A skew trapezoidal bipyramidal coordination geometry based on a C2S4 donor set is found in the structure of (C6H5)2Sn[S2CN(Me)CH2CH2OMe]2, with the SnIV atom lying on a mirror plane.
Context
Diphenyltin(IV) diallyldithiocarbamate compound (Compound
1
) and triphenyltin(IV) diallyldithiocarbamate compound (Compound
2
) are two newly synthesised compounds of organotin(IV) with diallyldithiocarbamate ligands.
Objective
To assess the cytotoxic effects of two synthesised compounds against HT-29 human colon adenocarcinoma cells and human CCD-18Co normal colon cells.
Materials and methods
Two successfully synthesised compounds were characterised using elemental (carbon, hydrogen, nitrogen, and sulphur) analysis, Fourier-Transform Infrared (FTIR), and
1
H,
13
C
119
Sn Nucleus Magnetic Resonance (NMR) spectroscopies. The single-crystal structure of both compounds was determined by X-ray single-crystal analysis. The cytotoxicity of the compounds was assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazholium bromide (MTT) assay upon 24 h of treatment. While the mode of cell death was determined based on the externalisation of phosphatidylserine using a flow cytometer.
Results
The elemental analysis data of the two compounds showed an agreement with the suggested formula of (C
6
H
5
)
2
Sn[S
2
CN(C
3
H
5
)
2
]
2
for Compound
1
and (C
6
H
5
)
3
Sn[S
2
CN(C
3
H
5
)
2
] for Compound
2
. The two major peaks of infrared absorbance, i.e., ν(C = N) and ν(C = S) were detected at the range of 1475–1479 cm
−1
and 972–977 cm
−1
, respectively. The chemical shift of carbon in NCS
2
group for Compound
1
and
2
were found at 200.82 and 197.79 ppm. The crystal structure of Compound
1
showed that it is six coordinated and crystallised in monoclinic, P2
1
/c space group. While the crystal structure of Compound
2
is five coordinated and crystallised in monoclinic, P2
1
/c space group. The cytotoxicity (IC
50
) of the two compounds against HT-29 cell were 2.36 μM and 0.39 μM. Meanwhile, the percentage of cell death modes between 60% and 75% for compound
1
and compound
2
were mainly due to apoptosis, suggesting that both compounds induced growth arrest.
Conclusion
Our study concluded ...
The metal coordination geometry in each of the title molecules, [Sn(C6H5)3(C8H16NS2)] (I) and [Sn(C6H5)3(C10H12NOS2)] (II), is based on a heavily distorted tetrahedron owing to the asymmetric mode of coordination of the dithiocarbamate ligand. The persence of C—H⋯π(phenyl) interactions in the crystals lead to dimeric aggregates in (I) and supramolecular chains (II).
Two distinct coordination geometries, each based on a C2S4 donor set, are found in the title compounds, being based on an octahedron in (C6H5)2Sn(S2CN(Me)CH2CH2OMe)2 and a skew trapezoidal bipyramid in (C6H5)2Sn[S2CN(CH2CH2OMe)2]2.
Dibutyltin(IV) (2-methoxyethyl) methyldithiocarbamate (Compound 1) and tricyclohexyltin(IV) (2-methoxyethyl) methyldithiocarbamate (Compound 2) were used to evaluate their cytotoxicity against three human leukemic cell lines namely Jurkat E6.1, K562, and HL-60. The cytotoxicity of these compounds was assessed using MTT assay for treatment duration of 24 hours. The morphological changes were also observed upon the induction of these compounds with the IC 50 value for 24 hours. Both compounds demonstrated high cytotoxicity towards the cell lines tested, with IC 50 values of 0.14-1.30 µM (Jurkat E6.1), 0.06-0.18 µM (HL-60) and 5.20-5.40 µM (K562). The morphological changes of the cell lines induced by both compounds mostly showed characteristics of cell death via apoptosis. In conclusion, both compounds exhibited good cytotoxicity towards the cell lines tested. However, further studies are needed to identify the exact mode of cell death and the mechanisms of action of these compounds in induced human leukemic cell lines.
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