Synthesis and cytotoxic activity of organotin(IV) diallyldithiocarbamate compounds as anticancer agent towards colon adenocarcinoma cells (HT-29)

Abstract

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 ...

Toxicity and anti-tumour activity of organotin (IV) compounds

“…Structures, and biological actions of organotin(IV) compounds have lately been plotted. 1 Organotin carboxylates are often used because they have cytotoxic and biocidal potential, in addition to their agriculture and industrial applications. Generally, the coordination number and molecular structures of the tin atom are the main important aspect to specify the biocidal activity of organotin (IV) complexes.…”

An integrated mass production of a copepod Acanthocyclops trajani to determine its biochemical composition and evaluate its extract for antimicrobial and anticancer activity

“…If the SI value of the compound is more than 2, it means that the compound has selective toxicity towards cancer cells (Berrington and Lall 2012, Demirgan et al 2016, Haezam et al 2021. Also the results of the ANOVA showed a signi cant effect of the extract (P < 0.005) between A549 and WI38; and between MCF7 and MCF10a.…”

Anthracene appended organotin (IV) compounds: Synthesis, structure elucidation and their cytotoxicity against A549 and RBL cancer cell lines

“…10 Organotin (IV) compounds have also shown promising results as potential anticancer agents due to their ability to inhibit cancer cell growth and induce cell death in certain types of cancer. [11][12][13][14][15][16] Notably, their specific interactions with DNA's phosphate groups make them advanced anti-cancer anti-proliferative agents. Extensive research has been conducted on the bioactivity potency of organotin (IV) compounds, with studies indicating that the effectiveness follows the order R 4 Sn < RSnL3 < R 2 SnL2 < R 3 SnL (L = ligand).…”