Synthesis, Characterization, in vitro Antifungal Activities and Calf Thymus DNA Interactions of Two Different Hydroxy Benzaldehyde Derivative Schiff Bases from Sulfamethizole: Electrochemical, Spectroscopic and Biological Study
- 9 Downloads
In the present work, the Schiff bases were synthesized by reacting sulfamethizole (SMTZ) with two different hydroxy benzaldehydes (2,3-dihydroxy benzaldehyde (DHBA) and 2,4,6-trihydroxy benzaldehyde (THBA)) and characterized by elemental analysis, 1H-NMR and IR spectroscopies. From the obtained data, it was suggested that 4,6-dihydroxy salicylaldehyde reacted with both primary and secondary amine groups of SMTZ. The binding properties between the synthesized Schiff bases and calf thymus DNA (CT-DNA) at the physiological pH (7.4) was investigated by using cyclic voltammetry and UV-Vis spectroscopy techniques. The experimental results verify that the Schiff bases can bind to CT-DNA by electrostatic mode in 1 : 1 stoichiometry. Antifungal activities of the synthesized Schiff bases against Candida albicans ATCC 10231 were studied and their minimum inhibitory concentrations (MIC) were also determined. The MIC value of the Schiff base 1 synthesized from DHBA is smaller than that of the Schiff base 2 obtained from THBA. Although Schiff base 2 binds to CT-DNA with a higher affinity than Schiff base 1, it is less effective than Schiff base 1 against Candida albicans.
Keywordscalf thymus DNA interaction salicylaldehyde derivatives Schiff bases sulfamethizole
Unable to display preview. Download preview PDF.
This study was presented in part and in poster form at International Eurasian Conference on Biological and Chemical Sciences (EurasianBioChem 2018), 26–27 April 2018, Ankara/TURKEY.
- 1.Khan, F., Khan, S., Athar, A., Ahmed, W., Zia-ul-Haq, and Khan, Z., Synthesis, spectral characterization and antibacterial study of a Schiff base metal complexes derived from N-[(E)-(5-chloro-2-hydroxyphenyl)methylidene]-4-nitrobenzenesulfonamide, Amer.- Eur. J. Agric. Environ. Sci., 2015, vol. 15, p. 216.Google Scholar
- 3.Xiao, Y.-J., Diao, Q.-C., Liang, Y.-H., and Zeng, K., Two novel Co(II) complexes with two different Schiff bases: inhibiting growth of human skin cancer cells, Braz. J. Med. Biol. Res., 2017, vol. 50, p. e6390.Google Scholar
- 9.Ahmadi, F., Alizadeh, A.A., Bakhshandeh-Saraskanrood, F., Jafari, B., and Khodadadian, M., Experimental and computational approach to the rational monitoring of hydrogen-bonding interaction of 2-imidazoli-dinethione with DNA and guanine, Food Chem. Toxicol., 2010, vol. 48, p. 29.CrossRefGoogle Scholar
- 10.Ahmadi, F. and Jafari, B., Voltammetry and spectroscopy study of in vitro interaction of fenitrothion with DNA, Electroanalysis, 2011, vol. 23, p. 675.Google Scholar
- 11.Cox, P.J., Psomas, G., and Bolos, C.A., Characterization and DNA-interaction studies of 1,1-dicyano-2,2-ethylene dithiolate Ni(II) mixed-ligand complexes with 2-amino-5-methyl thiazole, 2-amino-2-thiazoline and imidazole. Crystal structure of [Ni(i-MNT)(2a-5mt)2], Bioorg. Med. Chem., 2009, vol. 17, p. 6054.CrossRefGoogle Scholar
- 12.Gao, F., Wang, Q., Zheng, M., Li, S., Chen, G., Jiao, K., and Gao, F., Electrochemical studies on the recognition of a ternary copper complex to single-stranded DNA and double-stranded DNA, Int. J. Electrochem. Sci, 2011, vol. 6, p. 1508.Google Scholar
- 14.https://pubchem.ncbi.nlm.nih.gov/compound/sulfamethizole#section=Pharmacology-and-Biochemistry. Accessed Feb. 20, 2018.
- 15.Petrikaitè, V., Tarasevičius, E., and Pavilonis, A., New thiazolidones-4 with sulfamethizole-2 substituent as potential antifungal and antimicrobial preparations, Biologija, 2007, vol. 53, p. 45.Google Scholar
- 16.Pehlivan, V, Biçer, E., Genç Bekiroğlu, Y., and Dege, N., Synthesis, in vitro antibacterial activity and calf thymus DNA binding of sulfamethizole-based Schiff bases, Abstract E-Book, 4th Int. Türk-Pak Conf. on Chemical Sciences (ITPCCS 2017), Konya, Oct. 26–28, 2017, PP017.Google Scholar
- 17.Omanović, D. and Branica, M., Automation ofvoltammetric measurements by polarographic analyser PAR 384B, Croat. Chem. Acta, 1998, vol. 71, p. 421.Google Scholar
- 19.Naik, T.R.R. and Naik, H.S.B., Electrochemical investigation of DNA binding on carbaldehyde oxime by cyclic voltammetry, Int. J. Electrochem. Sci., 2008, vol. 3, p. 409.Google Scholar
- 30.Clinical and Laboratory Standards Institute (CLSI). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, 3rd ed., Wayne: Clinical and Laboratory Standards Institute, 2008. Approved Standard no. M27-S3.Google Scholar
- 32.Gosser, D.K., Cyclic Voltammetry:Simulation and Analysis of Reaction Mechanisms, New York: VCH, 1993, p. 43.Google Scholar
- 35.Coşkun, E. and Biçer, E., Sülfatiazolün Ni(II) iyonlariyla etkileşiminin voltametrik incelenmesi, Erciyes Univ. J. Inst. Sci. Technol., 2014, vol. 30, p. 296.Google Scholar
- 39.Chambers, J.Q., Organic sulphur compounds, in Encyclopedia of Electrochemistry of the Elements, Bard, A.J. and Lund, H., Eds., vol. XII: Organic Section, New York: M. Dekker, 1979, chapter XII-3, p. 371.Google Scholar
- 44.Pakravan, P. and Masoudian, S., Study on the interaction between isatin-ß-thiosemicarbazone and calf thymus DNA by spectroscopic techniques, Iran. J. Pharm. Res., 2015, vol. 14, p. 111.Google Scholar
- 45.Mallappa, M., Gowda, B.G., and Mahesh, R.T., Mechanism of interaction of antibacterial drug moxifloxacin with herring sperm DNA: electrochemical and spectroscopic studies, Der Pharma Chem., 2014, vol. 6, p. 398.Google Scholar
- 46.Jiang, Y., Yuan, Y., Wang, K., Li, H., Xu, C., and Yang, X., Spectroscopic and electrochemical studies on the binding of pyrocatechol violet with telomere DNA and its application, Int. J. Electrochem. Sci., 2012, vol. 7, p. 10933.Google Scholar