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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

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Abstract

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.

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Acknowledgments

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.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, Atakum-Samsun, 55139, Turkey

    Ender Biçer & Vahide Pehlivan

  2. Department of Herbal and Animal Production, Bafra Vocational School, Ondokuz Mayıs University, Bafra-Samsun, 55400, Turkey

    Yeliz Genç Bekiroğlu

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  1. Ender Biçer
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  2. Vahide Pehlivan
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Correspondence to Ender Biçer.

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Published in Russian in Elektrokhimiya, 2019, Vol. 55, No. 5, pp. 587–598.

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Biçer, E., Pehlivan, V. & Bekiroğlu, Y.G. 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. Russ J Electrochem 55, 419–428 (2019). https://doi.org/10.1134/S1023193519050045

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