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Study of the Anticancer Properties of Tin(IV) Carboxylate Complexes on a Panel of Human Tumor Cell Lines

Published on Feb 6, 2012in ChemMedChem3.016
· DOI :10.1002/cmdc.201100432
Lourdes Rocamora-Reverte8
Estimated H-index: 8
(Universidad Miguel Hernández de Elche),
Estefanía Carrasco-García10
Estimated H-index: 10
(Universidad Miguel Hernández de Elche)
+ 4 AuthorsSantiago Gómez-Ruiz25
Estimated H-index: 25
(URJC: King Juan Carlos University)
Abstract
A group of organotin(IV) complexes were prepared: [SnCy3(DMNI)] (1), [SnCy3(BZDO)] (2), [SnCy3(DMFU)] (3), and [SnPh2(BZDO)2] (4), for which DMNIH=2,6-dimethoxynicotinic acid, BZDOH=1,4-benzodioxane-6-carboxylic acid, and DMFUH=2,5-dimethyl-3-furoic acid. The cytotoxic activities of compounds 1–4 were tested against pancreatic carcinoma (PANC-1), erythroleukemia (K562), and two glioblastoma multiform (U87 and LN-229) human cell lines; they show very high antiproliferative activity, with IC50 values in the 150–700 nM range after incubation for 72 h. Distribution of cellular DNA upon treatment with 1–4 revealed that whereas compounds 1–3 induce apoptosis in most of the cell lines, compound 4 does not affect cell viability in any cell line tested, indicating a possible difference in cytotoxic mechanism. Studies with the daunomycin-resistant K562/R cell line expressing P-glycoprotein (Pgp) showed that compounds 1–4 are not substrates of this protein efflux pump, indicating that these compounds do not induce acquisition of multidrug resistance, which is associated with the overexpression of Pgp.
  • References (62)
  • Citations (26)
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References62
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#1Goran N. Kaluđerović (University of Belgrade)H-Index: 26
#2Damián Pérez-Quintanilla (URJC: King Juan Carlos University)H-Index: 19
Last. Santiago Gómez-Ruiz (URJC: King Juan Carlos University)H-Index: 25
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The reaction of [Ti(η5-C5H5)2Cl2] (1), with 3-mercaptopropyltrimethoxysilane or 3-mercaptopropyltriethoxysilane in the presence of triethylamine leads to the formation of the thiolate complexes [Ti(η5-C5H5)2{SCH2CH2CH2Si(OMe)3}2] (2) and [Ti(η5-C5H5)2{SCH2CH2CH2Si(OEt)3}2] (3), respectively. Complexes 2 and 3 have been characterized by traditional methods, in addition, structural studies based on DFT calculations are reported. 1–3 have been grafted onto dehydroxylated MCM-41 to give the novel ma...
31 CitationsSource
#1Milena R. Kaluđerović (Leipzig University)H-Index: 8
#2Santiago Gómez-Ruiz (URJC: King Juan Carlos University)H-Index: 25
Last. Goran N. Kaluđerović (University of Belgrade)H-Index: 26
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Abstract The reaction of 3-methoxyphenylacetic acid, 4-methoxyphenylacetic acid, mesitylthioacetic acid, 2,5-dimethyl-3-furoic acid and 1,4-benzodioxane-6-carboxylic acid with trimethylgallium (1:1) yielded the dimeric complexes [Me 2 Ga(μ-O 2 CCH 2 C 6 H 4 -3-OMe)] 2 ( 1 ), [Me 2 Ga(μ-O 2 CCH 2 C 6 H 4 -4-OMe)] 2 ( 2 ), [Me 2 Ga(μ-O 2 CCH 2 SMes)] 2 ( 3 ) (Mes = 2,4,6-Me 3 C 6 H 2 ), [Me 2 Ga{μ-O 2 C(Fur)}] 2 ( 4 ) (Fur = 2,5-dimethylfuran) and [Me 2 Ga{μ-O 2 C(Bdo)}] 2 ( 5 ) (Bdo = 1,4-benzodi...
32 CitationsSource
#1Goran N. Kaluđerović (University of Belgrade)H-Index: 26
#2Damián Pérez-Quintanilla (URJC: King Juan Carlos University)H-Index: 19
Last. Santiago Gómez-Ruiz (URJC: King Juan Carlos University)H-Index: 25
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Four different titanocene complexes, [Ti(η5-C5H5)2Cl2] (1), [Ti(η5-C5H5)(η5-C5H4Pri)Cl2] (2), [Ti(η5-C5H5)(η5-C5H4But)Cl2] (3) and [Ti(η5-C5H5){η5-C5H3(SiMe3)2}Cl2] (4), have been grafted onto dehydroxylated MCM-41 to give the novel materials MCM-41/[Ti(η5-C5H5)2Cl2] (S1), MCM-41/[Ti(η5-C5H5)(η5-C5H4Pri)Cl2] (S2), MCM-41/[Ti(η5-C5H5)(η5-C5H4But)Cl2] (S3) and MCM-41/[Ti(η5-C5H5){η5-C5H3(SiMe3)2}Cl2] (S4), which have been characterized by powder X-ray diffraction, X-ray fluorescence, nitrogen gas ...
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#2Sanjiv Prashar (URJC: King Juan Carlos University)H-Index: 21
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Abstract The organotin compounds, [SnPh 3 (C 5 H 4 R)] (R = Bu t ( 1 ), CMe 2 (CH 2 CH 2 CH CH 2 ) ( 2 )) and [SnPh 3 (C 5 Me 4 R)] (R = H ( 3 ), SiMe 3 ( 4 )), were prepared by the reaction of SnPh 3 Cl with the lithium derivative of the corresponding cyclopentadiene. 1 – 4 have been characterized by multinuclear NMR spectroscopy ( 1 H, 13 C{ 1 H} and 119 Sn{ 1 H}). In addition, the molecular structures of 1 , 2 and 4 were determined by single-crystal X-ray diffraction studies. The cytotoxic ac...
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#2Beatriz Gallego (Leipzig University)H-Index: 6
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Abstract Four titanium(IV) carboxylate complexes [Ti(η5-C5H5)2(O2CCH2SMes)2] (1), [Ti(η5-C5H4Me)2(O2CCH2SMes)2] (2), [Ti(η5-C5H5)(η5-C5H4SiMe3)(O2CCH2SMes)2] (3) and [Ti(η5-C5Me5)(O2CCH2SMes)3] (4; Mes = 2,4,6-Me3C6H2) have been synthesised by the reaction of the corresponding titanium derivatives [Ti(η5-C5H5)2Cl2], [Ti(η5-C5H4Me)2Cl2], [Ti(η5-C5H5)(η5-C5H4SiMe3)Cl2] and [Ti(η5-C5Me5)Cl3] and two (for 1–3) or three (for 4) equivalents of mesitylthioacetic acid. Complexes 1–4 have been characteri...
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#1Pieter C. A. Bruijnincx (Warw.: University of Warwick)H-Index: 34
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The reaction of N-phthaloylglycine and N-phthaloyl-DL-alanine with trimethylgallium (1:1) yielded the dinuclear complexes [Me 2 Ga(μ-O 2 CCH 2 N(CO) 2 C 6 H 4 )] 2 (1) and RS-[Me 2 Ga(μ-O 2 CCHMeN(CO) 2 C 6 H 4 )] 2 (2), respectively. The molecular structure of 2 was determined by X-ray diffraction studies. The cytotoxic activity of the organogallium(III) complexes (1 and 2) was tested against human tumour cell lines 8505C anaplastic thyroid cancer, A253 head and neck tumour, A549 lung carcinoma...
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The next generation: The grafting of titanocene complexes on the surfaces of MCM-41 and SBA-15 led to a new generation of anticancer drugs, which are very active against human cancer cells. Dehydroxylated MCM-41 and SBA-15 surfaces were modified by the grafting of two different titanocene complexes ([Ti(η5-C5H4Me)2Cl2] and [Ti{Me2Si(η5-C5Me4)(η5-C5H4)}Cl2]) to give new materials, which have been characterized by powder X-ray diffraction, X-ray fluorescence, nitrogen gas sorption, MAS-NMR spectro...
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