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Review: Organotin compounds and their therapeutic potential: a report from the Organometallic Chemistry Department of the Free University of Brussels

Published on Sep 1, 2002in Applied Organometallic Chemistry 3.26
· DOI :10.1002/aoc.331
Marcel Gielen34
Estimated H-index: 34
(Free University of Brussels)
Cite
Abstract
An overview of the development of antitumour organotin derivatives is presented and discussed for selected classes of compounds, such as tetraorganodicarboxylatodistannoxanes and related diorganotin dicarboxylates, and for triorganotin carboxylates. Among the carboxylate groups used are steroidcarboxylates and other biologically relevant carboxylates. High to very high in vitro activities have been found, sometimes equalling that of doxorubicin. Solubility in water is an important issue, dominating the in vivo testing of compounds. Polar substituents, like fluorine or polyoxaalkyl moieties, improve the water solubility. Although organotin derivatives constitute a separate class of compounds, the comparison with cisplatin is inevitable. Among the observed toxicities, neurotoxicity, known from platinum cytostatics, and gastrointestinal toxicity, typical for many oncology drugs, have been detected, but to a lower extent. Further research to develop novel useful organotin antitumour compounds needs to be carried out. Copyright © 2002 John Wiley & Sons, Ltd.
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  • Citations (406)
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References84
Newest
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen34
Estimated H-index: 34
(Free University of Brussels),
Abdelaziz El Khloufi8
Estimated H-index: 8
(Free University of Brussels)
+ 3 AuthorsRudolph Willem38
Estimated H-index: 38
(Free University of Brussels)
Bis(di-n-butyl)(2,3,6-trifluorobenzoato)- and bis(di-n-butyl)(2,3,4,5-tetrafluorobenzoato)tin oxides were synthesized and characterized by 1H, 13C, 19F and 119Sn NMR as well as by 119mSn Mossbauer spectroscopy. They were screened in vitro against six human tumour cell lines. MCF-7 and EVSAT. breast cancers, WiDr, a colon carcinoma, IGROV, an ovarian cancer, M19 MEL, a melanoma and A498, a renal cancer.
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Ludo De L.D. Clercq1
Estimated H-index: 1
(Vrije Universiteit Brussel),
Rudolph Willem38
Estimated H-index: 38
(Vrije Universiteit Brussel)
+ 1 AuthorsGhanem Atassi33
Estimated H-index: 33
(Institut Jules Bordet)
The synthesis and characterisation of fifteen new organotin compounds containing at least two CF3(CF2)5CH2‐CH2 groups bound to tin are described. The activity of six of these compounds towards the murine P388 lymphocytic leukaemia tumour is given. Copyright © 1984 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Abdelkader Meriem6
Estimated H-index: 6
(ULB: Université libre de Bruxelles),
Monique Biesemans34
Estimated H-index: 34
(Vrije Universiteit Brussel)
+ 4 AuthorsMarcel Gielen34
Estimated H-index: 34
(Vrije Universiteit Brussel)
Four compounds of the type [(o-RNH-C6H4COO)(CH3CH2CH2CH2)2Sn]2O and [(o-CH3NH-C6H4COO)(CH3)2Sn]2O have been prepared, characterized by H-1, C-13, Sn-119 NMR, and by Mossbauer and mass spectrometry. They have been tested in vitro against two human tumour cell lines, nl. MCF-7 (mammary tumour) and WiDr (colon carcinoma), and found to score slightly better than cis-platin but markedly less than other cytostatic agents.
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen34
Estimated H-index: 34
(Free University of Brussels),
A. Elkhloufi1
Estimated H-index: 1
(Free University of Brussels)
+ 2 AuthorsR. Willem1
Estimated H-index: 1
(Catholic University of Leuven)
Diethyl- and di-n-butyltin(IV) oxides react with 3-amino-4-methylbenzoic acid in a 1:2 (a) and 1:1 (b) molar ratio to yield dialkyltin compounds of the types R2Sn[O2C-C6H3-3-NH2-4-CH3]2 (a) and {[R2Sn(O2C-C6H3-3-NH2-4-CH3)]2O}2 (b). The compounds obtained were characterized by H-1, C-13, Sn-119 NMR and by Mossbauer spectroscopy. Compound 1a was tested in vitro against two human tumor cell lines, MCF-7, a mammary tumor, and WiDr, a colon carcinoma.
Published on Jul 1, 2001in Journal of Inorganic Biochemistry 3.22
Angela Casini58
Estimated H-index: 58
(UniFI: University of Florence),
Luigi Messori51
Estimated H-index: 51
(UniFI: University of Florence)
+ 3 AuthorsRudolph Willem38
Estimated H-index: 38
(Free University of Brussels)
The reactions with DNA of two antitumor active organotin(IV) compounds, the dimer of bis[(di-n-butyl 3,6-dioxaheptanoato)tin] (C52H108Sn4O1·2H2O), compound 1, and tri-n-butyltin 3,6,9-trioxodecanoate (C19H40SnO5·1/2H2O), compound 2, were analysed by circular dichroism, DNA melting experiments and gel mobility shift assays. It is found that both complexes modify only slightly the B-type circular dichroism spectroscopy (CD) spectrum of calf thymus DNA. On the other hand, both complexes were found ...
Published on Mar 1, 2000in European Journal of Inorganic Chemistry 2.58
Laurent Ghys5
Estimated H-index: 5
(ULB: Université libre de Bruxelles),
Monique Biesemans34
Estimated H-index: 34
(Vrije Universiteit Brussel)
+ 4 AuthorsJosé Martins35
Estimated H-index: 35
(Vrije Universiteit Brussel)
The interactions between diethyltin dichloride and 5'-CMP, 5'-dCMP, and 5'-UMP in aqueous solution were investigated by multinuclear 1D and 2D NMR techniques including 119Sn, 15N and 31P nuclei. These studies were combined with electrospray mass spectrometry, infrared spectroscopy, solid state 13C, 31P and 117Sn CP-MAS NMR, and elemental analysis. As demonstrated by 31P-1H HOESY spectroscopy, the diethyltin moiety interacts with the phosphate group of the pyrimidic mononucleotides in the pH rang...
Published on Sep 1, 1999in Journal of Molecular Structure-theochem
Giampaolo Barone24
Estimated H-index: 24
,
Marina Cotta Ramusino5
Estimated H-index: 5
(ISS: Istituto Superiore di Sanità)
+ 1 AuthorsGianfranco La Manna12
Estimated H-index: 12
Abstract The interaction between a dinucleotide triphosphate duplex (DD), mimicking the DNA molecule, and the dimethyltin(IV) cation is studied by the semiempirical PM3 method. The results show that the interaction can occur involving the tin atom and the electron-donor centres of DD, requiring in some cases the presence of water molecules. In particular, the binding of the dimethyltin(IV) moiety with two adjacent phosphate oxygen atoms is allowed by the presence of water molecules coordinating ...
Published on Aug 1, 1999in Applied Organometallic Chemistry 3.26
R. Barbieri24
Estimated H-index: 24
(University of Palermo),
F. Huber20
Estimated H-index: 20
(Technical University of Dortmund)
+ 4 AuthorsAdriana Barbieri Paulsen4
Estimated H-index: 4
Complexes Me2SnCl(SPy) and Me2SnCl(SPym) (HSPy = 2-mercaptopyridine; HSPym = 2-mercaptopyrimidine), from ethanol solutions, interact with aqueous calf-thymus DNA yielding condensed phases with probable Me2Sn(SPy,SPym) (DNA monomer) stoichiometries of 1:1; the condensation of DNA is inferred originated from electrostatic bonding between complex cations Me2Sn(SPy,SPym)+ and the phosphate oxygen of the phosphodiester groups. Octahedral-or trigonal-bipyramidal tin environments are inferred from the ...
Published on Jul 1, 1999in Applied Organometallic Chemistry 3.26
Marcel Gielen34
Estimated H-index: 34
(Vrije Universiteit Brussel),
Hassan Dalil11
Estimated H-index: 11
(Vrije Universiteit Brussel)
+ 3 AuthorsRudolph Willem38
Estimated H-index: 38
(Vrije Universiteit Brussel)
Di-n-butyl-, triphenyl and tri-n-butyltin derivatives of 3S,4S-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl-4-[(R)-1-carboxyethyl]-2-azetidinone were synthesized and characterized. Their antitumour activity was screened against seven tumoural cell lines of human origin. Copyright (C) 1999 John Wiley & Sons, Ltd.
Published on Apr 1, 1999in Journal of the American Chemical Society 14.70
José Martins35
Estimated H-index: 35
,
Rudolph Willem38
Estimated H-index: 38
+ 2 AuthorsMonique Biesemans34
Estimated H-index: 34
The 9R,12S-[tBu2Sn]2O derivative of the macrolide antibiotic erythromycin A (ErySn-A) is obtained as the sole regio- and stereospecific reaction product from the condensation reaction of (tBu2SnOPr)2O with erythromycin A in benzene solution. Complete resonance assignments were achieved, and the covalent structure was derived using various one-dimensional and two-dimensional NMR techniques, including gradient enhanced 1H−119Sn heteronuclear multiple quantum correlation and heteronuclear multiple ...
Cited By406
Newest
Published on Jul 1, 2019in Journal of Molecular Structure 2.12
Rachana Joshi2
Estimated H-index: 2
(BHU: Banaras Hindu University),
Ankita Kumari (BHU: Banaras Hindu University)+ 2 AuthorsSandeep Pokharia2
Estimated H-index: 2
(BHU: Banaras Hindu University)
Abstract Two new triorganotin(IV) complexes of Schiff base, Bu 3 SnL ( 1 ) and Ph 3 SnL ( 2 ) (where, L is the monoanion of Schiff base (HL= (E)-4-amino-3-(2-(2-hydroxybenzylidene) hydrazinyl)-1H-1,2,4-triazole-5(4H)-thione)) have been synthesized and thoroughly characterized by elemental analysis, IR, NMR ( 1 H, 13 C, 119 Sn), ESI-MS and UV–Vis studies. The spectroscopic evidences suggest that both complexes adopt distorted trigonal bipyramidal geometry around tin atom with O phenolic and two o...
Published on Aug 1, 2019in Journal of Organometallic Chemistry 2.07
Safaa El-din H. Etaiw16
Estimated H-index: 16
,
Dina M. Abd El-Aziz6
Estimated H-index: 6
,
Elham A. Ali3
Estimated H-index: 3
Abstract The supramolecular complexes (SC) of the type [Me 2 SnCl 2 L], L = 2,2′-bipyridine (2,2′-bpy), SC 1 , 4,4′-bipyridine (4,4′-bpy), SC 2, and (1,10-phenanthroline), SC 3, have been synthesized and structurally characterized by elemental analysis, FT-IR, UV–Vis, 1 H and 13 C NMR spectra and X-ray single crystal. The X-ray data of SC 1 and SC 2 exhibited 1:1 stoichiometry for the dimethyltin dichloride: bipodal ligand. The structure of SC 1 extends along the a-axis in a parallel way forming...
Published on Mar 1, 2019in Journal of Inorganic Biochemistry 3.22
Qiong Zhang18
Estimated H-index: 18
(Anda: Anhui University),
Mingzhu Zhang5
Estimated H-index: 5
(Anda: Anhui University)
+ 7 AuthorsYupeng Tian35
Estimated H-index: 35
(Anda: Anhui University)
Abstract Compared to organotin (IV) compounds with biochemical activity, two-photon absorption (2PA) organotin (IV) complexes for targeting nuclear with anticancer activities are rarely reported. Here, two novel 2PA organotin (IV) cyano carboxylate complexes ( C1Sn - 1 , C1Sn - 2 ) are synthesized and characterized. The two-photon absorption cross section values (δ) in the near-infrared region are significantly enhanced for C1Sn - 2 compared to C1Sn - 1 , thus developing for targeting nuclear by...
Published on Mar 1, 2019in Applied Organometallic Chemistry 3.26
Jin Liu (Qufu Normal University), Yichao Lin (Qufu Normal University)+ 4 AuthorsLaijin Tian10
Estimated H-index: 10
(Qufu Normal University)
Published on Feb 16, 2019in Journal of Coordination Chemistry 1.69
Shilpa Kumari (HPU: Himachal Pradesh University), Neeraj Sharma6
Estimated H-index: 6
(HPU: Himachal Pradesh University)
Published on Feb 15, 2019in International Journal of Molecular Sciences 4.18
Enis Nadia Md Yusof3
Estimated H-index: 3
,
Muhammad A. M. Latif1
Estimated H-index: 1
+ 6 AuthorsThahira Begum S. A. Ravoof9
Estimated H-index: 9
Six new organotin(IV) compounds of Schiff bases derived from S-R-dithiocarbazate [R = benzyl (B), 2- or 4-methylbenzyl (2M and 4M, respectively)] condensed with 2-hydroxy-3-methoxybenzaldehyde (oVa) were synthesised and characterised by elemental analysis, various spectroscopic techniques including infrared, UV-vis, multinuclear (1H, 13C, 119Sn) NMR and mass spectrometry, and single crystal X-ray diffraction. The organotin(IV) compounds were synthesised from the reaction of Ph2SnCl2 or Me2SnCl2 ...
Published on Feb 1, 2019in Nucleosides, Nucleotides & Nucleic Acids 1.17
Nahid Shahabadi25
Estimated H-index: 25
(Razi University),
Badri Z. Momeni9
Estimated H-index: 9
(KNTU: K.N.Toosi University of Technology),
Saba Zendehcheshm (Razi University)
Published on Feb 1, 2019in Journal of Chemical Sciences 1.50
Ali Akremi1
Estimated H-index: 1
(Northern Borders University),
Ali Akremi (Northern Borders University), Adel Noubigh1
Estimated H-index: 1
(Northern Borders University)
Published on Jan 17, 2019in Journal of Chemistry 1.73
Nebojša Pantelić4
Estimated H-index: 4
(University of Belgrade),
Bojana B. Zmejkovski7
Estimated H-index: 7
(University of Belgrade)
+ 4 AuthorsGoran N. Kaluđerović8
Estimated H-index: 8
A novel triphenyltin(IV) compound with 1-(4-carboxyphenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione was synthesized and characterized by IR, NMR spectroscopy, mass spectrometry, and elemental analysis. In vitro anticancer activity of ligand precursor and synthesized organotin(IV) compound was determined against tumor cell lines: human adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human breast cancer (MDA-MB-453), using microculture tetrazolium test (MTT) assay. The results indicate ...