Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies
Six new tin(IV) compounds derived from tridentate dinegatively charged ONS dithiocarbazate Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde (H2L1, H2L2 and H2L3) and 2,3-dihydroxybenzaldehyde (H2L4, H2L5 and H2L6) (where H2Ln = di-acids of Schiff base) are reported. The compounds were chara...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2020
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| Online Access: | http://psasir.upm.edu.my/id/eprint/89199/1/TIN.pdf |
| _version_ | 1796982098662260736 |
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| author | Md Yusof, Enis Nadia Mohammad Latif, Muhammad Alif Mohamed Tahir, Mohamed Ibrahim Sakoff, Jennette A. Veerakumarasivam, Abhi Page, Alister J. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. |
| author_facet | Md Yusof, Enis Nadia Mohammad Latif, Muhammad Alif Mohamed Tahir, Mohamed Ibrahim Sakoff, Jennette A. Veerakumarasivam, Abhi Page, Alister J. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. |
| author_sort | Md Yusof, Enis Nadia |
| collection | UPM |
| description | Six new tin(IV) compounds derived from tridentate dinegatively charged ONS dithiocarbazate Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde (H2L1, H2L2 and H2L3) and 2,3-dihydroxybenzaldehyde (H2L4, H2L5 and H2L6) (where H2Ln = di-acids of Schiff base) are reported. The compounds were characterised by elemental analysis, FT-IR and multinuclear NMR (1H, 13C and 119Sn) spectroscopy. The crystal structures of tin(IV) [S-4-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene)dithiocarbazate] (2) and tin(IV) [S-benzyl-β-N-(2-hydroxy-3-methoxy benzylmethylene)dithiocarbazate] (3) were determined by X-ray single crystal diffraction analysis. X-ray crystallography showed the molecular geometries in homoleptic 2 and 3 to be quite similar in which the dinegative tridentate ligand coordinated the tin atoms via thiolate-S, phenoxide-O and imine-N atoms. The coordination geometries are based on an octahedron with like-atoms mutually trans. The experimental findings were validated by density functional theory (DFT) calculations at the B3LYP/LanL2DZ/6-311G(d,p) level of theory. All the tin(IV) compounds, except the insoluble compound 2 were screened for their in vitro cytotoxicity against a panel ten of cancer cell lines and one normal breast cell line (MCF-10 A) by MTT assay. Interestingly, the cytotoxicity of five tin(IV) compounds against HT29, MCF7 and MIA was higher than the reference drug, cisplatin. |
| first_indexed | 2024-03-06T10:47:21Z |
| format | Article |
| id | upm.eprints-89199 |
| institution | Universiti Putra Malaysia |
| language | English |
| last_indexed | 2024-03-06T10:47:21Z |
| publishDate | 2020 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | upm.eprints-891992021-09-03T20:49:51Z http://psasir.upm.edu.my/id/eprint/89199/ Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies Md Yusof, Enis Nadia Mohammad Latif, Muhammad Alif Mohamed Tahir, Mohamed Ibrahim Sakoff, Jennette A. Veerakumarasivam, Abhi Page, Alister J. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. Six new tin(IV) compounds derived from tridentate dinegatively charged ONS dithiocarbazate Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde (H2L1, H2L2 and H2L3) and 2,3-dihydroxybenzaldehyde (H2L4, H2L5 and H2L6) (where H2Ln = di-acids of Schiff base) are reported. The compounds were characterised by elemental analysis, FT-IR and multinuclear NMR (1H, 13C and 119Sn) spectroscopy. The crystal structures of tin(IV) [S-4-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene)dithiocarbazate] (2) and tin(IV) [S-benzyl-β-N-(2-hydroxy-3-methoxy benzylmethylene)dithiocarbazate] (3) were determined by X-ray single crystal diffraction analysis. X-ray crystallography showed the molecular geometries in homoleptic 2 and 3 to be quite similar in which the dinegative tridentate ligand coordinated the tin atoms via thiolate-S, phenoxide-O and imine-N atoms. The coordination geometries are based on an octahedron with like-atoms mutually trans. The experimental findings were validated by density functional theory (DFT) calculations at the B3LYP/LanL2DZ/6-311G(d,p) level of theory. All the tin(IV) compounds, except the insoluble compound 2 were screened for their in vitro cytotoxicity against a panel ten of cancer cell lines and one normal breast cell line (MCF-10 A) by MTT assay. Interestingly, the cytotoxicity of five tin(IV) compounds against HT29, MCF7 and MIA was higher than the reference drug, cisplatin. Elsevier 2020 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/89199/1/TIN.pdf Md Yusof, Enis Nadia and Mohammad Latif, Muhammad Alif and Mohamed Tahir, Mohamed Ibrahim and Sakoff, Jennette A. and Veerakumarasivam, Abhi and Page, Alister J. and Tiekink, Edward R. T. and Ravoof, Thahira B. S. A. (2020) Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies. Journal of Molecular Structure, 1205. art. no. 127635. pp. 1-9. ISSN 0022-2860 https://www.sciencedirect.com/science/article/pii/S0022286019317442 10.1016/j.molstruc.2019.127635 |
| spellingShingle | Md Yusof, Enis Nadia Mohammad Latif, Muhammad Alif Mohamed Tahir, Mohamed Ibrahim Sakoff, Jennette A. Veerakumarasivam, Abhi Page, Alister J. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies |
| title | Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies |
| title_full | Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies |
| title_fullStr | Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies |
| title_full_unstemmed | Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies |
| title_short | Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies |
| title_sort | homoleptic tin iv compounds containing tridentate ons dithiocarbazate schiff bases synthesis x ray crystallography dft and cytotoxicity studies |
| url | http://psasir.upm.edu.my/id/eprint/89199/1/TIN.pdf |
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