Study of interaction between human serum albumin and three antioxidants: Ascorbic acid, α-tocopherol, and proanthocyanidins

European Journal of Medicinal Chemistry

Volumn 70, Issue , 2013, Pages 22-36

  Li, Xiangrong ^a,b   Chen, Dejun ^a   Wang, Gongke ^a   Lu, Yan ^a  

^a HENAN NORMAL UNIVERSITY   (China)

^b XINXIANG MEDICAL UNIVERSITY   (China)

Author keywords

Antioxidants; Fluorescence spectroscopy; Fourier transform infrared (FT IR) spectroscopy; Human serum albumin; UV vis absorption spectroscopy

Indexed keywords

ALPHA TOCOPHEROL; ASCORBIC ACID; HUMAN SERUM ALBUMIN; PROANTHOCYANIDIN;

ARTICLE; BINDING SITE; CONFORMATIONAL TRANSITION; DRUG BINDING; FLUORESCENCE; HYDROPHOBICITY; INFRARED SPECTROSCOPY; STATIC ELECTRICITY; THERMODYNAMICS;

ANTIOXIDANTS; FLUORESCENCE SPECTROSCOPY; FOURIER TRANSFORM INFRARED (FT-IR) SPECTROSCOPY; HUMAN SERUM ALBUMIN; UV-VIS ABSORPTION SPECTROSCOPY;

ALPHA-TOCOPHEROL; ANTIOXIDANTS; ASCORBIC ACID; BINDING SITES; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR STRUCTURE; PROANTHOCYANIDINS; SERUM ALBUMIN; STATIC ELECTRICITY; THERMODYNAMICS;

EID: 84885467748     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.09.033     Document Type: Article

References (63)

1. N. Ibrahim, H. Ibrahim, S. Kim, J.P. Nallet, and F. Nepveu Interactions between antimalarial indolone-N-oxide derivatives and human serum albumin Biomacromolecules 11 2010 3341 3351
2. X.M. He, and D.C. Carter Atomic structure and chemistry of human serum albumin Nature 358 1992 209 215
3. G. Sudlow, D.F. Birkett, and D.N. Wade The characterization of two specific drug binding sites on human serum albumin Mol. Pharmacol. 11 1975 824 832
4. K. Aidas, J.M.H. Olsen, J. Kongsted, and H. Ågren Photoabsorption of acridine yellow and proflavin bound to human serum albumin studied by means of quantum mechanics/molecular dynamics J. Phys. Chem. B 117 2013 2069 2080
5. F. Samari, M. Shamsipur, B. Hemmateenejad, T. Khayamian, and S. Gharaghani Investigation of the interaction between amodiaquine and human serum albumin by fluorescence spectroscopy and molecular modeling Eur. J. Med. Chem. 54 2012 255 263
6. X. Liu, and Y. Du Study on the binding of chiral drug duloxetine hydrochloride to human serum albumin Eur. J. Med. Chem. 45 2010 4043 4049
7. N. Zaidi, E. Ahmad, M. Rehan, G. Rabbani, M.R. Ajmal, Y. Zaidi, N. Subbarao, and R.H. Khan Biophysical insight into furosemide binding to human serum albumin: a study to unveil its impaired albumin binding in uremia J. Phys. Chem. B 117 2013 2595 2604
8. N. Bijari, Y. Shokoohinia, M.R. Ashrafi-Kooshk, S. Ranjbar, S. Parvaneh, M. Moieni-Arya, and R. Khodarahmi Spectroscopic study of interaction between osthole and human serum albumin: Identification of possible binding site of the compound J. Lumin. 143 2013 328 336
9. N. Shahabadi, A. Khorshidi, and N.H. Moghadam Study on the interaction of the epilepsy drug, zonisamide with human serum albumin (HSA) by spectroscopic and molecular docking techniques Spectrochim. Acta Part A 114 2013 627 632
10. J. Baraka-Vidot, A. Guerin-Dubourg, F. Dubois, B. Payet, E. Bourdon, and P. Rondeau New insights into deleterious impacts of in vivo glycation on albumin antioxidant activities Biochim. Biophys. Acta 1830 2013 3532 3541
11. J.D.J. Ornelas-Paz, L.A. Cira-Chávez, A.A. Gardea-Béjar, J.C. Guevara-Arauza, D.R. Sepúlveda, J. Reyes-Hernández, and S. Ruiz-Cruz Effect of heat treatment on the content of some bioactive compounds and free radical-scavenging activity in pungent and non-pungent peppers Food Res. Int. 50 2013 519 525
12. X.Q. Lu, M.N. Nan, H.R. Zhang, X.H. Liu, H.Q. Yuan, and J.D. Yang Investigation of the antioxidant property of ascorbic acid J. Phys. Chem. C 111 2007 14998 15002
13. N. Na, J.R. Delanghe, Y.E.C. Taes, M. Torck, W.R.G. Baeyens, and J. Ouyang Serum vitamin C concentration is influenced by haptoglobin polymorphism and iron status in Chinese Clin. Chim. Acta 365 2006 319 324 (Pubitemid 43196454)
14. R.R. Yettella, and D.B. Min Effects of trolox and ascorbic acid on the riboflavin photosensitised oxidation of aromatic amino acids Food Chem. 118 2010 35 41
15. K. Krumova, S. Friedland, and G. Cosa How lipid unsaturation, peroxyl radical partitioning, and chromanol lipophilic tail affect the antioxidant activity of α-tocopherol: direct visualization via high-throughput fluorescence studies conducted with fluorogenic α-tocopherol analogues J. Am. Chem. Soc. 134 2012 10102 10113
16. M.G. Traber, and J. Atkinson Vitamin E, antioxidant and nothing more Free Radical Biol. Med. 43 2007 4 15 (Pubitemid 46874839)
17. M.G. Traber, and J.F. Stevens Vitamins C and E: beneficial effects from a mechanistic perspective Free Radical Biol. Med. 51 2011 1000 1013
18. A. Scalbert, and G. Williamson Dietary intake and bioavailability of polyphenols J. Nutr. 130 2000 2073 2085
19. C. Santos-Buelga, and A. Scalbert Proanthocyanidins and tanninlike compounds: nature, occurrence, dietary intake and effects on nutrition and health J. Sci. Food Agric. 80 2000 1094 1117 (Pubitemid 30319402)
20. R. Gonc-alves, N. Mateus, and V.D. Freitas Influence of carbohydrates on the interaction of procyanidin B3 with trypsin J. Agric. Food Chem. 59 2011 11794 11802
21. S. Nafisi, G.B. Sadeghi, and A. PanahYab Interaction of aspirin and vitamin C with bovine serum albumin J. Photochem. Photobiol. B 105 2011 198 202
22. Y. Zhang, S. Shi, X. Chen, W. Zhang, K. Huang, and M. Peng Investigation on the interaction between ilaprazole and bovine serum albumin without or with different C-ring flavonoids from the viewpoint of food-drug interference J. Agric. Food Chem. 59 2011 8499 8506
23. M.L. Hall, W.L. Jorgensen, and L. Whitehead Automated ligand- and structurebased protocol for in silico prediction of human serum albumin binding J. Chem. Inf. Model 53 2013 907 922
24. Z. Omidvar, A. Asoodeh, and J. Chamani Studies on the antagonistic behavior between cyclophosphamide hydrochloride and aspirin with human serum albumin: time-resolved fluorescence spectroscopy and isothermal titration calorimetry J. Solution Chem. 42 2013 1005 1017
25. A.Y. Khan, M. Hossain, and G.S. Kumar Binding of plant alkaloids berberine and palmatine to serum albumins: a thermodynamic investigation Mol. Biol. Rep. 40 2013 553 566
26. G.J. Zhang, B. Keita, C.T. Craescu, S. Miron, P.D. Oliveira, and L. Nadjo Polyoxometalate binding to human serum albumin: a thermodynamic and spectroscopic approach J. Phys. Chem. B 111 2007 11253 11259 (Pubitemid 47548378)
27. Y.Y. Yue, J.M. Liu, M.H. Yao, X.J. Yao, J. Fan, and H.X. Ji The investigation of the binding behavior between ethyl maltol and human serum albumin by multi-spectroscopic methods and molecular docking Spectrochim. Acta Part A 96 2012 316 323
28. A. Divsalar, M.J. Bagheri, A.A. Saboury, H. Mansoori-Torshizi, and M. Amani Investigation on the interaction of newly designed anticancer Pd(II) complexes with different aliphatic tails and human serum albumin J. Phys. Chem. B 113 2009 14035 14042
29. F. Samari, B. Hemmateenejad, M. Shamsipur, and M. Rashidi Affinity of two novel five-coordinated anticancer Pt(II) complexes to human and bovine serum albumins: a spectroscopic approach Inorg. Chem. 51 2012 3454 3464
30. O.K. Abou-Zied, and O.I.K. Al-Shihi 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 2008 10793 10801
31. J.R. Lakowicz Principles of Fluorescence Spectroscopy third ed. 2006 Springer Science & Business Media New York
32. I. Matei, and M. Hillebrand Interaction of kaempferol with human serum albumin: a fluorescence and circular dichroism study J. Pharm. Biomed. Anal. 51 2010 768 773
33. S. Soares, N. Mateus, and V.D. Freitas Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary α-Amylase (HSA) by fluorescence quenching J. Agric. Food Chem. 55 2007 6726 6735 (Pubitemid 47280052)
34. C. Tan, E. Atas, J.G. Muller, M.R. Pinto, V.D. Kleiman, and K.S. Schanze Amplified quenching of a conjugated polyelectrolyte by cyanine dyes J. Am. Chem. Soc. 126 2004 13685 13694 (Pubitemid 39407248)
35. G.W. Zhang, L. Wang, and J.H. Pan Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques J. Agric. Food Chem. 60 2012 2721 2729
36. 60-nanosensor Anal. Chem. 83 2011 8093 8100
37. M.E. Zweifel, and D. Barrick Studies of the ankyrin repeats of the drosophila melanogaster notch receptor. 1. solution conformational and hydrodynamic properties Biochemistry 40 2001 14344 14356 (Pubitemid 33111716)
38. Y. Shu, M.L. Liu, S. Chen, X.W. Chen, and J.H. Wang New insight into molecular interactions of imidazolium ionic liquids with bovine serum albumin J. Phys. Chem. B 115 2011 12306 12314
39. H. Iranfa, O. Rajabi, R. Salari, and J. Chamani Probing the interaction of human serum albumin with ciprofloxacin in the presence of silver nanoparticles of three sizes: multispectroscopic and ζ potential investigation J. Phys. Chem. B 116 2012 1951 1964
40. A.J.T. Smith, X. Zhang, A.G. Leach, and K.N. Houk Beyond picomolar affinities: quantitative aspects of noncovalent and covalent binding of drugs to proteins J. Med. Chem. 52 2009 225 233
41. A. Martínez, J. Suárez, T. Shand, R.S. Magliozzo, and R.A. Sánchez-Delgado Interactions of arene-Ru(II)-chloroquine complexes of known antimalarial and antitumor activity with human serum albumin (HSA) and transferring J. Inorg. Biochem. 105 2011 39 45
42. S.R. Feroz, S.B. Mohamad, N. Bujang, S.N.A. Malek, and S. Tayyab Multispectroscopic and molecular modeling approach to investigate the interaction of flavokawain B with human serum albumin J. Agric. Food Chem. 60 2012 5899 5908
43. D.A. Smith, L. Di, and E.H. Kerns The effect of plasma protein binding on in vivo efficacy: misconceptions in drug discovery Nat. Rev. Drug Discovery 9 2010 929 939
44. 1-acid-glycoprotein at a micro liquid-liquid interface Anal. Chem. 84 2012 2299 2304
45. L.M. Berezhkovskiy On the calculation of the concentration dependence of drug binding to plasma proteins with multiple binding sites of different affinities: determination of the possible variation of the unbound drug fraction and calculation of the number of binding sites of the protein J. Pharm. Sci. 96 2007 249 257 (Pubitemid 46363555)
46. Y.J. Hu, Y. Liu, and X.H. Xiao Investigation of the interaction between berberine and human serum albumin Biomacromolecules 10 2009 517 521
47. P.D. Ross, and S. Subramanian Thermodynamics of protein association reactions: forces contributing to stability Biochemistry 20 1981 3096 3102
48. Q. Zhao, X.Y. Xu, X.J. Sun, M. Liu, D.Z. Sun, and L.W. Li A calorimetric study on interactions of colchicine with human serum albumin J. Mol. Struct. 931 2009 31 34
49. W. He, Y. Li, C. Xue, Z. Hu, X. Chen, and F. Sheng Effect of Chinese medicine alpinetin on the structure of human serum albumin Bioorg. Med. Chem. 13 2005 1837 1845 (Pubitemid 40215271)
50. D.Z. Sun, L. Li, X.M. Qiu, F. Liu, and B.L. Yin Isothermal titration calorimetry and 1H NMR studies on host-guest interaction of paeonol and two of its isomers with beta-cyclodextrin Int. J. Pharm. 316 2006 7 13 (Pubitemid 43765694)
51. D.Z. Sun, S.B. Wang, M.Z. Song, X.L. Wei, and B.L. Yin A microcalorimetric study of hostguest complexes of α-cyclodextrin with alkyl trimethyl ammonium bromides in aqueous solutions J. Solution Chem. 34 2005 701 712
52. H.C. Wang, X.H. Jiang, L.M. Zhou, Z.J. Cheng, W.M. Yin, M. Duan, P.L. Liu, and X.M. Jiang Interaction of NAEn-s-n gemini surfactants with bovine serum albumin: a structure-activity probe J. Lumin. 134 2013 138 147
53. É.A. Enyedy, L. Horváth, A. Hetényi, T. Tuccinardi, C.G. Hartinger, B.K. Keppler, and T. Kiss Interactions of the carrier ligands of antidiabetic metal complexes with human serum albumin: a combined spectroscopic and separation approach with molecular modeling studies Bioorg. Med. Chem. 19 2011 4202 4210
54. Z. Chi, R. Liu, Y. Teng, X. Fang, and C. Gao Binding of oxytetracycline to bovine serum albumin: spectroscopic and molecular modeling investigations J. Agric. Food Chem. 58 2010 10262 10269
55. Z.X. Chi, and R.T. Liu Phenotypic characterization of the binding of tetracycline to human serum albumin Biomacromolecules 12 2011 203 209
56. X.C. Zhao, R.T. Liu, Z.X. Chi, Y. Teng, and P.F. Qin New insights into the behavior of bovine serum albumin adsorbed onto carbon nanotubes: comprehensive spectroscopic studies J. Phys. Chem. B 114 2010 5625 5631
57. Y. Lu, G.K. Wang, X.M. Lu, J. Lv, M.H. Xu, and W.W. Zhang Molecular mechanism of interaction between norfloxacin and trypsin studied by molecular spectroscopy and modeling Spectrochim. Acta Part A 75 2010 261 266
58. P.F. Qin, R.T. Liu, X.R. Pan, X.Y. Fang, and Y. Mou Impact of carbon chain length on binding of perfluoroalkyl acids to bovine serum albumin determined by spectroscopic methods J. Agric. Food Chem. 58 2010 5561 5567
59. J.N. Tian, J.Q. Liu, W.Y. He, Z.D. Hu, X.J. Yao, and X.G. Chen Probing the binding of scutellarin to human serum albumin by circular dichroism, fluorescence spectroscopy, FTIR, and molecular modeling method Biomacromolecules 5 2004 1956 1961
60. K. Rahmelow, and W. Hubner Secondary structure determination of proteins in aqueous solution by infrared spectroscopy: a comparison of multivariate data analysis methods Anal. Biochem. 241 1996 5 13 (Pubitemid 26337205)
61. Y.Q. Wang, X.Y. Wang, J. Wang, Y.M. Zhao, W.J. He, and Z.J. Guo Noncovalent interactions between a trinuclear monofunctional platinum complex and human serum albumin Inorg. Chem. 50 2011 12661 12668
62. S. Dubeau, P. Bourassa, T.J. Thomas, and H.A. Tajmir-Riahi Biogenic and synthetic polyamines bind bovine serum albumin Biomacromolecules 11 2010 1507 1515
63. J.S. Mandeville, H.A. Tajmir-Riahi, Complexes of dendrimers with bovine serum albumin, Biomacromolecules 11 (2010) 465e472.