Probing the Interaction of a Therapeutic Flavonoid, Pinostrobin with Human Serum Albumin: Multiple Spectroscopic and Molecular Modeling Investigations

PLoS ONE

Volumn 8, Issue 10, 2013, Pages

  Feroz, Shevin R ^a   Mohamad, Saharuddin B ^a   Bakri, Zarith S D ^a   Malek, Sri N A ^a   Tayyab, Saad ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

[No Author keywords available]

Indexed keywords

FLAVONOID; HUMAN SERUM ALBUMIN; PINOSTROBIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; CIRCULAR DICHROISM; COMPLEX FORMATION; DRUG ISOLATION; DRUG PROTEIN BINDING; DRUG PURIFICATION; FLUORESCENCE ANALYSIS; FLUORESCENCE SPECTROSCOPY; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; PROTEIN INTERACTION; QUANTITATIVE ANALYSIS; SPECTROSCOPY; STOICHIOMETRY; THERMODYNAMICS; THERMOSTABILITY; THREE DIMENSIONAL IMAGING;

CIRCULAR DICHROISM; FLAVANONES; HUMANS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; PROTEIN BINDING; PROTEIN CONFORMATION; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE;

EID: 84885088721     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0076067     Document Type: Article

References (42)

1. Fahey JW, Stephenson KK, (2002) Pinostrobin from honey and Thai ginger (Boesenbergia pandurata): A potent flavonoid inducer of mammalian phase 2 chemoprotective and antioxidant enzymes. J Agric Food Chem 50: 7472-7476.
2. Le Bail JC, Aubourg L, Habrioux G, (2000) Effects of pinostrobin on estrogen metabolism and estrogen receptor transactivation. Cancer Lett 156: 37-44.
3. Dangles O, Dufour C (2006) Flavonoid-protein interactions. In: Anderson ØM, Markham KR, editors. Flavonoids: Chemistry, biochemistry, and applications. Boca Raton: CRC Press. 443-464.
4. Wu N, Kong Y, Zu Y, Fu Y, Liu Z, et al. (2011) Activity investigation of pinostrobin towards herpes simplex virus-1 as determined by atomic force microscopy. Phytomedicine 18: 110-114.
5. Wu D, Nair MG, DeWitt DL, (2002) Novel compounds from Piper methysticum Forst (Kava Kava) roots and their effect on cyclooxygenase enzyme. J Agric Food Chem 50: 701-705.
6. Peters T (1996) All about Albumin: Biochemistry, genetics and medical applications. San Diego: Academic Press. 432 p.
7. Kragh-Hansen U, Chuang VTG, Otagiri M, (2002) Practical aspects of the ligand-binding and enzymatic properties of human serum albumin. Biol Pharm Bull 25: 695-704.
8. Sudlow G, Birkett DJ, Wade DN, (1975) The characterization of two specific drug binding sites on human serum albumin. Mol Pharmacol 11: 824-832.
9. Carter DC, Ho JX, (1994) Structure of serum albumin. Adv Protein Chem 45: 153-203.
10. Wallevik K, (1973) Reversible denaturation of human serum albumin by pH, temperature and guanidine hydrochloride. J Biol Chem 245: 2650-2655.
11. Twine SM, Gore MG, Morton P, Fish BC, Lee AG, et al. (2003) Mechanism of binding of warfarin enantiomers to recombinant domains of human albumin. Arch Biochem Biophys 414: 83-90.
12. Faizul FM, Kadir HA, Tayyab S, (2008) Spectroscopic studies on the binding of bromocresol purple to different serum albumins and its bilirubin displacing action. J Photochem Photobiol B 90: 1-7.
13. Jacobsen J, Wennberg RP, (1974) Determination of unbound bilirubin in the serum of newborns. Clin Chem 20: 783-789.
14. Saquib Q, Al-Khedhairy AA, Siddiqui MA, Roy AS, Dasgupta S, et al. (2011) Preferential binding of insecticide phorate with sub-domain IIA of human serum albumin induces protein damage and its toxicological significance. Food Chem Toxicol 49: 1787-1795.
15. Feroz SR, Mohamad SB, Bujang N, Malek SNA, Tayyab S, (2012) Multispectroscopic and molecular modeling approach to investigate the interaction of flavokawain B with human serum albumin. J Agric Food Chem 60: 5899-5908.
16. Lakowicz JR (2006) Principles of fluorescence spectroscopy. New York: Plenum Press. 954 p.
17. Abou-Zied OK, Al-Shihi OI, (2008) Characterization of subdomain IIA binding site of human serum albumin in its native, unfolded, and refolded states using small molecular probes. J Am Chem Soc 130: 10793-10801.
18. Bi S, Ding L, Tian Y, Song D, Zhou X, et al. (2004) Investigation of the interaction between flavonoids and human serum albumin. J Mol Struct 703: 37-45.
19. van der Weert M, Stella L, (2011) Fluorescence quenching and ligand binding: A critical discussion of a popular methodology. J Mol Struct 998: 144-150.
20. Trnková L, Boušová I, Staňková V, Dršata J, (2011) Study on the interaction of catechins with human serum albumin using spectroscopic and electrophoretic techniques. J Mol Struct 985: 243-250.
21. Demchenko AP (2009) Introduction to fluorescence sensing. Dordrecht: Springer. 586 p.
22. Goodsell DS, Morris GM, Olson AJ, (1999) Automated docking of flexible ligands: Applications of AutoDock. J Mol Recognit 9: 1-5.
23. Sanner MH, (1999) Python: A programming language for software integration and development. J Mol Graph Model 17: 57-61.
24. Pedretti A, Villa L, Vistoli G, (2002) VEGA: A versatile program to convert, handle and visualize molecular structure on Windows-based PCs. J Mol Graph Model 21: 47-49.
25. Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP, (1985) Development and use of quantum molecular models. 75. Comparative tests of theoretical procedures for studying chemical reactions. J Am Chem Soc 107: 3902-3909.
26. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, et al. (2000) The Protein Data Bank. Nucleic Acids Res 28: 235-242.
27. Khanna NC, Tokuda M, Waisman DM, (1986) Conformational changes induced by binding of divalent cations to calregulin. J Biol Chem 261: 8883-8887.
28. Olsson TSG, Williams MA, Pitt WR, Ladbury JE, (2008) The thermodynamics of protein-ligand interaction and solvation: Insights for ligand design. J Mol Biol 384: 1002-1017.
29. Ross PD, Rekharsky MV, (1996) Thermodynamics of hydrogen bond and hydrophobic interactions in cyclodextrin complexes. Biophys J 71: 2144-2154.
30. Ross PD, Subramanian S, (1981) Thermodynamics of protein association reactions: Forces contributing to stability. Biochemistry 20: 3096-3102.
31. Ahmad E, Rabbani G, Zaidi N, Singh S, Rehan M, et al. (2011) Stereo-selectivity of human serum albumin to enantiomeric and isoelectronic pollutants dissected by spectroscopy, calorimetry and bioinformatics. PLoS ONE 6: e26186.
32. Kalanur SS, Seetharamappa J, Kalalbandi VKA, (2010) Characterization of interaction and the effect of carbamazepine on the structure of human serum albumin. J Pharm Biomed Anal 53: 660-666.
33. Freitas PG, Barbosa AF, Saraiva LA, Camps I, da Silveira NJF, et al. (2012) Mangiferin binding to serum albumin is non-saturable and induces conformational changes at high concentrations. J Lumin 132: 3027-3034.
34. Zaroog MS, Tayyab S, (2012) Formation of molten globule-like state during acid denaturation of Aspergillus niger glucoamylase. Process Biochem 47: 775-784.
35. 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.
36. Petitpas I, Bhattacharya AA, Twine S, East M, Curry S, (2001) Crystal structure analysis of warfarin binding to human serum albumin. J Biol Chem 276: 22804-22809.
37. Shrake A, Ross PD, (1990) Ligand-induced biphasic protein denaturation. J Biol Chem 265: 5055-5059.
38. Celej MS, Montich GG, Fidelio GD, (2003) Protein stability induced by ligand binding correlates with changes in protein flexibility. Protein Sci 12: 1496-1506.
39. Vermeer AWP, Norde W, (2000) The thermal stability of immunoglobulin: Unfolding and aggregation of a multi-domain protein. Biophys J 78: 394-404.
40. Trynda-Lemiesz L, (2004) Paclitaxel-HSA interaction. Binding sites on HSA molecule. Bioorg Med Chem 12: 3269-3275.
41. Watanabe H, Tanase S, Nakajou K, Maruyama T, Kragh-Hansen U, et al. (2000) Role of Arg-410 and Tyr-411 in human serum albumin for ligand binding and esterase-like activity. Biochem J 349: 813-819.
42. Sugio S, Kashima A, Mochizuki S, Noda M, Kobayashi K, (1999) Crystal structure of human serum albumin at 2.5 Å resolution. Protein Eng 12: 439-446.