Synthesis, Crystal Structure, Antibacterial and In Vitro Anticancer Activity of Novel Macroacyclic Schiff Bases and Their Cu (II) Complexes Derived from <i>S</i>-Methyl and <i>S</i>-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 <i>S</i>-methyl dithiocarbazate (SMDTC) and <i>S</i>-benzyl dithiocarbazate (SBDTC) followed by coordination with Cu (II) ion...
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| Format: | Article |
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MDPI AG
2023-06-01
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| Online Access: | https://www.mdpi.com/1420-3049/28/13/5009 |
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| author | Mohammed Khaled Bin Break Tan Yew Fung May Zie Koh Wan Yong Ho Mohamed Ibrahim Mohamed Tahir Omar Ashraf Elfar Rahamat Unissa Syed Weam M. A. Khojali Turki Mubarak Alluhaibi Bader Huwaimel Christophe Wiart Teng-Jin Khoo |
| author_facet | Mohammed Khaled Bin Break Tan Yew Fung May Zie Koh Wan Yong Ho Mohamed Ibrahim Mohamed Tahir Omar Ashraf Elfar Rahamat Unissa Syed Weam M. A. Khojali Turki Mubarak Alluhaibi Bader Huwaimel Christophe Wiart Teng-Jin Khoo |
| author_sort | Mohammed Khaled Bin Break |
| collection | DOAJ |
| description | A series of novel macroacyclic Schiff base ligands and their Cu (II) complexes were synthesised via reacting dicarbonyls of varying chain lengths with <i>S</i>-methyl dithiocarbazate (SMDTC) and <i>S</i>-benzyl dithiocarbazate (SBDTC) followed by coordination with Cu (II) ions. X-ray crystal structures were obtained for compound <b>4</b>, an SBDTC-diacetyl analogue, and <b>Cu7</b>, an SMDTC-hexanedione Cu (II) complex. Anticancer evaluation of the compounds showed that <b>Cu1</b>, an SMDTC-glyoxal complex, demonstrated the highest cytotoxic activity against MCF-7 and MDA-MB-231 breast cancer cells with IC<sub>50</sub> 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 <i>K. rhizophila</i> was the most susceptible bacteria to the compounds, followed by <i>S. aureus</i>. Compound <b>4</b> and the SMDTC-derived analogues <b>3</b>, <b>5</b>, <b>Cu7</b> and <b>Cu9</b> possessed the highest antibacterial activity. These active analogues were further assessed, whereby <b>3</b> possessed the highest antibacterial activity with an MIC of <24.4 µg/mL against <i>K. rhizophila</i> and <i>S. aureus</i>. Further antibacterial studies showed that at least compounds <b>4</b> and <b>5</b> were bactericidal. Thus, <b>Cu1</b> and <b>3</b> were the most promising anticancer and antibacterial agents, respectively. |
| first_indexed | 2024-03-11T01:34:40Z |
| format | Article |
| id | doaj.art-e75e33d31c7d4645a5dd533c859cec6a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T01:34:40Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e75e33d31c7d4645a5dd533c859cec6a2023-11-18T17:06:50ZengMDPI AGMolecules1420-30492023-06-012813500910.3390/molecules28135009Synthesis, Crystal Structure, Antibacterial and In Vitro Anticancer Activity of Novel Macroacyclic Schiff Bases and Their Cu (II) Complexes Derived from <i>S</i>-Methyl and <i>S</i>-Benzyl DithiocarbazateMohammed Khaled Bin Break0Tan Yew Fung1May Zie Koh2Wan Yong Ho3Mohamed Ibrahim Mohamed Tahir4Omar Ashraf Elfar5Rahamat Unissa Syed6Weam M. A. Khojali7Turki Mubarak Alluhaibi8Bader Huwaimel9Christophe Wiart10Teng-Jin Khoo11Department of Pharmaceutical Chemistry, College of Pharmacy, University of Hail, Hail 55473, Saudi ArabiaSchool of Pharmacy, Faculty of Science and Engineering, University of Nottingham Malaysia, Semenyih 43500, Selangor, MalaysiaDivision of Biomedical Sciences, School of Pharmacy, Faculty of Science and Engineering, University of Nottingham Malaysia, Semenyih 43500, Selangor, MalaysiaDivision of Biomedical Sciences, School of Pharmacy, Faculty of Science and Engineering, University of Nottingham Malaysia, Semenyih 43500, Selangor, MalaysiaDepartment of Chemistry, Faculty of Science, University Putra Malaysia, Serdang 43400, Selangor, MalaysiaSchool of Pharmacy, Faculty of Science and Engineering, University of Nottingham Malaysia, Semenyih 43500, Selangor, MalaysiaMedical and Diagnostic Research Centre, University of Hail, Hail 55473, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, University of Hail, Hail 55473, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, University of Hail, Hail 55473, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, University of Hail, Hail 55473, Saudi ArabiaInstitute for Tropical Biology & Conservation, University Malaysia Sabah, Kota Kinabalu 88400, Sabah, MalaysiaSchool of Pharmacy, Faculty of Science and Engineering, University of Nottingham Malaysia, Semenyih 43500, Selangor, MalaysiaA series of novel macroacyclic Schiff base ligands and their Cu (II) complexes were synthesised via reacting dicarbonyls of varying chain lengths with <i>S</i>-methyl dithiocarbazate (SMDTC) and <i>S</i>-benzyl dithiocarbazate (SBDTC) followed by coordination with Cu (II) ions. X-ray crystal structures were obtained for compound <b>4</b>, an SBDTC-diacetyl analogue, and <b>Cu7</b>, an SMDTC-hexanedione Cu (II) complex. Anticancer evaluation of the compounds showed that <b>Cu1</b>, an SMDTC-glyoxal complex, demonstrated the highest cytotoxic activity against MCF-7 and MDA-MB-231 breast cancer cells with IC<sub>50</sub> 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 <i>K. rhizophila</i> was the most susceptible bacteria to the compounds, followed by <i>S. aureus</i>. Compound <b>4</b> and the SMDTC-derived analogues <b>3</b>, <b>5</b>, <b>Cu7</b> and <b>Cu9</b> possessed the highest antibacterial activity. These active analogues were further assessed, whereby <b>3</b> possessed the highest antibacterial activity with an MIC of <24.4 µg/mL against <i>K. rhizophila</i> and <i>S. aureus</i>. Further antibacterial studies showed that at least compounds <b>4</b> and <b>5</b> were bactericidal. Thus, <b>Cu1</b> and <b>3</b> were the most promising anticancer and antibacterial agents, respectively.https://www.mdpi.com/1420-3049/28/13/5009antibacterialanticancercoppercrystallographySchiff base |
| spellingShingle | Mohammed Khaled Bin Break Tan Yew Fung May Zie Koh Wan Yong Ho Mohamed Ibrahim Mohamed Tahir Omar Ashraf Elfar Rahamat Unissa Syed Weam M. A. Khojali Turki Mubarak Alluhaibi Bader Huwaimel Christophe Wiart Teng-Jin Khoo Synthesis, Crystal Structure, Antibacterial and In Vitro Anticancer Activity of Novel Macroacyclic Schiff Bases and Their Cu (II) Complexes Derived from <i>S</i>-Methyl and <i>S</i>-Benzyl Dithiocarbazate Molecules antibacterial anticancer copper crystallography Schiff base |
| title | Synthesis, Crystal Structure, Antibacterial and In Vitro Anticancer Activity of Novel Macroacyclic Schiff Bases and Their Cu (II) Complexes Derived from <i>S</i>-Methyl and <i>S</i>-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 <i>S</i>-Methyl and <i>S</i>-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 <i>S</i>-Methyl and <i>S</i>-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 <i>S</i>-Methyl and <i>S</i>-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 <i>S</i>-Methyl and <i>S</i>-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 i s i methyl and i s i benzyl dithiocarbazate |
| topic | antibacterial anticancer copper crystallography Schiff base |
| url | https://www.mdpi.com/1420-3049/28/13/5009 |
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