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Research Articles

Study on the interaction of taiwaniaquinoids with FTO by spectroscopy and molecular modeling

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Pages 3182-3193 | Received 29 Jul 2016, Accepted 11 Oct 2016, Published online: 28 Oct 2016

References

  • Abdelhameed, A. S., Alanazi, A. M., Bakheit, H., Darwish, H. W., Ghabbour, H. A., & Darwish, I. A. (2017). Fluorescence spectroscopic andmolecular docking studies of the binding interaction between the new anaplastic lymphoma kinase inhibitor crizotinib and bovine serum albumin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 171, 174–182.10.1016/j.saa.2016.08.005
  • Alvarez-Manzaneda, E., Chahboun, R., Alvarez, E., Tapia, R., & Alvarez-Manzaneda, R. (2010). Enantioselective total synthesis of cytotoxic taiwaniaquinones A and F. Chemical Communications, 46, 9244–9246.10.1039/c0cc03763j
  • Becke, A. D. (1993). Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 98, 5648–5652.10.1063/1.464913
  • Bolli, A., Marino, M., Rimbach, G., Fanali, G., Fasano, M., & Ascenzi, P. (2010). Flavonoid binding to human serum albumin. Biochemical and Biophysical Research Communications, 398, 444–449.10.1016/j.bbrc.2010.06.096
  • Chang, C. I., Chang, J. Y., Kuo, C. C., Pan, W. Y., & Kuo, Y. H. (2005). Four New 6-Nor-5(6→7) abeo -abietane Type Diterpenes and Antitumoral Cytotoxic Diterpene Constituents from the Bark of Taiwania cryptomerioides. Planta Medica, 71, 72–76.10.1055/s-2005-837754
  • Chaudhuri, S., Chakraborty, S., & Sengupta, P. K. (2011). Probing the interactions of hemoglobin with antioxidant flavonoids via fluorescence spectroscopy and molecular modeling studies. Biophysical Chemistry, 154, 26–34.10.1016/j.bpc.2010.12.003
  • Chaves, O. A., Jesus, C., Cruz, P., & Sant’Anna, C., Brito R., & Serpa, C. (2016). Evaluation by fluorescence, STD-NMR, docking and semi-empirical calculations of the o-NBA photo-acid interaction with BSA. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 169, 175–181.10.1016/j.saa.2016.06.028
  • Chi, Z. X., & Liu, R. T. (2011). Phenotypic characterization of the binding of tetracycline to human serum albumin by fluorescence spectroscopy and molecular modeling. Biomacromolecules, 12, 203–209.10.1021/bm1011568
  • Chi, Z., Liu, R., Yang, B., & Zhang, H. (2010). Toxic interaction mechanism between oxytetracycline and bovine hemoglobin. Journal of Hazardous Materials, 180, 741–747.10.1016/j.jhazmat.2010.04.110
  • Deng, J., Li, R., Luo, Y., Li, J., Zhou, S., Li, Y., Hu, J., & Li, A. (2013). Divergent total synthesis of taiwaniaquinones A and F and taiwaniaquinols B and D. Organic Letters, 15, 2022–2025.10.1021/ol400717h
  • Fischer, J., Koch, L., Emmerling, C., Vierkotten, J., Peters, T., Bruning, J. C., & Ruther, U. (2009). Inactivation of the Fto gene protects from obesity. Nature, 458, 894–898.10.1038/nature07848
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., & Scuseria, G. E. (2010). Gaussian 09 revision C.01. Wallingford, CT: Gaussian Inc.
  • Gerken, T., Girard, C. A., Tung, Y. C., Webby, C. J., Saudek, V., Hewitson, K. S., … Schofield, C. J. (2007). The obesity-associated FTO gene encodes a 2-oxoglutarate-dependent nucleic acid demethylase. Science, 318, 1469–1472.10.1126/science.1151710
  • Han, Z., Niu, T., Chang, J., Lei, X., Zhao, M., Wang, Q., … Chai, J. (2010). Crystal structure of the FTO protein reveals basis for its substrate specificity. Nature, 464, 1205–1209.10.1038/nature08921
  • Jia, G. F., Yang, C. G., Yang, S. D., Jian, X., Yi, C. Q., Zhou, Z. Q., & He, C. (2008). Oxidative demethylation of 3-methylthymine and 3-methyluracil in single-stranded DNA and RNA by mouse and human FTO. FEBS Letters, 582, 3313–3319.10.1016/j.febslet.2008.08.019
  • Jiang, Y. L. (2008). Design, synthesis and spectroscopic studies of resveratrol aliphatic acid ligands of human serum albumin. Bioorganic & Medicinal chemistry letters, 16, 6406–6414.10.1016/j.bmc.2008.05.002
  • Kandagal, P. B., Seetharamappa, J., Shaikh, S. M. T., & Manjunatha, D. H. (2007). Binding of trazodone hydrochloride with human serum albumin: A spectroscopic study. Journal of Photochemistry and Photobiology A: Chemistry, 185, 239–244.10.1016/j.jphotochem.2006.06.015
  • Kawazoe, K., Yamamoto, M., Takaishi, Y., Honda, G., Fujita, T., Sezik, E., & Yesilada, E. (1999). Rearranged abietane-type diterpenes from Salvia dichroantha. Phytochemistry, 50, 493–497.10.1016/S0031-9422(98)00471-3
  • Lakowicz, J. R. (2006). Principles of Fluorescence Spectroscopy (3rd ed.). New York, NY: Springer, pp. 278–290.
  • Lehrer, S. S. (1971). Solute perturbation of protein fluorescence. Quenching of the tryptophyl fluorescence of model compounds and of lysozyme by iodide ion. Biochemistry, 10, 3254–3263.10.1021/bi00793a015
  • Li, X. X., Yan, Y. X., & Ye, L. (2010). Study on the interaction of raloxifene and bovine serum albumin by the tachiya model. Journal of Solution Chemistry, 39, 1187–1199.10.1007/s10953-010-9571-4
  • Liao, X., Stanley, L. M., & Hartwig, J. F. (2011). Enantioselective total syntheses of (-)-taiwaniaquinone H and (-)-taiwaniaquinol B by iridium-catalyzed borylation and palladium-catalyzed asymmetric α-arylation. Journal of the American Chemical Society, 133, 2088–2091.10.1021/ja110215b
  • Lin, W. H., Fang, J. M., & Cheng, Y. S. (1995). Uncommon diterpenes with the skeleton of six-five-six fused-rings from Taiwania cryptomerioides. Phytochemistry, 40, 871–873.10.1016/0031-9422(95)00358-E
  • Liu, J. M., Yue, Y. Y., Wang, J., Yan, X. Y., Liu, R., Sun, Y. Y., & Li, X. G. (2015). Study of interaction between human serum albumin and three phenanthridine derivatives: Fluorescence spectroscopy and computational approach. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 145, 473–481.10.1016/j.saa.2015.03.069
  • Liu, B. M., Zhang, J., Bai, C. L., Wang, X., Qiu, X. Z., Wang, X. L., … Liu, B. (2015). Spectroscopic study on flavonoid-drug interactions: Competitive binding for human serum albumin between three flavonoid compounds and ticagrelor, a new antiplatelet drug. Journal of Luminescence, 168, 69–76.10.1016/j.jlumin.2015.07.037
  • Majetich, G., & Shimkus, J. M. (2010). The taiwaniaquinoids: A review. Journal of Natural Products, 73, 284–298.10.1021/np9004695
  • Meng, Y. G., Liu, Y. Z., Lv, Z. G., Wang, J. Q., Wang, Y. Y., Song, C. J., & Chang, J. B. (2015). Concise synthesis of taiwaniaquinol B and 5-epi-taiwaniaquinone G. Natural Product Communications, 10, 2031–2032.
  • Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. K. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30, 2785–2791.10.1002/jcc.v30:16
  • Ohtsu, H., Iwamoto, M., Ohishi, H., Matsunaga, S., & Tanaka, R. (1999). Standishinal, a novel carbon skeletal diterpene from the bark of Thuja standishii (Gord.) Carr. Tetrahedron Letters, 40, 6419–6422.10.1016/S0040-4039(99)01191-0
  • Ozeki, M., Satake, M., Toizume, T., Fukutome, S., Arimitsu, K., Hosoi, S., … Yamashita, M. (2013). First asymmetric total synthesis of (+)-taiwaniaquinol D and (-)-taiwaniaquinone D by using intramolecular Heck reaction. Tetrahedron, 69, 3841–3846.10.1016/j.tet.2013.03.051
  • Ross, P. D., & Subramanian, S. J. (1981). Thermodynamics of protein association reactions: Forces contributing to stability. Biochemistry, 20, 3096–3102.10.1021/bi00514a017
  • Samari, F., Shamsipur, M., Hemmateenejad, B., Khayamian, T., & Gharaghani, S. (2012). Investigation of the interaction between amodiaquine and human serum albumin by fluorescence spectroscopy and molecular modeling. European Journal of Medicinal Chemistry, 54, 255–263.10.1016/j.ejmech.2012.05.007
  • Song, S. M., Hou, X. L., Wu, Y. B., Shuang, S. M., Yang, C., & Inoue, Y. (2009). Study on the interaction between methyl blue and human serum albumin by fluorescence spectrometry. Journal of Luminescence, 129, 169–175.10.1016/j.jlumin.2008.09.008
  • Stratigopoulos, G., Padilla, S. L., LeDuc, C. A., Watson, E., Hattersley, A. T., McCarthy, M. I., … Leibel, R. L. (2008). Regulation of Fto/Ftm gene expression in mice and humans. American Journal of Physiology Regulatory, Integrative and Comparative Physiology, 294, R1185–R1196.10.1152/ajpregu.00839.2007
  • Tapia, R., Guardia, J. J., Alvarez, E., Haidöur, A., Ramos, J. M., Alvarez-Manzaneda, R., Chahboun, R., & Alvarez-Manzaneda, E. (2012). General access to taiwaniaquinoids based on a hypothetical abietane C7–C8 cleavage biogenetic pathway. The Journal of Organic Chemistry, 77, 573–584.10.1021/jo202163y
  • Tiwari, A., Krzysik-Walker, S. M., & Ramachandran, R. (2012). Domestic Animal Endocrinology, 42, 1–10.10.1016/j.domaniend.2011.08.001
  • Wang, R., Chai, Y., Wang, R., Zhang, L., Wu, J., & Chang, J. (2012). Study of the interaction between bovine serum albumin and analogs of Biphenyldicarboxylate by spectrofluorimetry. Spectrochimica Acta A, 96, 324–331.10.1016/j.saa.2012.05.030
  • Wang, J. Q., Wang, J., Li, C. W., Meng, Y. G., Wu, J., Song, C. J., & Chang, J. B. (2014). Synthesis of 5-epi-Taiwaniquinone G. Journal of Organic Chemistry, 9, 1911–1921.
  • Yang, L., Yu, W., Li, Z., Zhang, X., Ren, T., Zhang, L., … Chang, J. (2016). Comparative study of the binding between FTO protein and five pyrazole derivatives by spectrofluorimetry. Journal of Molecular Liquids, 218, 156–165.10.1016/j.molliq.2016.02.031
  • Yaseen, Z., Banday, A. R., Hussain, M. A., Tabish, M., & Kabir-ud-Din (2014). Determination of the cationic amphiphilic drug-DNA binding mode and DNA-assisted fluorescence resonance energy transfer amplification. Spectrochimica Acta Part A, 122, 553–564.10.1016/j.saa.2013.11.030
  • Zhang, Q. D., Huang, Y. Y., Zhao, R., Liu, G. Q., & Chen, Y. (2008). Determining binding sites of drugs on human serum albumin using FIA-QCM. Biosensors & Bioelectronics, 24, 48–54.10.1016/j.bios.2008.03.009
  • Zhang, X., & Jin, J. (2008). Binding analysis of pazufloxacin mesilate to catalase using spectroscopic methods. Journal of Molecular Structure, 882, 96–100.
  • Zhang, H. M., Wang, Y. Q., & Zhou, Q. H. (2010). Fluorimetric study of interaction of benzidine with trypsin. Journal of Luminescence, 130, 781–786.10.1016/j.jlumin.2009.11.032

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