(<i>N</i>,<i>N</i>-Diisopropyldithiocarbamato)triphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

Haezam, Farah Natasha; Awang, Normah; Kamaludin, Nurul Farahana; Jotani, Mukesh M.; Tiekink, Edward R. T.

doi:10.1107/s2056989019012490

Cited by 5 publications

(3 citation statements)

References 29 publications

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“…A study by Balas et al [18] similarly showed cell cycle inhibition occurring in the S phase when leiomyosarcoma cells were treated with triphenyltin (IV) compounds. In addition, triphenyltin (IV) compounds have a greater toxic effect than diphenyltin (IV) compounds on human colorectal cancer, according to a study by Haezam et al [19]. Adeyemi et al [20] stated that the functional groups linked to tin atoms had in vitro toxic effects on the examined cells.…”

Section: Resultsmentioning

confidence: 99%

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2023

J. Med. Chem. Sci.

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Introduction:A chemotherapeutic agent known as the etoposide is used to treat acute lymphoblastic leukaemia (ALL). Over the years, the etoposide usage in treating ALL has yielded positive outcomes. Nevertheless, it has been discovered that a number of ALL patients experience side-effects and are susceptible to cancer cells. Accordingly, drug research for improved chemotherapy becomes necessary. The results of numerous investigations using compounds containing organotin (IV) dithiocarbamate were encouraging. Aim: The objective of this study is to examine the genotoxicity effects on Jurkat E6.1 cells, derivatives of the aforementioned substances were chosen for this investigation. Materials and Methods: The assessment of cell cycle arrest and genotoxic effects on Jurkat E6.1 cell lines was accomplished using the substances triphenyltin (IV) diisopropyldithiocarbamate (C1) and triphenyltin (IV) dialkyldithiocarbamate (C2). The cell cycle arrest was established using cell cycle analysis. The average DNA tail moment score was used to calculate the genotoxic effects of DNA damage. Inhibitory concentration (IC50) was used to conduct both analyses. C1 has an IC50 of 0.1 M, while C2 has an IC50 of 0.2 M. On the other hand, the etoposide, which served as a positive control, has an IC50 of 0.87 M. Results:The research findings demonstrated that after four hours of treatment, both triphenyltin (IV) dithiocarbamate and etoposide compounds prompted cell cycle arrest, with a significant difference (p < 0.05) in the S phase. Following a four-hour etoposide treatment, the findings of genotoxicity assessment revealed substantial DNA damage (p < 0.05). Furthermore, the C1 and C2 treatments revealed a similar level of DNA damage. However, when a statistical analysis of the comet assay results was accomplished, no discernible change (p > 0.05) was observed. Conclusion: In summary, DNA damage and cell cycle trapping were caused by etoposide, C1, and C2 in Jurkat E6.1 cells.

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Section: Resultsmentioning

confidence: 99%

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2023

J. Med. Chem. Sci.

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“…The aforementioned report on tin diallyldithiocarbamate compounds (Adeyemi et al, 2019) also presented the first crystal-structure determinations for tin compounds of diallyldithiocarbamate. In a continuation of recent structural studies in this area (Mohamad et al, 2017(Mohamad et al, , 2018aHaezam et al, 2019), herein, two organotin compounds of diallyldithiocarbamate, (C 6 H 5 ) 3 Sn[S 2 CN(CH 2 C(H) CH 2 ) 2 ], (I), and (C 6 H 5 ) 2 Sn[S 2 CN(CH 2 C(H) CH 2 ) 2 ] 2 , (II), have been synth-esized and studied by X-ray crystallography. In addition, the supramolecular associations in their crystals have been evaluated by Hirshfeld surface analyses and computational chemistry.…”

Section: Chemical Contextmentioning

confidence: 85%

(N,N-Diallyldithiocarbamato-κ² S,S′)triphenyltin(IV) and bis(N,N-diallyldithiocarbamato-κ² S,S′)diphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

Haezam¹,

Awang²,

Kamaludin³

et al. 2020

Acta Cryst E

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The crystal and molecular structures of the title organotin dithiocarbamate compounds, [Sn(C6H5)3(C7H10NS2)] (I) and [Sn(C6H5)2(C7H10NS2)2] (II), present very distinct tin atom coordination geometries. In (I), the dithiocarbamate ligand is asymmetrically coordinating with the resulting C3S2 donor set defining a coordination geometry intermediate between square-pyramidal and trigonal–bipyramidal. In (II), two independent molecules comprise the asymmetric unit, which differ in the conformations of the allyl substituents and in the relative orientations of the tin-bound phenyl rings. The dithiocarbamate ligands in (II) coordinate in an asymmetric mode but the Sn—S bonds are more symmetric than observed in (I). The resulting C2S4 donor set approximates an octahedral coordination geometry with a cis-disposition of the ipso-carbon atoms and with the more tightly bound sulfur atoms approximately trans. The only directional intermolecular contacts in the crystals of (I) and (II) are of the type phenyl-C—H...π(phenyl) and vinylidene-C—H...π(phenyl), respectively, with each leading to a supramolecular chain propagating along the a-axis direction. The calculated Hirshfeld surfaces emphasize the importance of H...H contacts in the crystal of (I), i.e. contributing 62.2% to the overall surface. The only other two significant contacts also involve hydrogen, i.e. C...H/H...C (28.4%) and S...H/H...S (8.6%). Similar observations pertain to the individual molecules of (II), which are clearly distinguishable in their surface contacts, with H...H being clearly dominant (59.9 and 64.9%, respectively) along with C...H/H...C (24.3 and 20.1%) and S...H/H...S (14.4 and 13.6%) contacts. The calculations of energies of interaction suggest dispersive forces make a significant contribution to the stabilization of the crystals. The exception is for the C—H...π contacts in (II) where, in addition to the dispersive contribution, significant contributions are made by the electrostatic forces.

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“…Seven organotin(IV) dithiocarbamate compounds, which are diphenyltin(IV) diisopropyl dithiocarbamate (ODTC 1), diphenyltin(IV) diallyl dithiocarbamate (ODTC 2), triphenyltin(IV) diisopropyl dithiocarbamate (ODTC 3), triphenyltin(IV) diallyl dithiocarbamate (ODTC 4), triphenyltin(IV) diethyl dithiocarbamate (ODTC 5), dimethyltin(IV) diisopropyl dithiocarbamate (ODTC 6) and dimethyltin(IV) diethyl dithiocarbamate (ODTC 7) were synthesized and characterized by our team (Haezam et al) [22,47,48] at the School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Bangi, Malaysia.…”

Section: Compoundsmentioning

confidence: 99%

Series of Organotin(IV) Compounds with Different Dithiocarbamate Ligands Induced Cytotoxicity, Apoptosis and Cell Cycle Arrest on Jurkat E6.1, T Acute Lymphoblastic Leukemia Cells

et al. 2023

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The discovery of cisplatin has influenced scientists to study the anticancer properties of other metal complexes. Organotin(IV) dithiocarbamate compounds are gaining attention as anticancer agents due to their potent cytotoxic properties on cancer cells. In this study, a series of organotin compounds were assessed for their toxic effects on the Jurkat E6.1 cell line. WST-1 assay was used to determine the cytotoxic effect of the compounds and showed that six out of seven organotin(IV) dithiocarbamate compounds exhibited potent cytotoxic effects toward T-lymphoblastic leukemia cells, Jurkat E6.1 with the concentration of IC50 ranging from 0.67–0.94 µM. The apoptosis assay by Annexin V-FITC/PI staining showed that all tested compounds induced cell death mainly via apoptosis. Cell cycle analysis assessed using RNase/PI staining showed that organotin(IV) dithiocarbamate compounds induced cell cycle arrest at different phases. In conclusion, the tested organotin(IV) dithiocarbamate compounds demonstrated potent cytotoxicity against Jurkat E6.1 cells via apoptosis and cell cycle arrest at low IC50 value. However, further studies on the mechanisms of action are required to probe the possible potential of these compounds on leukemia cells before they can be developed into anti-leukemic agents.

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(N,N-Diisopropyldithiocarbamato)triphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

Cited by 5 publications

References 29 publications

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(N,N-Diallyldithiocarbamato-κ² S,S′)triphenyltin(IV) and bis(N,N-diallyldithiocarbamato-κ² S,S′)diphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

Series of Organotin(IV) Compounds with Different Dithiocarbamate Ligands Induced Cytotoxicity, Apoptosis and Cell Cycle Arrest on Jurkat E6.1, T Acute Lymphoblastic Leukemia Cells

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(N,N-Diisopropyldithiocarbamato)triphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

Cited by 5 publications

References 29 publications

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(N,N-Diallyldithiocarbamato-κ2 S,S′)triphenyltin(IV) and bis(N,N-diallyldithiocarbamato-κ2 S,S′)diphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

Series of Organotin(IV) Compounds with Different Dithiocarbamate Ligands Induced Cytotoxicity, Apoptosis and Cell Cycle Arrest on Jurkat E6.1, T Acute Lymphoblastic Leukemia Cells

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(N,N-Diallyldithiocarbamato-κ² S,S′)triphenyltin(IV) and bis(N,N-diallyldithiocarbamato-κ² S,S′)diphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study