Preferential binding of fisetin to the native state of bovine serum albumin: Spectroscopic and docking studies

Molecular Biology Reports

Volumn 40, Issue 4, 2013, Pages 3239-3253

  Singha Roy, Atanu ^a   Pandey, Nitin Kumar ^a   Dasgupta, Swagata ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Binding; Bovine serum albumin; Docking; Fisetin; Thermodynamic parameters

Indexed keywords

BOVINE SERUM ALBUMIN; CARRIER PROTEIN; FISETIN; IBUPROFEN; UREA; WARFARIN;

ARTICLE; BINDING AFFINITY; BINDING SITE; CRYSTAL STRUCTURE; DRUG BINDING; DRUG STRUCTURE; ENERGY TRANSFER; ENTROPY; FLUORESCENCE ANALYSIS; FLUORESCENCE SPECTROSCOPY; HYDROPHOBICITY; INFRARED SPECTROSCOPY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR DOCKING; PROTEIN BINDING; PROTEIN DENATURATION; SPECTROSCOPY; STATIC ELECTRICITY; STEADY STATE; THERMODYNAMICS;

ANIMALS; BINDING SITES; CATTLE; CIRCULAR DICHROISM; ENTROPY; FLAVONOIDS; MOLECULAR DOCKING SIMULATION; PROTEIN BINDING; PROTEIN CONFORMATION; SERUM ALBUMIN, BOVINE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SPECTRUM ANALYSIS; THERMODYNAMICS;

BOVINAE;

EID: 84878385058     PISSN: 03014851     EISSN: 15734978     Source Type: Journal    
DOI: 10.1007/s11033-012-2399-9     Document Type: Article

References (64)

1. Peters T (1985) Serum albumin. Adv Protein Chem 37:161-245
2. Kragh-Hansen U (1981) Molecular aspects of ligand binding serum albumin. Pharmacol Rev 33:17-53
3. Wright AK, Thompson MR (1975) Hydrodynamic structure of bovine serum albumin determined by transient electric birefringence. Biophys J 15:137-141
4. 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
5. Carter DC, Chang B, Ho JX, Keeling K, Krishnasami Z (1994) Preliminary crystallographic studies of four crystal forms of serum albumin. Eur J Biochem 226:1049-1052
6. He HM, Carter DC (1992) Atomic structure and chemistry of human serum albumin. Nature 358:209-215
7. Petitpas I, Bhattacharya AA, Twine S, East M, Curry S (2001) Crystal structure analysis of warfarin binding to human serum albumin. Anatomy of drug site I. J Biol Chem 276:22804-22809
8. Peterman BF, Laidler KJ (1980) Study of reactivity of tryptophan residues in serum albumins and lysozyme by N-bromosuccinamide fluorescence quenching. Arch Biochem Biophys 199:158-164
9. Williams RJ, Spencer JPE, Rice-Evans C (2004) Flavonoids: antioxidants or signalling molecules? Free Radic Biol Med 36:838-849
10. Geraets L, Haegens A, Brauers K, Haydock JA, Vernooy JHJ, Wouters EFM, Bast A, Hageman GJ (2009) Inhibition of LPS-induced pulmonary inflammation by specific flavonoids. Biochem Biophys Res Commun 382:598-603
11. Lim DY, Park JHY (2009) Induction of p53 contributes to apoptosis of HCT-116 human colon cancer cells induced by the dietary compound fisetin. Am J Physiol Gastrointest Liver Physiol 296:1060-1068
12. Khan N, Afaq F, Syed DN, Mukhtar H (2008) Fisetin, a novel dietary flavonoid, causes apoptosis and cell cycle arrest in human prostate cancer LNCaP cells. Carcinogenesis 29:1049-1056
13. Pamela M, Dargusch R, Ehren JL, Okada S, Sharma K, Schubert D (2011) Fisetin lowers methylglyoxal dependent protein glycation and limits the complications of diabetes. PLoS ONE 6:e21226
14. Hanneken A (2006) Flavonoids protect human retinal pigment epithelial cells from oxidative-stress-induced death. Invest Ophthalmol Vis Sci 47:3164-3177
15. Tripathi R, Samadder T, Gupta S, Surolia A, Shaha C (2011) Anticancer activity of a combination of cisplatin and fisetin in embryonal carcinoma cells and xenograft. Mol Cancer Ther 10:255-268
16. Ragelle H, Crauste-Manciet S, Seguin J, Brossard D, Scherman D, Arnaud P, Chabot GG (2012) Nanoemulsion formulation of fisetin improves bioavailability and antitumour activity in mice. Int J Pharm 427:452-459
17. Sentchouk VV, Bondaruk EV (2007) Fluorescent analysis of interaction of flavonols with hemoglobin and bovine serum albumin. J Appl Spectrosc 74:659-664
18. Pace N, Vajdos F, Fee L, Grimsley G, Gray T (1995) How to measure and predict the molar absorption coefficient of a protein. Protein Sci 4:2411-2423
19. Perry JL, Goldsmith MR, Williams TR, Radack KP, Christensen T, Gorham J, Pasquinelli MA, Toone EJ, Beratan DN, Simon JD (2006) Binding of warfarin influences the acid-base equilibrium of H242 in sudlow site I of human serum albumin. Photochem Photobiol 82:1365-1369
20. Du L, Liu X, Huang W, Wang E (2006) A study on the interaction between ibuprofen and bilayer lipid membrane. Electrochem Acta 51:5754-5760
21. Singha Roy A, Dinda AK, Dasgupta S (2012) Study the interaction of fisetin with human serum albumin: a biophysical approach. Protein Pept Lett 19:604-615
22. Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer, New York
23. Jiang M, Xie MX, Zheng D, Liu Y, Li XY, Cheng X (2004) Spectroscopic studies on interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin. J Mol Struct 692:71-80
24. Whitmore L, Wallace BA (2004) DICHROWEB: an online server for protein secondary structure analyses from circular dichroism spectroscopic data. Nucleic Acids Res 32:W668-W673
25. Byler S, Susi H (1986) Examination of the secondary structure of proteins by deconvolved FTIR spectra. Biopolymers 25:469-487
26. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE (2000) The protein data bank. Nucleic Acids Res 28:235-242
27. DeLano WL (2004) The PyMoL molecular graphics system. San Carlos: DeLano Scientific, http://www.pymol.sourceforge.net
28. Hubbard SJ, Thornton JM (1993). NACCESS. Computer program, Department of Biochemistry and Molecular Biology, University College of London
29. Han LY, Lin HH, Li ZR, Zheng CJ, Cao ZW, Xie B, Chen YZ (2006) PEARLS: program for energetic analysis of receptor-ligand system. J Chem Inf Model 46:445-450
30. Mabry TJ, Markham KR, Thomas MB (1970) The systematic identification of flavonoids. Springer-Verlag, New York
31. Zhang G, Wang A, Jiang T, Guo J (2008) Interaction of irisflorentin with bovine serum albumin: a fluorescence quenching study. J Mol Struct 891:93-97
32. Ross PD, Subramanian S (1981) Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 20:3096-3102
33. Sudlow G, Birkett DJ, Wade DN (1975) The characterization of two specific drug binding sites on human serum albumin. Mol Pharmacol 11:824-832
34. Sudlow G, Birkett DJ, Wade DN (1976) Further characterization of specific drug binding sites on human serum albumin. Mol Pharmacol 12:1052-1061
35. Singha Roy A, Tripathy DR, Chatterjee A, Dasgupta S (2013) The influence of common metal ions on the interactions of the isoflavone genistein with bovine serum albumin. Spectrochim Acta A 102:393-402
36. Singha Roy A, Tripathy DR, Chatterjee A, Dasgupta S (2010) A spectroscopic study of the interaction of the antioxidant naringin with bovine serum albumin. J Biophys Chem 1:141-152
37. Förster T (1948) Intermolecular energy migration and fluorescence. Ann Phys 2:55-75
38. Ji Ma, Yin YM, Liu HL, Xie MX (2011) Interactions of flavonoids with biomacromolecules. Curr Org Chem 15:2627-2640
39. Gokara M, Sudhamalla B, Amroou DG, Subramanyam R (2010) Molecular interaction studies of trimethoxy flavone with human serum albumin. PLoS ONE 5:e8834
40. Sudhamalla B, Gokara M, Ahalawat N, Amroou DG, Subramanyam R (2010) Molecular dynamics simulation and binding studies of β-sitosterol with human serum albumin and its biological relevance. J Phys Chem B 114:9054-9062
41. 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
42. Uversky VN, Narizhneva NV, Ivanova TV, Tomashevski AY, Omashevski AY (1997) Rigidity of human α-fetoprotein tertiary structure is under ligand control. Biochemistry 494:13638-13645
43. Elliott A, Ambrose EJ (1950) Structure of synthetic polypeptides. Nature 165:921-922
44. Krimm S, Bandekar J (1986) Vibrational spectroscopy and conformation of peptides, polypeptides, and proteins. Adv Protein Chem 38:181-364
45. Singha Roy A, Ghosh KS, Dasgupta S (2012) An investigation into the altered binding mode of green tea polyphenols with human serum albumin on complexation with copper. J Biomol Struct Dyn. http://dx.doi.org/10.1080/ 07391102.2012.729158
46. Bourassa P, Kanakis CD, Tarantilis P, Pollissiou MG, Tajmir-Riahi HA (2010) Resveratrol, genistein, and curcumin bind bovine serum albumin. J Phys Chem B 114(2010):3348-3354
47. Gonzalez-Jimenez J, Cortijo M (2002) Urea-induced denaturation of human serum albumin labeled with acrylodan. J Protein Chem 21:75-79
48. Khan MY, Agarwal SK, Hangloo SJ (1987) Urea-induced structural transformations in bovine serum albumin. Biochemistry 102:313-317
49. Ahmad B, Khan MKA, Haq SK, Khan RH (2004) Intermediate formation at lower urea concentration in ''B" isomer of human serum albumin: a case study using domain specific ligands. Biochem Biophys Res Commun 314:166-173
50. Sułkowskaa A, Bojkoa B, Rownickaa J, Pentakb D, Sułkowskib W (2003) Effect of urea on serum albumin complex with antithyroid drugs: fluorescence study. J Mol Struct 651:237-243
51. Liepinsh E, Otting G (1994) Specificity of urea binding to proteins. J Am Chem Soc 116:9670-9674
52. Sengupta B, Banerjee A, Sengupta PK (2005) Interactions of the plant flavonoid fisetin with macromolecular targets: insights from fluorescence spectroscopic studies. J Photochem Photobiol B 80:76-79
53. Qin C, Xie MX, Liu Y (2007) Characterization of the myricetin-human serum albumin complex by spectroscopic and molecular modeling approaches. Biomacromolecules 8:2182-2189
54. Zsila F, Bikadi Z, Simonyi M (2003) Probing the binding of flavonoid, quercetin to human serum albumin by circular dichroism, electronic absorption spectroscopy and molecular modelling methods. Biochem Pharmacol 65:447-456
55. Paul BK, Samanta A, Guchhait N (2010) Exploring hydrophobic subdomain IIA of the protein bovine serum albumin in the native, intermediate, unfolded, and refolded states by a small fluorescence molecular reporter. J Phys Chem B 114:6183-6196
56. Patra D, Barakat C, Tafech RM (2012) Study on effect of lipophilic curcumin on sub-domain IIA site of human serum albumin during unfolded and refolded states: a synchronous fluorescence spectroscopic study. Colloids Surf B 94:351-361
57. Ojha B, Das G (2010) The Interaction of 5-(Alkoxy)naphthalen-1-amine with bovine serum albumin and its effect on the conformation of protein. J Phys Chem B 114:3979-3986
58. Barakat C, Patra D (2012) Combining time-resolved fluorescence with synchronous fluorescence spectroscopy to study bovine serum albumin-curcumin complex during unfolding and refolding processes. Luminescence. doi: 10.1002/bio.2354
59. Li D, Wang Y, Chen J, Ji B (2011) Characterization of the interaction between farrerol and bovine serum albumin by fluorescence and circular dichroism. Spectrochim Acta A 79:680-686
60. Sandhya B, Hedge AH, Klankur SS, Katrahalli U, Seetharamappa J (2011) Interaction of triprolidine hydrochloride with serum albumins: thermodynamic and binding characteristics, and influence of site probes. J Pharm Biomed Anal 54:1180-1186
61. Sytnik A, Lritvinyuk I (1996) Energy transfer to a proton-transfer fluorescence probe: tryptophan to a flavonol in human serum albumin. Proc Natl Acad Sci USA 93:12959-12963
62. Roy D, Dutta S, Maity SS, Ghosh S, Singha Roy A, Ghosh KS, Dasgupta S (2012) Spectroscopic and docking studies of the binding of two stereoisomeric antioxidant catechins to serum albumins. J Lumin 132:1364-1375
63. Singha Roy A, Tripathy DR, Ghosh AK, Dasgupta S (2012) An alternate mode of binding of the polyphenol quercetin with serum albumins when complexed with Cu(II). J Lumin 132:2943-2951
64. Zhang Y, Li Y, Dong L, Li J, He W, Chen X, Hu Z (2008) Investigation of the interaction between naringin and human serum albumin. J Mol Struct 875:1-8