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Synthesis and characterization of a novel o-tolyltelluronic trimethyltin ester and its cytotoxic assessment in vitro

Published on Jan 1, 2014in Dalton Transactions4.05
· DOI :10.1039/C3DT52326H
Chunlin Ma14
Estimated H-index: 14
(Liaocheng University),
Shuang Cheng7
Estimated H-index: 7
(Liaocheng University)
+ 3 AuthorsShao-Liang Zhang6
Estimated H-index: 6
(Liaocheng University)
Cite
Abstract
A new arenetelluronic triorganotin ester, namely (Me3Sn)4[o-Me-PhTe(μ-O)(OH)O2)]2 (1) has been prepared by the reaction of o-tolyltelluronic acid and Me3SnCl in the presence of potassium hydroxide. The complex was fully characterized by elemental analysis, FT-IR, NMR (1H, 13C, 119Sn) spectroscopy and X-ray crystallography. Structure analysis revealed that the complex crystallized as Sn4Te2 units and a 1D linear chain was formed by intermolecular C–H⋯O interactions. Cytotoxic assessments showed that the complex can induce apoptotic cell death via accumulation of ROS, collapse of the MMP and activating caspase-3. The results indicated that ROS is crucial to the cytotoxicity induced by the complex.
  • References (44)
  • Citations (6)
Cite
References44
Newest
Published on Feb 11, 2013in Organometallics4.10
Lukas K. Filak6
Estimated H-index: 6
,
Simone Göschl11
Estimated H-index: 11
+ 6 AuthorsVladimir B. Arion40
Estimated H-index: 40
Six novel ruthenium(II)− and osmium(II)− arene complexes with three modified indolo(3,2-c)quinolines have been synthesized in situ starting from 2-amino- indoloquinolines and 2-pyridinecarboxaldehyde in the pres- ence of (M(p-cymene)Cl2)2 (M = Ru, Os) in ethanol. All complexes have been characterized by elemental analysis, spectroscopic techniques ( 1 H, 13 C NMR, IR, UV−vis), and ESI mass spectrometry, while four complexes were investigated by X-ray diffraction. The complexes have been tested f...
Published on Feb 1, 2013in Toxicology in Vitro3.07
Rui Ge6
Estimated H-index: 6
(Shanxi Medical University),
Wen-Hua Ma1
Estimated H-index: 1
(Shanxi Medical University)
+ 1 AuthorsQingshan Li7
Estimated H-index: 7
(Shanxi Medical University)
Abstract The severe toxicity of antitumor organotin (IV) compounds limits their application in clinic, however, the toxic mechanism is still unclear. Di-n-butyl-di-(4-chlorobenzohydroxamato) Tin (IV) (DBDCT), an antitumor agent with high activity and obvious neurotoxicity was chosen as a typical diorganotin (IV) compound to investigate its neurotoxic mechanism using PC12 cells and comprehensive methods. Treatment with DBDCT resulted in a dose- and time-dependent growth inhibition of PC12 cells. ...
Published on Jan 1, 2013in Dalton Transactions4.05
Alexey A. Nazarov30
Estimated H-index: 30
(EPFL: École Polytechnique Fédérale de Lausanne),
Daniel Gardini1
Estimated H-index: 1
(EPFL: École Polytechnique Fédérale de Lausanne)
+ 5 AuthorsPaul J. Dyson87
Estimated H-index: 87
(EPFL: École Polytechnique Fédérale de Lausanne)
Two hybrid compounds comprising an antimetastatic ruthenium–arene fragment tethered to an indazole-3-carboxylic acid derivative that inhibits aerobic glycolysis in cancer cells have been prepared and evaluated in a variety of cancer cell lines, including highly relevant human glioblastoma cells, with an apparent synergistic action between the two components observed.
Published on Feb 1, 2012in Seminars in Cancer Biology9.66
Benjamin Sredni38
Estimated H-index: 38
(BIU: Bar-Ilan University)
Abstract Tellurium is a rare element, which has been regarded as a toxic, non-essential trace element; its biological role, if any, has not been clearly established to date. The investigation of therapeutic activities of tellurium compounds is rather limited in the literature, despite the relative abundance of tellurium in the human body. Nevertheless, the varied activities of tellurium agents in both malignant and normal cells are extremely exciting, though very complex. Not surprisingly, an in...
Published on Jan 1, 2012in Dalton Transactions4.05
Edward R. T. Tiekink45
Estimated H-index: 45
(UM: University of Malaya)
Despite being disparaged for their malodorous and toxic demeanour, compounds of selenium, a bio-essential element, and tellurium, offer possibilities as therapeutic agents. Herein, their potential use as drugs, for example, as anti-viral, anti-microbial, anti-inflammatory agents, etc., will be surveyed along with a summary of the established biological functions of selenium. The natural biological functions of tellurium remain to be discovered.
Published on Jan 1, 2012in Frontiers in Bioscience2.21
M. Schmitt Sara1
Estimated H-index: 1
,
Frezza M1
Estimated H-index: 1
,
Q. P. Dou2
Estimated H-index: 2
Published on Jun 1, 2011in Cell Biology and Toxicology5.10
Armando Varela-Ramirez17
Estimated H-index: 17
(UTEP: University of Texas at El Paso),
Mc Costanzo2
Estimated H-index: 2
(UTEP: University of Texas at El Paso)
+ 2 AuthorsRenato J. Aguilera21
Estimated H-index: 21
(UTEP: University of Texas at El Paso)
In this report, we have tested the cytotoxicity of two organotin (OT) compounds by flow cytometry on a panel of immortalized cancer cell lines of human and murine origin. Although the OT compounds exhibited varying levels of cytotoxicity, diphenylmethyltin chloride was more toxic than 1,4-bis (diphenylchlorostannyl)p-xylene on all cell lines tested. The OT compounds were found to be highly cytotoxic to lymphoma cell lines with lower toxicity toward the HeLa cervical cancer cell line. In order to...
Published on Apr 1, 2011in Journal of Neuroscience Research4.14
Nobuyuki Kuramoto12
Estimated H-index: 12
(Setsunan University),
Keiichi Seko4
Estimated H-index: 4
(Setsunan University)
+ 2 AuthorsKiyokazu Ogita28
Estimated H-index: 28
(Setsunan University)
The organotin trimethyltin (TMT) is well known to cause neuronal damage in the central nervous system. To elucidate the mechanisms underlying the toxicity of TMT toward neurons, we prepared primary cultures of neurons from the neocortex of mouse embryos. A continuous exposure to TMT produced a decrease in cell viability as well as an increase in the number of cells with nuclear condensation/shrinkage at the exposure time window up to 24 hr. In addition to the events at the early time window, lac...
Published on Mar 1, 2011in Apoptosis4.02
Nyree Crawford14
Estimated H-index: 14
('QUB': Queen's University Belfast),
Alexander D. Chacko2
Estimated H-index: 2
('QUB': Queen's University Belfast)
+ 4 AuthorsDean A. Fennell21
Estimated H-index: 21
('QUB': Queen's University Belfast)
Resistance to cisplatin chemotherapy remains a major hurdle preventing effective treatment of many solid cancers. BAX and BAK are pivotal regulators of the mitochondrial apoptosis pathway, however little is known regarding their regulation in cisplatin resistant cells. Cisplatin induces DNA damage in both sensitive and resistant cells, however the latter exhibits a failure to initiate N-terminal exposure of mitochondrial BAK or mitochondrial SMAC release. Both phenotypes are highly sensitive to ...
Published on Jan 13, 2011in Journal of Medicinal Chemistry1.51
Gilles Gasser31
Estimated H-index: 31
,
Ingo Ott38
Estimated H-index: 38
,
Nils Metzler-Nolte34
Estimated H-index: 34
The quest for alternative drugs to the well-known cisplatin and its derivatives, which are still used in more than 50% of the treatment regimes for patients suffering from cancer, is highly needed.1,2 Despite their tremendous success, these platinum compounds suffer from two main disadvantages: they are inefficient against platinum-resistant tumors, and they have severe side effects such as nephrotoxicity. The latter drawback is the consequence of the fact that the ultimate target of these drugs...
Cited By6
Newest
Published on Jan 1, 2019in New Journal of Chemistry3.07
Shuai Chen , Jiajia Nie1
Estimated H-index: 1
+ 4 AuthorsChunlin Ma14
Estimated H-index: 14
A new series of fluorobenzenetelluronic triorganotin(IV) esters, namely (R3Sn)4H2L (H6L1 = [3-FC6H4TeO(OH)3]2, R = Me: 1, R = Ph: 2; H6L2 = [3,4-F2C6H3TeO(OH)3]2, R = Me: 3, R = Ph: 4; H6L3 = [3,4,5-F3C6H2TeO(OH)3]2, R = Me: 5, R = Ph: 6), have been synthesized by the reaction of deprotonated fluorobenzenetelluronic acid ligands with the corresponding R3SnCl (R = Me, Ph). All the complexes have been characterized by means of elemental analysis, FT-IR, NMR (1H, 13C, 119Sn) spectroscopy and X-ray ...
Published on Jun 6, 2019in Dalton Transactions4.05
Anand Gupta1
Estimated H-index: 1
(IITB: Indian Institute of Technology Bombay),
Rajesh Deka1
Estimated H-index: 1
(IITB: Indian Institute of Technology Bombay)
+ 2 AuthorsRay J. Butcher21
Estimated H-index: 21
(UW: University of Washington)
The oxidation reaction of unsymmetrical diorganotellurides, namely, bis[2-{(dimethylamino)methyl}aryl]tellurides [aryl = phenyl (6), 2-methylphenyl (7), 2,6-dimethylphenyl (8) and 2,6-diisopropylphenyl (9)] with meta-chloroperbenzoic acid afforded the first examples of tetraorganoditelluronic acids, [RR′Te(μ-O)(OH)2]2, where R = 2-NMe2CH2C6H4, R′ = C6H5 (10), 2-MeC6H4 (11), 2,6-MeC6H3 (12) and 2,6-iPrC6H3 (13). The structures of tetraorganoditelluronic acids 10–13 were authenticated by single cr...
Published on Apr 1, 2018in Journal of Organometallic Chemistry2.07
Kriti Srivastava8
Estimated H-index: 8
,
Arunashree Panda16
Estimated H-index: 16
(BITS: Birla Institute of Technology and Science)
+ 1 AuthorsHarkesh B. Singh40
Estimated H-index: 40
Abstract This review discusses the syntheses, structures and applications of organotelluroxanes. These compounds have found applications in many areas such as catalysis, oxidation, hydrolysis etc. Weak intermolecular O⋯Te interactions are common features in this class of compounds and play an important role in the aggregation, reactivity and properties of such compounds. However, monomeric species could be isolated by employing bulky groups or intramolecular interactions in the system. The highl...
Published on Jan 1, 2017in New Journal of Chemistry3.07
Ya-Ru Qiu1
Estimated H-index: 1
(Liaocheng University),
Rufen Zhang19
Estimated H-index: 19
(Liaocheng University)
+ 3 AuthorsChunlin Ma14
Estimated H-index: 14
(Liaocheng University)
A cluster of novel organotin(IV) complexes with the formulas [Me3Sn(O2CCH2SeC6H4F-p)]n (1), [(Me2Sn)4(μ3-O)2(O2CCH2SeC6H4F-p)4] (2), [n-Bu3Sn(O2CCH2SeC6H4F-p)]n (3) and [n-Bu2Sn(O2CCH2SeC6H4F-p)2] (4) were designed, synthesized, and characterized by elemental analysis, FT-IR, and NMR (1H, 13C, and 119Sn) spectroscopy as well as single-crystal X-ray diffraction. Complexes 1 and 3 represent one-dimensional (1D) coordination polymers composed of alternate [Sn–O]2. The molecular spatial structure of...
Published on Oct 1, 2016in Journal of Photochemistry and Photobiology B-biology4.07
Zhen Li5
Estimated H-index: 5
(Liaocheng University),
Hui Yan2
Estimated H-index: 2
(Liaocheng University)
+ 3 AuthorsMeiju Niu12
Estimated H-index: 12
(Liaocheng University)
Abstract A series of novel copper (II) and nickel (II) complexes derived from chiral Schiff-base ligands [( R )/( S )-H 2 L 1 = ( R )/( S )-2-[(1-Hydroxymethyl-propylimino)-methyl]-5-methoxy-phenol and ( R )/( S )-H 2 L 2 = ( R )/( S )-2-[(1-Hydroxymethyl-2-phenyl-ethylimino)-methyl]-5-methoxy-phenol], were synthesized and characterized by elemental analyses, 1 H NMR spectra, FT-IR spectrum. The crystal structures of complexes 1 – 5 were determined through single crystal X-ray diffraction (SXRD)...
Published on Sep 1, 2016in Journal of Organometallic Chemistry2.07
Rufen Zhang19
Estimated H-index: 19
(Liaocheng University),
Jiajia Nie1
Estimated H-index: 1
(Liaocheng University)
+ 3 AuthorsChunlin Ma14
Estimated H-index: 14
(Liaocheng University)
Abstract Reactions of R 2 SnCl 2 (R = Me) or R 3 SnCl (R = Me, Ph) with the respective dinuclear aryltellurinic acid (H 6 L 1 = [3,4-Me 2 C 6 H 3 TeO(OH) 3 ] 2 and H 6 L 2 = [3,5-Me 2 C 6 H 3 TeO(OH) 3 ] 2 ) afforded two types of aryltelluronic organotin esters: [R 2 Sn(CH 3 OH)(R 2 SnCl)] 2 L (L 1 = [3,4-Me 2 C 6 H 3 TeO 4 ] 2 , R = Me: 1 ; L 2 = [3,5-Me 2 C 6 H 3 TeO 4 ] 2 , R = Me: 4 ) and [(R 3 Sn) 2 H] 2 L (L 1 = [3,4-Me 2 C 6 H 3 TeO 4 ] 2 , R = Me: 2 , R = Ph: 3 ; L 2 = [3,5-Me 2 C 6 H 3 ...
Published on Jan 1, 2016in New Journal of Chemistry3.07
Min Hong14
Estimated H-index: 14
(Liaocheng University),
Guoliang Chang5
Estimated H-index: 5
(Liaocheng University)
+ 1 AuthorsMeiju Niu12
Estimated H-index: 12
(Liaocheng University)
Five new mono- or di-organotin(IV) complexes, Me2SnL (1), Ph2SnL (2), n-Bu2SnL (3), n-Oct2SnL (4) and n-BuSnCl(H2O)L·CH3CH2OH (5), where H2L is 2-hydroxy-N′-[(2-hydroxy-3-methoxyphenyl)methylidene]-benzohydrazone, were synthesized and characterized by elemental analysis and spectroscopic techniques (IR and 1H, 13C, 119Sn NMR). The crystal structures of all compounds were established by X-ray diffraction, showing the hydrazone Schiff base ligand bound to the tin atom as ONO tridentate chelate. In...
Published on Jan 1, 2016in New Journal of Chemistry3.07
Chunlin Ma14
Estimated H-index: 14
(Liaocheng University),
Xinglong Liu2
Estimated H-index: 2
(Liaocheng University)
+ 2 AuthorsRufen Zhang19
Estimated H-index: 19
(Liaocheng University)
A novel 4-fluorobenzenetelluronic trimethyltin ester (Me3Sn)4[p-F-PhTe(μ-O)(OH)O2]2 (1) has been prepared and fully characterized using elemental analysis, FT-IR, NMR (1H, 13C, 119Sn) spectroscopy, XRD and X-ray crystallography. Structural analysis shows that the complex is crystallized as a Sn4Te2 molecule, in which an asymmetric four-membered Te2(μ2-O)2 unit is situated in the center. The geometry of tellurium is described as a distorted octahedron and for each tin it is described as a distort...
View next paperA novel 4-fluorobenzenetelluronic trimethyltin ester: synthesis, characterization and in vitro cytotoxicity assessment