Study on the interaction of phthalate esters to human serum albumin by steady-state and time-resolved fluorescence and circular dichroism spectroscopy

Journal of Hazardous Materials

Volumn 192, Issue 3, 2011, Pages 1291-1298

  Xie, Xiaoyun ^a   Wang, Zhaowei ^a   Zhou, Ximin ^a   Wang, Xiaoru ^a   Chen, Xingguo ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Circular dichroism; Fluorescence; Human serum albumin; Molecular modelling; Phthalate esters

Indexed keywords

ASSOCIATION CONSTANT; BINDING AFFINITIES; BINDING CONSTANT; BINDING REACTIONS; CD SPECTROSCOPY; DIMETHYL PHTHALATE; ENDOCRINE DISRUPTOR; HIGH AFFINITY; HUMAN SERUM ALBUMINS; HYDROGEN INTERACTION; HYDROPHOBIC FORCES; PHTHALATE ESTER; PHTHALATES; PRIORITY POLLUTANTS; PROTEIN SECONDARY STRUCTURE; REGRESSION CURVE; SCATCHARD PLOTS; STEADY STATE; STERN-VOLMER; THERMODYNAMIC PARAMETER; TIME-RESOLVED FLUORESCENCE;

BINDING ENERGY; BINDING SITES; BODY FLUIDS; CIRCULAR DICHROISM SPECTROSCOPY; DICHROISM; ESTERIFICATION; FLUORESCENCE; MOLECULAR MODELING; ULTRAVIOLET SPECTROSCOPY; ULTRAVIOLET VISIBLE SPECTROSCOPY;

ESTERS;

HUMAN SERUM ALBUMIN; HYDROGEN; PHTHALIC ACID BENZYL BUTYL ESTER; PHTHALIC ACID BIS(2 ETHYLHEXYL) ESTER; PHTHALIC ACID DIMETHYL ESTER; PHTHALIC ACID ESTER;

CHEMICAL BINDING; ENDOCRINE DISRUPTOR; FLUORESCENCE SPECTROSCOPY; HOMINID; MOLECULAR ANALYSIS; ORGANIC POLLUTANT; PHTHALATE; PROTEIN; REACTION KINETICS; SERUM; TEMPERATURE PROFILE; ULTRAVIOLET RADIATION;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL INTERACTION; CIRCULAR DICHROISM; FLUORESCENCE; HUMAN; MOLECULAR MODEL; PROTEIN SECONDARY STRUCTURE; STEADY STATE; TEMPERATURE; THERMODYNAMICS; ULTRAVIOLET SPECTROSCOPY;

BINDING SITES; CIRCULAR DICHROISM; ESTERS; HUMANS; HYDROGEN; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, CHEMICAL; MODELS, MOLECULAR; PHTHALIC ACIDS; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; REGRESSION ANALYSIS; SERUM ALBUMIN; SPECTROPHOTOMETRY, ULTRAVIOLET; THERMODYNAMICS;

EID: 80052037905     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2011.06.038     Document Type: Article

References (32)

1. Zeng F., Wen J.X., Cui K.Y., Wu L.N., Liu M., Li Y.J., Lin Y.J., Zhu F., Ma Z.L., Zeng Z.X. Seasonal distribution of phthalate esters in surface water of the urban lakesin the subtropical city, Guangzhou, China. J. Hazard. Mater. 2009, 169:719-725.
2. Staples C.A., Peterson D.R., Parkerton T.F., Adams W.J. The environmental fate of phthalate esters: a literature review. Chemosphere 1997, 35:667-749.
3. Mackintosh C.E., Maldonado J.A., Ikonomou M.G., Gobas F.A.P.C. Sorption of phthalate esters and PCBs in a marine ecosystem. Environ. Sci. Technol. 2006, 40:3481-3488.
4. Salima C.J., Liua S.H., Kennedy J.F. Comparative study of the adsorption on chitosan beads of phthalate esters and their degradation products. Carbohydr. Polym. 2010, 81:640-644.
5. Blair J.D., Ikonomou M.G., Kelly B.C., Surridge B., Frank A.P.C., Gobas F.A.P.C. Ultra-trace determination of phthalate ester metabolites in seawater, sediments, and biota from an urbanized marine inlet by LC/ESI-MS/MS. Environ. Sci. Technol. 2009, 43:6262-6268.
6. 2 process. J. Hazard. Mater. 2009, 162:954-959.
7. Xu Z.W., Zhang W.M., Lv L., Pan B.C., Lan P., Zhang Q.X. A new approach to catalytic degradation of dimethyl phthlate by a macroporous OH-type strongly basic anion exchange resin. Environ. Sci. Technol. 2010, 44:3130-3135.
8. Suzuki T., Yaguchi K., Suzuki S. Monitoring of phthalic acid monoesters in river water by solid-phase extraction and GC-MS determination. Environ. Sci. Technol. 2001, 35:3757-3763.
9. Yuan S.Y., Huang I.C., Chang B.V. Biodegradation of dibutyl phthalate and di-(2-ethylhexyl) phthalate and microbial community changes in mangrove sediment. J. Hazard. Mater. 2010, 184:826-831.
10. US EPA, Exposure and risk assessment for phthalate esters: di(2-ethylhexyl) phthalate, di-n-butyl phthalate, dimethyl phthalate, diethyl phthalate, din-octyl phthalate, butyl benzyl phthalate, Final Report, US Environmental Protection Agency, EPA-440/4-81-020, 1981b,Washington, DC, 1981.
11. Kabdaşh I., Keleş A., Ölmez-Hanci{dotless} T., Tünay O., Arslan-Alaton I. Treatment of phthalic acid esters by electrocoagulation with stainless steel electrodes using dimethyl phthalate as a model compound. J. Hazard. Mater. 2009, 171:932-940.
12. Hu Y.J., Liu Y., Xiao X.H. Investigation of the interaction between berberine and human serum albumin. Biomacromolecules 2009, 10:517-521.
13. Zolese G., Falcioni G., Bertoli E., Galeazzi R., Wozniak M., Wypych Z., Gratton E., Ambrosini A. Steady-state and time resolved fluorescence of albumins interacting with N-Oleylethanolamine, a component of the endogenous N-Acylethanolamines. Proteins: Struct. Funct. Genet. 2000, 40:39-48.
14. Divsalar A., Bagheri M.J., Saboury A.A., Mansoori-Torshizi H., Amani M. Investigation on the interaction of newly designed anticancer Pd(II) complexes with different aliphatic tails and human serum albumin. J. Phys. Chem. B 2009, 113:14035-14042.
15. Petitpas I., Bhattacharya A.A., Twine S., East M., Curry S. Crystal structure analysis of warfarin binding to human serum albumin - Anatomy of drug site I. J. Biol. Chem. 2001, 276:22804-22809.
16. G. Morris, SYBYL Software, Version 6.9, Tripos Associates Inc., St. Louis, 2002.
17. Lakowicz J.R. Principles of Fluorescence Spectroscopy 1999, Kluwer/Plenum, New York. 2nd ed.
18. Scatchard G., Ann N.Y. The attraction of proteins for small molecules. Acad. Sci. 1949, 51:660-672.
19. Papadopoulou A., Green R.J., Frazier R.A. Interaction of flavonoids with bovine serum albumin: a fluorescence quenching study. J. Agric. Food Chem. 2005, 53:158-163.
20. Sjoholm I., Ekman B., Kober A. Binding of drugs to human serum albumin: XI. The specificity of three binding sites as studied with albumin immobilized in microparticles. Mol. Pharmacol. 1979, 16:767-777.
21. Froehlich E., Mandeville J.S., Jennings C.J., Sedaghat-Herati R., Tajmir-Riahi H.A. Dendrimers bind human serum albumin. J. Phys. Chem. B. 2009, 113:6986-6993.
22. Sulkowska A. Interaction of drugs with bovine and human serum albumin. J. Mol. Struct. 2002, 614:227-232.
23. Soares S., Mateus N., Freitas V.D. Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary α-amylase (HSA) by fluorescence quenching. J. Agric. Food Chem. 2007, 55:6726-6735.
24. Chen G.Z., Huang X.Z., Xu J.G., Zheng Z.Z., Wang Z.B. The Methods of Fluorescence Analysis 1990, Science Press, Beijing.
25. Bertucci C., Domenici E. Reversible and covalent binding of drugs to human serum albumin: methodological approaches and physiological relevance. Curr. Med. Chem. 2002, 9:1463-1481.
26. Ambrosetti R., Bianchini R., Fischella S., Fichera M., Zandomeneghi M. Resolution of the absorbance and CD spectra and formation constants of the complexes between human serum albumin and methyl orange. Chem. Eur. J. 1996, 2:149-156.
27. Rahman M.H., Maruyama T., Okada T., Yamasaki K., Otagiri M. Study of interaction of carprofen and its enantiomers with human serum albumin-I: mechanism of binding studied by dialysis and spectroscopic methods. Biochem. Pharmacol. 1993, 46:1721-1731.
28. Ross P.D., Subramanian S. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 1981, 20:3096-3102.
29. Hirshfield K.M., Toptygin D., Grandhige G., Kim H., Packard B.Z., Brand L. Steady-state and time-resolved fluorescence measurements for studying molecular interactions: interaction of a calcium-binding probe with proteins. Biophys. Chem. 1996, 62:25-38.
30. Flora K., Brennan J.D., Baker G.A., Doody M.A., Bright F.V. Unfolding of acrylodan-labeled human serum albumin probed by steady-state and time-resolved fluorescence methods. Biophys. J. 1998, 75:1084-1096.
31. Wolfbeis O.S., Leiner M., Hochmuth P., Geiger H. Absorption and fluorescence spectra, pKa values, and fluorescence lifetimes of monohydroxyflavones and monomethoxyflavones. Ber. Bunsenge. Phys. Chem. 1984, 88:759-767.
32. Yang P., Gao F. The Principle of Bioinorganic Chemistry 2002, Science Press, p. 349.