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Butyltin(IV) 5-sulfosalicylates: Structural characterization and their cytostatic activity

Published on Jan 1, 2013in Polyhedron 2.28
· DOI :10.1016/j.poly.2012.10.025
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)
Cite
Abstract
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. The complex 1 in solid state is a chain compound with bridging ligand O 3 SC 6 H 3 (OH)COOH − coordinated to two adjacent SnBu 3 units via SO 3 and COOH groups and complex 2 is a dinuclear compound with O 3 SC 6 H 3 (OH)COO 2− bridging ligand bound to the SnBu 3 moieties through SO 3 and COO groups. The spectroscopic data indicate that 3 is probably a trinuclear complex containing bridging oxido and Hssal ligands containing two five-coordinate and one six-coordinate tin atoms. The complexes effectively interact with ATP and DAMP nucleotides forming Sn–OP bonds and O′–H′…O and N…H–O (nucleotide–Hssal) hydrogen bonds. All compounds are very effective cytotoxic agents against tumor cells. The cytotoxic activity changes in the order 2  >  1  >  3 . Their activity toward non-tumor NHDF cells is much lower. They show also antibacterial and antifungal activity.
  • References (36)
  • Citations (10)
Cite
References36
Newest
Published on Jun 1, 2012in Journal of Inorganic Biochemistry 3.22
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 ChemMedChem 3.02
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 Feb 1, 2011in Polyhedron 2.28
Cengiz Yenikaya9
Estimated H-index: 9
,
Musa Sarı10
Estimated H-index: 10
(Gazi University)
+ 2 AuthorsOrhan Büyükgüngör29
Estimated H-index: 29
(OMU: Ondokuz Mayıs University)
Abstract A novel amino salicylato salt, 2-amino-6-methylpyridinium 2-hydroxy-5-sulfonatobenzoate ( 1 ), and its Cu(II) complex, 2-ammonio-6-methylpyridinium bis(μ 6 -5-sulfonatosalicylatoaquacopper(II)) ( 2 ), have been synthesized from free ligands, namely 5-sulfosalicylic acid (H 3 ssa) and 2-amino-6-methylpyridine (amp). Compounds 1 and 2 have been characterized by elemental, spectral ( 1 H NMR, IR and UV–Vis) and thermal analyses. Additionally, magnetic measurements and the single crystal X-...
Published on Feb 1, 2011in Journal of Inorganic Biochemistry 3.22
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 Biochemistry 3.22
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 Jan 1, 2010in Journal of Health Science
Hiromu Sakurai12
Estimated H-index: 12
(Suzuka University of Medical Science)
This review introduces the development of metal-containing pharmaceutics (metallopharmaceutics) such as anticancer agents containing platinum (Pt) and ruthenium (Ru), and superoxide dismutase (SOD) mimetic, focusing on the recent topics on antidiabetic vanadium (V) and zinc (Zn) complexes as well as antioxidative copper (Cu) and Zn complexes. From the ancient ages, people used many types of inorganic compounds to treat physical disorders or diseases. Since the modern concept of chemotherapy was ...
Published on Sep 1, 2009in European Journal of Inorganic Chemistry 2.58
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 Reviews 13.48
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.
Published on Jan 1, 2009in Dalton Transactions 4.05
Philip C. Andrews24
Estimated H-index: 24
(Monash University, Clayton campus),
Glen B. Deacon44
Estimated H-index: 44
(Monash University, Clayton campus)
+ 4 AuthorsJonathan G. MacLellan11
Estimated H-index: 11
(Monash University, Clayton campus)
Treatment of 5-sulfosalicylic acid (H3Ssal) with BiPh3 results in the formation of the first dianionic carboxylate–sulfonate bismuth complex, [PhBi(HSsal)H2O]∞1a, and its ethanol analogue [PhBi(HSsal)EtOH]∞1b (space groupP21/c), while Bi(OAc)3 gives the mixed monoanionic and dianionic complex, {[Bi(HSsal)(H2Ssal)(H2O)3]2·2H2O}∞2 (space groupP). The three complexes are all polymeric in the solid state as determined by single crystal X-ray diffraction, with extended frameworks constructed from dim...
Published on Jan 1, 2009in Medical Mycology 2.85
Mariusz Dyląg5
Estimated H-index: 5
(UWr: University of Wrocław),
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences)
+ 2 AuthorsStanisław Ułaszewski11
Estimated H-index: 11
(UWr: University of Wrocław)
We investigated the susceptibility of 96 well-characterized strains of yeast-like and filamentous fungi towards new organotin compounds: (1) [Sn(C4H9)3(OOCC6H4SO3H-2)], (2) Sn(C4H9)3{OOC(CH2)3P(C6H5)3}]Br, and (3) [Sn(C6H5)3[OOC(CH2)3N(CH3)3}]Cl. In the case of yeast-like fungi, the in vitro susceptibility tests were carried out according to the Clinical Laboratory Standards Institute (CLSI, formerly NCCLS) reference method M27-A2, while for filamentous fungi the investigations were conducted ac...
Cited By10
Newest
Published on Dec 1, 2018in The Journal of Membrane Biology 1.75
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Aleksandra Włoch5
Estimated H-index: 5
(Wroclaw University of Environmental and Life Sciences)
+ 1 AuthorsHalina Kleszczyńska15
Estimated H-index: 15
(Wroclaw University of Environmental and Life Sciences)
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 i...
Published on Oct 1, 2018in Journal of Thermal Analysis and Calorimetry 2.47
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...
Saqib Ali29
Estimated H-index: 29
(QAU: Quaid-i-Azam University),
Saira Shahzadi16
Estimated H-index: 16
(QAU: Quaid-i-Azam University),
Imtiaz-ud-Din10
Estimated H-index: 10
(QAU: Quaid-i-Azam University)
The excellent anticarcinogenicity and toxicity of organotin(IV) complexes of certain acrylates, methylenedioxyphenylpropenoic acid, piperonylic acid, phenylethanoates, carboxylic acid, acetic acid, benzohydroxamato, peptides, dipeptides, benzoates, schiff bases, xylene, nicotinic acid, pyrimidine, and aminoalcohols have been reviewed here. The high cytotoxic activity of complexes is affected by (1) the availability of coordination positions at Sn and (2) the occurrence of relatively stable ligan...
Published on Jan 1, 2017in Journal of Thermal Analysis and Calorimetry 2.47
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 Nov 1, 2016in Journal of Organometallic Chemistry 2.07
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Małgorzata Latocha12
Estimated H-index: 12
(Medical University of Silesia)
+ 1 AuthorsFlorian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
Abstract New pentamethylcyclopentadienyl complexes [M(C 5 Me 5 )Cl 2 (TCEP)] (M = Rh 1 , M = Ir 2 ) with P(C 2 H 4 COOH) 3 (TCEP) were investigated using IR, 1 H, 13 C, 31 P NMR and ESI-MS spectroscopies. Geometry optimization in the gas phase at the B3LYP/3-21G** level indicated that complex 1 has stable pseudooctahedral structure with large HOMO–LUMO gap. Calculated and experimental IR spectra of 1 agree very well. Cytostatic activity of compounds 1 and 2 was investigated against melanoma and ...
Published on Mar 1, 2016in Journal of Inorganic Biochemistry 3.22
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Tadeusz Lis30
Estimated H-index: 30
(UWr: University of Wrocław)
+ 2 AuthorsFlorian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
Abstract Water soluble and air stable P(RCOOH) 3 (R = C 2 H 4 ) (TCEP) is an efficient reducing agent used in biochemistry to break S–S bond in peptides, proteins and other compounds containing S–S bonds. The similarity between the coordination chemistry of Pd(II) and Pt(II) led to the investigations of antitumor activity of palladium(II) compounds however the Pd(II) complexes with TCEP were not investigated. New palladium(II) complexes with (TCEP): trans -[PdCl 2 (TCEP) 2 ] ( 1 ) and trans -[Pd...
Published on Jan 1, 2016in Chemico-Biological Interactions 3.41
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)
+ 4 AuthorsMartin Hof32
Estimated H-index: 32
Abstract New 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) (DBTsbz), [Sn(C 4 H 9 ) 3 {O 3 SC 6 H 4 COOH-2}] (TBTsbz) and [Sn 2 (C 4 H 9 ) 6 {μ-O 3 SC 6 H 4 COO-2}] (DTBTsbz) are very effective cytotoxic agents against tumor cells. The molecular interaction of these complexes with lipid membranes and DNA has been investigated. The IR spectra and changes of 1 H, 13 C chemical shifts suggest that SO 3 and COO groups of 2-sulfobenzoato ligand ...
Published on Feb 1, 2015in Journal of Organometallic Chemistry 2.07
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Tadeusz Lis30
Estimated H-index: 30
(UWr: University of Wrocław)
+ 2 AuthorsFlorian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
Abstract Reaction between 2,2′-bipyridine-3,3′,6,6′-tetracarboxylic acid (bptcH 4 ) ( 1 ) and [Sn 2 Bu 6 O] in mild conditions proceeds with Sn-Bu bond cleavage giving polynuclear compounds. Complexes [(H 2 O)SnBu 2 (bptc)Sn 2 Bu 6 ]·H 2 O ( 2 ), [(CH 3 OH)SnBu 2 (bptc)Sn 2 Bu 6 ]·H 2 O ( 2a ), [(DMF)SnBu 2 (bptc)Sn 2 Bu 6 ] ( 2b ) and [(DMF)SnBu 2 (bptc)Sn 2 Bu 6 ]·0.5DMF·0.5H 2 O ( 3 ) were characterized using IR, NMR and ESI-MS spectroscopies. The X-ray structures of 1 ·H 2 O and ( 3 ) have b...
Published on Nov 1, 2014in Journal of Thermal Analysis and Calorimetry 2.47
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 Apr 1, 2013in Journal of Organometallic Chemistry 2.07
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Florian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
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 ...