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Butyltin(IV) citrates and tartrates: Structural characterization and their interaction with nucleotides

Published on Apr 1, 2013in Journal of Organometallic Chemistry2.07
· DOI :10.1016/j.jorganchem.2013.01.015
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Florian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
Cite
Abstract
Abstract Butyltin complexes with biologically important hydroxyacids, citric HOOCCH 2 C(OH)(COOH)CH 2 COOH (C 6 H 8 O 7 ) acid and (2 R ,3 R )-(+)-tartaric HOOCCH(OH)CH(OH)COOH (C 4 H 6 O 6 ) acid: [Sn(C 4 H 9 ) 2 (C 6 H 6 O 7 )] ( 1 ), [Sn(C 4 H 9 ) 3 (C 6 H 7 O 7 )] ( 2 ), (phenH) 2 [Sn(C 4 H 9 ) 3 (C 6 H 5 O 7 )] ( 3 ), [Sn(C 4 H 9 ) 2 (C 4 H 4 O 6 )] ( 4 ), [Sn(C 4 H 9 ) 3 (C 4 H 5 O 6 )] ( 5 ), (phenH)[Sn(C 4 H 9 ) 3 (C 4 H 4 O 6 )] ( 6 ) and [{Sn(C 4 H 9 ) 3 } 2 (C 4 H 4 O 6 )] ( 7 ) have been synthesized and characterized by ESI–MS, IR and 1 H, 13 C and 119 Sn NMR spectra. Their structures and properties in solid state and solutions were proposed on the basis of the spectroscopic data and density functional theory (DFT) calculations at B3LYP/3-21G** level. Complexes in solutions in polar solvents are five-coordinate as evidenced by 13 C and 119 Sn NMR spectra. Geometries of the five-coordinate complexes were optimized with B3LYP/3-21G** calculations. The 13 C, 31 P and 119 Sn NMR spectra prove that complexes effectively interact with AMP, ATP and DAMP nucleotides forming Sn–OP bonds and N⋯H–O (nucleotide–carboxylate ligand) hydrogen bonds. In the case of dibutyltin complexes ( 1 and 4 ) nucleotides may also be coordinated as a chelating ligands via phosphate group and N7 atom of adenine residue.
  • References (42)
  • Citations (5)
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References42
Newest
Published on Jan 1, 2013in Polyhedron2.28
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Małgorzata Latocha12
Estimated H-index: 12
(Medical University of Silesia)
+ 2 AuthorsFlorian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
Abstract Butyltin complexes with 5-sulfosalicylic acid (H 3 ssal) [Sn(C 4 H 9 ) 3 {O 3 SC 6 H 3 (OH)COOH}] ( 1 ), [Sn 2 (C 4 H 9 ) 6 (OOCC 6 H 3 OHSO 3 )] ( 2 ) and [Sn 3 (C 4 H 9 ) 6 (OOCC 6 H 3 (OH)SO 3 ) 2 O] ( 3 ) have been synthesized and characterized by ESI-MS, IR and 1 H, 13 C and 119 Sn NMR spectra. Their structures and properties in solid state and solutions were proposed on the basis of the spectroscopic data and density functional theory (DFT) calculations at B3LYP/3-21G ∗∗ level. Th...
Published on Jun 1, 2012in Journal of Inorganic Biochemistry3.22
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Tadeusz Lis30
Estimated H-index: 30
(UWr: University of Wrocław)
+ 4 AuthorsFlorian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
Abstract Three butyltin complexes with 2-sulfobenzoic acid [Sn(C 4 H 9 ) 2 {O 3 SC 6 H 4 COO-2}(H 2 O)]·(C 2 H 5 OH) ( 1 ), [Sn(C 4 H 9 ) 3 {O 3 SC 6 H 4 COOH-2}] ( 2 ) and [Sn 2 (C 4 H 9 ) 6 {μ-O 3 SC 6 H 4 COO-2}] ( 3 ) have been synthesized and characterized by IR and 1 H, 13 C and 119 Sn NMR spectra. They show interesting properties in solid state and solutions because there are many modes of coordination of the Sbz ligand. The structure of complex 1 has been determined by X-ray crystallogra...
Published on Feb 6, 2012in ChemMedChem3.02
Lourdes Rocamora-Reverte8
Estimated H-index: 8
(Universidad Miguel Hernández de Elche),
Estefanía Carrasco-García10
Estimated H-index: 10
(Universidad Miguel Hernández de Elche)
+ 4 AuthorsSantiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University)
A group of organotin(IV) complexes were prepared: [SnCy3(DMNI)] (1), [SnCy3(BZDO)] (2), [SnCy3(DMFU)] (3), and [SnPh2(BZDO)2] (4), for which DMNIH=2,6-dimethoxynicotinic acid, BZDOH=1,4-benzodioxane-6-carboxylic acid, and DMFUH=2,5-dimethyl-3-furoic acid. The cytotoxic activities of compounds 1–4 were tested against pancreatic carcinoma (PANC-1), erythroleukemia (K562), and two glioblastoma multiform (U87 and LN-229) human cell lines; they show very high antiproliferative activity, with IC50 val...
Published on Jan 1, 2012in Journal of Molecular Structure2.12
Laura Cecilia Bichara6
Estimated H-index: 6
,
María V. Fiori Bimbi2
Estimated H-index: 2
+ 2 AuthorsSilvia Antonia Brandán19
Estimated H-index: 19
Abstract We studied the Sn(IV)-complex, [Sn(C 6 H 4 O 7 ) 2 ] 2− formed after anodic dissolution of a tin surface through its passive oxide film in citric–citrate aqueous solution buffer pH 3. Tin-complex was experimentally characterized using infrared spectroscopy while ab initio calculations were made to study its structure and vibrational properties. These calculations gave us a precise knowledge of the normal modes of vibration taking into account that in the complex the molecule comprises a...
Published on Jan 1, 2012in Organic and Biomolecular Chemistry3.49
Mario Waser17
Estimated H-index: 17
(Johannes Kepler University of Linz),
Katharina Gratzer5
Estimated H-index: 5
(Johannes Kepler University of Linz)
+ 1 AuthorsNorbert Müller31
Estimated H-index: 31
(Johannes Kepler University of Linz)
A novel class of tartaric acid-derived N-spiro quaternary ammonium salts was synthesised starting from known TADDOLs. These compounds were found to catalyse the asymmetric α-alkylation of glycine Schiff bases with high enantioselectivities and in good yields.
Published on Feb 1, 2011in Journal of Inorganic Biochemistry3.22
Vaso Dokorou8
Estimated H-index: 8
(UoI: University of Ioannina),
Alexandra Primikiri4
Estimated H-index: 4
(UoI: University of Ioannina),
Dimitra Kovala-Demertzi36
Estimated H-index: 36
(UoI: University of Ioannina)
Abstract The novel triphenyltin(IV) esters of flufenamic acid ( 1 ), Hflu, [Ph 3 Sn(flu)] ( 2 ), and of [2-(2,3-dichlorophenylamino)benzoic acid] ( 3) , Hdcpa, [Ph 3 Sn(dcpa)] ( 4 ) have been structurally characterized by means of vibrational and 1 H, 13 C NMR spectroscopic studies. The crystal and molecular structures of [SnPh 3 (dcpa)(DMSO)] 4a are described. The molecular structure of 4a reveals that the Sn atom has a distorted trigonal bipyramidal coordination geometry with equatorial phenyl...
Published on Sep 1, 2010in Journal of Inorganic Biochemistry3.22
Tushar S. Basu Baul23
Estimated H-index: 23
(NEHU: North Eastern Hill University),
Anup Paul6
Estimated H-index: 6
(NEHU: North Eastern Hill University)
+ 8 AuthorsRajeshwar P. Verma21
Estimated H-index: 21
(Pomona College)
Abstract A series of tributyltin(IV) complexes based on 2/4-[( E )-2-(aryl)-1-diazenyl]benzoate ligands was synthesized, wherein the position of the carboxylate and aryl substituents (methyl, tert -butyl and hydroxyl) varies. The complexes, Bu 3 SnL 1–4 H ( 1 – 4 ), have been structurally characterized by elemental analysis and IR, NMR ( 1 H, 13 C, and 119 Sn) and 119 Sn Mossbauer spectroscopy. All have a tetrahedral geometry in solution and a trigonal bipyramidal geometry in the solid-state, ex...
Published on Jun 30, 2010in Talanta4.92
Regina de Carvalho Oliveira1
Estimated H-index: 1
(Federal Fluminense University),
Ricardo Erthal Santelli28
Estimated H-index: 28
(Federal Fluminense University)
Abstract Environmental concerns regarding organotin compounds have increased remarkably in the past 20 years, due in large part to the use of these compounds as active components in antifouling paints [mainly tributyltin (TBT)] and pesticide formulations [mainly triphenyltin (TPhT)]. Their direct introduction into the environment, their bio-accumulation and the high toxicity of these compounds towards “non-target” organisms (for example: oysters and mussels) causes environmental and economic dam...
Published on Sep 1, 2009in European Journal of Inorganic Chemistry2.58
Malgorzata Gajewska2
Estimated H-index: 2
(IST: Instituto Superior Técnico),
Konstantin V. Luzyanin22
Estimated H-index: 22
(IST: Instituto Superior Técnico)
+ 3 AuthorsArmando J. L. Pombeiro58
Estimated H-index: 58
(IST: Instituto Superior Técnico)
The reactions between equimolar amounts of R2SnO (R = Me 1, nBu 2) and N,2-dihydroxy-5-[N-hydroxyethanimidoyl]benzamide (H2L) under solvent reflux conditions (in toluene for 1 and methanol for 2) for ca. 4 h led to the formation of the trinuclear tin complexes [R2Sn(L)]3 (R = Me 3, nBu 4) isolated as colourless crystalline solids in ca. 85 % yield, which were characterized by IR, 1H, 13C and 119Sn NMR spectroscopy, elemental analysis and (for 4) by X-ray diffraction. The trinuclear Sn core is st...
Published on Jan 1, 2009in Coordination Chemistry Reviews13.48
Sotiris K. Hadjikakou34
Estimated H-index: 34
(UoI: University of Ioannina),
Nick Hadjiliadis36
Estimated H-index: 36
(UoI: University of Ioannina)
Tin compounds and their therapeutic potentials are under consideration from many research groups, while a number of early reviews recording advances in the screening for antiproliferative potential of organotins are also available. This review focuses upon results obtained on the antiproliferative activity of tin compounds in the past 5 years.
Cited By5
Newest
Published on May 1, 2019in Polyhedron2.28
I. I. Seifullina6
Estimated H-index: 6
,
E. E. Martsinko6
Estimated H-index: 6
+ 3 AuthorsS. V. Shishkina11
Estimated H-index: 11
Abstract This study describes supramolecular assemblies of Cu(II) and Ni(II) 2,2′-bipyridine cations with dimeric tartratogermanate anions, namely [CuCl(bipy) 2 ] 2 [Ge 2 (OH) 2 (Tart) 2 ]·4H 2 O ( I ) and [Ni(bipy) 3 ] 4 [{Ge 2 (OH) 2 (Tart) 2 } 3 Cl 2 ]·15H 2 O ( II ). The compounds were characterized by elemental analysis, mass-spectrometry, IR-spectroscopy and X-ray analysis. The chloride ion coordinates to the Cu atom in cation I and two chloride ions together with the [Ge 2 (OH) 2 (Tart) 2...
Published on Oct 1, 2018in Journal of Thermal Analysis and Calorimetry2.47
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Teresa Kral9
Estimated H-index: 9
(Wroclaw University of Environmental and Life Sciences),
Martin Hof32
Estimated H-index: 32
The aim of the study was to investigate and compare the interaction of tributyltin (TBTA) and triphenyltin (TPhTA) 2-[4 (dimethylamino)phenylazo]benzoates complexes with the lipid membrane and plasmid DNA. Both TBTA and TPhTA belong to the group of promising anticancer agents. Differential scanning calorimetry method was employed to examine the heat signal associated with phase transitions of liposomes formed from dipalmitoylphosphatidylcholine (DPPC) or DPPC/cholesterol and modified with TBTA a...
Published on Jan 1, 2017in Journal of Thermal Analysis and Calorimetry2.47
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences)
In the previous study, we showed that butyltin complexes with 2-sulfobenzoic acid (commonly referred to as BTsbz) exhibit a very wide biological activity. The BTsbz in vitro are very active cytotoxic agents against tumor cells—more effective than cisplatin and carboplatin (traditional anticancer drugs). These complexes are antibacterial agents against gram-positive and gram-negative bacteria, as well. The aim of the present study was to investigate the influence of BTsbz on the thermotropic phas...
Published on Jun 26, 2015
Four organotin (IV) derivatives of Hexanedioic acid: potassium dibutyltin (IV) hexanedioate (1), potassium tributyltin (IV) hexanedioate (2), potassium diphenyltin (IV) hexanedioate (3) and potassium triphenyltin (IV) hexanedioate (4) were synthesized by reacting hexanedioic acid with potassium hydroxide to give the potassium hydrogen salt followed by reaction between the salt and an organotin oxide/hydroxide to give the potassium organotin dicarboxylates. The compounds were characterized by tin...
Published on Nov 1, 2014in Journal of Thermal Analysis and Calorimetry2.47
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Teresa Kral9
Estimated H-index: 9
(Wroclaw University of Environmental and Life Sciences),
Martin Hof32
Estimated H-index: 32
Organotin(IV) complexes show a wide variety of biological activity: bactericidal, fungicidal, caricidal, and pesticidal. Many of them are more effective than traditional heavy metal anticancer drugs. The aim of the present study was to investigate the interaction of a new dibutyltin complex with citric acid (DBTC) with lipid membrane and plasmid DNA. The effect of this compound on the multilamellar liposomes formed with dipalmitoylphosphatidylcholine, dimyristoylphosphatidylcholine, and dimyrist...
Published on Nov 1, 2014in Polyhedron2.28
Fang-Lin Li (Shihezi University), Qi Chen (NKU: Nankai University)+ 2 AuthorsLiang-Fu Tang12
Estimated H-index: 12
(NKU: Nankai University)
Abstract Bis(pyrazol-1-yl)methane-tetracarboxylic acid and tris(pyrazol-1-yl)methane-hexacarboxylic acid, namely bis(3,5-dicarboxypyrazol-1-yl)methane (CH 2 [3,5-Pz(CO 2 H) 2 ] 2 ) and tris(3,5-dicarboxypyrazol-1-yl)methane (CH[3,5-Pz(CO 2 H) 2 ] 3 ), have been synthesized by the oxidation reaction of bis(3,5-dimethylpyrazol-1-yl)methane and tris(3,5-dimethylpyrazol-1-yl)methane with an excess of KMnO 4 . Reaction of CH 2 [3,5-Pz(CO 2 H) 2 ] 2 with (R 3 Sn) 2 O yielded the corresponding organoti...