Novel organotin(IV) compounds derived from bis(organostannyl)methanes: Synthesis and crystal structures of bis[diphenyl(pyridin-2-onato)stannyl]methane and bis[bromophenyl(pyrimidine-2-thionato)stannyl]methane·C7H8

Hadjikakou, Sotiris K.; Jurkschat, Klaus; Schürmann, Markus

doi:10.1016/j.jorganchem.2005.11.056

Cited by 10 publications

(8 citation statements)

References 36 publications

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“…During the last decades the anticancer activity of organotin compounds (OTCs) has been well studied [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. Therefore, the investigation of new OTCs of low toxicity and improved anticancer activity are known to induce apoptosis in several cancer cell lines [ 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

“…In the course of our studies on the design and synthesis of new metallodrugs [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ], the known {[R 3 Sn(CH 3 COO)] n } where R = n -Bu– ( 1 ) and R = Ph– ( 2 ) compounds were isolated from the reaction between acetic acid with tributyltin or triphenyltin oxides. The compounds were characterized via their physical properties and their FT-IR, 119 Sn Mössbauer, and 1 H NMR spectroscopic data, while their structures were verified by single-crystal X-Ray diffraction crystallography.…”

Section: Introductionmentioning

confidence: 99%

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Poly Organotin Acetates against DNA with Possible Implementation on Human Breast Cancer

Latsis

Banti

Kourkoumelis

et al. 2018

IJMS

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Two known tin-based polymers of formula {[R3Sn(CH3COO)]n} where R = n-Bu– (1) and R = Ph– (2),were evaluated for their in vitro biological properties. The compounds were characterized via their physical properties and FT-IR, 119Sn Mössbauer, and 1H NMR spectroscopic data. The molecular structures were confirmed by single-crystal X-Ray diffraction crystallography. The geometry around the tin(IV) ion is trigonal bi-pyramidal. Variations in O–Sn–O···Sn′ torsion angles lead to zig-zag and helical supramolecular assemblies for 1 and 2, respectively. The in vitro cell viability against human breast adenocarcinoma cancer cell lines: MCF-7 positive to estrogens receptors (ERs) and MDA-MB-231 negative to ERs upon their incubation with 1 and 2 was investigated. Their toxicity has been studied against normal human fetal lung fibroblast cells (MRC-5). Compounds 1 and 2 exhibit 134 and 223-fold respectively stronger antiproliferative activity against MDA-MB-231 than cisplatin. The type of the cell death caused by 1 or 2 was also determined using flow cytometry assay. The binding affinity of 1 and 2 towards the CT-DNA was suspected from the differentiation of the viscosity which occurred in the solution containing increasing amounts of 1 and 2. Changes in fluorescent emission light of Ethidium bromide (EB) in the presence of DNA confirmed the intercalation mode of interactions into DNA of both complexes 1 and 2 which have been ascertained from viscosity measurements. The corresponding apparent binding constants (Kapp) of 1 and 2 towards CT-DNA calculated through fluorescence spectra are 4.9 × 104 (1) and 7.3 × 104 (2) M−1 respectively. Finally, the type of DNA binding interactions with 1 and 2 was confirmed by docking studies.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Poly Organotin Acetates against DNA with Possible Implementation on Human Breast Cancer

Latsis

Banti

Kourkoumelis

et al. 2018

IJMS

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“…Ru(II), Ti(IV), Au(III), Ga(III), Sn(IV)) because they can have different targets in cells and might exhibit mechanisms of action in cancer cells other than those of platinum‐based ones. Tin(IV) compounds are interesting because of well‐known multiple applications: industrial and agricultural applications as well as biological (biocides, antimicrobials and potential antiviral and anticancer agents) . In the last few decades the anti‐tumour activity of organotin(IV) compounds has been quite well investigated .…”

Section: Introductionmentioning

confidence: 99%

Preparation and in vitro investigations of triphenyl[ω‐(tetrahydro‐2H‐pyran‐2‐yloxy)alkyl]tin(IV) compounds

Edeler

Bensing

Schmidt

et al. 2016

Applied Organom Chemis

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authors equally contributed.The reaction of SnPh 3 Li with X(CH 2 ) n O-THP (THP = tetrahydro-2H-pyran-2-yl; n = 3, 4, 6, 8, 11; X = Cl, Br) afforded organotin(IV) compounds with the general formula Ph 3 Sn(CH 2 ) n O-THP (1-5). The tetraorganotin(IV) compounds were characterized using multinuclear NMR and infrared spectroscopies and high-resolution mass spectrometry. Anticancer activity of the synthesized compounds was tested in vitro against the A2780 (ovarian), A549 (lung), HeLa (adenocarcinoma) and SW480 (colon) tumour cell lines with SRB assay. The in vitro investigations revealed that when a shorter chain was present a higher activity was achieved; however compounds 1-5 were found to be less active than cisplatin. In addition, the most active compound, 1, enters A2780 cells and causes apoptosis by triggering both intrinsic and extrinsic caspase pathways.

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“…In particular, the cytotoxic and biological activity of organotin compounds is well documented [2e12]. Organotin(IV) complexes with ligands containing phenolic -OH groups and heterocyclic nitrogen donor atoms such as 2-thiobarbituric acid comprise an interesting class of such complexes because they contain an amide group [4,13,14]. Thus, the chemistry that join together organotin moieties and hydroxyl derivatives (e.g.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization and biological studies of the triphenyltin(IV) complex with 2-thiobarbituric acid

Balas

Verginadis

Geromichalos

et al. 2011

European Journal of Medicinal Chemistry

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Novel organotin(IV) compounds derived from bis(organostannyl)methanes: Synthesis and crystal structures of bis[diphenyl(pyridin-2-onato)stannyl]methane and bis[bromophenyl(pyrimidine-2-thionato)stannyl]methane·C7H8

Cited by 10 publications

References 36 publications

Poly Organotin Acetates against DNA with Possible Implementation on Human Breast Cancer

Poly Organotin Acetates against DNA with Possible Implementation on Human Breast Cancer

Preparation and in vitro investigations of triphenyl[ω‐(tetrahydro‐2H‐pyran‐2‐yloxy)alkyl]tin(IV) compounds

Synthesis, structural characterization and biological studies of the triphenyltin(IV) complex with 2-thiobarbituric acid

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