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Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases

A series of tridentate ONS Schiff bases were synthesised via condensation by reacting 2,3-dihydroxybenzaldehyde with S-2-methylbenzyldithiocarbazate (S2MBDTC) (1), S-4-methylbenzyldithiocarbazate (S4MBDTC) (2) and S-benzyldithiocarbazate (SBDTC) (3) in an equimolar ratio (10 mmol). The Schiff bases...

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Main Authors: Md Yusof, Enis Nadia, Mohamad Ishak, Nurul Nabihah, Mohammad Latif, Muhammad Alif, Mohamed Tahir, Mohamed Ibrahim, Sakoff, Jennette A., Page, Alister J., Tiekink, Edward R. T., Ravoof, Thahira B. S. A.
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Published: Springer 2020
Online Access:http://psasir.upm.edu.my/id/eprint/87552/
https://link.springer.com/article/10.1007/s11164-020-04095-x
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spelling my.upm.eprints.875522022-11-23T03:21:23Z http://psasir.upm.edu.my/id/eprint/87552/ Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases Md Yusof, Enis Nadia Mohamad Ishak, Nurul Nabihah Mohammad Latif, Muhammad Alif Mohamed Tahir, Mohamed Ibrahim Sakoff, Jennette A. Page, Alister J. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. A series of tridentate ONS Schiff bases were synthesised via condensation by reacting 2,3-dihydroxybenzaldehyde with S-2-methylbenzyldithiocarbazate (S2MBDTC) (1), S-4-methylbenzyldithiocarbazate (S4MBDTC) (2) and S-benzyldithiocarbazate (SBDTC) (3) in an equimolar ratio (10 mmol). The Schiff bases were then reacted with diphenyltin(IV) and dimethyltin(IV) dichloride in an equimolar ratio (1 mmol) yielding six new organotin(IV) compounds (4–9). All the compounds were successfully characterised by elemental analysis, FT-IR, multinuclear NMR, UV–Vis, mass spectroscopy and molar conductivity. The molecular geometries for five compounds, 3, 5, 6, 8 and 9, have been established by X-ray crystallography. The five-coordinate geometry for each of the diorganotin molecules was defined by two carbon atoms from the tin-bound substituents as well as three donor atoms derived from the dinegative, tridentate dithiocarbazate ligands, namely thiolate-S, phenoxide-O and imine-N atoms. The resultant five-coordinate C2NOS geometries were intermediate between ideal square pyramidal and trigonal bipyramidal geometries. The diphenyltin(IV) compounds (4–6) exhibited particularly promising and selective cytotoxicity against the A2780 (ovarian), BE2-C (neuroblastoma), SJ-G2 (glioblastoma) and MIA (pancreas) cancer cell lines. The interactions of the compounds (4–9) with calf thymus (CT-DNA) were evaluated using an electronic absorption method, and 7, 8, 9 were found to have good DNA binding affinity. The molecular docking studies of compounds (4–9) with DNA revealed that the compounds interacted with duplex DNA via hydrogen bonding, hydrophobic and electrostatic interactions. Springer 2020-02-05 Article PeerReviewed Md Yusof, Enis Nadia and Mohamad Ishak, Nurul Nabihah and Mohammad Latif, Muhammad Alif and Mohamed Tahir, Mohamed Ibrahim and Sakoff, Jennette A. and Page, Alister J. and Tiekink, Edward R. T. and Ravoof, Thahira B. S. A. (2020) Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases. Research on Chemical Intermediates volume, 46. 2351 - 2379. ISSN 0922-6168; ESSN: 1568-5675 https://link.springer.com/article/10.1007/s11164-020-04095-x 10.1007/s11164-020-04095-x
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
description A series of tridentate ONS Schiff bases were synthesised via condensation by reacting 2,3-dihydroxybenzaldehyde with S-2-methylbenzyldithiocarbazate (S2MBDTC) (1), S-4-methylbenzyldithiocarbazate (S4MBDTC) (2) and S-benzyldithiocarbazate (SBDTC) (3) in an equimolar ratio (10 mmol). The Schiff bases were then reacted with diphenyltin(IV) and dimethyltin(IV) dichloride in an equimolar ratio (1 mmol) yielding six new organotin(IV) compounds (4–9). All the compounds were successfully characterised by elemental analysis, FT-IR, multinuclear NMR, UV–Vis, mass spectroscopy and molar conductivity. The molecular geometries for five compounds, 3, 5, 6, 8 and 9, have been established by X-ray crystallography. The five-coordinate geometry for each of the diorganotin molecules was defined by two carbon atoms from the tin-bound substituents as well as three donor atoms derived from the dinegative, tridentate dithiocarbazate ligands, namely thiolate-S, phenoxide-O and imine-N atoms. The resultant five-coordinate C2NOS geometries were intermediate between ideal square pyramidal and trigonal bipyramidal geometries. The diphenyltin(IV) compounds (4–6) exhibited particularly promising and selective cytotoxicity against the A2780 (ovarian), BE2-C (neuroblastoma), SJ-G2 (glioblastoma) and MIA (pancreas) cancer cell lines. The interactions of the compounds (4–9) with calf thymus (CT-DNA) were evaluated using an electronic absorption method, and 7, 8, 9 were found to have good DNA binding affinity. The molecular docking studies of compounds (4–9) with DNA revealed that the compounds interacted with duplex DNA via hydrogen bonding, hydrophobic and electrostatic interactions.
format Article
author Md Yusof, Enis Nadia
Mohamad Ishak, Nurul Nabihah
Mohammad Latif, Muhammad Alif
Mohamed Tahir, Mohamed Ibrahim
Sakoff, Jennette A.
Page, Alister J.
Tiekink, Edward R. T.
Ravoof, Thahira B. S. A.
spellingShingle Md Yusof, Enis Nadia
Mohamad Ishak, Nurul Nabihah
Mohammad Latif, Muhammad Alif
Mohamed Tahir, Mohamed Ibrahim
Sakoff, Jennette A.
Page, Alister J.
Tiekink, Edward R. T.
Ravoof, Thahira B. S. A.
Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases
author_facet Md Yusof, Enis Nadia
Mohamad Ishak, Nurul Nabihah
Mohammad Latif, Muhammad Alif
Mohamed Tahir, Mohamed Ibrahim
Sakoff, Jennette A.
Page, Alister J.
Tiekink, Edward R. T.
Ravoof, Thahira B. S. A.
author_sort Md Yusof, Enis Nadia
title Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases
title_short Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases
title_full Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases
title_fullStr Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases
title_full_unstemmed Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases
title_sort selective cytotoxicity of organotin(iv) compounds with 2,3-dihydroxybenzyldithiocarbazate schiff bases
publisher Springer
publishDate 2020
url http://psasir.upm.edu.my/id/eprint/87552/
https://link.springer.com/article/10.1007/s11164-020-04095-x
_version_ 1751538215856111616
score 13.211869

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