Organotins and quantitative-structure activity/property relationships

Song, Xueqing; Zapata, Alejandra; Eng, George

doi:10.1016/j.jorganchem.2005.12.003

Cited by 44 publications

(11 citation statements)

References 38 publications

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“…The activity of organotin(IV) compounds can be readily modified by the choice of ligand coordinated to the central Sn(IV) ion. Organotin(IV) centres coordinated to hetero-donor atoms, especially oxygen, nitrogen and sulphur, have been investigated with a particular focus on their structure-activity correlations [34,35,36]. Coordination of metals to multidentate Schiff bases have, in most cases, enhanced the biological activity of these compounds [37,38,39].…”

Section: Introductionmentioning

confidence: 99%

o-Vanillin Derived Schiff Bases and Their Organotin(IV) Compounds: Synthesis, Structural Characterisation, In-Silico Studies and Cytotoxicity

Yusof

Latif

Tahir

et al. 2019

IJMS

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Six new organotin(IV) compounds of Schiff bases derived from S-R-dithiocarbazate [R = benzyl (B), 2- or 4-methylbenzyl (2M and 4M, respectively)] condensed with 2-hydroxy-3-methoxybenzaldehyde (oVa) were synthesised and characterised by elemental analysis, various spectroscopic techniques including infrared, UV-vis, multinuclear (1H, 13C, 119Sn) NMR and mass spectrometry, and single crystal X-ray diffraction. The organotin(IV) compounds were synthesised from the reaction of Ph2SnCl2 or Me2SnCl2 with the Schiff bases (S2MoVaH/S4MoVaH/SBoVaH) to form a total of six new organotin(IV) compounds that had a general formula of [R2Sn(L)] (where L = Schiff base; R = Ph or Me). The molecular geometries of Me2Sn(S2MoVa), Me2Sn(S4MoVa) and Me2Sn(SBoVa) were established by X-ray crystallography and verified using density functional theory calculations. Interestingly, each experimental structure contained two independent but chemically similar molecules in the crystallographic asymmetric unit. The coordination geometry for each molecule was defined by thiolate-sulphur, phenoxide-oxygen and imine-nitrogen atoms derived from a dinegative, tridentate dithiocarbazate ligand with the remaining positions occupied by the methyl-carbon atoms of the organo groups. In each case, the resulting five-coordinate C2NOS geometry was almost exactly intermediate between ideal trigonal-bipyramidal and square-pyramidal geometries. The cytotoxic activities of the Schiff bases and organotin(IV) compounds were investigated against EJ-28 and RT-112 (bladder), HT29 (colon), U87 and SJ-G2 (glioblastoma), MCF-7 (breast) A2780 (ovarian), H460 (lung), A431 (skin), DU145 (prostate), BE2-C (neuroblastoma) and MIA (pancreatic) cancer cell lines and one normal breast cell line (MCF-10A). Diphenyltin(IV) compounds exhibited greater potency than either the Schiff bases or the respective dimethyltin(IV) compounds. Mechanistic studies on the action of these compounds against bladder cancer cells revealed that they induced the production of reactive oxygen species (ROS). The bladder cancer cells were apoptotic after 24 h post-treatment with the diphenyltin(IV) compounds. The interactions of the organotin(IV) compounds with calf thymus DNA (CT-DNA) were experimentally explored using UV-vis absorption spectroscopy. This study revealed that the organotin(IV) compounds have strong DNA binding affinity, verified via molecular docking simulations, which suggests that these organotin(IV) compounds interact with DNA via groove-binding interactions.

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Section: Introductionmentioning

confidence: 99%

o-Vanillin Derived Schiff Bases and Their Organotin(IV) Compounds: Synthesis, Structural Characterisation, In-Silico Studies and Cytotoxicity

Yusof

Latif

Tahir

et al. 2019

IJMS

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“…The model quickly became quite successful and has been applied to problems ranging from its original purpose, quantifying substituent effects, 3 to redox potentials, 7 dipole moments, 8 orbital energies of metallorganic complexes, 9 aromaticity, [10][11][12][13][14][15][16][17][18][19][20][21] ion stabilization, 22 mechanicistic investigation, 23,24 catalyst activity of nanoparticles, 25 proton-electron coupling in radicals, 26 molecular conductance, 27 excited singlet state, 28 and even toxicities. 29 More recent approaches have also tried to apply the models to nonbenzyl systems. 9,[30][31][32] It is, however, less satisfying because the linear relationship postulated by Hammett lacks a motivation based on physical effects.…”

Section: Introductionmentioning

confidence: 99%

Data enhanced Hammett-equation: reaction barriers in chemical space

2020

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“…While there are a number of reviews pertaining to QSAR of organotins in the literature, the intent of this review is to update the present state of knowledge and trends in this area. Due to the majority of organotin QSARs involving biological systems, this aspect will be discussed first.…”

Section: Introductionmentioning

confidence: 99%

Review: Quantitative structure–activity/property relationships as related to organotin chemistry

Eng

2017

Applied Organom Chemis

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The aim of this review is to examine the current status of quantitative structure–activity/property relationships (QSAR/QSPR) as related to organotin chemistry. QSAR/QSPR are mathematical models that relate some measurable biological activity or physical property in a series of similar compounds to a descriptor or descriptors associated with the molecules. Descriptors used in QSAR/QSPR studies are endless, from traditional parameters to newly developed ones. They range from quantum chemical descriptors to physicochemical parameters while QSAR/QSPR studies range from predicting bio‐toxicity of various species to estimating chromatographic parameters. The intent of the review is to provide investigators with the current state of knowledge and trends in this area.

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Organotins and quantitative-structure activity/property relationships

Cited by 44 publications

References 38 publications

o-Vanillin Derived Schiff Bases and Their Organotin(IV) Compounds: Synthesis, Structural Characterisation, In-Silico Studies and Cytotoxicity

o-Vanillin Derived Schiff Bases and Their Organotin(IV) Compounds: Synthesis, Structural Characterisation, In-Silico Studies and Cytotoxicity

Data enhanced Hammett-equation: reaction barriers in chemical space

Review: Quantitative structure–activity/property relationships as related to organotin chemistry

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