Triphenyltin(IV) benzoates with diazenyl/imino scaffold exhibiting remarkable apoptosis mediated by reactive oxygen species

Baul, Tushar S. Basu; Dutta, Dhrubajyoti; Duthie, Andrew; Prasad, Rajkishore; Rana, Nishant Kumar; Koch, Biplob; Tiekink, Edward R. T.

doi:10.1016/j.jinorgbio.2017.04.020

Cited by 23 publications

(37 citation statements)

References 60 publications

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“…[20] The identityo fL1 was established using ac ombination of spectroscopica nd analytical methods, including a single crystal molecular structure. [21] Along the same lines, ligand L2 {2-((4-methoxybenzylidene)amino)benzoic acid} and L3 {2-((4methylbenzylidene)amino)benzoic acid} formed readily upon mixinga nthranilic acid with para-anisaldehyde and 4-methylbenzaldehyde, respectively. The NMR findings were corroborated by mass analysis, which revealed am olecular ion peak at m/z = 256.09 [M+ +H] + Da (Figure S5).…”

Section: Resultsmentioning

confidence: 95%

Pd‐Iminocarboxylate Complexes and Their Behavior in Ethylene Polymerization

Deshmukh

Gaikwad

Gonnade

et al. 2020

Chemistry An Asian Journal

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Designingc o-catalyst-free late transition metal complexes for ethylene polymerization is ac hallenging task at the interface of organometallic and polymerc hemistry. Herein, as et of new,co-catalyst-free,s ingle-component catalytic systemsf or ethylene polymerizationh ave been unraveled. Treatmento fa nthranilica cid with various aldehydes produced four iminocarboxylate ligands (L1-L4)i nv ery good to excellent yield (75-92 %). The existence of 2-((2-methoxybenzylidene)amino) benzoica cid (L1)h as been unambiguously demonstrated using NMR spectroscopy,M Sa nd single-crystal X-ray diffraction. An eutralP d-iminocarboxylate complex [{N O}PdMe(L1)] (N O = k 2 -N,O-ArCHNC 6 H 4 CO 2 with Ar = 2-MeOC 6 H 4 ) C1 was prepared by treating stoichiometric amount of L1.Na with palladium precursor.T he identity of C1 was confirmed by 1-2D NMR spectroscopy and singlecrystal X-ray diffraction studies. Along the same lines,p alladium complexes C2-C4 were prepared from ligands L2-L4 respectively.I n-situ high-pressure NMR investigations revealed that these Pd complexes are amenable to ethylene insertiona nd undergo facile b-H elimination to produce propylene. These palladium complexes were then evaluated in ethylene polymerizationr eaction and various reactionp arameters were screened. When C1-C4 were exposed to ethylene pressures of 10-50bar,f ormationo fl ow-molecularweightpolyethylene wasobserved.

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Section: Resultsmentioning

confidence: 95%

Pd‐Iminocarboxylate Complexes and Their Behavior in Ethylene Polymerization

Deshmukh

Gaikwad

Gonnade

et al. 2020

Chemistry An Asian Journal

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“…The presence of an imine moiety (‐C=N‐) in the ligand skeleton can greatly influence the biological properties of the metal compounds…”

Section: Synthesis Structure and Anti‐cancer Activity Of Triphenymentioning

confidence: 99%

“…The 2/3/4‐[( E )‐{[4‐dimethylamino)phenyl]methylidene}amino]benzoic acids HL 13 , HL 13a and HL 13b were used as pro‐ligands for the syntheses of 28–30 (Table , entry 7; Scheme ) . The metal source was Ph 3 SnOH and the reaction took place in anhydrous toluene.…”

Section: Synthesis Structure and Anti‐cancer Activity Of Triphenymentioning

confidence: 99%

Biological Evaluation of Azo‐ and Imino‐Based Carboxylate Triphenyltin(IV) Compounds

et al. 2020

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Azo (‐N=N‐)‐ and imino (‐C=N‐)‐carboxylate triphenyltin(IV) compounds, which are well known for their promising biological activities, are usually synthesized by reacting a triphenyltin(IV) compound (oxide, hydroxide or chloride) with a suitably substituted carboxylic acid, under appropriate conditions. Their biological properties are influenced by the type/position of the functional azo or imino group in the carboxylate ligand skeleton. They are very effective in anticancer studies, being often better than the standard drug cisplatin in terms of cytotoxicity. A few of the azo‐appended carboxylate triphenyltin(IV) compounds also display anti‐bacterial, anti‐fungal and anti‐diabetic activities. The present manuscript highlights the syntheses, structures, and biological (i.e., anti‐cancer, anti‐bacterial, anti‐fungal and anti‐diabetic) activities of such triphenyltin(IV) compounds.

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“…Some organotin(IV) complexes were found to have much higher activity in vitro than the currently used anticancer drugs; in particular, the highest activity was ascribed to tributyltin(IV) and triphenyltin(IV) compounds (mostly in nM concentration) (Gielen and Tiekink 2005; Pellerito and Nagy 2002; Nath et al 2013; Williams et al 2016; Baile et al 2015; Edeler et al 2017; Pruchnik et al 2013, 2015, 2016). However, many of them show severe toxicity, which prompted a search for new compounds with high activity against tumor cells and decreased side effects (Hadjikakou and Hadjiliadis 2009; de Carvalho Oliveira and Santelli 2010; Ndagi et al 2017; Basu Baul et al 2017). The subjects of the research are tributyltin (TBTA) and triphenyltin (TPhTA) 2-[4 (dimethylamino)phenylazo]benzoate complexes (Fig.…”

Section: Introductionmentioning

confidence: 99%

An In Vitro Study of the Effect of Cytotoxic Triorganotin Dimethylaminophenylazobenzoate Complexes on Red Blood Cells

et al. 2018

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Interactions of tributyltin (TBTA) and triphenyltin (TPhTA) 2-[4 (dimethylamino)phenylazo]benzoates, showing promising cytostatic activity against tumor cells, with erythrocytes and with erythrocyte membranes and model lipid membranes have been investigated. The effect of TBTA and TPhTA on the erythrocyte and its model membrane was investigated by the microscopic and spectroscopic methods. Interaction of tin complexes with the membrane was determined on the basis of hemolytic activity, changes induced in the shape of erythrocytes, as well as physicochemical parameters of the membrane, such as fluidity. The studies showed that the compounds in higher concentration induce hemolysis; however, TBTA is more toxic than TPhTA. Both TBTA and TPhTA induce morphological alterations in red blood cells—from discocytes to spherocytes and from discocytes to echinocytes. The results suggest that investigated complexes interact with the erythrocyte membrane, change its properties, and probably locate themselves in the hydrophilic part of the membrane, which agrees with conclusions drawn from investigation of erythrocyte membranes and model lipid membranes with the help of fluorescence and infrared spectroscopy.

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Triphenyltin(IV) benzoates with diazenyl/imino scaffold exhibiting remarkable apoptosis mediated by reactive oxygen species

Abstract: The cytotoxic potency of a series of triphenyltin(IV) compounds of general composition [Ph 3 compounds-based drugs as potential anti-cancer therapies should be pursued.

Cited by 23 publications

References 60 publications

Pd‐Iminocarboxylate Complexes and Their Behavior in Ethylene Polymerization

Pd‐Iminocarboxylate Complexes and Their Behavior in Ethylene Polymerization

Biological Evaluation of Azo‐ and Imino‐Based Carboxylate Triphenyltin(IV) Compounds

An In Vitro Study of the Effect of Cytotoxic Triorganotin Dimethylaminophenylazobenzoate Complexes on Red Blood Cells

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