G., Zini, R., Urien, S., Albengres, E., Barre, J., & Sebille, B. (1984). The binding of drugs to blood plasma macromolecules: Recent advances and therapeutic significance. Advances in Drug Research, 13, 59-90.
60. Tokoro, A., Takewaki, N., Suzuki, K. O., Mikami, T., Suzuki, S., & Suzuki, M. (1988). Growth-inhibitory effect of hexa- N-acetylchitohexanse and chitohexaose against Meth-A solid tumor. Chemical and Pharmaceutical Bulletin, 36, 784-790.
61. Trynda-Lemiesz, L. (2004). Paclitaxel-HSA interaction. Binding sites on HSA molecule. Bioorganic and Medicinal Chemistry, 12, 3269-3275.
62. Van Gunsteren, W. F., Daura, X., & Mark, A. E. (1998). GROMOS force field. Encyclopedia of Computational Chemistry, 2, 1211-1216.
63. Varshney, A., Sen, P., Ahmad, E., Rehan, M., Subbarao, N., & Khan, R. H. (2010). Ligand binding strategies of human serum albumin: How can the cargo be utilized? Chirality, 22, 77-87.
64. Wallace, A. C., Laskowski, R. A., & Thornton, J. M. (1995). LIGPLOT: A program to generate schematic diagrams of protein-ligand interactions. Protein Engineering, 8, 127-134.
65. Yamasaki, K., Chuang, V. T., Maruyama, T., & Otagiri, M. (in press). Albumin-drug interaction and its clinical implication. Biochimica et Biophysica Acta, 1830, 5435-5443.
66. Yang, X., Ye, Z., Yuan, Y., Zheng, Z., Shi, J., Ying, Y., & Huang, P. (2013). Insights into the binding of paclitaxel to human serum albumin: Multispectroscopic studies. Luminescence, 28, 427-434.
67. Zhang, G., Que, Q., Pan, J., & Guo, J. (2008). Study of the interaction between icariin and human serum albumin by fluorescence spectroscopy. Journal of Molecular Structure, 881, 132-138.
68. Zsila, F., Bikádi, Z., & Simonyi, M. (2003). Probing the binding of the flavonoid, quercetin to human serum albumin by circular dichroism, electronic absorption spectroscopy and molecular modelling methods. Biochemical Pharmacology, 65, 447-456.
69. Zunszain, P. A., Ghuman, J., Komatsu, T., Tsuchida, E., & Curry, S. (2003). Crystal structural analysis of human serum albumin complexed with hemin and fatty acid. BMC Structural Biology, 3, 1-9.