Abstract
The interaction between 3-thiol-4-(2,4-dichlorobenzylideneamino)-5-methyl-4H-1,2,4-triazole (CBTZ) and bovine serum albumin (BSA) under physiological conditions was investigated by fluorescence, UV-vis absorption and circular dichroism (CD) spectroscopy as well as molecular modeling methods. The result of fluorescence experiment indicates the static quenching as a result of the formation of the CBTZ-BSA complex. The binding constants (K a) at different temperatures were calculated according to the modified Stern-Volmer equation. The enthalpy change (ΔH) and entropy change (ΔS) were determined based on the van’t Hoff equation. Both negative ΔH and ΔS indicated that van der Waals and hydrogen-bonding forces were the dominant intermolecular forces to stabilize the CBTZ-BSA complex. Site marker competitive replacement experiments demonstrated that binding of CBTZ to BSA primarily took place in sub-domain IIA (Sudlow’s site I). The binding distance (r = 7.2 nm) between CBTZ and the tryptophan residue of BSA was estimated according to the theory of fluorescence resonance energy transfer (FRET). The conformational studies by circular dichroism (CD) and three-dimensional fluorescence spectroscopy showed that the presence of CBTZ induced minor changes of the secondary structure of BSA. Molecular modeling study further confirmed the binding mode obtained experimentally.
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Flarakos J, Morand KL, Vouros P. High-throughput solution-based medicinal library screening against human serum albumin. Anal Chem, 2005, 77: 1345–1353
Mourik J, de Jong LPA. Binding of the organophosphates parathion and paraoxon to bovine and human serum albumin. Arch Toxicol, 1978, 41: 43–48
Hu YJ, Liu Y, Xiao XH. Investigation of the interaction between berberine and human serum albumin. Biomacromolecules, 2009, 10: 517–521
Duan YQ, Lei HG, Min SG, Duan ZQ. Spectroscopic study on interaction of rodenticide brodifacoum with bovine serum albumin. Spectrosc Spect Anal, 2009, 29: 2998–3002
Marzano C, Pellei M, Colavito D, Alidori S, Lobbia GG, Gandin V, Tisato F, Santini C. Synthesis, characterization, and in vitro antitumor properties of tris(hydroxymethyl)phosphine copper (I) complexes containing the new bis(1,2,4-triazol-1-yl)acetate ligand. J Med Chem, 2009, 49: 7317–7324
Jantova S, Letasiova S, Ovadekova R, Múcková M. Cytotoxic/antiproliferative effects of new [1,2,4]triazolo[4,3,c] quinazolines in tumor cell lines HeLa and B16. Neoplasma, 2006, 53: 291–300
Kritsanida M, Mouroutsou A, Marakos P, Nicole P, Spyroula P-G, Christophe P, Myriam W, Erik DC. Synthesis and antiviral activity evaluation of some new 6-substituted 3-(1-adamantyl)-1,2,4-triazolo [3,4-b][1,3,4]thiadiazoles. Farmaco, 2002, 57: 253–257
Sun XH, Tao Y, Liu YF, Jia YQ, Chen B. Synthesis and biological activities of 4,5-dihydro-3-methyl-4-amino-1,2,4-triazole-5-thione Schiff bases (in Chinese). Acta Chimica Sinica, 2008, 66: 234–238
Lakowicz JR. Principles of Fluorescence Spectroscopy. 3rd ed. New York: Springer, 2006
Zhang YZ, Xiang X, Mei P, Dai J, Zhang LL, Liu Y. Spectroscopic studies on the interaction of Congo Red with bovine serum albumin. Spectrochim Acta A, 2009, 72: 907–914
Hu YJ, Liu Y, Sun TQ, Hu YJ, Liu Y, Sun TQ, Bai AM, Lü JQ, Pi ZB. Binding of anti-inflammatory drug cromolyn sodium to bovine serum albumin. Int J Biol Macromol, 2006, 39: 280–285
Zhang YZ, Zhou B, Zhang XP, Huang P, Li CH, 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
Zhang YZ, Zhou B, Liu YX, Zhou CX, Ding XL, Liu Y. Fluorescence study on the interaction of bovine serum albumin with p-aminoazobenzene. J Fluoresc, 2008, 18: 109–118
Timaseff SN. Thermodynamics of Protein Interactions: Proteins of Biological Fluids. Oxford: Pergamon Press, 1972, 511–519
Klotz IM, Urouhart JM. The binding of organic ions by proteins. Effect of temperature. J Am Chem Soc, 1949, 71: 847–851
Ross PD, Subramanian S. Thermodynamics of protein association reactions: Forces contributing to stability. Biochemistry, 1981, 20: 3096–3120
Liu JQ, Tian JN, Zhang JY, Hu ZD, Chen XG. Isolation and determination of p-hydroxybenzoylcholine in traditional Chinese medicine Semen sinapis Albae. Anal Bioanal Chem, 2003, 376: 864–867
Sudlow G, Birkett DJ, Wade DN. Characterization of two specific drug binding sites on human serum albumin. Mol Pharmacol, 1975, 11: 824–832
Sudlow G, Birkett DJ, Wade DN. Further characterization of specific drug binding sites on human serum albumin. Mol Pharmacol, 1976, 12: 1052–1061
Förster T. Delocalized excitation and excitation transfer, In: Sinanoglu O, Ed. Modern Quantum Chemistry. New York: Academic Press, 1965, 93–137
Mahammed A, Weaver JJ, Gray HB, Sorasaenee K, Gross Z. Amphiphilic corroles bind tightly to human serum albumin. Bioconjugate Chem, 2004, 15: 738–746
Yang P, Gao F. The Principle of Bioinorganic Chemistry. Beijing: Science Press, 2002
Kamat BP. In vitro study on the interaction of mechanism of tricyclic compounds with bovine serum albumin. J Pharm Biomed Anal, 2004, 35: 655–664
Zhang HX, Huang X, Mei P, Li KH, Yan CN. Studies on the interaction of tricyclazole with β-cyclodextrin and human serum albumin by spectroscopy. J Fluoresc, 2006, 16: 287–294
Sulkowska A. Interaction of drugs with bovine and human serum albumin. J Mol Struct, 2002, 614: 227–232
Yang P, Gao F. The Principle of Bioinorganic Chemistry. Beijing: Science Press, 2002. 489–494
Cui FL, Yan YH, Zhang QZ, Yao XJ, Qu GR, Lu Y. Characterization of the interaction between 8-bromoadenosine with human serum albumin and its analytical application. Spectrochim Acta A, 2009, 74: 964–971
Li YS, Ge YS, Zhang Y, Zhang AQ, Sun SF, Jiang FL, Liu Y. Interaction of coomassie brilliant blue G250 with human serum albumin: Probing of the binding mechanism and binding site by spectroscopic and molecular modeling methods. J Mol Struct, 2010, 968: 24–31
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Fu, J., Wang, K., Ge, Y. et al. Biophysical studies of the interaction between a triazole derivative and bovine serum albumin by multi-spectroscopic and molecular modeling methods. Sci. China Chem. 54, 788–796 (2011). https://doi.org/10.1007/s11426-011-4260-8
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DOI: https://doi.org/10.1007/s11426-011-4260-8