Synthesis, computational and biological studies of alkyltin(IV) N-methyl- N-hydroxyethyl dithiocarbamate complexes

Jerry O Adeyemi; Gbemisola M Saibu; Lukman O Olasunkanmi; Adewale O Fadaka; Mervin Meyer; Nicole R S Sibuyi; Damian C Onwudiwe; Adebola O Oyedeji

doi:10.1016/j.heliyon.2021.e07693

Synthesis, computational and biological studies of alkyltin(IV) N-methyl- N-hydroxyethyl dithiocarbamate complexes

Heliyon. 2021 Aug 2;7(8):e07693. doi: 10.1016/j.heliyon.2021.e07693. eCollection 2021 Aug.

Authors

Jerry O Adeyemi^{1

2}, Gbemisola M Saibu³, Lukman O Olasunkanmi⁴, Adewale O Fadaka⁵, Mervin Meyer⁵, Nicole R S Sibuyi⁵, Damian C Onwudiwe^{1

2}, Adebola O Oyedeji⁶

Affiliations

¹ Material Science Innovation and Modelling (MaSIM) Research Focus Area, Faculty of Natural and Agricultural Science, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho, South Africa.
² Department of Chemistry, Faculty of Natural and Agricultural, Science, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa.
³ Risk & Vulnerability Science Centre, Walter Sisulu University, Nelson Mandela Drive, Mthatha, Private Bag X1, 5099, South Africa.
⁴ Department of Chemistry, Faculty of Science, Obafemi Awolowo University, Ile-Ife 220005, Nigeria.
⁵ Department of Science and Innovation/Mintek Nanotechnology Innovation Centre, Biolabels Node, Department of Biotechnology, Faculty of Natural Sciences, University of the Western Cape, Private Bag X17, Bellville, 7535 Cape Town, South Africa.
⁶ Department of Chemical & Physical Sciences, Faculty of Natural Sciences, Walter Sisulu University, Mthatha, South Africa.

Abstract

Methyltin(IV) of butyltin(IV)-N-hydroxyethyl dithiocarbamate complexes, represented as [(CH₃)₂Sn(L(OH))₂] and [(C₄H₉)₂Sn(L(OH))₂] respectively were synthesized and characterized using spectroscopic techniques (¹H, ¹³C and ¹¹⁹Sn NMR) and elemental analysis. Both infrared and NMR data showed that, the complexes were formed via two sulphur atoms of the dithiocarbamate group. This mode of coordination was further supported by the DFT calculation, which suggested the formation of a distorted octahedral geometry around the tin atom. The complexes were screened for their antioxidant, cytotoxicity and anti-inflammatory properties. Four different assays including DPPH, nitric oxide, reducing power and hydrogen peroxides were used for the antioxidant studies, while an in vitro anti-inflammatory study was done using albumin denaturation assay. The complexes showed good antioxidant activity, especially in the DPPH assay. Butyltin(IV)-N-hydroxyethyl dithiocarbamate showed better cytotoxicity activity compared to methyltin(IV)-N-hydroxyethyl dithiocarbamate in the selected cell lines, which included KMST-6, Caco-2 and A549 cell lines. The anti-inflammatory activities revealed that the two complexes have useful activities better than diclofenac used as control drug.

Keywords: Anti-inflammatory; Antioxidant; Computational study; Cytotoxicity; Dithiocarbamate; Organotin.