Interaction of (-)-epigallocatechin-3-gallate with human serum albumin: Fluorescence, Fourier transform infrared, circular dichroism, and docking studies

Proteins: Structure, Function and Genetics

Volumn 64, Issue 2, 2006, Pages 355-362

  Maiti, Tushar Kanti ^a   Ghosh, Kalyan Sundar ^a   Dasgupta, Swagata ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

( ) epigallocatechin 3 gallate; Accessible surface area; Circular dichroism; FlexX single molecule docking; Fluorescence quenching; FTIR; Human serum albumin

Indexed keywords

ARGININE; ASPARAGINE; ASPARTIC ACID; EPIGALLOCATECHIN GALLATE; GLUTAMINE; HUMAN SERUM ALBUMIN; TRYPTOPHAN;

ANTIOXIDANT ACTIVITY; ARTICLE; CALCULATION; CIRCULAR DICHROISM; DRUG BINDING SITE; DRUG PROTEIN BINDING; ENTROPY; FLUORESCENCE SPECTROSCOPY; HYDROGEN BOND; HYDROPHOBICITY; INFRARED SPECTROSCOPY; LIGAND BINDING; MOLECULAR INTERACTION; PRIORITY JOURNAL; SURFACE PROPERTY; TEA; THERMODYNAMICS;

CATECHIN; CIRCULAR DICHROISM; HUMANS; HYDROGEN BONDING; KINETICS; MODELS, MOLECULAR; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN STRUCTURE, SECONDARY; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMODYNAMICS;

EID: 33745610160     PISSN: 08873585     EISSN: 10970134     Source Type: Journal    
DOI: 10.1002/prot.20995     Document Type: Article

References (39)

1. Cutter H, Wu LY, Kim C, Morre DJ, Morre DM. Is the cancer protective effect correlated with growth inhibitions by green tea (-)-epigallocatechin gallate mediated through an antioxidant mechanism? Cancer Lett 2001;162:149-154.
2. Pietta PG. Flavonoids as antioxidants. J Nat Prod 2000;63:1035-1042.
3. Balentine DA. Manufacturing and chemistry of tea. In: Ho C-T, Huang M-T, Lee CY, editors. Phenolic compounds in food and their effects on health, analysis, occurrence, and chemistry. Washington, DC: American Chemical Society; 1992. p 102-117.
4. Tosetti F, Ferrari N, De Flora S, Albini A. Angioprevention: angiogenesis is a common and key target for cancer chemopreventive agents. FASEB J 2002;16:2-14.
5. Lambert JD, Yang CS. Cancer chemopreventive activity and bioavailability of tea and tea polyphenols. Mutat Res 2003;523:201-208.
6. Fujiki H, Suganuma M, Imai K, Nakachi K. Green tea: cancer preventive beverage and/or drug [mini-review]. Cancer Lett 2002;188:9-13.
7. Cao Y, Cao R. Angiogenesis inhibited by drinking tea. Nature 1999;398:381.
8. Zhong Z, Connor HD, Froh M, et al. Polyphenols from Camellia sinenesis prevent primary graft failure after transplantation of ethanol-induced fatty livers from rats. Free Radic Biol Med 2004;36:1248-1258.
9. Narumi S, Mikae O, Masahiro I, Koji F. Differences in antioxidative efficiency of catechins in various metal-induced lipid peroxidations in cultured hepatocytes. J Health Sci 2001;47:99-106.
10. 2+ ions: implications for their antioxidant properties. Biochem J 1998;330:1173-1178.
11. Kragh-Hansen U. Molecular aspects of ligand binding to serum albumin. Pharmacol Rev 1981;33:17-53.
12. Muller WE, Wollert U. Human serum albumin as a 'silent receptor' for drugs and endogenous substances. Pharmacology 1979;19:56-59.
13. He XM, Carter DC. Atomic structure and chemistry of human serum albumin. Nature 1992;358:209-215.
14. Sugio S, Kashima A, Mochizuki S, Noda M, Kobayashi K. Crystal structure of human serum albumin at 2.5 A resolution. Protein Eng 1999;12:439-446.
15. Lamson SW, Brignall MS. Antioxidants and cancer. Part 3. Quercetin. Altern Med Rev 2000;5:196-208.
16. Sengupta B, Sengupta PK. The interaction of quercetin with human serum albumin: a fluorescence spectroscopic study. Biochem Biophys Res Commun 2002;299:400-403.
17. 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;65:447-456.
18. Boulton DW, Walle UK, Walle T. Extensive binding of the bioflavonoid quercetin to human plasma proteins. J Pharm Pharmacol 1998;50:243-249.
19. Dangles O, Dufour C, Manach C, Morand C, Remesy C. Binding of flavonoids to plasma proteins. Methods Enzymol 2001;335:319-333.
20. Dufour C, Dangles O. Flavonoid-serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy. Biochim Biophys Acta 2005;1721:164-173.
21. Manach C, Morand C, Crespy V, et al. Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett 1998;426:331-336.
22. Kaldas MI, Walle UK, van der Woude H, McMillan JM, Walle T. Covalent binding of the flavonoid quercetin to human serum albumin. J Agric Food Chem 2005;53:4194-4197.
23. Smith DM, Daniel KG, Wang Z, Guida WC, Chan T-H, Dou PQ. Docking studies and model development of tea polyphenol proteasome inhibitors: applications to rational drug design. Proteins 2004;54:58-70.
24. Gonzalez-Jimenez J, Frutos G, Cayre I, Cortijo M. Chlophenir amine binding to human serum albumin by fluorescence quenching measurements. Biochimie 1991;73:551-556.
25. Pelillo M, Cuvelier ME, Biguzzi B, Toschi TG, BersetC, Lercker G. Calculation of the molar absorptivity of polyphenols by using liquid chromatography with diode array detection: the case of carnosic acid. J Chromatogr A 2004;1023:225-229.
26. Scatchard G. The attractions of proteins for small molecules and ions. Ann NY Acad Sci 1949;51:660-673.
27. Lakowicz JR. Principles of fluorescence spectroscopy. New York: Plenum Press; 1991.
28. Byler D, Susi H. Examination of the secondary structure of proteins by deconvolved FT-IR spectra. Biopolymers 1986;25:469-487.
29. Dong AC, Huang P, Caughey WS. Protein secondary structures in water from second-derivative amide I infrared spectra. Biochemistry 1990;29:3303-3308.
30. Susi H, Byler DM. Protein structure by Fourier transform infrared spectroscopy: second derivative spectra. Biochem Biophys Res Commun 1983;115:391-397.
31. Susi H, Byler DM. Resolution-enhanced Fourier transform infrared spectroscopy of enzymes. Methods Enzymol 1986;130:290-311.
32. Whitmore L, Wallace BA. DICHROWEB: an online server for protein secondary structure analyses from circular dichroism spectroscopic data. Nucleic Acids Res 2004;32:W668-W673.
33. Berman M, Westbrook J, Feng Z, et al. The Protein Data Bank. Nucleic Acids Res 2000;28:235-242.
34. Rarey M, Kramer B, Lengauer T, Klebe G. A fast flexible docking method using an incremental construction algorithm. J Mol Biol 1996;261:470-489.
35. DeLano WL. The PyMOL molecular graphics system. San Carlos, CA: DeLano Scientific; 2004. http://www.pymol.sourceforge.net.
36. Hubbard SJ, Thornton JM. 'NACCESS.' Computer Program, Department of Biochemistry and Molecular Biology, University College London; 1993.
37. Neault JF, Tajmir-Riahi HA. Interaction of cisplatin with human serum albumin. Drug binding mode and protein secondary structure. Biochim Biophys Acta 1998;1384:153-159.
38. Timaseff SN. Thermodynamics of protein interactions. In: Peeters H, editor. Proteins of biological fluids. Oxford: Pergamon Press; 1972. p 511-519.
39. Ross PD, Subramanian S. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 1981;20:3096-3102.