Synthesis, characterization, crystal structure and antitumor activity of organotin(IV) compounds bearing ferrocenecarboxylic acid

Zhu, Chengchen; Liguo, Yang; Li, Dacheng; Zhang, Qingfu; Dou, Jianmin; Wang, Daqi

doi:10.1016/j.ica.2011.04.049

Cited by 25 publications

(10 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…7-9) or the nitrogen atom of a pyridine moiety. The intermolecular Sn···N interaction occurs opposite to the covalent Sn-O bond, and discrete trimers [98] (Fig. 16, top) or one-dimensional [99][100][101][102] (Fig.…”

Section: Nitrogen Atoms As Tb Acceptorsmentioning

confidence: 99%

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

et al. 2018

View full text Add to dashboard Cite

Modeling indicates the presence of a region of low electronic density (a Bσ-hole^) on group 14 elements, and this offers an explanation for the ability of these elements to act as electrophilic sites and to form attractive interactions with nucleophiles. While many papers have described theoretical investigations of interactions involving carbon and silicon, such investigations of the heavier group 14 elements are relatively scarce. The purpose of this review is to rectify, to some extent, the current lack of experimental data on interactions formed by germanium and tin with nucleophiles. A survey of crystal structures in the Cambridge Structural Database is reported. This survey reveals that close contacts between Ge or Sn and lone-pair-possessing atoms are quite common, they can be either intra-or intermolecular contacts, and they are usually oriented along the extension of the covalent bond formed by the tetrel with the most electron-withdrawing substituent. Several examples are discussed in which germanium and tin atoms bear four carbon residues or in which halogen, oxygen, sulfur, or nitrogen substituents replace one, two, or three of those carbon residues. These close contacts are assumed to be the result of attractive interactions between the involved atoms and afford experimental evidence of the ability of germanium and tin to act as electrophilic sites, namely tetrel bond (TB) donors. This ability can govern the conformations and the packing of organic derivatives in the solid state. TBs can therefore be considered a promising and robust tool for crystal engineering.

show abstract

Section: Nitrogen Atoms As Tb Acceptorsmentioning

confidence: 99%

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

et al. 2018

View full text Add to dashboard Cite

show abstract

“…21 With respect to mixed carboxylate methoxide tetraorganodistannoxanes, [(R 2 SnCOOR=)(R 2 SnOMe)O] 2 , which are equivalent to 6, all exhibit the same structural feature of monodentate, terminally bonded carboxylate groups. [22][23][24][25][26][27] When hydroxyl groups are lacking, no hydrogen bonds are formed. Interactions between different molecules, therefore, are restricted to van der Waals and very weak tin nitrate interactions (Fig.…”

Section: (N-bu 2 Snno 3 )(N-bu 2 Snome)o (6)mentioning

confidence: 99%

Reaction products of diorganotin(IV) oxides, R₂SnO, with nitric acid. Part 2 – R = n-butyl and t-butyl

ReuterHans

ReicheltMartin

2014

Can. J. Chem.

View full text Add to dashboard Cite

The reaction of diorganotin(IV) oxides, R 2 SnO with R = n-butyl and t-butyl, with nitric acid in different stoichiometric ratios resulted in the formation of different products depending on the organic groups attached to the tin atom: the diorganotin(IV) dinitrate dihydrates, n-Bu 2 Sn(NO 3 ) 2 ·2H 2 O (2d) and t-Bu 2 Sn(NO 3 ) 2 ·2H 2 O (2e), the mixed diorganotin(IV) nitrate methoxide oxide n-Bu 2 Sn(NO 3 ) (n-Bu 2 SnOMe)O (6), and the diorganotin(IV) nitrate hydroxide hydrate t-Bu 2 Sn(NO 3 )(OH)·H 2 O = [t-Bu 2 Sn(OH)(H 2 O)][NO 3 ] (7). On examination of the solubility of the primary reaction products in different solvents, the three additional compounds t-Bu 2 Sn(NO 3 )(OH)·DMSO (8), t-Bu 2 Sn(NO 3 )(OH)·THF, and 2-t-Bu 2 Sn(NO 3 )(OH)·DMF = [t-Bu 2 Sn(OH)dmf] 2 [NO 3 ] 2 ·[t-Bu 2 Sn(NO 3 )OH] 2 (9) could be isolated. All compounds have been structurally characterized by single crystal X-ray diffraction (primary results for 7) with special attention paid to dimensionality (2d and 2c = monomeric, hydrogen bonded molecules; 6 = dimeric molecules of ladder-type structure; 7 = dimeric cation; 8 = dimeric molecule with hydrogen bonded solvent molecules; 9 = both components dimeric), tin coordination (6, 7, 8, and 9 = trigonal bipyramidal; 2d and 2e = eightfold), and nitrate bonding modes (7 and 9 = isolated, hydrogen bonded; 6, 8, and 9 (component 2) = monodentate; 2d and 2e = symmetrical bidentate), the latter one being analyzed using both Sn-O and N-O distances.Résumé : La réaction des oxydes de diorganoétain(IV), de formule R 2 SnO (où R = n-Butyl et t-Butyl), avec l'acide nitrique, dans diverses proportions stoechiométriques a conduit à la formation de différents produits dont la nature dépendait des groupes organiques liés à l'atome d'étain : les dinitrates de diorganétain (IV) dihydratés, nBu 2 Sn(NO 3 ) 2 ·2H 2 O (2d) et tBu 2 Sn(NO 3 ) 2 ·2H 2 O (2e), le composé mixte d'oxyde méthanolate de diorganoétain(IV) et nitrate de diorganoétain(IV), nBu 2 Sn(NO 3 )(nBu 2 SnOMe)O (6) et l'hydroxyde nitrate de diorganoétain(IV) hydraté, tBu 2 Sn(NO 3 )(OH)·H 2 O = [tBu 2 Sn(OH)(H 2 O)][NO 3 ] (7). Après examen de la solubilité des produits primaires de réaction dans différents solvants, trois autres composés ont pu être isolés : tBu 2 Sn(NO 3 )(OH)·DMSO (8), tBu 2 Sn(NO 3 )(OH)·THF et 2tBu 2 Sn(NO 3 )(OH)·DMF = [tBu 2 Sn(OH)dmf] 2 [NO 3 ] 2 ·[tBu 2 Sn(NO 3 )OH] 2 (9). La structure de ces composés a été déterminée par cristallographie aux rayons X (premiers résultats obtenus pour 7), en particulier la dimensionnalité (2d et 2c = molécules monomériques à liaisons hydrogènes, 6 = molécules dimériques de structure en échelle; 7 = cation dimérique, 8 = molécule dimérique associée à des molécules de solvant à liaisons hydrogène; 9 = deux composants dimériques), la coordination de l'étain (6, 7, 8, 9 = trigonalebipyramidale; 2d, 2e = à huit plis) et les modes de liaisons du nitrate (7, 9 = isolé, à liaisons hydrogène; monodentate, avec les composants dimériques 6, 8 et 9; bidentate symétrique, avec 2d et 2e), le composé ...

show abstract

“…Organotin carboxylates can be chemically customized by directly introducing carboxylic acid group(s) into the organometallic ligands. From this perspective, a significant number of organotin(IV) complexes based on ferrocenecarboxylic acid have been structurally characterized by single crystal X-ray crystallography, revealing a diverse range of structures, such as monomers, dimers, ladders, drums, and polymers. − Organostannoxane-supported ferrocene assemblies were also extended to 1,1′-ferrocenedicarboxylic acid (Fc{COOH} 2 ), resulting in heterobimetallic compounds with interesting structures that include mixed-valence Sn(II)–Sn(III) and macrocycles with large cavities. − …”

Section: Introductionmentioning

confidence: 99%

Syntheses, Structural Snapshots, Solution Redox Properties, and Cytotoxic Performances of Designated Ferrocene Scaffolds Appended with Organostannyl(IV) benzoates en Route for Human Hepatic Carcinoma

et al. 2018

View full text Add to dashboard Cite

Although several strategies have been established to circumvent the limitations of platinum-based chemotherapy, the basic problems still persist. For this purpose, the new series of heterobimetallic formulations [FcL n SnPh 3 ] (1, 3, and 9)], [FcL n SnBu 3 ] n (2, 4 and 8), [FcL 3 SnCy 3 ] (10), and [FcL 3 SnR 3 (MeOH)] (R = Me (5), Et (6), or Pr (7)), where FcL n (n = 1−3) refers to the isomeric 2-/3-/4-ferrocenylbenzoates, was synthesized which can target cancer cells and successively support functional iron deficiencies during chemotherapy. Compounds 1−10 have been characterized by elemental analysis, and their spectroscopic properties were investigated using IR, NMR, electronic, and fluorescence techniques. The molecular structures of metallo proligands FcL 1 H and FcL 3 H and the six heterobimetallic compounds 2, 3, 5−7, and 10 have been determined by X-ray crystallography. The redox properties of FcL n H and their compounds 1−10 were also investigated by cyclic voltammetry. In vitro cytotoxic activities of compounds 1−4, 8, and 9 were assessed by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against human hepatic carcinoma (HepG2) cells, with IC 50 values revealing high activity better than that of doxorubicin. More importantly, compound 2 demonstrated maximum inhibition in HepG2 cells (IC 50 = 0.10 μM) among other studied cell lines of human origin, e.g. embryonic kidney (HEK-293T), breast (MDA-MB-231), and lung (A-549) cancer cells, with negligible effect on human peripheral blood mononuclear cells (PBMC). Compound 2 effectively inhibited cell viability, and the apoptosis proceeded via activation of caspases and cleavages of caspase-dependent proteins, as revealed from a PARP cleavage assay. Membrane microviscosity results point toward changes in fluidity that are sufficient to stop biological activities mediated by growth factors.

show abstract

Synthesis, characterization, crystal structure and antitumor activity of organotin(IV) compounds bearing ferrocenecarboxylic acid

Cited by 25 publications

References 45 publications

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

Reaction products of diorganotin(IV) oxides, R₂SnO, with nitric acid. Part 2 – R = n-butyl and t-butyl

Syntheses, Structural Snapshots, Solution Redox Properties, and Cytotoxic Performances of Designated Ferrocene Scaffolds Appended with Organostannyl(IV) benzoates en Route for Human Hepatic Carcinoma

Contact Info

Product

Resources

About

Synthesis, characterization, crystal structure and antitumor activity of organotin(IV) compounds bearing ferrocenecarboxylic acid

Cited by 25 publications

References 45 publications

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

Reaction products of diorganotin(IV) oxides, R2SnO, with nitric acid. Part 2 – R = n-butyl and t-butyl

Syntheses, Structural Snapshots, Solution Redox Properties, and Cytotoxic Performances of Designated Ferrocene Scaffolds Appended with Organostannyl(IV) benzoates en Route for Human Hepatic Carcinoma

Contact Info

Product

Resources

About

Reaction products of diorganotin(IV) oxides, R₂SnO, with nitric acid. Part 2 – R = n-butyl and t-butyl