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Cell proliferation inhibition and antitumor activity of novel alkyl series of diorganotin(IV) compounds.

Published on May 1, 2008in Journal of Applied Toxicology3.06
· DOI :10.1002/jat.1290
Biplob Koch17
Estimated H-index: 17
(NEHU: North Eastern Hill University),
Tushar S. Basu Baul23
Estimated H-index: 23
(NEHU: North Eastern Hill University),
Anupam Chatterjee17
Estimated H-index: 17
(NEHU: North Eastern Hill University)
Cite
Abstract
Diorganotin(IV) compounds, R2SnCl2 are often tetrahedral, and structurally resemble the active platinum compounds, i.e. cisplatin, and consequently a large number of such complexes have been tested for antitumor activity. A structural correlation with biological activity for diorganotin(IV) complexes has shown that active species are associated with complexes having Sn–N bonds longer than 2.39 A which in turn determines the formation of a tin–DNA complex. In view of these, a series of diorganotin(IV) dichloride complexes of N-(2-pyridylmethylene)arylamine (nitrogen-chelating ligands) has been synthesized and characterized on the basis of IR, NMR and 119Sn-Mossbauer studies. In the present study, an attempt was made to determine the comparative antiproliferative and antitumor effect of diorganotin(IV) complexes with different alkyl groups [Me2SnCl2·L1 (OTC-1), Et2SnCl2·L2 (OTC-2) and nBu2SnCl2·L2 (OTC-3)]. The present study in human lymphocytes demonstrated that these diorganotin(IV) complexes could block the cell cycle progression and induce sister chromatid exchanges (SCEs) significantly, however, with respect to the induction of chromosome aberrations (CAs) it was very mild. Both the levels of p53 and p16 proteins were raised after diorganotin(IV) treatment and such induction was maximum in the OTC-3 treated samples. The antitumor activity was determined in accordance with the US National Cancer Institute (NCI) standard protocol for primary screening in Dalton's lymphoma that was maintained by serial intraperitoneal transplantation. The T/C (treated/control) value was increased (186% with OTC-3) when diorganotin(IV) was given after transplantation. The data suggest that the OTC-3 has better antiproliferative and antitumor activity and endogenous glutathione level has no influence on the effect of OTC-3. Copyright © 2007 John Wiley & Sons, Ltd.
  • References (31)
  • Citations (30)
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References31
Newest
Published on Dec 20, 2005
Marcel Gielen34
Estimated H-index: 34
(Vrije Universiteit Brussel),
Edward R. T. Tiekink45
Estimated H-index: 45
(NUS: National University of Singapore)
Published on Nov 1, 2003in International Journal of Cancer4.98
Yann Schneider9
Estimated H-index: 9
(French Institute of Health and Medical Research),
Philippe Chabert3
Estimated H-index: 3
(CNRS: Centre national de la recherche scientifique)
+ 6 AuthorsRaul F33
Estimated H-index: 33
(French Institute of Health and Medical Research)
Resveratrol (3,5,4′-trihydroxystilbene) a natural polyphenol present in medicinal plants, grapes and wines, has potent chemopreventive properties on intestinal carcinogenesis. A methylated derivative (Z-3,5,4′-trimethoxystilbene: R3) was synthesized. R3 at 0.3 μM exerted a 80% growth inhibition of human colon cancer Caco-2 cells and arrested growth completely at 0.4 μM (R3 was 100-fold more active than resveratrol). The cis conformation of R3 was also 100-fold more potent than the trans isomer. ...
Published on Jul 15, 2003in Nucleic Acids Research11.15
Jianmin Zhou3
Estimated H-index: 3
(Columbia University),
Carol Prives76
Estimated H-index: 76
(Columbia University)
The tumor suppressor protein p53 may have other roles and functions in addition to its well-documented ability to serve as a sequence-specific transcriptional activator in response to DNA damage. We showed previously that p53 can block the replication of polyomavirus origin-containing DNA (Py ori-DNA) in vitro when p53 binding sites are present on the late side of the Py ori. Here we have both further extended these observations and have also examined whether p53 might be able to bind directly t...
Christine Syng-ai3
Estimated H-index: 3
(NEHU: North Eastern Hill University),
Tushar S. Basu Baul23
Estimated H-index: 23
(NEHU: North Eastern Hill University),
Anupam Chatterjee17
Estimated H-index: 17
(NEHU: North Eastern Hill University)
Abstract Organotin compounds are organometallic compounds showing various toxicological properties. Several organotin compounds also showed an antineoplastic effect. However, their relative mutagenic potential is not well established. In this study Et 2 SnCl 2 ·L [L= N -(2-pyridylmethylene)-4-toluidine] (OTC) has been subjected to investigation for its cytotoxic effect in mouse bone marrow cells (BMCs) and human peripheral blood lymphocyte cells (HPBLs). The SnN bond in OTC is 2.46 A which is g...
Published on Jan 1, 2002in Coordination Chemistry Reviews13.48
L. Pellerito22
Estimated H-index: 22
(University of Palermo),
László Nagy24
Estimated H-index: 24
(University of Szeged)
Abstract The organotin(IV) cations form complexes with ligands containing {O}, {N}, {S}, or {phosphorus(O)} donor atoms with various composition and stability. The emergence of new experimental techniques (EXAFS, multinuclear 1 H-, 13 C-, 119 Sn-NMR, 119 Sn Mossbauer, etc., spectroscopic techniques) provided useful information about the structure and stabilities of the complexes formed. We reviewed the literature on these type of complexes taking into account the biological aspects of the comple...
Christine Syng-ai3
Estimated H-index: 3
(NEHU: North Eastern Hill University),
Tushar S. Basu Baul23
Estimated H-index: 23
(NEHU: North Eastern Hill University),
Anupam Chatterjee17
Estimated H-index: 17
(NEHU: North Eastern Hill University)
Organotin compounds showed more antineoplastic effect against P388 leukemia in mice than any other class of compounds. However, they have not received as much attention as the platinum compounds. The present compound, Et 2 SnCl 2 .L [L = N-(2-pyridylmethylene)-4-toluidine] (OTC), showed an Sn-N bond length of 2.46 A which, because it is bigger than 2.39 A, is expected to achieve better formation of tin-DNA complexes. We previously reported on the synthesis and biological activity of this compoun...
Published on Jan 1, 2000in Cell Biochemistry and Biophysics2.32
Kurt W. Kohn81
Estimated H-index: 81
,
Rhong-Guang Shao1
Estimated H-index: 1
,
Yves Pommier100
Estimated H-index: 100
Recent results suggest that potentially lethal DNA lesions may result when replication forks encounter trapped topoisomerase-DNA complexes or some other types of DNA damage. Such events produce what are called replication-encounter lesions. These lesions have the characteristic that they may allow single stranded DNA-associated replication protein A (RPA) to become juxtaposed to dsDNA end-associated DNA-protein kinase. Our results suggest that DNA-protein kinases may then hyperphosphorylate the ...
Published on Oct 1, 1999in Human & Experimental Toxicology2.17
A De Santiago1
Estimated H-index: 1
,
Miguel Aguilar-Santelises17
Estimated H-index: 17
Organotin compounds (OTC) are organometallic compounds with vast industrial and agriculture applications that give rise to ubiquitous environmental contamination. OTC are immunotoxic, but most studies have been performed in rodents and almost exclusively focused on T cell immunity. Humans can be exposed to OTC by inhalation, absorption, and consumption of contaminated food and water. To analyse the effects of OTC in human immune tissue, we isolated B cells from tonsils and exposed them to five O...
Published on Apr 1, 1999in Toxicology and Applied Pharmacology3.58
Hélène Stridh6
Estimated H-index: 6
(KI: Karolinska Institutet),
Sten Orrenius119
Estimated H-index: 119
(KI: Karolinska Institutet),
Mark B. Hampton46
Estimated H-index: 46
Organotin compounds such as tributyltin (TBT) and triphenyltin (TPT) can kill target cells by triggering apoptosis. The mechanism by which these environmental toxicants activate the apoptotic program is currently unclear. We have studied the effect of TBT and TPT in the human Hut-78 and Jurkat T-lymphocyte cell lines. Within 1 h there was a 30-fold increase in caspase activity, as measured by the cleavage of the fluorescent peptide DEVD-AMC. Morphological changes characteristic of apoptosis, suc...
Published on Jan 1, 1999in Zeitschrift Fur Kristallographie1.09
Ch. A. Geiger1
Estimated H-index: 1
,
Th. Armbruster12
Estimated H-index: 12
The crystal structure of a synthetic solid-solution garnet, Gr90Py10, of composition (Ca 0.9 Mg 0.1 ) 3 Al 2 [SiO 4 ] 3 was refined at 100 K and 295 K from single-crystal X-ray data. The difference displacement parameters were examined in order to investigate static and dynamic disorder of Ca and Mg in the dodecahedral E-site of 222 point symmetry. The difference displacement parameters for the E-site, derived from the diffraction experiment, are compared to those calculated from two juxtaposed ...
Cited By30
Newest
Published on Sep 10, 2019in Applied Organometallic Chemistry3.26
Badri Z. Momeni9
Estimated H-index: 9
(KNTU: K.N.Toosi University of Technology),
Nastaran Fathi2
Estimated H-index: 2
(KNTU: K.N.Toosi University of Technology)
+ 1 AuthorsJan Janczak26
Estimated H-index: 26
(PAN: Polish Academy of Sciences)
Published on Jun 1, 2018in Inorganica Chimica Acta2.43
Hassan Keypour22
Estimated H-index: 22
,
Masoumeh Mahmoudabadi3
Estimated H-index: 3
+ 4 AuthorsRobert W. Gable20
Estimated H-index: 20
Abstract Trigonal-prismatic structures among different transition metal complexes according to the Cambridge Structural Database (CSD) are rare. The number of trigonal prisms throughout the transition-metal series is less than 1% of all six-coordinate metal centers and only 0.4% of cobalt complexes. Herein we report a novel macroacyclic Schiff base complexes incorporating piperazine moiety with Trigonal-Prismatic coordination were prepared via the metal templated of the 2,2′-(piperazine-1,4-diyl...
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 May 1, 2018in Inorganic Chemistry Communications1.79
Jai Devi5
Estimated H-index: 5
(Guru Jambheshwar University of Science and Technology),
Sushila Pachwania1
Estimated H-index: 1
(Guru Jambheshwar University of Science and Technology)
Abstract DNA interaction studies of organotin(IV) complexes have got tremendous attention during the recent years due to their anticancer and antitumor properties. Most of the chemotherapeutic organotins are DNA-targeted as they recognize specific DNA sequences, alter the local DNA structure, inhibit access to the activator or repressor protein and ultimately affect the gene expression process. The binding ability of organotin(IV) compounds with DNA depends on the coordination number and the nat...
D. Mourelatos16
Estimated H-index: 16
(A.U.Th.: Aristotle University of Thessaloniki)
Sister Chromatid Exchanges (SCEs) are known to enhance as a consequence of exposure to various mutagenic agents and appear to indicate DNA damaging effects and/or subsequent repair by homologous recombination (HR). DNA damage plays an interesting role in the majority of mechanisms underlying the effects of antitumor drugs, since the genetic activity of the plethora of these agents is due to their ability to damage the DNA. The DNA-effects of antitumor agents towards normal cells (genotoxicity) a...
Published on Apr 11, 2016
Md. Shamsuddin Sultan Khan1
Estimated H-index: 1
(Universiti Sains Malaysia),
Md. Abdus Salam1
Estimated H-index: 1
(Universiti Sains Malaysia)
+ 5 AuthorsYaseer M. Tabana1
Estimated H-index: 1
(Universiti Sains Malaysia)
AbstractBackground and Objective: Toxicity of the chemotherapeutic compounds is widely investigated. An organotin (IV) derivative was designed to modulate the toxicity and long-term anticancer efficacy of the single dose. Materials and Methods: The reaction of dimethyltin(IV) dichloride with N(4)-methylthiosemicarbazone derived by condensation of 4-methylthiosemicarbazone with 5-bromo-2-hydroxybenzaldehyde was prepared in 1:1 M ratio in absolute methanol. The newly synthesized complex was charac...
Published on Feb 1, 2016in Canadian Journal of Chemistry1.25
Arti Sharma4
Estimated H-index: 4
,
Asha Jain7
Estimated H-index: 7
,
Sanjiv Saxena9
Estimated H-index: 9
Diorganotin(IV) complexes of flexible N-protected amino acids and ketoximes having the compositions Me2Sn [CHRCOO][ON = C6H10] (where R = –CH2CH(CH3)2, –CH(CH3)C2H5,–CH2C6H5, –CH(CH3)2) and Me2Sn[CHRCOO][ON=CR′R″] (where R = –CH2CH(CH3)2, –CH(CH3)C2H5, –CH2C6H5, R′ = R″ = CH3; R = –CH(CH3)C2H5, –CH2C6H5, –CH(CH3)2, R′ = CH3, R″ = C6H5) were prepared by the reaction of dimethyltin(IV) dichloride with sodium salts of flexible N-protected amino acids and ketoximes in 1:1:1 molar ratio in refluxing ...
Published on Jan 1, 2016
Nasry Jassim Hussien1
Estimated H-index: 1
(UKM: National University of Malaysia),
Yang Farina9
Estimated H-index: 9
,
Mohamad J. Al-Jeboori9
Estimated H-index: 9
(UOB: University of Baghdad)
The diorganotin(IV) complexes of the type Me2SnL, Bu2SnL and Ph2SnL (L) with the anion of the semicarbazone ligand formed by condensation reaction of 3,4-dihydroxybenzaldehyde with semicarbazide were synthesized using 1:1 metal to ligand reactant ratios. The newly synthesized complexes were characterized using elemental analysis, infrared and nuclear magnetic resonance (1H, 13C,119Sn) spectroscopic techniques. Complex formation between the organotin(IV) moiety and the anion of 3,4-dihydroxybenza...
The present work comprises the synthesis of ofloxacin (OFL) complexes with various transition metals. Two types of complexes [Cu(OFL)Cl2].H2O, [Pt(OFL)CI2].3H2O, [Zn(OFL)2]2CI.4H2O, [Ru(OFL)2ClH2O]2CI.4H2O, and [Fe(OFL)2Cl]2CI.5H2O were obtained. The complexes were characterized by different physicochemical, spectroscopic, and elemental analysis. The thermal decomposition behaviors of metal complexes were investigated in nitrogen atmosphere using TG and DTA techniques. Results suggest that OFL i...
Published on Nov 1, 2014in Inorganica Chimica Acta2.43
Farukh Arjmand28
Estimated H-index: 28
(AMU: Aligarh Muslim University),
Sabiha Parveen4
Estimated H-index: 4
(AMU: Aligarh Muslim University)
+ 1 AuthorsClaudio Pettinari39
Estimated H-index: 39
(University of Camerino)
Abstract Toxicity-related problems, drug resistance and broad spectrum of action have hindered the success pathway of platinum antitumor chemotherapeutic drugs, although the survival rates for patients suffering from solid cancers treated by platinum drugs, notably ‘cisplatin’ is considerably high. Therefore, many non-platinum metal-based chemical entities are gaining attention and have also entered preclinical testing and clinical trails, yet at a later stage they fail to qualify as drugs and c...