Interaction of prometryn to human serum albumin: Insights from spectroscopic and molecular docking studies

Pesticide Biochemistry and Physiology

Volumn 108, Issue 1, 2014, Pages 66-73

  Wang, Yaping ^a   Zhang, Guowen ^a   Wang, Langhong ^a  

^a NANCHANG UNIVERSITY   (China)

Author keywords

Binding mode; Human serum albumin; Molecular modeling; Prometryn; Spectroscopy

Indexed keywords

HERBICIDE; HUMAN SERUM ALBUMIN; PROMETRYN; SERUM ALBUMIN;

ARTICLE; BINDING MODE; BINDING SITE; CHEMICAL PHENOMENA; CHEMISTRY; CIRCULAR DICHROISM; HUMAN; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR DOCKING; MOLECULAR MODEL; PROTEIN BINDING; PROTEIN SECONDARY STRUCTURE; PROTEIN TERTIARY STRUCTURE; SPECTROSCOPY;

BINDING MODE; HUMAN SERUM ALBUMIN; MOLECULAR MODELING; PROMETRYN; SPECTROSCOPY;

BINDING SITES; CIRCULAR DICHROISM; HERBICIDES; HUMANS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR DOCKING SIMULATION; PROMETRYNE; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; PROTEIN STRUCTURE, TERTIARY; SERUM ALBUMIN; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84895058751     PISSN: 00483575     EISSN: 10959939     Source Type: Journal    
DOI: 10.1016/j.pestbp.2013.12.006     Document Type: Article

References (42)

1. Wang J.F., Du Z.X., Yu W.L., Qu S.P. Detection of seven pesticides in cucumbers using hollow fibre-based liquid-phase microextraction and ultra-high pressure liquid chromatography coupled to tandem mass spectrometry. J. Chromatogr. A 2012, 1247:10-17.
2. Zhou Q.X., Xiao J.P., Ding Y.J. Sensitive determination of fungicides and prometryn in environmental water samples using multiwalled carbon nanotubes solid-phase extraction cartridge. Anal. Chim. Acta 2007, 602:223-228.
3. Wu Q.H., Li Z., Wu C.X., Wang C., Wang Z. Application of ultrasound-assisted emulsification microextraction for the determination of triazine herbicides in soil samples by high performance liquid chromatography. Microchim. Acta 2010, 170:59-65.
4. Cabanillas A.G., Díaz T.G., Díez N.M.M., Salinas F., Burguillos J.M.O., Viré J.C. Resolution by polarographic techniques of atrazine-simazine and terbutryn-prometryn binary mixtures by using PLS calibration and artificial neural networks. Analyst 2000, 125:909-914.
5. Khan S.U., Hamilton H.A. Extractable and bound (nonextractable) residues of prometryn and its metabolites in an organic soil. J. Agric. Food Chem. 1980, 28:126-132.
6. Molin W.T., Khan R.A. Differential tolerance of cotton (Gossypium sp.) cultivars to the herbicide prometryn. Pestic. Biochem. Physiol. 1996, 56:1-11.
7. Feroz S.R., Mohamad S.B., Bujang N., Malek S.N.A., Tayyab S. Multispectroscopic and molecular modeling approach to investigate the interaction of flavokawain b with human serum albumin. J. Agric. Food Chem. 2012, 60:5899-5908.
8. Ran D.H., Wu X., Zheng J.H., Yang J.H., Zhou H.P., Zhang M.F., Tang Y.J. Study on the interaction between florasulam and bovine serum albumin. J. Fluoresc. 2007, 17:721-726.
9. Shaw A.K., Pal S.K. Resonance energy transfer and ligand binding studies on pH-induced folded states of human serum albumin. J. Photochem. Photobiol. B: Biol. 2008, 90:187-197.
10. Li D.J., Hong D.F., Guo H., Chen J.J., Ji B.M. Probing the influences of urea on the interaction of sinomenine with human serum albumin by steady-state fluorescence. J. Photochem. Photobiol. B: Biol. 2012, 117:126-131.
11. Wang G.K., Wang D.C., Li X., Lu Y. Exploring the binding mechanism of dihydropyrimidinones to human serum albumin: spectroscopic and molecular modeling techniques. Colloids Surf. B 2011, 84:272-279.
12. Zhang G.W., Zhao N., Wang L. Fluorescence spectrometric studies on the binding of puerarin to human serum albumin using warfarin, ibuprofen and digitoxin as site markers with the aid of chemometrics. J. Lumin. 2011, 131:2716-2724.
13. Han C., Fang S.B., Cao H.M., Lu Y., Ma Y.Q., Wei D.F., Xie X.Y., Liu X.H., Li X., Fei D.Q., Zhao C.Y. Molecular interaction of PCB153 to human serum albumin: insights from spectroscopic and molecular modeling studies. J. Hazard. Mater. 2013, 248-249:313-321.
14. Li J.H., Liu X.Y., Ren C.L., Li J.Z., Sheng F.L., Hu Z.D. In vitro study on the interaction between thiophanate methyl and human serum albumin. J. Photochem. Photobiol. B: Biol. 2009, 94:158-163.
15. Bi S.Y., Sun Y.T., Qiao C.Y., Zhang H.Q., Liu C.M. Binding of several anti-tumor drugs to bovine serum albumin: fluorescence study. J. Lumin. 2009, 129:541-547.
16. Ding F., Li X.N., Diao J.X., Sun Y., Zhang L., Sun Y. Chiral recognition of metalaxyl enantiomers by human serum albumin: evidence from molecular modeling and photophysical approach. Chirality 2012, 24:471-480.
17. Li Y.Q., Jia B.X., Wang H., Li N.N., Chen G.P., Lin Y.J., Gao W.H. The interaction of 2-mercaptobenzimidazole with human serum albumin as determined by spectroscopy, atomic force microscopy and molecular modeling. Colloids Surf. B 2013, 104:311-317.
18. Lakowicz J.R. Principles of Fluorescence Spectroscopy 1983, Springer, New York, p. 257. first ed.
19. Zhang G.W., Ma Y.D., Wang L., Zhang Y.P., Zhou J. Multispectroscopic studies on the interaction of maltol, a food additive, with bovine serum albumin. Food Chem. 2012, 133:264-270.
20. Feroz S.R., Mohamad S.B., Bakri Z.S., Malek S.N., Tayyab S. Probing the interaction of a therapeutic flavonoid, pinostrobin with human serum albumin: multiple spectroscopic and molecular modeling investigations. PLOS One 2013, 8(10):e76067.
21. Kandagal P.B., Ashoka S., Seetharamappa J., Shaikh S.M.T., Jadegoud Y., Ijare O.B. Study of the interaction of an anticancer drug with human and bovine serum albumin: spectroscopic approach. J. Pharm. Biomed. Anal. 2006, 41:393-399.
22. Lehrer S. Quenching of the tryptophyl fluorescence of model compounds and of lysozyme by iodide ion. Biochemistry 1971, 10:3254-3263.
23. Cheng Z.J., Zhao H.M., Xu Q.Y., Liu R. Investigation of the interaction between indigotin and two serum albumins by spectroscopic approaches. J. Pharm. Anal. 2013, 3:257-269.
24. Jiang C.Q., Gao M.X., Meng X.Z. Study of the interaction between daunorubicin in blood serum samples. Spectrochim. Acta A 2003, 59:1605-1610.
25. Cheng Z.J. Studies on the interaction between scopoletin and two serum albumins by spectroscopic methods. J. Lumin. 2012, 132:2719-2729.
26. Ross P.D., Subramanian S. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 1981, 20:3096-3102.
27. Zhang G.W., Wang L., Pan J.H. Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques. J. Agric. Food Chem. 2012, 60:2721-2729.
28. Sudlow G., Birkett D.J., Wade D.N. Further characterization of specific drug binding sites on human serum albumin. Mol. Pharmacol. 1976, 12:1052-1061.
29. Sjoholm I., Ekman B., Kober A., Pahlman I.L., Seiving B., Sjodin T. Binding of drugs to human serum albumin: the specificity of three binding sites as studied with albumin immobilized in microparticles. Mol. Pharmacol. 1979, 16:767-777.
30. Naik P.N., Chimatadar S.A., Nandibewoor S.T. Interaction between a potent corticosteroid drug-dexamethasone with bovine serum albumin and human serum albumin: a fluorescence quenching and Fourier transformation infrared spectroscopy study. J. Photochem. Photobiol. B: Biol. 2010, 100:147-159.
31. Zhang G.W., Ma Y.D. Mechanistic and conformational studies on the interaction of food dye amaranth with human serum albumin by multispectroscopic methods. Food Chem. 2013, 136:442-449.
32. Polet H., Steinhardt J. Binding-induced alterations in ultraviolet absorption of native serum albumin. Biochemistry 1968, 7:1348-1356.
33. Glazer A.N., Smith E.L. Studies on the ultraviolet difference spectra of proteins and polypeptides. J. Biol. Chem. 1961, 236:2942-2947.
34. Zhou X.M., Lu W.J., Su L., Shan Z.J., Chen X.G. Binding of phthalate plasticizers to human serum albumin in vitro: a multispectroscopic approach and molecular modeling. J. Agric. Food Chem. 2012, 60:1135-1145.
35. Besley N.A., Hirst J.D. Theoretical studies toward quantitative protein circular dichroism calculations. J. Am. Chem. Soc. 1999, 121:9636-9644.
36. Han X.L., Tian F.F., Ge Y.S., Jiang F.L., Lai L., Li D.W., Yu Q.L.Y., Wang J., Chen L., Liu Y. Spectroscopic, structural and thermodynamic properties of chlorpyrifos bound to serum albumin: a comparative study between BSA and HSA. J. Photochem. Photobiol. B: Biol. 2012, 109:1-11.
37. Li Y., Ma X.R., Lu G.H. Systematic investigation of the toxic mechanism of difenoconazole on protein by spectroscopic and molecular modeling. Pestic. Biochem. Physiol. 2013, 105:155-160.
38. Wang Y.Q., Zhang H.M., Zhou Q.H. Investigation of the interaction between pentachlorophenol and human serum albumin using spectral methods. J. Mol. Struct. 2009, 932:31-37.
39. Darwish S.M., Abu sharkh S.E., Abu Teir M.M., Makharza S.A., Abu-hadid M.M. Spectroscopic investigations of pentobarbital interaction with human serum albumin. J. Mol. Struct. 2010, 963:122-129.
40. Rahmelow K., Hübner W. Secondary structure determination of proteins in aqueous solution by infrared spectroscopy: a comparison of multivariate data analysis methods. Anal. Biochem. 1996, 241:5-13.
41. Surewicz W.K., Mantsch H.H., Chapman D. Determination of protein secondary structure by Fourier transform infrared spectroscopy: a critical assessment. Biochemistry 1993, 2:389-394.
42. Wang X.R., Xie X.Y., Ren C.L., Yang Y., Xu X.M., Chen X.G. Application of molecular modelling and spectroscopic approaches for investigating binding of vanillin to human serum albumin. Food Chem. 2011, 127:705-710.