European Journal of Chemistry 2015, 6(4), 451-460 | doi: https://doi.org/10.5155/eurjchem.6.4.451-460.1318 | Get rights and content






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New N(4)-methylthiosemicarbazone derivatives: Synthesis, characterization, structural properties, DNA interactions and antiproliferative activity


Mouayed Hussein (1,*) , Teoh Siang Guan (2)

(1) Department of Chemistry, College of Science, University of Basrah, Basrah, 61001, Iraq
(2) School of Chemical Science, Universiti Sains Malaysia, Minden, Pulau Pinang, 11800, Malaysia
(*) Corresponding Author

Received: 11 Sep 2015 | Revised: 01 Oct 2015 | Accepted: 10 Oct 2015 | Published: 31 Dec 2015 | Issue Date: December 2015

Abstract


Five new thiosemicarbazone compounds derived from N(4)-methylthiosemicarbazide and 5-bromo-2-hydroxybenzaldehyde (1), 2,4-dihydroxybenzaldehyde (2), 3-ethoxy-2-hydroxy benzaldehyde (3), 3-tert-butyl-2-hydroxybenzaldehyde (4), and 2-acetylpyridine (5) have been synthesized. The molecular structures of the prepared compounds were identified using by single crystal X-ray crystallography. The binding properties of the compounds with calf thymus DNA were analyzed by UV, fluorescence titration, and viscosity measurements. The cytotoxic properties of the compounds were tested against human colorectal cell lines (HCT 116). The compounds showed greater pronounced activity than the standard reference drug 5-fluorouracil (IC50 = 7.3 μM). The results showed that the activity strength of these compounds depends on the lipophilic properties that provided by the terminal N(4)-substituent and aromatic ring-substituent, as well as the planarity that provided by the geometrical and conformational structures of the compounds.


Keywords


DNA binding; Electronic transitions; X-ray crystal structure; Fluorescence emissions; Antiproliferative activity; N(4)-Methylthiosemicarbazone

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DOI: 10.5155/eurjchem.6.4.451-460.1318

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Funding information


Universiti Sains Malaysia and the Malaysian Government for a Research Grant, Malaysia

Citations

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[1]. Md. Azharul Arafath, Huey Chong Kwong, Farook Adam
(E)-2-(2-Hydroxy-3-methylbenzylidene)-N-methylhydrazine-1-carbothioamide: supramolecular assemblies in two-dimensions mediated by N—H...S and C—H...π interactions
Acta Crystallographica Section E Crystallographic Communications  75(5), 571, 2019
DOI: 10.1107/S2056989019004444
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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Hussein, M.; Guan, T. Eur. J. Chem. 2015, 6(4), 451-460. doi:10.5155/eurjchem.6.4.451-460.1318
Hussein, M.; Guan, T. New N(4)-methylthiosemicarbazone derivatives: Synthesis, characterization, structural properties, DNA interactions and antiproliferative activity. Eur. J. Chem. 2015, 6(4), 451-460. doi:10.5155/eurjchem.6.4.451-460.1318
Hussein, M., & Guan, T. (2015). New N(4)-methylthiosemicarbazone derivatives: Synthesis, characterization, structural properties, DNA interactions and antiproliferative activity. European Journal of Chemistry, 6(4), 451-460. doi:10.5155/eurjchem.6.4.451-460.1318
Hussein, Mouayed, & Teoh Siang Guan. "New N(4)-methylthiosemicarbazone derivatives: Synthesis, characterization, structural properties, DNA interactions and antiproliferative activity." European Journal of Chemistry [Online], 6.4 (2015): 451-460. Web. 31 May. 2020
Hussein, Mouayed, AND Guan, Teoh. "New N(4)-methylthiosemicarbazone derivatives: Synthesis, characterization, structural properties, DNA interactions and antiproliferative activity" European Journal of Chemistry [Online], Volume 6 Number 4 (31 December 2015)

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DOI Link: https://doi.org/10.5155/eurjchem.6.4.451-460.1318

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