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Novel organotin complexes containing the 2,2′-bipyridine-3,3′,6,6′-tetracarboxylate. Helical supramolecular structure and cytostatic activity

Published on Feb 1, 2015in Journal of Organometallic Chemistry2.07
· DOI :10.1016/j.jorganchem.2014.11.027
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)
Cite
Abstract
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 been determined. Compound ( 3 ) is an exceptional polymer with seven-coordinate and five-coordinate Sn atoms. The Sn atoms are connected via screw-shaped C 10 H 4 N 2 (COO) 4 bridges giving 3D helical network. The NMR and ESI-MS spectra reveal, that complexes in solutions dissociate giving mainly dinuclear complexes. Complex 2 interacts with adenosine 5′-monophosphate (AMP) via phosphate group. Compounds ( 2 ), ( 2a ) and ( 2b ) are very effective cytostatic agents against C-32, SNB-19, SH-4 and Colo-829 tumor cells.
  • References (29)
  • Citations (7)
Cite
References29
Newest
Published on May 1, 2014in Zeitschrift für anorganische und allgemeine Chemie1.34
Kandasamy Gopal14
Estimated H-index: 14
(Central University of Rajasthan),
Subrata Kundu11
Estimated H-index: 11
(IITK: Indian Institute of Technology Kanpur)
+ 1 AuthorsVadapalli Chandrasekhar47
Estimated H-index: 47
(TIFR: Tata Institute of Fundamental Research)
The reaction of bis(tri-n-butyltin)oxide, [nBu3Sn]2O, with HO2C–C6H4–4-CF3 (RfTol-CO2H) affords a coordination polymer [nBu3SnO2C–RfTol]n (1). 1 undergoes hydrolysis in the presence of atmospheric moisture, at room temperature, resulting in the formation of the diorgano stannoxane [{nBu2SnO2C–RfTol}2O]2 (2). The transformation of 1 to 2 is accompanied by a Sn–C bond cleavage reaction. Formation of 2 also occurs in a direct reaction, involving [nBu3Sn]2O and RfTol–CO2H in the presence of water. 2...
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 Oct 1, 2012in Inorganic Chemistry Communications1.79
Andrzej Kochel13
Estimated H-index: 13
(UWr: University of Wrocław),
Małgorzata Hołyńska16
Estimated H-index: 16
(University of Marburg),
Kamil Twaróg1
Estimated H-index: 1
(UWr: University of Wrocław)
Abstract A new system is reported, where solvothermal conditions lead to a cleavage of a C C bond in 2,2′-bipyridine-3,3′,6,6′-tetracarboxylic acid, that might be catalyzed by the starting rhenium salt, ammonium hexachloridorhenate(IV). The resulting product ( 1 ) is a rhenium(III) complex, including the applied ligand and its decomposition product in the Re 3 + ion coordination sphere. 1 is characterized by X-ray diffraction, magnetic and spectroscopic, as well as TGA property measurements.
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 Apr 1, 2012in Journal of Neuro-oncology3.13
Derek R. Johnson14
Estimated H-index: 14
(Mayo Clinic),
Brian Patrick O’Neill56
Estimated H-index: 56
(Mayo Clinic)
The standard-of-care treatment for newly diagnosed glioblastoma changed in 2005, when radiation therapy plus temozolomide chemotherapy replaced radiation therapy alone. It is not yet clear how this change in treatment has influenced patient survival in routine clinical practice, or if a survival benefit extends to patients older than those enrolled in the trial. Data from the Surveillance, Epidemiology, and End Results (SEER) Program was analyzed to compare survival of adult glioblastoma patient...
Published on Feb 20, 2012in Inorganic Chemistry4.85
Baoming Ji22
Estimated H-index: 22
,
Dongsheng Deng9
Estimated H-index: 9
+ 7 AuthorsXianfei Li2
Estimated H-index: 2
A series of novel one-dimensional (1-D) lanthanide coordination polymers (CPs), with the general formula {[Ln(bptcH)(H2O)2]·H2O}n (Ln = NdIII (1), EuIII (2), GdIII (3), TbIII (4), DyIII (5), HoIII (6), or ErIII (7)) have been synthesized by the solvothermal reactions of the corresponding lanthanide(III) picrates and 2,2′-bipyridine-3,3′,6,6′-tetracarboxylic acid (bptcH4). These polymers have been structurally characterized by single-crystal X-ray diffraction, IR, PXRD, thermogravimetric (TGA), a...
Published on Jan 1, 2012in Inorganic Chemistry Communications1.79
Wu Ming-Yan2
Estimated H-index: 2
(CAS: Chinese Academy of Sciences),
Jiang Feilong2
Estimated H-index: 2
(CAS: Chinese Academy of Sciences)
+ 3 AuthorsHong Maochun6
Estimated H-index: 6
(CAS: Chinese Academy of Sciences)
Abstract Four isostructural lanthanide(III) complexes, [Ln 2 (HL) 2 (H 2 O) 4 ] n ·2nH 2 O (H 4 L = 3,3′,6,6′-tetracarboxyl-2,2′-bipyridine) (Sm ( 1 ), Eu ( 2 ), Gd ( 3 ), Tb ( 4 )), have been synthesized under the hydrothermal condition and characterized by single-crystal X-ray diffractions, powder X-ray diffractions (PXRD), thermal analyses (TGA) and elemental analyses (EA). These four complexes all exhibit 1D chain-like structures containing di-nuclear lanthanide(III) units, which are further...
Published on Jan 1, 2012in Inorganic Chemistry Communications1.79
Jie Wu18
Estimated H-index: 18
(Zhengzhou University),
Pei Wang3
Estimated H-index: 3
(Zhengzhou University)
+ 4 AuthorsJunbiao Chang18
Estimated H-index: 18
(Zhengzhou University)
Abstract Use of a C 3 -symmetric facial ligand N,N’,N”-tris(3-pyridyl)-1,3,5-benzenetricarboxamide (L1), three porous MOFs, [CdCl 2 ( aas -L1)] n ( 1 ), [HgI 2 ( sss -L1)] n ( 2 ) and [CoCl 2 ( ass -L1)(EtOH)] 2 ( 3 ), were obtained under solvothermal conditions. Complex 1 exhibits a fascinating 2D two interwoven nets consisting of sandwich-like channels. Compound 2 shows an infinite 1D polymeric chain in herringbone fashion running along a -axis. The hydrogen-bonding interactions further link t...
Published on May 1, 2010in CA: A Cancer Journal for Clinicians223.68
Erwin G. Van Meir68
Estimated H-index: 68
(Emory University),
Constantinos G. Hadjipanayis21
Estimated H-index: 21
(Emory University)
+ 3 AuthorsJeffrey L. Olson53
Estimated H-index: 53
(Emory University)
Malignant gliomas are the most common and deadly brain tumors. Nevertheless, survival for patients with glioblastoma, the most aggressive glioma, although individually variable, has improved from an average of 10 months to 14 months after diagnosis in the last 5 years due to improvements in the standard of care. Radiotherapy has been of key importance to the treatment of these lesions for decades, and the ability to focus the beam and tailor it to the irregular contours of brain tumors and minim...
Published on Jun 1, 2009in Inorganica Chimica Acta2.43
Chunlin Ma14
Estimated H-index: 14
(Liaocheng University),
Qian-Li Li7
Estimated H-index: 7
(Liaocheng University),
Rufen Zhang19
Estimated H-index: 19
(Liaocheng University)
Abstract The self-assembled reaction of 2-hydroxynicotinic acid, KOH and tri- n -butyltin chloride in CH 3 OH and H 2 O (V/V = 5:1) under solvothermal condition (150 °C) affords a novel mixed tri- and dibutyltin macrocyclic complex 1 . Characterization of the complex 1 was achieved using elemental analysis, IR, NMR ( 1 H, 13 C and 119 Sn) spectroscopy, TGA and X-ray crystallography diffraction analysis. X-ray data revealed that it is an unusual 16-membered macrocycle containing eight tin atoms, ...
Cited By7
Newest
Published on Dec 1, 2018in The Journal of Membrane Biology1.75
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 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...
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 Dec 1, 2017in Applied Organometallic Chemistry3.26
Mostafa M. Amini30
Estimated H-index: 30
(Shahid Beheshti University),
Ezzatollah Najafi4
Estimated H-index: 4
(PNU: Payame Noor University)
+ 3 AuthorsSeik Weng Ng36
Estimated H-index: 36
(UM: University of Malaya)
Published on Apr 18, 2017in Zeitschrift für anorganische und allgemeine Chemie1.34
Phil Liebing6
Estimated H-index: 6
(Otto-von-Guericke University Magdeburg),
Asrial A. Husien1
Estimated H-index: 1
(Jambi University)
+ 2 AuthorsFrank T. Edelmann44
Estimated H-index: 44
(Otto-von-Guericke University Magdeburg)
The new organotin(IV) squarates and croconates [SnMe2(H2O)2]C4O4 (1), [SnMe3]2C4O4 (2), and [SnMe3(H2O)]2C5O5 (3), were prepared by salt metathesis from the appropriate sodium salts, and characterized by single-crystal X-ray diffraction and infrared spectroscopy. While 1 and 2 are coordination polymers with bridging C4O42– anions, compound 3 exists as a monomer in the solid state. In the hydrated compounds 1 and 3, the molecules are interconnected by various types of O–H···O bridges between non-...
Haoyang Zhang1
Estimated H-index: 1
,
Jie Hu1
Estimated H-index: 1
+ 1 AuthorsYu Zhang1
Estimated H-index: 1
Abstract The molecular structure of a new complex of copper (II) with (E)-9-ethyl-3-(2-(6-(4-methylpyridin-2-yl)pyridin-3-yl)vinyl)-9H-carbazole ([Cu 2 (emppc) 2 Cl 2 ]Cl 2 ) was optimized with B3LYP/LanL2DZ, PBE1PBE/LanL2DZ and M062X/LanL2DZ theoretical level. The ligand, (E)-9-ethyl-3-(2-(6-(4-methylpyridin-2-yl)pyridin-3-yl)vinyl)-9H-carbazole (emppc), binds to Cu(II) ions with a bi-dentate mode, two Cl − serve as bridging ligand, each Cu(II) ion has a highly distorted tetrahedron coordinatio...
View next paperTriorganotin coordination polymers based on three dicarboxylate ligands containing flexible S S bonds: synthesis, structures and in vitro anti-tumor activity