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

A series of novel macroacyclic Schiff base ligands and their Cu (II) complexes were synthesised via reacting dicarbonyls of varying chain lengths with -methyl dithiocarbazate (SMDTC) and -benzyl dithiocarbazate (SBDTC) followed by coordination with Cu (II) ions. X-ray crystal structures were obtaine...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2023-06, Vol.28 (13), p.5009
Main Authors: Break, Mohammed Khaled Bin, Fung, Tan Yew, Koh, May Zie, Ho, Wan Yong, Tahir, Mohamed Ibrahim Mohamed, Elfar, Omar Ashraf, Syed, Rahamat Unissa, Khojali, Weam M A, Alluhaibi, Turki Mubarak, Huwaimel, Bader, Wiart, Christophe, Khoo, Teng-Jin
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemistry
antibacterial
Antibacterial activity
Antibacterial agents
anticancer
Antineoplastic Agents - chemistry
Antitumor activity
Bacteria
Biological activity
Breast cancer
Cancer
Coordination Complexes - chemistry
copper
Copper - chemistry
Crystal structure
Crystallography
Cytotoxicity
Diacetyl
Imines
Ligands
Nitrogen
Protons
Schiff base
Schiff Bases - chemistry
Spectrum analysis
Staphylococcus aureus
Sulfur
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Summary:A series of novel macroacyclic Schiff base ligands and their Cu (II) complexes were synthesised via reacting dicarbonyls of varying chain lengths with -methyl dithiocarbazate (SMDTC) and -benzyl dithiocarbazate (SBDTC) followed by coordination with Cu (II) ions. X-ray crystal structures were obtained for compound , an SBDTC-diacetyl analogue, and , an SMDTC-hexanedione Cu (II) complex. Anticancer evaluation of the compounds showed that , an SMDTC-glyoxal complex, demonstrated the highest cytotoxic activity against MCF-7 and MDA-MB-231 breast cancer cells with IC 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 was the most susceptible bacteria to the compounds, followed by . Compound and the SMDTC-derived analogues , , and possessed the highest antibacterial activity. These active analogues were further assessed, whereby possessed the highest antibacterial activity with an MIC of
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28135009