Synthesis, Crystal Structure, Antibacterial and In Vitro Anticancer Activity of Novel Macroacyclic Schiff Bases and Their Cu (II) Complexes Derived from S-Methyl and S-Benzyl Dithiocarbazate

Mohammed Khaled Break and Tan, Yew Fung and Koh, May Zie and Wan, Yong Ho and Mohamed Ibrahim Mohamed Tahir and Omar Ashraf Elfar and Rahamat Unissa Syed and Weam M. A. Khojali and Turki Mubarak Alluhaibi and Bader Huwaimel and Christophe Patrice Andie Wiart and Khoo, Teng-Jin (2023) Synthesis, Crystal Structure, Antibacterial and In Vitro Anticancer Activity of Novel Macroacyclic Schiff Bases and Their Cu (II) Complexes Derived from S-Methyl and S-Benzyl Dithiocarbazate. Molecules, 28. pp. 1-19.

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URL: https://www.mdpi.com/1420-3049/28/13/5009

Abstract

A series of novel macroacyclic Schiff base ligands and their Cu (II) complexes were synthesised via reacting dicarbonyls of varying chain lengths with S-methyl dithiocarbazate (SMDTC) and S-benzyl dithiocarbazate (SBDTC) followed by coordination with Cu (II) ions. X-ray crystal structures were obtained for compound 4, an SBDTC-diacetyl analogue, and Cu7, an SMDTC-hexanedione Cu (II) complex. Anticancer evaluation of the compounds showed that Cu1, an SMDTC-glyoxal complex, demonstrated the highest cytotoxic activity against MCF-7 and MDA-MB-231 breast cancer cells with IC50 values of 1.7 µM and 1.4 µM, respectively. There was no clear pattern observed between the effect of chain length and cytotoxic activity; however, SMDTC-derived analogues were more active than SBDTC-derived analogues against MDA-MB-231 cells. The antibacterial assay showed that K. rhizophila was the most susceptible bacteria to the compounds, followed by S. aureus. Compound 4 and the SMDTC-derived analogues 3, 5, Cu7 and Cu9 possessed the highest antibacterial activity. These active analogues were further assessed, whereby 3 possessed the highest antibacterial activity with an MIC of <24.4 µg/mL against K. rhizophila and S. aureus. Further antibacterial studies showed that at least compounds 4 and 5 were bactericidal. Thus, Cu1 and 3 were the most promising anticancer and antibacterial agents, respectively.

Item Type:	Article
Keyword:	Antibacterial, Anticancer, Copper, Crystallography, Schiff base
Subjects:	R Medicine > R Medicine (General) > R5-920 Medicine (General) R Medicine > RC Internal medicine > RC31-1245 Internal medicine > RC254-282 Neoplasms. Tumors. Oncology Including cancer and carcinogens
Department:	INSTITUTE > Institute for Tropical Biology and Conservation
Depositing User:	SITI AZIZAH BINTI IDRIS -
Date Deposited:	06 Sep 2023 15:41
Last Modified:	06 Sep 2023 15:41
URI:	https://eprints.ums.edu.my/id/eprint/36743

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