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...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English English |
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MDPI
2023
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| Online Access: | https://eprints.ums.edu.my/id/eprint/36743/1/ABSTRACT.pdf https://eprints.ums.edu.my/id/eprint/36743/2/FULL%20TEXT.pdf |
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| author | Mohammed Khaled Break Tan, Yew Fung Koh, May Zie Wan, Yong Ho Mohamed Ibrahim Mohamed Tahir Omar Ashraf Elfar Rahamat Unissa Syed Weam M. A. Khojali Turki Mubarak Alluhaibi Bader Huwaimel Christophe Patrice Andie Wiart Khoo, Teng-Jin |
| author_facet | Mohammed Khaled Break Tan, Yew Fung Koh, May Zie Wan, Yong Ho Mohamed Ibrahim Mohamed Tahir Omar Ashraf Elfar Rahamat Unissa Syed Weam M. A. Khojali Turki Mubarak Alluhaibi Bader Huwaimel Christophe Patrice Andie Wiart Khoo, Teng-Jin |
| author_sort | Mohammed Khaled Break |
| collection | UMS |
| 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 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. |
| first_indexed | 2024-03-06T03:25:11Z |
| format | Article |
| id | ums.eprints-36743 |
| institution | Universiti Malaysia Sabah |
| language | English English |
| last_indexed | 2024-03-06T03:25:11Z |
| publishDate | 2023 |
| publisher | MDPI |
| record_format | dspace |
| spelling | ums.eprints-367432023-09-06T07:41:31Z https://eprints.ums.edu.my/id/eprint/36743/ 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 Tan, Yew Fung Koh, May Zie Wan, Yong Ho Mohamed Ibrahim Mohamed Tahir Omar Ashraf Elfar Rahamat Unissa Syed Weam M. A. Khojali Turki Mubarak Alluhaibi Bader Huwaimel Christophe Patrice Andie Wiart Khoo, Teng-Jin R5-920 Medicine (General) RC254-282 Neoplasms. Tumors. Oncology Including cancer and carcinogens 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. MDPI 2023 Article NonPeerReviewed text en https://eprints.ums.edu.my/id/eprint/36743/1/ABSTRACT.pdf text en https://eprints.ums.edu.my/id/eprint/36743/2/FULL%20TEXT.pdf 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. https://doi.org/10.3390/molecules28135009 |
| spellingShingle | R5-920 Medicine (General) RC254-282 Neoplasms. Tumors. Oncology Including cancer and carcinogens Mohammed Khaled Break Tan, Yew Fung Koh, May Zie Wan, Yong Ho Mohamed Ibrahim Mohamed Tahir Omar Ashraf Elfar Rahamat Unissa Syed Weam M. A. Khojali Turki Mubarak Alluhaibi Bader Huwaimel Christophe Patrice Andie Wiart 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 | R5-920 Medicine (General) RC254-282 Neoplasms. Tumors. Oncology Including cancer and carcinogens |
| url | https://eprints.ums.edu.my/id/eprint/36743/1/ABSTRACT.pdf https://eprints.ums.edu.my/id/eprint/36743/2/FULL%20TEXT.pdf |
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