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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 S-methyl dithiocarbazate (SMDTC) and S-benzyl dithiocarbazate (SBDTC) followed by coordination with Cu (II) ions. X-ray crystal structures were obtai...
Autores principales: | , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343930/ https://www.ncbi.nlm.nih.gov/pubmed/37446670 http://dx.doi.org/10.3390/molecules28135009 |
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author | 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 |
author_facet | 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 |
author_sort | Break, Mohammed Khaled Bin |
collection | PubMed |
description | 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 IC(50) 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. |
format | Online Article Text |
id | pubmed-10343930 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-103439302023-07-14 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 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 Molecules Article 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 IC(50) 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. MDPI 2023-06-26 /pmc/articles/PMC10343930/ /pubmed/37446670 http://dx.doi.org/10.3390/molecules28135009 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article 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 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 |
title | 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 |
title_full | 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 |
title_fullStr | 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 |
title_full_unstemmed | 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 |
title_short | 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 |
title_sort | 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 |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343930/ https://www.ncbi.nlm.nih.gov/pubmed/37446670 http://dx.doi.org/10.3390/molecules28135009 |
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