The interaction between 4-aminoantipyrine and bovine serum albumin: Multiple spectroscopic and molecular docking investigations

Journal of Hazardous Materials

Volumn 190, Issue 1-3, 2011, Pages 574-581

  Teng, Yue ^a   Liu, Rutao ^a   Li, Chao ^b   Xia, Qing ^a   Zhang, Pengjun ^a  

^a SHANDONG UNIVERSITY   (China)

^b Key Laboratory of Cardiovascular Proteomics of Shandong Province   (China)

Author keywords

4 Aminoantipyrine; Bovine serum albumin; Multi spectroscopic techniques; Toxicity evaluation

Indexed keywords

4-AMINOANTIPYRINE; AROMATIC POLLUTANTS; AROMATIC RINGS; BINDING CONSTANT; BIOCHEMICAL EXPERIMENTS; BOVINE SERUM ALBUMINS; ENVIRONMENTAL MONITORING; HUMAN HEALTH; INNER FILTER EFFECTS; INTRINSIC FLUORESCENCE; MOLECULAR DOCKING; MULTI-SPECTROSCOPIC TECHNIQUES; PHARMACEUTICAL INDUSTRY; PROTEIN LEVEL; SKELETAL STRUCTURES; SPECTROSCOPIC TECHNIQUE; STATIC QUENCHING; SUBDOMAIN; THERMODYNAMIC PARAMETER;

AMINO ACIDS; AROMATIC COMPOUNDS; BINDING SITES; DOCKING; HEALTH RISKS; MOLECULAR MODELING; TOXICITY;

BODY FLUIDS;

4 AMINOPHENAZONE; BOVINE SERUM ALBUMIN;

AMINO ACID; AROMATIC HYDROCARBON; BIOCHEMICAL COMPOSITION; DRUG; EXPERIMENTAL STUDY; FLUORESCENCE; HEALTH RISK; HYDROPHOBICITY; PROTEIN; PUBLIC HEALTH; SERUM; SPECTROSCOPY; TOXICITY TEST;

ABSORPTION SPECTROSCOPY; ARTICLE; BINDING AFFINITY; BINDING SITE; CIRCULAR DICHROISM; FLUORESCENCE SPECTROSCOPY; MOLECULAR DOCKING; POLLUTANT; STATIC ELECTRICITY; THERMODYNAMICS; TOXICITY; ULTRAVIOLET SPECTROSCOPY;

AMPYRONE; ANIMALS; CATTLE; COMPUTER SIMULATION; MODELS, MOLECULAR; PROTEIN BINDING; PROTEIN CONFORMATION; SERUM ALBUMIN, BOVINE; SPECTRUM ANALYSIS; TOXICITY TESTS;

BOVINAE;

EID: 79956133302     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2011.03.084     Document Type: Article

References (49)

1. Carter D.C., Ho J.X. Structure of serum albumin. Adv. Protein Chem. 1994, 45:153-176.
2. Varshney A., Sen P., Ahmad E., Rehan M., Subbarao N., Khan R.H. Ligand binding strategies of human serum albumin: how can the cargo be utilized?. Chirality 2010, 22:77-87.
3. 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.
4. Neelam S., Gokara M., Sudhamalla B., Amooru D.G., Subramanyam R. Interaction studies of coumaroyltyramine with human serum albumin and its biological importance. J. Phys. Chem. B 2010, 114:3005-3012.
5. Gulden M., Morchel S., Tahan S., Seibert H. Impact of protein binding on the availability and cytotoxic potency of organochlorine pesticides and chlorophenols in vitro. Toxicology 2002, 175:201-213.
6. Chi Z., Liu R., Teng Y., Fang X., Gao C. Binding of oxytetracycline to bovine serum albumin: spectroscopic and molecular modeling investigations. J. Agric. Food Chem. 2010, 58:10262-10269.
7. Turro N.J., Lei X.-G. Spectroscopic probe analysis of protein-surfactant interactions: the BSA/SDS system. Langmuir 1995, 11:2525-2533.
8. Tian J., Liu J., Hu Z., Chen X. Interaction of Wogonin with bovine serum albumin. Bioorg. Med. Chem. 2005, 13:4124-4129.
9. Liu R., Sun F., Zhang L., Zong W., Zhao X., Wang L., Wu R., Hao X. Evaluation on the toxicity of nanoAg to bovine serum albumin. Sci. Total Environ. 2009, 407:4184-4188.
10. Jones M.N. Surfactant interactions with biomembranes and proteins. Chem. Soc. Rev. 1992, 21:127-136.
11. Wang N., Ye L., Yan F., Xu R. Spectroscopic studies on the interaction of azelnidipine with bovine serum albumin. Int. J. Pharm. 2008, 351:55-60.
12. MacManus-Spencer L.A., Tse M.L., Hebert P.C., Bischel H.N., Luthy R.G. Binding of perfluorocarboxylates to serum albumin: a comparison of analytical methods. Anal. Chem. 2010, 82:974-981.
13. Chen Y.M., Chen Y.P. Measurements for the solid solubilities of antipyrine, 4-aminoantipyrine and 4-dimethylaminoantipyrine in supercritical carbon dioxide. Fluid Phase Equilib. 2009, 282:82-87.
14. Lang A., Hatscher C., Wiegert C., Kuhl P. Protease-catalysed coupling of N-protected amino acids and peptides with 4-aminoantipyrine. Amino Acids 2009, 36:333-340.
15. Cunha S., Oliveira S.M., Rodrigues M.T., Bastos R.M., Ferrari J., de Oliveira C.M.A., Kato L., Napolitano H.B., Vencato I., Lariucci C. Structural studies of 4-aminoantipyrine derivatives. J. Mol. Struct. 2005, 752:32-39.
16. Prasad S., Agarwal R.K. Cobalt(II) complexes of various thiosemicarbazones of 4-aminoantipyrine: syntheses, spectral, thermal and antimicrobial studies. Transit. Met. Chem. 2007, 32:143-149.
17. Van Staden J.F., Beyene N.W., Stefan R.I., Aboul-Enein H.Y. Sequential injection spectrophotometric determination of ritodrine hydrochloride using 4-aminoantipyrine. Talanta 2005, 68:401-405.
18. Kasthuri J., Santhanalakshmi J., Rajendiran N. Platinum nanoparticle catalysed coupling of phenol derivatives with 4-aminoantipyrine in aqueous medium. Transit. Met. Chem. 2008, 33:899-905.
19. Katsaounos C.Z., Paleologos E.K., Giokas D.L., Karayannis M.I. The 4-aminoantipyrine method revisited: determination of trace phenols by micellar assisted preconcentration. Int. J. Environ. Anal. Chem. 2003, 83:507-514.
20. Vinagre A.M., Collares E.F. Effect of 4-aminoantipyrine on gastric compliance and liquid emptying in rats. Braz. J. Med. Biol. Res. 2007, 40:903-909.
21. Sunderji S.G., El Badry A., Poore E.R., Figueroa J.P., Nathanielsz P.W. The effect of myometrial contractures on uterine blood flow in the pregnant sheep at 114 to 140 days' gestation measured by the 4-aminoantipyrine equilibrium diffusion technique. Am. J. Obstet. Gynecol. 1984, 149:408-412.
22. El Badry A., Figueroa J.P., Poore E.R., Sunderji S., Levine S., Mitchell M.D., Nathanielsz P.W. Effect of fetal intravascular 4-aminoantipyrine infusions on myometrial activity (contractures) at 125 to 143 days' gestation in the pregnant sheep. Am. J. Obstet. Gynecol. 1984, 150:474-479.
23. Pierre S.C., Schmidt R., Brenneis C., Michaelis M., Geisslinger G., Scholich K. Inhibition of cyclooxygenases by dipyrone. Br. J. Pharmacol. 2007, 151:494-503.
24. Teng Y., Liu R., Yan S., Pan X., Zhang P., Wang M. Spectroscopic investigation on the toxicological interactions of 4-aminoantipyrine with bovine hemoglobin. J. Fluoresc. 2010, 20:381-387.
25. Berman H.M., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., Shindyalov I.N., Bourne P.E. The Protein Data Bank. Nucleic Acids Res. 2000, 28:235-242.
26. Karchin R., Cline M., Karplus K. Evaluation of local structure alphabets based on residue burial. Proteins 2004, 55:508-518.
27. Karchin R., Cline M., Mandel-Gutfreund Y., Karplus K. Hidden Markov models that use predicted local structure for fold recognition: alphabets of backbone geometry. Proteins 2003, 51:504-514.
28. Sahoo B.K., Ghosh K.S., Dasgupta S. Investigating the binding of curcumin derivatives to bovine serum albumin. Biophys. Chem. 2008, 132:81-88.
29. Sur S.S., Rabbani L.D., Libman L., Breslow E. Fluorescence studies of native and modified neurophysins. Effects of peptides and pH. Biochemistry 1979, 18:1026-1036.
30. Mandeville J.S., Tajmir-Riahi H.A. Complexes of dendrimers with bovine serum albumin. Biomacromolecules 2010, 11:465-472.
31. Zhang Y.Z., Zhou B., Zhang X.P., Huang P., Li C.H., Liu Y. Interaction of malachite green with bovine serum albumin: determination of the binding mechanism and binding site by spectroscopic methods. J. Hazard. Mater. 2009, 163:1345-1352.
32. Soares S., Mateus N., Freitas V. Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary alpha-amylase (HSA) by fluorescence quenching. J. Agric. Food Chem. 2007, 55:6726-6735.
33. Lakowicz J.R., Weber G. Quenching of fluorescence by oxygen. A probe for structural fluctuations in macromolecules. Biochemistry 1973, 12:4161-4170.
34. Chi Z.X., Liu R.T., Yang B.J., Zhang H. Toxic interaction mechanism between oxytetracycline and bovine hemoglobin. J. Hazard. Mater. 2010, 180:741-747.
35. Liu X.H., Xi P.X., Chen F.J., Xu Z.H., Zeng Z.Z. Spectroscopic studies on binding of 1-phenyl-3-(coumarin-6-yl)sulfonylurea to bovine serum albumin. J. Photochem. Photobiol. B 2008, 92:98-102.
36. Paramaguru G., Kathiravan A., Selvaraj S., Venuvanalingam P., Renganathan R. Interaction of anthraquinone dyes with lysozyme: evidences from spectroscopic and docking studies. J. Hazard. Mater. 2010, 175:985-991.
37. Ross P.D., Subramanian S. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 1981, 20:3096-3102.
38. Khan S.N., Islam B., Yennamalli R., Sultan A., Subbarao N., Khan A.U. Interaction of mitoxantrone with human serum albumin: spectroscopic and molecular modeling studies. Eur. J. Pharm. Sci. 2008, 35:371-382.
39. Hu X.Y., Yang J.A., Yang C.Z., Zhang J.D. UV/H2O2 degradation of 4-aminoantipyrine: a voltammetric study. Chem. Eng. J. 2010, 161:68-72.
40. Paul B.K., Samanta A., Guchhait N. 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 2010, 114:6183-6196.
41. Zhou N., Liang Y.Z., Wang P. 18beta-Glycyrrhetinic acid interaction with bovine serum albumin. J. Photochem. Photobiol. A 2007, 185:271-276.
42. Bian H., Li M., Yu Q., Chen Z., Tian J., Liang H. Study of the interaction of artemisinin with bovine serum albumin. Int. J. Biol. Macromol. 2006, 39:291-297.
43. Lu J.Q., Jin F., Sun T.Q., Zhou X.W. Multi-spectroscopic study on interaction of bovine serum albumin with lomefloxacin-copper(II) complex. Int. J. Biol. Macromol. 2007, 40:299-304.
44. Wang Y.Q., Zhang H.M., Zhang G.C., Liu S.X., Zhou Q.H., Fei Z.H., Liu Z.T. Studies of the interaction between paraquat and bovine hemoglobin. Int. J. Biol. Macromol. 2007, 41:243-250.
45. Guo M., Lu W.J., Li M.H., Wang W. Study on the binding interaction between carnitine optical isomer and bovine serum albumin. Eur. J. Med. Chem. 2008, 43:2140-2148.
46. Yang Q., Liang J., Han H. Probing the interaction of magnetic iron oxide nanoparticles with bovine serum albumin by spectroscopic techniques. J. Phys. Chem. B 2009, 113:10454-10458.
47. Hu Y.J., Liu Y., Wang H.B., Xiao X.H., Qu S.S. Study of the interaction between monoammonium glycyrrhizinate and bovine serum albumin. J. Pharm. Biomed. Anal. 2004, 36:915-919.
48. De Jonge H.R. Toxicity of tetracyclines in rat-small-intestinal epithelium and liver. Biochem. Pharmacol. 1973, 22:2659-2677.
49. Shaikh S.M.T., Seetharamappa J., Kandagal P.B., Manjunatha D.H., Ashoka S. Spectroscopic investigations on the mechanism of interaction of bioactive dye with bovine serum albumin. Dyes Pigments 2007, 74:665-671.