Synthesis, characterization and DNA binding study of silver(I) complexes with 2'-thiazolylazo aminoanisole compounds (TAAA)
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Published
May 6, 2021
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Abstract
Bioinorganic chemistry has been attracted for many years on the biological studies of transition metal complexes, including those based on the silver(I) ion. Since azo compounds have significant biological activity, the development of new silver(I) complexes with such compounds might be of interest. Azo dyes 2-(2'-thiazolylazo)-5-aminoanisole (p-TAAA) and 4-(2'-thiazolylazo)-3-aminoanisole (o-TAAA) and their silver(I) complexes; [Ag-(p-TAAA)] and [Ag-(o-TAAA)] have been prepared and characterized by elemental analysis, mass spectrometry, IR spectroscopy, 1H and 13C NMR spectroscopy. The results reveal structures of the synthesized complexes in which silver(I) ion have bound to two molecules of 2'-thiazolylazo aminoanisole compounds with nitrogen of azo group and sulfur of thiazole ring as donor atoms. The biological activity of such complexes was examined using calf thymus DNA (CT-DNA). The mode of DNA binding interaction was investigated by electronic absorption titration. The results indicate that the synthesized silver(I) complexes bind to CT-DNA via intercalative mode of binding with binding constants of 1.44 x 105 M-1 for [Ag-(p-TAAA)] and 9.77 x 104 M-1 for [Ag-(o-TAAA)], respectively.
Keywords: Thiazolylazo, Silver(I) complexes, DNA binding, Electronic absorption titration, Binding constants (Kb)
References
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Tang, T. C., & Huang, H. J. (1999). Electrochemical Studies of the Intercalation of Ethidium Bromide to DNA. Electroanalysis, 11(16), 1185-1190.
Wolfe, A., Shimer Jr., G. H., & Meehan, T. (1987). Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry, 26(20), 6392–6396.
Zeglis, B. M., Pierre, V. C., & Barton, J. K. (2007). Metallo-intercalators and metallo-insertors. Chemical Communications, 44, 4565-4579. doi: 10.1039/b710949k
Zollinger, H. (2003). Color Chemistry Syntheses, Properties, Application of Organic Dyes and Pigments. New York: Wiley-VCH.
Benkhaya, S., El Harfi, S., & El Harf, A. (2017). Classifications, properties and applications of textile dyes: A review. Applied Journal of Environmental Engineering Science, 3, 311-320.
Cavicchioli, M., Massabni, A. C., Heinrich, T. A., Costa-Neto, C. M., Abrão, E. P., Fonseca, B. A. L., … Leite, C. Q. F. (2010). Pt(II) and Ag(I) complexes with acesulfame: Crystal structure and a study of their antitumoral, antimicrobial and antiviral activities. Journal of Inorganic Biochemistry, 104(5), 533-540.
Chhetri, A., Chettri, S., Rai, P., Mishra, D. K., Sinha, B., & Brahman, D. (2021). Synthesis, characterization and computational study on potential inhibitory action of novel azo imidazole derivatives against COVID-19 main protease (Mpro: 6LU7). Journal of Molecular Structure, 1225, 129230.
Clark, M. (2011). Handbook of Textile and Industrial Dyeing: Volume 1 Principles, Processes and Types of Dyes. Oxford: Woodhead Publishing.
El-Sonbati, A. Z., Diab, M. A., El-Bindary, A. A., Shoair, A. F., Hussein, M. A., & El-Boz, R. A. (2017). Spectroscopic, thermal, catalytic and biological studies of Cu(II) azo dye complexes. Journal of Molecular Structure, 1141, 186-203. doi: 10.1016/j.molstruc.2017.03.082
El-Wakiel, N. A., Rizk, H. F., & Ibrahim, S. A. (2017). Synthesis and characterization of metal complexes of azo dye based on 5-nitro-8-hydroxyquinoline and their applications in dyeing polyester fabrics. Applied Organometallic Chemistry, 31(10), 3723.
Li, Y. T., Song, C. H., Wang, Y. Q., Wei, Y., Wei, Y. J., & Hu, Y. Z. (2007). High photoluminescence quantum yield of TiO2 nanocrystals prepared using an alcohothermal method. Luminescence, 22(6), 540-545. doi: 10.1002/bio.997
Mahmoud, W. H., Omar, M. M., & Sayed, F. N. (2016). Synthesis, spectral characterization, thermal, anticancer and antimicrobial studies of bidentate azo dye metal complexes. Journal of Thermal Analysis and Calorimetry, 124(2), 1071-1089. doi: 10.1007/s10973-015-5172-1
Mathur, S., & Tabassum, S. (2008). Template synthesis of novel carboxamide dinuclear copper (II) complex: spectral characterization and reactivity towards calf-thymus DNA. Biometals, 21(3), 299-310. doi: 10.1007/s10534-007-9119-2
Mittal, A., Kurup, L., & Mittal, J. (2007). Freundlich and Langmuir adsorption isotherms and kinetics for the removal of Tartrazine from aqueous solutions using hen feathers. Journal of Hazardous Materials, 146(1-2), 243-248. doi: 10.1016/j.jhazmat.2006.12.012
Nath, M., Singh, H., Eng, G., & Song, X. Q. (2008). New di- and triorganotin(IV) derivatives of tyrosinylphenylalanine as models for metal-protein interactions: Synthesis and structural characterization. Crystal structure of Me2Sn(Tyr-Phe)MeOH. Journal of Organometallic Chemistry, 693(15), 2541-2550. doi: 10.1016/j.jorganchem.2008.04.032
Nawaz, S., Isab, A. A., Merz, K., Vasylyeva, V., Metzler-Nolte, N., Saleem, M., & Ahmad, S. (2011). Synthesis, characterization and antimicrobial studies of mixed ligand silver(I) complexes of triphenylphosphine and heterocyclic thiones: Crystal structure of bis[{(mu(2)-diazinane-2-thione)(diazinane-2-thione)(triphenylphosphine)silver(I) nitrate}]. Polyhedron, 30(9), 1502-1506. doi: 10.1016/j.poly.2011.02.054
Prakash, S., Somiya, G., Elavarasan, N., Subashini, K., Kanaga, S., Dhandapani, R., … Sujatha, V. (2020). Synthesis and characterization of novel bioactive azo compounds fused with benzothiazole and their versatile biological applications. Journal of Molecular Structure, 1224, 129016.
Pyle, A. M., Rehmann, J. P., Meshoyrer, R., Kumar, C. V., Turro, N. J., & Barton J. K. (1989). Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA. Journal of the American Chemical Society, 111 (8), 3051-3058.
Reichmann, M. E., Rice, C. A., Thomas, C. A., & Doty, P. (1954). A Further Examination of the Molecular Weight and Size of Deoxypentose Nucleic Acid. Journal of the American Chemical Society, 76, 3047-3053.
Rendosova, M., Vargova, Z., Sabolova, D., Imrichova, N., Hudecova, D., Gyepes, R., & Elefantova, K. (2018). Silver pyridine-2-sulfonate complex-its characterization, DNA binding, topoisomerase I inhibition, antimicrobial and anticancer response. Journal of Inorganic Biochemistry, 186, 206-216. doi: 10.1016/j.jinorgbio.2018.06.006
Robert, T. M., Robert, N. B., & Bhattacharjee, S. K. (2011). Organic Chem. New Delhi: Prentice Hall.
Tang, T. C., & Huang, H. J. (1999). Electrochemical Studies of the Intercalation of Ethidium Bromide to DNA. Electroanalysis, 11(16), 1185-1190.
Wolfe, A., Shimer Jr., G. H., & Meehan, T. (1987). Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry, 26(20), 6392–6396.
Zeglis, B. M., Pierre, V. C., & Barton, J. K. (2007). Metallo-intercalators and metallo-insertors. Chemical Communications, 44, 4565-4579. doi: 10.1039/b710949k
Zollinger, H. (2003). Color Chemistry Syntheses, Properties, Application of Organic Dyes and Pigments. New York: Wiley-VCH.
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How to Cite
PINCHAIPAT, Bussaba et al.
Synthesis, characterization and DNA binding study of silver(I) complexes with 2'-thiazolylazo aminoanisole compounds (TAAA).
Naresuan University Journal: Science and Technology (NUJST), [S.l.], v. 29, n. 4, p. 62-72, may 2021.
ISSN 2539-553X.
Available at: <https://www.journal.nu.ac.th/NUJST/article/view/Vol-29-No-4-2021-62-72>. Date accessed: 19 apr. 2024.
doi: https://doi.org/10.14456/nujst.2021.36.