3-D QSAR studies on new dibenzyltin(IV) anticancer agents by comparative molecular field analysis (CoMFA)

Published on Jan 1, 2002in Bioorganic & Medicinal Chemistry Letters 2.44
· DOI :10.1016/S0960-894X(01)00684-9
Purnima M. Samuel3
Estimated H-index: 3
(Indian Institute of Chemical Technology),
Dick de Vos1
Estimated H-index: 1
+ 2 AuthorsSujit Roy29
Estimated H-index: 29
(Indian Institute of Technology Kharagpur)
Abstract
Abstract Dibenzyltin(IV)dichloride and dibenzyltin(IV)diisothiocyanate derivatives with N,S-donor ligands show significant cytotoxic activities against human cancer cell lines, and are well compared to analogous dialkyltin(IV) derivatives. CoMFA models were generated for the first time for these organotin derivatives using the cytotoxic activities (against two human tumor cell lines, MCF-7, a mammary carcinoma and WiDr, a colon carcinoma) of 21 complexes. High r 2 and r 2 cv values for both CoMFA models indicate good predictive power for the models.
  • References (20)
  • Citations (37)
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References20
Published on Dec 16, 1980in Journal of Organometallic Chemistry 1.95
S.L. Chadha1
Estimated H-index: 1
(University of Nottingham),
Philip G. Harrison30
Estimated H-index: 30
(University of Nottingham),
Kieran Molloy7
Estimated H-index: 7
(University of Nottingham)
Abstract The reaction between [ClEt 2 SnOSnEt 2 Cl] 2 and 2,2′-bipyridyl has been shown to give Et 2 SnCl 2 · bipyridyl and the tristannoxane adduct [ClEt 2 SnOEt 2 -SnOSnEt 2 Cl] · 1 2 bipyridyl. Tin-119 Mossbauer data for the tristannoxane indicate a trigonal bipyramidal geometry for all tin atoms. Crystals of Et 2 SnCl 2 - bipy are monoclinic, space group P 2 1 / n with a  18.803(1), b  14.549(6), c  8.294(2) A, and β  134.47(2)°. The complex has the expected octahedral geometry with tran...
27 Citations Source Cite
Published on Jan 1, 1989
Vincent T. DeVita72
Estimated H-index: 72
,
Samuel Hellman43
Estimated H-index: 43
,
Steven A. Rosenberg182
Estimated H-index: 182
Part I: Molecular Biology of Cancer Molecular Methods in Oncology Section 1. Amplification Techniques Section 2. RNA Interference Section 3. cDNA arrays Section 4. Tissue arrays Section 5. Cytogenetics Section 6. Bioinformatics Genomics and Proteomics Molecular Targets in Oncology Section 1. Signal transduction systems Section 2. Cell cycle Section 3. Apoptosis Section 4. Telomerase Invasion and Metastases Angiogenesis Cancer Immunology Part II: Principles of Oncology Etiology of Cancer: Viruses...
8,722 Citations
Published on May 1, 1988in Inorganica Chimica Acta 2.26
Jiazhu Wan2
Estimated H-index: 2
,
Jingshuo Huang1
Estimated H-index: 1
+ 2 AuthorsSheng-Zhi Hu7
Estimated H-index: 7
(Xiamen University)
Abstract The antitumor agent Et 2 SnCl 2 (phen) (phen = phenanthroline) reacts with 5-fluorouracil (UF) to form Et 2 Sn(phen)UF)Cl by a basic catalytic process. The reaction may be characterized as nucleophilic attack on H + N(3) in the 5-fluorouracil ring by the cis -chloro in Et 2 SnCl 2 (phen). The product has been identified by microanalysis, IR, UV and NMR spectra and these results are consistent with the expected complex. The binding of the 5-fluorouracil ligand to the cis -chloro in Et 2 ...
15 Citations Source Cite
Published on Sep 1, 1999in Journal of Inorganic Biochemistry 3.06
José S. Casas24
Estimated H-index: 24
(University of Santiago de Compostela),
Alfonso Castiñeiras37
Estimated H-index: 37
(University of Santiago de Compostela)
+ 9 AuthorsAntonio Bonati24
Estimated H-index: 24
(University of Parma)
Abstract Reaction of the title ligands (HPyTSC and HS(S)PPh 2 , respectively) with R 2 SnO (R=Me, Et, Bu) in ethanol (EtOH) afforded the complexes [SnMe 2 (PyTSC)(S 2 PPh 2 )]·EtOH ( 1 ) and [SnR 2 (PyTSC)(S 2 PPh 2 )] (R=Et ( 2 ), Bu ( 3 )). The structures of 1 and 2 were determined by single-crystal X-ray diffractometry. In both these complexes the tin atom is coordinated to an N,N,S-dentate thiosemicarbazonate ligand, an anisobidentate dithiophosphinato ligand and the two R groups. The coordi...
28 Citations Source Cite
Published on Jul 1, 1990in Inorganica Chimica Acta 2.26
Sheng-Zhi Hu7
Estimated H-index: 7
(Xiamen University),
Dashuang Shi2
Estimated H-index: 2
(Xiamen University)
+ 4 AuthorsChenghui Xu1
Estimated H-index: 1
(Academia Sinica)
Le complexe forme a partir de SnEt 2 Cl 2 cristallise dans le systeme Pca2 1 avec a=13,912 A, b=13,074 A, c=11,186 A
22 Citations Source Cite
Published on Nov 1, 1996in Journal of Inorganic Biochemistry 3.06
Qingshan Li1
Estimated H-index: 1
(Nanjing University),
Pin Yang9
Estimated H-index: 9
(Shanxi University)
+ 1 AuthorsMaolin Guo3
Estimated H-index: 3
Abstract This contribution reports a solution and solid-state study of the aqueous nucleotide coordination chemistry of the dieihyltin(IV) antitumor agent, (C 2 H 5 )2SnC1 2 (phen). [trans-en 2 OS(η-H 2 ] (CF 3 SO 3 ) 2 , a versatile 1 H NMR probe for biomolecules, is first used to investigate the interaction of (C 2 H 5 ) 2 SnC1 2 (phen) with DGMP in neutral aqueous solution, and then the synthesis of mixed-ligands complexes formulated as (C 2 Hn5) S nC1(phenXNu) (Nu is nucleotide) by reactions...
172 Citations Source Cite
Published on Sep 1, 1998in Journal of Applied Toxicology 2.91
Purnima M. Samuel3
Estimated H-index: 3
(Indian Institute of Chemical Technology),
Sujit Roy29
Estimated H-index: 29
(Indian Institute of Chemical Technology)
+ 1 AuthorsJ. Venkateswara Rao1
Estimated H-index: 1
(Indian Institute of Chemical Technology)
In vitro effects of six dibenzyltin dichloride (A-series) and another six dibenzyltin diisothiocyanate (Bseries) complexes on Na 1 /K 1 -ATPase were studied. The rat brain synaptic membranes were prepared and significant ATPase inhibition was observed with all the complexes in a dose-dependent manner. The order of potency on Na 1 /K 1 -ATPase activity of the chloride complexes was found to be higher than that of the isothiocyanate complexes. The ic50 values range from 64 mM to 252 mM for the chl...
16 Citations Source Cite
Published on Aug 1, 1984in Cancer Letters 6.49
Alan J. Crowe11
Estimated H-index: 11
,
Peter John Smith3
Estimated H-index: 3
+ 2 AuthorsFrank E. Smith18
Estimated H-index: 18
(Laurentian University)
An examination of crystallographic data has indicated that the structure/activity relationship for diorganotin dihalide complexes is different from that of other metal dihalides, in that the SnN bond lengths appear to determine the antitumour activity.
107 Citations Source Cite
Published on Mar 1, 1990in Journal of Computer-aided Molecular Design 2.36
James J. P. Stewart14
Estimated H-index: 14
(United States Air Force Academy)
1,801 Citations Source Cite
Published on Apr 1, 1969in Nature 41.58
Barnett Rosenberg35
Estimated H-index: 35
,
Loretta VanCamp3
Estimated H-index: 3
+ 1 AuthorsVirginia H. Mansour2
Estimated H-index: 2
(Michigan State University)
CERTAIN platinum compounds completely but reversibly iiihibit cell division in Gram-negative rods1–4. These compounds have been tested for antitumour activity and we report some of the preliminary results. The platinum compounds inhibit sarcoma 180 and leukaemia L1210 in mice.
2,423 Citations Source Cite
Cited By37
Tidiane Diop2
Estimated H-index: 2
(Cheikh Anta Diop University),
Libasse Diop8
Estimated H-index: 8
(Cheikh Anta Diop University)
+ 1 AuthorsAmanda C. Keeley4
Estimated H-index: 4
(Keene State College)
In the structure of the title monomeric coordination salt, (C3H10N)[Sn(C6H5)3Cl2], the SnIV atom is five coordinate, with the SnC3Cl2 entity in a trans trigonal–bipyramidal arrangement and the chlorine atoms in apical positions. In the crystal, the cations and anions are connected by N—H⋯Cl hydrogen bonds.
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Published on Apr 1, 2008in Chemical Biology & Drug Design 2.33
Prashant R. Murumkar16
Estimated H-index: 16
(Maharaja Sayajirao University of Baroda),
Rajani Giridhar19
Estimated H-index: 19
(Maharaja Sayajirao University of Baroda),
Mange Ram Yadav21
Estimated H-index: 21
(Maharaja Sayajirao University of Baroda)
A set of 29 benzothiadiazepine hydroxamates having selective tumor necrosis factor-α converting enzyme inhibitory activity were used to compare the quality and predictive power of 3D-quantitative structure–activity relationship, comparative molecular field analysis, and comparative molecular similarity indices models for the atom-based, centroid/atom-based, data-based, and docked conformer-based alignment. Removal of two outliers from the initial training set of molecules improved the predictivi...
31 Citations Source Cite
Rajeev Singh10
Estimated H-index: 10
(University of Delhi),
Narender Kumar Kaushik15
Estimated H-index: 15
(University of Delhi)
Abstract Some complexes of 2-phenylethyl dithiocarbamate, thiohydrazides and thiodiamines with dibenzyltin(IV) chloride, tribenzyltin(IV) chloride and di( para -chlorobenzyl)tin(IV) dichloride have been synthesized and investigated in 1:2 and 1:1 molar ratio. The dithiocarbamate ligand act as monoanionic bidentate and thiohydrazide, thiodiamines act as neutral bidentate ligand. The synthesized complexes have been characterized by elemental analysis and molecular weight determination studies and ...
37 Citations Source Cite
Published on Aug 1, 2008in Applied Organometallic Chemistry 3.58
Flaviana T. Vieira5
Estimated H-index: 5
(Universidade Federal de Minas Gerais),
Daniele C. Menezes8
Estimated H-index: 8
(Universidade Federal de Minas Gerais)
+ 5 AuthorsJ.R. da S. Maia3
Estimated H-index: 3
(Universidade Federal de Viçosa)
The in vitro anti-fungal activity of diorganotin(V) carboxylate complexes, [N-(2-carboxyphenyl)salicylideneiminato] dimethyltin(IV) (1), bis(µ3-oxo)bis(µ-O-aminobenzoato-O,O′)bis(O-aminobenzoato)tetrakis[dimethyltin(IV)] (2) and bis(O- aminobenzoato-O,O′)di-n-butyltin(IV) (3) has been screened against Candida albicans. The complexes, prepared by minor modifications of a literature method, have been fully characterized. The biological activities of complexes 1–3 on cultures of Candida albicans ha...
16 Citations Source Cite
Mala Nath22
Estimated H-index: 22
(Indian Institute of Technology Roorkee),
Hitendra Singh5
Estimated H-index: 5
(Indian Institute of Technology Roorkee)
+ 1 AuthorsXueqing Song17
Estimated H-index: 17
(University of the District of Columbia)
Abstract New triorganotin(IV) derivatives of dipeptides with general formulae, R3Sn(HL), where R = Me and Ph, and HL is the monoanion of histidinylalanine and histidinylleucine, have been synthesized and characterized on the basis of infrared (IR), multinuclear NMR (1H, 13C, and 119Sn), and 119Sn Mossbauer spectroscopic studies. These derivatives exhibit distorted trigonal-bipyramidal geometry around tin in which dipeptide anion acts as bidentate ligand coordinating through carboxyl oxygen and a...
2 Citations Source Cite
Published on Oct 21, 2009in Materials 2.47
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
Organotin polyethers are easily synthesized employing interfacial polymerization systems involving the reaction of hydroxyl-containing Lewis bases and organotin halides. A wide variety of organotin-containing polymeric products have been synthesized including those derived from natural and synthetic polymers such as lignin, xylan, cellulose, dextran, and poly(vinyl alcohol). Others have been synthesized employing known drug diols such as dicumarol, DES, and dienestrol and a wide variety of synth...
24 Citations Source Cite
Published on Oct 1, 2010in Investigational New Drugs 3.50
Tushar S. Basu Baul23
Estimated H-index: 23
(North Eastern Hill University),
Anup Paul6
Estimated H-index: 6
(North Eastern Hill University)
+ 4 AuthorsDick de Vos23
Estimated H-index: 23
Triphenyltin(IV) complexes of composition [Ph3SnL1H]n (1) and [Ph3SnL2H]n (2) (where L1H = 2-[(E)-2-(3-formyl-4-hydroxyphenyl)-1-diazenyl]benzoate and L2H = 2-[(E)-2-(4-Hydroxy-5-methylphenyl)-1-diazenyl]benzoate) were synthesized and characterized by spectroscopic (1H, 13C and 119Sn NMR, IR, 119Sn Mossbauer) techniques in combination with elemental analysis. The molecular structures and geometries of the complexes (1 and 2) were fully optimized using the quantum mechanical method (PM3). Complex...
18 Citations Source Cite
Girish Barot11
Estimated H-index: 11
(Florida Atlantic University),
Kimberly Shahi10
Estimated H-index: 10
(University of Texas at Arlington)
+ 1 AuthorsCharles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University)
A series of organotin poly(ethylene glycols) were synthesized including the first water soluble organotin polymers. These products are all polymeric with weight average molecular weights about 105. Infrared spectroscopy shows the presence of moieties from both reactants and the formation of the Sn–O linkage. F MALDI MS shows the presence of up to over a hundred units and by isotopic abundance the presence of one, two, and three tin-containing ion fragments. The polymers inhibit the growth of can...
34 Citations Source Cite
Published on Apr 1, 2011in Journal of Organometallic Chemistry 1.95
Safaa El-din H. Etaiw16
Estimated H-index: 16
(Tanta University),
Ahmed S. Sultan4
Estimated H-index: 4
(Alexandria University),
Mohamed M. El-bendary12
Estimated H-index: 12
(Tanta University)
Abstract Two novel organotin supramolecular coordination polymers (SCP), namely, 3 ∞ [Me 3 SnCu(CN) 2 ·(EN) 2 ], 1 and 3 ∞ [Ph 3 SnCu(CN) 2 ·(3-mpy) 2 ], 2 are obtained by the reactions of K 3 [Cu(CN) 4 ], ethyl nicotinate (EN) or 3-methylpyridine (3-mpy) and Me 3 SnCl or Ph 3 SnCl in H 2 O/acetonitrile solution at room temperature. 2D-layers are constructed via H-bonds between the parallel 1D-puckered chains which contain nanometer-sized [–CN(R 3 Sn)NC-] spacers connecting the tetrahedral (T-4)...
34 Citations Source Cite
Tidiane Diop2
Estimated H-index: 2
(Cheikh Anta Diop University),
Libasse Diop8
Estimated H-index: 8
(Cheikh Anta Diop University),
Arie van der Lee4
Estimated H-index: 4
(University of Montpellier)
In the structure of the title coordination polymer, {(C8H20N)[Sn3(CH3)9(SO4)2]}n, each of the three SnIV atoms is coordinated in a trigonal–bipyramidal manner by three methyl groups in the equatorial plane and by two O atoms of SO4 2− anions in the axial positions. The μ3-bridging mode of the sulfate anions leads to the formation of corrugated anionic layers parallel to (100). The uncoordinating O atom of one of the two SO4 2− anions is N—H⋯O hydrogen-bonded to the dibutyl­ammonium cation inter­...
2 Citations Source Cite