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Original Articles

Insights into the binding of thiosemicarbazone derivatives with human serum albumin: spectroscopy and molecular modelling studies

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Pages 1264-1281 | Received 20 May 2015, Accepted 20 Jul 2015, Published online: 03 Nov 2015

References

  • Ali, S., & Alam, M. (1994). Potential antimicrobial agents-I: Structural modifications and antimicrobial activity of some isatin derivatives. Archives of Pharmacal Research, 17, 131–133.10.1007/BF02974237
  • Anand, P., & Kunnumakara, A. B. (2008). Cancer is a preventable disease that requires major lifestyle changes. Pharmaceutical Research, 25, 2097–2116.10.1007/s11095-008-9661-9
  • Blumenkopf, T. A., Harrington, J. A., Koble, C. S., Bankston, D. D., Morrison, R. W., Bigham, E. C., … Spector, T. (1992). 2-Acetylpyridine thiocarbonohydrazones. Potent inactivators of herpes simplex virus ribonucleotide reductase. Journal of Medicinal Chemistry, 35, 2306–2314.10.1021/jm00090a022
  • Carter, D., He, X. M., Munson, S. H., Twigg, P. D., Gernert, K. M., Broom, M. B., & Miller, T. Y. (1989). Three-dimensional structure of human serum albumin. Science, 244, 1195–1198.10.1126/science.2727704
  • Chamani, J., Movahed, H. V., & Saberi, M. R. (2011). Lomefloxacin promotes the interaction between human serum albumin and transferrin: A mechanistic insight into the emergence of antibiotic’s side effects. Journal of Pharmaceutical and Biomedical. Analysis, 55, 114–124.10.1016/j.jpba.2010.12.029
  • Chinnathambi, S., Velmurugan, D., Hanagata, N., Aruna, P., & Ganesan, S. (2014). Investigations on the interactions of 5-fluorouracil with bovine serum albumin: Optical spectroscopic and molecular modeling studies. Journal of Luminescence, 151, 1–10.10.1016/j.jlumin.2014.01.063
  • Cui, F. L., Wang, J. L., Cui, Y. R., & Li, J. P. (2006). Fluorescent investigation of the interactions between N-(p-chlorophenyl)-N′-(1-naphthyl) thiourea and serum albumin: Synchronous fluorescence determination of serum albumin. Analytica Chimica Acta, 571, 175–183.10.1016/j.aca.2006.05.002
  • Curry, S., Brick, P., & Franks, N. P. (1999). Fatty acid binding to human serum albumin: New insights from crystallographic studies. Biochimica et Biophysica Acta (BBA) – Molecular and Cell Biology of Lipids, 1441, 131–140.10.1016/S1388-1981(99)00148-1
  • Curry, S., Mandelkow, H., Brick, P., & Franks, N. (1998). Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nature Structural Biology, 5, 827–835.10.1038/1869
  • Cyril, L., Earl, J. K., & Sperry, W. M. (1961). Biochemists’ handbook. London: E. & F.N. Spon, p. 84.
  • Dilovic, I., Ruccic, M., Vrdoljak, V., Karaljevic, S., & Cindric, M. (2008). Novel thiosemicarbazone derivatives as potential antitumor agents: Synthesis, physicochemical and structural properties, DNA interactions and ant proliferative activity. Bioorganic & Medicinal Chemistry, 6, 5189–5198.
  • Ding, F., Huang, J., Lin, J., Li, Z. H., Liu, F., Jiang, Z. H., & Sun, Y. (2009). A study of the binding of C.I. Mordant Red 3 with bovine serum albumin using fluorescence spectroscopy. Dyes Pigments, 82, 65–70.10.1016/j.dyepig.2008.11.003
  • Ding, F., Zhang, L., Diao, J. X., Li, X. N., Ma, L., & Sun, Y. (2012). Human serum albumin stability and toxicity of anthraquinone dye alizarin complexone: An albumin–dye model. Ecotoxicology and Environmental Safety, 79, 238–246.10.1016/j.ecoenv.2012.01.009
  • Domotor, O., Tuccinardi, T., Karcz, D., Walsh, M., Creaven, B. S., & Enyedy, É. A. (2014). Interaction of anticancer reduced Schiff base coumarin derivatives with human serum albumin investigated by fluorescence quenching and molecular modeling. Bioorganic Chemistry, 52, 16–23.10.1016/j.bioorg.2013.10.003
  • Elford, H. L., Frees, M., Passamani, E., & Morris, H. P. (1970). Ribonucleotide reductase and cell proliferation: Variations of ribonucleotide reductase activity with tumor growth rate in a series of rat hepatomas. Journal of Biological Chemistry, 245, 5228–5233.
  • Förster, T. (1965). Delocalized excitation and excitation transfer. In O. Sinanoglu (Ed.), Modern quantum chemistry (Vol. 3, pp. 93–137). New York, NY: Academic Press.
  • Garg, A., Mark Manidhar, D., Gokara, M., Malleda, C., Suresh Reddy, C., & Subramanyam, R. (2013). Elucidation of the binding mechanism of coumarin derivatives with human serum albumin. PLoS One, 8, e63805.10.1371/journal.pone.0063805
  • Garland, C. W., & Nibler, J. W., Shoemaker, D. P. (2003). Experiments in physical chemistry (7th ed.). Boston, MA: McGraw-Hill.
  • Ge, F., Chen, C. H., Liu, D., Han, B., Xiong, X., & Zhao, S. H. (2010). Study on the interaction between theasinesin and human serum albumin by fluorescence spectroscopy. Journal of Luminescence, 130, 168–173.10.1016/j.jlumin.2009.08.003
  • Guo, X., Li, X., Jiang, Y., Yi, L., Wu, Q., Chang, H., … Zhou, N. (2014). A spectroscopic study on the interaction between p-nitrophenol and bovine serum albumin. Journal of Luminescence, 149, 353–360.10.1016/j.jlumin.2014.01.036
  • Iranfar, H., Rajabi, O., Salari, R., & Chamani, J. (2012). Probing the interaction of human serum albumin with ciprofloxacin in the presence of silver nanoparticles of three sizes: Multispectroscopic and potential investigation. The Journal of Physical Chemistry B, 116, 1951–1964.10.1021/jp210685q
  • Kalinowski, D. S., & Richardson, R. (2005). The evolution of iron chelators for the treatment of iron overload disease and cancer. Pharmacological Reviews, 57, 547–583.10.1124/pr.57.4.2
  • Karthikeyan, S., Chinnathambi, S., Kannan, A., Rajakumar, P., Velmurugan, D., Bharanidharan, G., … Ganesan, S. (2015). Investigation of optical spectroscopic and computational binding mode of bovine serum albumin with 1, 4-bis ((4-((4-heptylpiperazin-1-yl) methyl)-1H-1, 2, 3-triazol-1-yl) methyl) benzene. Journal of Biochemical and Molecular Toxicology, 29, 373–381. doi:10.1002/jbt.21704
  • Katrahalli, U., Jaldappagari, S., & Kalanur, S. H. S. (2010). Study of the interaction between fluoxetine hydrochloride and bovine serum albumin in the imitated physiological conditions by multi-spectroscopic methods. Journal of Luminescence, 130, 211–216.10.1016/j.jlumin.2009.07.033
  • Klayman, D. L., Bartosevich, J. P., Griffin, T. S., & Mason, C. J. (1979). 2-Acetylpyridine thiosemicarbazones. 1. A new class of potential antimalarial agents. Journal of Medicinal Chemistry, 22, 855–862.10.1021/jm00193a020
  • Kuznetsova, I. M., Sulatskaya, A, I., Povarova, O. I., & Turoverov, K, K. (2012). Reevaluation of ANS binding to human and bovine serum albumins: Key role of equilibrium microdialysis in ligand–receptor binding characterization. PLoS One, 7, e40845.10.1371/journal.pone.0040845
  • Lakowicz, J. R. (2006). Principles of fluorescence spectroscopy (3rd ed.). New York, NY: Springer Science+Business Media.10.1007/978-0-387-46312-4
  • Mylonas, S., & Mamalis, A. (2005). Synthesis and antitumor activity of new thiosemicarbazones of 2-acetylimidazo[4,5-b]pyridine. Journal of Heterocyclic Chemistry, 42, 1273–1281.10.1002/jhet.v42:7
  • Paramaguru, G., Kathiravan, A., Selvaraj, S., Venuvanalingam, P., & Renganathan, R. (2010). Interaction of anthraquinone dyes with lysozyme: Evidences from spectroscopic and docking studies. Journal of Hazardous Materials, 175, 985–991.10.1016/j.jhazmat.2009.10.107
  • Peters, T. (1995). All about albumin: biochemistry, genetics and medical applications. Cooperstown, NY: The Mary Imogene Bassett Hospital.
  • Prichard, M. N., & Shipman, C. (1995). Ribonucleotide reductase: An important enzyme in the replication of herpes simplex virus type 1 and a target for antiviral chemotherapy. Chemotherapy, 41, 384–395.10.1159/000239371
  • Qian, X., Dan-Dan, D., Zhi-Juan, C., Qiong, X., Jian-Ying, L., & Jian-ZhongChin, L. (2010). Interaction between serum albumin and four flavones by fluorescence spectroscopy and molecular docking. Journal of Analytical Chemistry, 38, 483–487.
  • Rinco, O., Brenton, J., Douglas, A., Maxwell, A., Henderson, M., Indrelie, K., … Widin, J. (2009). The effect of porphyrin structure on binding to human serum albumin by fluorescence spectroscopy. Journal of Photochemistry and Photobiology A: Chemistry, 208, 91–96.10.1016/j.jphotochem.2009.08.009
  • Równicka-Zubik, J., Sułkowska, A., Bojko, B., Maciążek-Jurczyk, M., Pożycka, J., Pentak, D., & Sułkowski, W. W. (2009). Binding of 6-propyl-2-thiouracil to human serum albumin destabilized by chemical denaturants. Journal of Photochemistry and Photobiology B: Biology, 97, 54–59.10.1016/j.jphotobiol.2009.08.001
  • Sarzehi, S., & Chamani, J. (2010). Investigation on the interaction between tamoxifen and human holo-transferrin: Determination of the binding mechanism by fluorescence quenching, resonance light scattering and circular dichroism methods. International Journal of Biological Macromolecules, 47, 558–569.10.1016/j.ijbiomac.2010.08.002
  • Sattar, Z., Iranfar, H., Asoodeh, A., Saberi, M. R., Mazhari, M., & Chamani, J. (2012). Interaction between holo transferrin and HSA–PPIX complex in the presence of lomefloxacin: An evaluation of PPIX aggregation in protein–protein interactions. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, 1089–1100.10.1016/j.saa.2012.07.034
  • Sebastian, L., Desai, A., Shampur, M. N., Perumal, Y., Sriram, D., & Vasanthapuram, R. (2008). N-methylisatin-beta-thiosemicarbazone derivative (SCH 16) is an inhibitor of Japanese encephalitis virus infection in vitro and in vivo. Virology Journal, 5–64, 1–12. doi:10.1186/1743-422X-5-64.10.1186/1743-422X-5-64
  • Shao, J., Zhou, B., Di Billo, A. J., Zhu, L. J., Wang, T., Qi, C., … Yen, Y. (2006). A ferrous-triapine complex mediates formation of reactive oxygen species that inactivate human ribonucleotide reductase. Molecular Cancer Therapeutics, 5, 586–592.10.1158/1535-7163.MCT-05-0384
  • Sidwell, R. W., Huffman, J. H., Schafer, T. W., & Shipman, C. (1990). Influence of vehicle on topical efficacy of 2-acetylpyridine thiosemicarbazone and related derivatives on in vivo type 2 herpes simplex virus infections. Chemotherapy, 36, 58–69.10.1159/000238749
  • Sudlow, G., Birkett, D., & Wade, D. (1976). Further characterization of specific drug binding sites on human serum albumin. Molecular Pharmacology, 12, 1052–1061.
  • Sugio, S., Kashima, A., Mochizuki, S., Noda, M., & Kobayashi, K. (1999). Crystal structure of human serum albumin at 2.5 A resolution. Protein Engineering Design and Selection, 12, 439–446.10.1093/protein/12.6.439
  • Tang, J., Luan, F., & Chen, F. (2006). Binding analysis of glycyrrhetinic acid to human serum albumin: Fluorescence spectroscopy, FTIR, and molecular modelling. Bioorganic & Medicinal Chemistry, 14, 3210–3217.
  • Teitz, Y., Ronen, D., Vansover, A., Stematsky, T., & Riggs, J. L. (1994). Inhibition of human immunodeficiency virus by N-methylisatin-β4′:4′-diethylthiosemicarbazone and N-allylisatin-β-4′:4′-diallythiosemicarbazone. Antiviral Research, 24, 305–314.10.1016/0166-3542(94)90077-9
  • Valeur, B., & Brochon, J. C. (1999). New trends in fluorescence spectroscopy (6th ed.). Berlin: Springer Press. p. 25.
  • Wallace, A. C., Laskowski, R. A., & Thornton, J. M. (1995). LIGPLOT: A program to generate schematic diagrams of protein–ligand interactions. Protein Engineering, 8, 127–134.10.1093/protein/8.2.127
  • Wang, Z. M., Ho, J. X., Ruble, J. R., Rose, J., Rüker, F., Ellenburg, M., … Carter, D. C. (2013). Structural studies of several clinically important oncology drugs in complex with human serum albumin. Biochimica et Biophysica Acta (BBA) – General Subjects, 1830, 5356–5374.10.1016/j.bbagen.2013.06.032
  • Wang, Y. Q., Zhang, H. M., & Zhou, Q. H. (2009). Investigation of the interaction between pentachlorophenol and human serum albumin using spectral methods. Journal of Molecular Structure, 932, 31–37.10.1016/j.molstruc.2009.05.036
  • Wei, Y., Li, J., Dong, C., Shuang, S., Liu, D., & Huie, C. (2006). Investigation of the association behaviors between biliverdin and bovine serum albumin by fluorescence spectroscopy. Talanta, 70, 377–382.10.1016/j.talanta.2006.02.052
  • World Health Organization. Cancer: Data and country profiles. Retrieved from http://www.who.int/cancer/country/en/
  • Wu, F., Ji, Z., Wu, Y., & Wan, X. (2006). Interaction of ICT receptor with serum albumins in aqueous buffer. Chemical Physics Letters, 424, 387–393.10.1016/j.cplett.2006.05.019
  • Xiang, Y., & Wu, F. (2010). Study of the interaction between a new Schiff-base complex and bovine serum albumin by fluorescence spectroscopy. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 77, 430–436.10.1016/j.saa.2010.06.010
  • Yan-qing, W., Bo-ping, T., Hong-mei, Z., Qiu-hua, Z., & Gen-cheng, Z. J. (2009). Studies on the interaction between imidacloprid and human serum albumin: Spectroscopic approach. Journal of Photochemistry and Photobiology B: Biology, 94, 183–190.
  • Yeggoni, D. P., Gokara, M., Mark Manidhar, D., Rachamallu, A., Nakka, S., Reddy, C. S., & Subramanyam, R. (2014). Binding and molecular dynamics studies of 7-hydroxycoumarin derivatives with human serum albumin and its pharmacological importance. Molecular Pharmaceutics, 11, 1117–1131.10.1021/mp500051f
  • Yu, Y., Wong, J., Lovejoy, D. B., Kalinowski, D. S., & Richardson, D. R. (2006). Chelators at the cancer coalface: Desferrioxamine to triapine and beyond. Clinical Cancer Research, 12, 6876–6883.10.1158/1078-0432.CCR-06-1954
  • Yue, Y., Zhang, Y., Zhou, L., Qin, J., & Chen, X. (2008). In vitro study on the binding of herbicide glyphosate to human serum albumin by optical spectroscopy and molecular modeling. Journal of Photochemistry and Photobiology B: Biology, 90, 26–32.10.1016/j.jphotobiol.2007.10.003
  • Zhang, H., Chen, T., Zhou, Q., & Wang, Y. (2009). Binding of caffeine, theophylline, and theobromine with human serum albumin: A spectroscopic study. Journal of Molecular Structure, 938, 221–228.10.1016/j.molstruc.2009.09.032
  • Zhang, Y., Li, J. H., Ge, S. H., Liu, X. R., Jiang, F. L., & Liu, Y. (2010). Biophysical studies on the interactions of a classic mitochondrial uncoupler with bovine serum albumin by spectroscopic, isothermal titration calorimetric and molecular modeling methods. Journal of Fluorescence, 21, 475–485.
  • Zhang, G., Que, Q., Pan, J., & Guo, J. (2008). Study of the interaction between icariin and human serum albumin by fluorescence spectroscopy. Journal of Molecular Structure, 881, 132–138.10.1016/j.molstruc.2007.09.002

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