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New organotin(IV) dithiolate complexes derived from 2-methoxyphenylacetonitrile: Synthesis, DFT studies, docking, and cytotoxic activity against A549 cells.

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Title: New organotin(IV) dithiolate complexes derived from 2-methoxyphenylacetonitrile: Synthesis, DFT studies, docking, and cytotoxic activity against A549 cells.
Authors: Gupta, Kiran1 (AUTHOR), Verma, Deepika1 (AUTHOR), Parveen, Sana2 (AUTHOR), Fatma, Mariyam2 (AUTHOR), Mir, Snober S.1,2 (AUTHOR) smir@iul.ac.in, Sabah, Zia-Ul3 (AUTHOR), Prakash, Om1 (AUTHOR) prakash_om@lkouniv.ac.in
Source: Journal of Molecular Structure. Aug2026, Vol. 1368, pN.PAG-N.PAG. 1p.
Subjects: Organotin compounds, Density functional theory, Cell lines, Chemical synthesis, Molecular docking, Ligands (Chemistry), Oxidative stress, Cytotoxins
Abstract: • New cyanoarylvinyl dithiolate organotin(IV) complexes were synthesized. • Steric and electronic tuning of Sn–S coordination influences reactivity and bioactivity. • DFT analysis links frontier orbitals with optimized molecular geometries. • Complexes induce oxidative stress and mitochondrial dysfunction in A549 cells. • Docking studies suggest substituent dependent target affinity trends. Three new tetra-coordinated organotin(IV)dithiolate complexes of the type [ R 2 SnL ] , where R = CH 3 (Me 2 SnL), n‑butyl (Bu 2 SnL), pH (Ph 2 SnL), and L = [CH 3 OPhC(CN)=CS 2 2–] are synthesized via in situ complexation. The complexes are characterized by elemental analysis, FT-IR, ¹H, ¹³C and 119Sn NMR, UV–Vis, as well as ESI–MS that support the formation of organotin(IV)dithiolates frameworks. Density functional theory calculations confirm a distorted tetrahedral geometry around Sn(IV), with bidentate S,S-chelation producing small S–Sn–S bite angles (76.62–76.80°) and substituent-dependent Sn–S bond asymmetry. Complex Ph 2 SnL exhibits the maximum HOMO–LUMO energy gap, indicating greater electronic stability relative to the alkyl-substituted analogues. In vitro cytotoxic evaluation against A549 cells reveals substituent dependent antiproliferative activity, with Ph 2 SnL showing the lowest IC₅₀ (15 µM), followed by Me 2 SnL (30 µM) and Bu 2 SnL (50 µM). Notably, Ph 2 SnL induces pronounced cell de-adhesion accompanied by mitochondrial and nuclear perturbation, suggesting involvement of adhesion-dependent cytotoxic stress rather than a purely redox-driven mechanism. Biological responses show clear correlations with substituent dependent electronic structure of the complexes. Overall, these results demonstrate that substituent-dependent factors like steric, electronic, including cellular interactions and target engagement, modulate the apoptotic response within this organotin(IV) dithiolate series. Three organotin(IV) dithiolate complexes were synthesized and characterized by spectroscopic and analytical methods. In vitro cytotoxic activity was evaluated against selected cancer cell lines, and molecular docking rationalized binding interactions with target proteins. DFT calculations provided complementary electronic and vibrational descriptors consistent with the proposed structural assignments. [Display omitted] [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
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Abstract:• New cyanoarylvinyl dithiolate organotin(IV) complexes were synthesized. • Steric and electronic tuning of Sn–S coordination influences reactivity and bioactivity. • DFT analysis links frontier orbitals with optimized molecular geometries. • Complexes induce oxidative stress and mitochondrial dysfunction in A549 cells. • Docking studies suggest substituent dependent target affinity trends. Three new tetra-coordinated organotin(IV)dithiolate complexes of the type [ R 2 SnL ] , where R = CH 3 (Me 2 SnL), n‑butyl (Bu 2 SnL), pH (Ph 2 SnL), and L = [CH 3 OPhC(CN)=CS 2 2–] are synthesized via in situ complexation. The complexes are characterized by elemental analysis, FT-IR, ¹H, ¹³C and 119Sn NMR, UV–Vis, as well as ESI–MS that support the formation of organotin(IV)dithiolates frameworks. Density functional theory calculations confirm a distorted tetrahedral geometry around Sn(IV), with bidentate S,S-chelation producing small S–Sn–S bite angles (76.62–76.80°) and substituent-dependent Sn–S bond asymmetry. Complex Ph 2 SnL exhibits the maximum HOMO–LUMO energy gap, indicating greater electronic stability relative to the alkyl-substituted analogues. In vitro cytotoxic evaluation against A549 cells reveals substituent dependent antiproliferative activity, with Ph 2 SnL showing the lowest IC₅₀ (15 µM), followed by Me 2 SnL (30 µM) and Bu 2 SnL (50 µM). Notably, Ph 2 SnL induces pronounced cell de-adhesion accompanied by mitochondrial and nuclear perturbation, suggesting involvement of adhesion-dependent cytotoxic stress rather than a purely redox-driven mechanism. Biological responses show clear correlations with substituent dependent electronic structure of the complexes. Overall, these results demonstrate that substituent-dependent factors like steric, electronic, including cellular interactions and target engagement, modulate the apoptotic response within this organotin(IV) dithiolate series. Three organotin(IV) dithiolate complexes were synthesized and characterized by spectroscopic and analytical methods. In vitro cytotoxic activity was evaluated against selected cancer cell lines, and molecular docking rationalized binding interactions with target proteins. DFT calculations provided complementary electronic and vibrational descriptors consistent with the proposed structural assignments. [Display omitted] [ABSTRACT FROM AUTHOR]
ISSN:00222860
DOI:10.1016/j.molstruc.2026.146248