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Synthesis, characterization and in vitro antitumor activity of di- and triorganotin derivatives of polyoxa- and biologically relevant carboxylic acids.

Published on Apr 1, 2000in Journal of Inorganic Biochemistry 3.22
· DOI :10.1016/S0162-0134(99)00161-0
Marcel Gielen25
Estimated H-index: 25
(Vrije Universiteit Brussel),
Monique Biesemans34
Estimated H-index: 34
(Vrije Universiteit Brussel)
+ 1 AuthorsRudolph Willem38
Estimated H-index: 38
(Vrije Universiteit Brussel)
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Abstract
Abstract An overview of the development of anti-tumor organotin derivatives, sometimes as active in vitro as doxorubicin, is presented and discussed. Solubility in water is an important issue, dominating the in vivo testing of compounds with promising in vitro properties. Several water-soluble organotin compounds gave the best in vitro activities. Novel, useful organotin anti-tumor compounds should be designed toward improved water solubility.
  • References (44)
  • Citations (157)
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References44
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 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 in Coordination Chemistry Reviews 13.48
Bernhard Lippert48
Estimated H-index: 48
(Technical University of Dortmund)
Abstract An overview is presented on recent developments in selected areas of Pt coordination chemistry which were a direct consequence of the discovery of the antitumor activity of cis -Pt(NH 3 ) 2 Cl 2 (Cisplatin). These include complexes of Pt II with oxygen donor atoms, mixed-valence state Pt compounds as well as diplatinum(III) complexes, and compounds containing nucleobases as well as a limited number of other heterocyclic ligands. Both the potential biological relevance of these compounds...
Published in Chemical Reviews 54.30
Scott R. Rajski9
Estimated H-index: 9
,
Robert M. Williams51
Estimated H-index: 51
Published on Dec 1, 1998in Inorganica Chimica Acta 2.43
Eduard G. Talman3
Estimated H-index: 3
(LEI: Leiden University),
Yoshinori Kidani1
Estimated H-index: 1
(LEI: Leiden University)
+ 1 AuthorsJan Reedijk73
Estimated H-index: 73
(LEI: Leiden University)
Abstract Platinum antitumour drugs have been used for a number of years routinely as Pt(II) amine compounds, the prototype being cis -PtCl 2 (NH 3 ) 2 . More recently, Pt(IV) compounds have been shown to be active, and one of them is being introduced into clinical use. The present study deals with the question of whether such compounds are real drugs, or whether they act as prodrugs, being reduced to Pt(II) before reaching their DNA target. A few Pt(IV) amine complexes with the chelating ligand ...
Published on Dec 1, 1998in Applied Organometallic Chemistry 3.26
Marcel Gielen34
Estimated H-index: 34
(Vrije Universiteit Brussel),
Hassan Dalil11
Estimated H-index: 11
(Vrije Universiteit Brussel)
+ 2 AuthorsRudolph Willem38
Estimated H-index: 38
(Vrije Universiteit Brussel)
The synthesis and characterization of di-n-butyl-, tri-n-butyl- and triphenyltin gibberellates are reported. Their antitumour activities in vitro against a panel of seven human tumour cell lines are given and compared with those of drugs used clinically. (C) 1998 John Wiley & Sons, Ltd.
Published on Aug 1, 1998in Journal of Inorganic Biochemistry 3.22
S. Shamsuddin7
Estimated H-index: 7
(University of Texas MD Anderson Cancer Center),
Claudia C. Santillan1
Estimated H-index: 1
(University of Texas MD Anderson Cancer Center)
+ 3 AuthorsAbdul R. Khokhar26
Estimated H-index: 26
(University of Texas MD Anderson Cancer Center)
Abstract A series of novel platinum(IV) cisplatin analogues of the type [Pt( cis -1,4-DACH) trans -(L) 2 Cl 2 ] (where cis -1,4-DACH= cis -1,4-diaminocyclohexane and L=acetate, propionate, butyrate, valerate, hexanoate, heptanoate, octanoate, nonanoate, or decanoate) was synthesized and characterized by elemental analysis, IR, 13 C-NMR, and 195 Pt-NMR spectroscopy. The structure of [Pt( cis -1,4-DACH) trans -(acetate) 2 Cl 2 ] ( 1 ) was determined by X-ray crystallography. The crystals were mono...
Published on May 1, 1998in Inorganic Chemistry 4.85
Sunhee Choi14
Estimated H-index: 14
,
Catherine Filotto1
Estimated H-index: 1
+ 9 AuthorsJennifer Willingham1
Estimated H-index: 1
A series of PtIV anticancer complexes with chloro leaving groups have been investigated for the effects of axial and carrier ligands on the reduction and cytotoxicity. The reduction rates of the PtIV complexes such as Pt(d,l)(1,2-(NH2)2C6H10)Cl4 (tetraplatin, Pt(dach)Cl4; dach = diaminocyclohexane), cis,trans,cis-[Pt((CH3)2CHNH2)2(OH)2Cl2] (iproplatin, Pt(ipa)(OH)2Cl2; ipa = isopropylamine), cis,trans,cis-[Pt(NH3)(C6H11NH2)(OCOCH3)2Cl2] (JM-216, Pt(a,cha)(OCOCH3)2Cl2; a = ammine, cha = cyclohexy...
Published on May 1, 1998in Journal of Inorganic Biochemistry 3.22
Adoración G. Quiroga19
Estimated H-index: 19
(UAM: Autonomous University of Madrid),
José M. Pérez32
Estimated H-index: 32
(UAM: Autonomous University of Madrid)
+ 3 AuthorsCarmen Navarro-Ranninger28
Estimated H-index: 28
(UAM: Autonomous University of Madrid)
Abstract In the present paper we report the synthesis and characterization by 1 H NMR, 13 C NMR and heteronuclear 2D NMR spectroscopies of two new metallic complexes derived from phenylacetaldehyde thiosemicarbazone: Pt(C 9 H 11 N 3 S)Cl 2 , compound 2 , and Pd(C 9 H 11 N 3 S)Cl 2 , compound 3 . The testing of the cytotoxic activity of these compounds against several human and murine cell lines sensitive and resistant to cis -DDP suggests that compounds 2 and 3 may be considered potential antica...
Cited By157
Newest
Published on Jun 1, 2019in Journal of Molecular Structure 2.12
Oumaima Ben Moussa (Tunis University), Hammouda Chebbi3
Estimated H-index: 3
(Tunis University)
+ 3 AuthorsMohamed Faouzi Zid8
Estimated H-index: 8
(Tunis University)
Abstract In this work, a novel compound bis(2,6-diaminopyridinium) hexachloridostannate(IV), formulated as (C 5 H 8 N 3 ) 2 [SnCl 6 ], has been synthesized and characterized by powder and single crystal X-ray diffraction (XRD), IR and UV–Vis spectroscopies, and Hirshfeld surface analysis. The title compound crystallizes in the monoclinic system, P 2 1 /c space group with a = 7.1481(2) A, b = 11.1164 (3) A, c = 12.4535(1) A, β = 104.688(4)⁰ and V = 957.23(4) A 3 . Its crystal structure can be des...
Published on Jul 1, 2018in Applied Organometallic Chemistry 3.26
T.A. Antonenko3
Estimated H-index: 3
(MSU: Moscow State University),
D.B. Shpakovsky8
Estimated H-index: 8
(MSU: Moscow State University)
+ 9 AuthorsA.G. Iksanova (Kazan: Kazan Federal University)
Published on Jun 1, 2018in Structural Chemistry 1.62
Bharti Badhani3
Estimated H-index: 3
(DU: University of Delhi),
Rita Kakkar15
Estimated H-index: 15
(DU: University of Delhi)
The present work explores the probable parameters responsible for the potent anticancer activity of tin-based organometallic compounds. The characteristic structural, electronic, and reactivity features of some recently synthesized triorganotin(IV) carboxylates are identified by employing the density functional theory (DFT). The influence of solvent on these parameters is analyzed. In general, the stability of the complex is found to be governed by the donor ligand, alkyl/aryl group at the tin c...
Published on Jan 1, 2018in Journal of Organometallic Chemistry 2.07
Susanta Hazra22
Estimated H-index: 22
(IST: Instituto Superior Técnico),
Nuno Martins15
Estimated H-index: 15
(IST: Instituto Superior Técnico)
+ 3 AuthorsArmando J. L. Pombeiro4
Estimated H-index: 4
(IST: Instituto Superior Técnico)
Abstract The synthesis and crystal structure of the new tetranuclear diphenyltin(IV) compound [{SnPh 2 }{SnPh 2 (OCOMe)}(μ 2 -OMe)(μ 3 -O)] 2 ( 1 ), generated from the reaction of [SnPh 2 Cl 2 ] and NaOCOMe, are described. Single crystal X-ray diffraction revealed that 1 is a tetranuclear complex with four diphenyltin(IV) units which are inter-connected by μ 3 -oxido and μ 2 -methoxido bridges leading to a ladder-like Sn 4 O 4 cluster. Structural comparison with related compounds found in crysta...
Published on Sep 1, 2017in Journal of Inorganic Biochemistry 3.22
Anup Paul11
Estimated H-index: 11
(IST: Instituto Superior Técnico),
Susanta Hazra22
Estimated H-index: 22
(IST: Instituto Superior Técnico)
+ 3 AuthorsArmando J. L. Pombeiro58
Estimated H-index: 58
(IST: Instituto Superior Técnico)
Abstract Synthesis, inter-conversions and biological study of the dichloro bridged dicopper(II) compound [CuLCl] 2 ( 1 ) and its two mononuclear derivatives [CuLCl(H 2 O)]·H 2 O ( 2 ) and [CuLCl(py)] ( 3 ) (HL = 2-(2-pyridylmethyleneamino)benzenesulfonic acid) are described. The dimeric compound 1 collapses into monomers 2 and 3 in the presence of coordinating solvents, water and pyridine, respectively, and 1 is regenerated upon simple stirring of 2 or 3 in methanol. The reactions of 1 with neut...
Published on May 4, 2017in Phosphorus Sulfur and Silicon and The Related Elements 0.78
Zeinab Ansari-Asl2
Estimated H-index: 2
(Shahid Chamran University of Ahvaz),
Tahereh Sedaghat14
Estimated H-index: 14
(Shahid Chamran University of Ahvaz)
+ 2 AuthorsElham Hoveizi13
Estimated H-index: 13
(Shahid Chamran University of Ahvaz)
Published on Jan 17, 2017in Journal of Coordination Chemistry 1.69
Keisham Surjit Singh3
Estimated H-index: 3
(NITA: National Institute of Technology Agartala),
Manojit Roy3
Estimated H-index: 3
(NITA: National Institute of Technology Agartala)
+ 4 AuthorsLo Kong Mun1
Estimated H-index: 1
(UM: University of Malaya)
AbstractTriorganotin(IV) complexes with polyaromatic azo-azomethine carboxylate ligands viz. 2-{4-hydroxy-3-[(2/4-hydroxyphenylimino)methyl]phenylazo}benzoic acids [H3L1/H3L2] were synthesized by reacting the ligands with either bis-tri-n-butyltin(IV) oxide (for 1 and 4) or trimethyltin(IV) chloride in presence of triethylamine (for 2 and 5) or triphenyltin(IV) hydroxide (for 3 and 6). The complexes were characterized by elemental analysis, UV, IR, NMR, and mass spectrometry. NMR spectroscopic s...
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...