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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 ChemMedChem3.02
· 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-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University)
Cite
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 (25)
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References62
Newest
Published on Feb 1, 2010in European Journal of Medicinal Chemistry4.83
Milena R. Kaluđerović8
Estimated H-index: 8
(Leipzig University),
Santiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University)
+ 3 AuthorsGoran N. Kaluđerović19
Estimated H-index: 19
(University of Belgrade)
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...
Published on Jan 1, 2010in Polyhedron2.28
Santiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University),
Sanjiv Prashar21
Estimated H-index: 21
(URJC: King Juan Carlos University)
+ 4 AuthorsGoran N. Kaluđerović19
Estimated H-index: 19
(University of Belgrade)
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...
Published on Jan 1, 2010in Polyhedron2.28
Santiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University),
Beatriz Gallego6
Estimated H-index: 6
(Leipzig University)
+ 3 AuthorsGoran N. Kaluđerović19
Estimated H-index: 19
(University of Belgrade)
Abstract Four titanium(IV) carboxylate complexes [Ti(η 5 -C 5 H 5 ) 2 (O 2 CCH 2 SMes) 2 ] ( 1 ), [Ti(η 5 -C 5 H 4 Me) 2 (O 2 CCH 2 SMes) 2 ] ( 2 ), [Ti(η 5 -C 5 H 5 )(η 5 -C 5 H 4 SiMe 3 )(O 2 CCH 2 SMes) 2 ] ( 3 ) and [Ti(η 5 -C 5 Me 5 )(O 2 CCH 2 SMes) 3 ] ( 4 ; Mes = 2,4,6-Me 3 C 6 H 2 ) have been synthesised by the reaction of the corresponding titanium derivatives [Ti(η 5 -C 5 H 5 ) 2 Cl 2 ], [Ti(η 5 -C 5 H 4 Me) 2 Cl 2 ], [Ti(η 5 -C 5 H 5 )(η 5 -C 5 H 4 SiMe 3 )Cl 2 ] and [Ti(η 5 -C 5 Me ...
Published on Jan 1, 2010in Dalton Transactions4.05
Goran N. Kaluđerović19
Estimated H-index: 19
(University of Belgrade),
Damián Pérez-Quintanilla19
Estimated H-index: 19
(URJC: King Juan Carlos University)
+ 2 AuthorsSantiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University)
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...
Published on Jan 1, 2010in Journal of Materials Chemistry10.73
Goran N. Kaluđerović19
Estimated H-index: 19
(University of Belgrade),
Damián Pérez-Quintanilla19
Estimated H-index: 19
(URJC: King Juan Carlos University)
+ 6 AuthorsSantiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University)
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 ...
Published on Jul 7, 2009in Advances in Inorganic Chemistry2.30
Pieter C. A. Bruijnincx33
Estimated H-index: 33
(Warw.: University of Warwick),
Peter J. Sadler89
Estimated H-index: 89
(Warw.: University of Warwick)
Publisher Summary Transition-metal complexes provide enormously versatile platforms for drug design. Many variations in the metal itself, the types, and numbers of coordinated ligands and hence in the strengths of coordination bonds and in the kinetics of ligand-substitution processes are available. This chapter discusses the efforts towards the development of photoactive platinum anticancer agents and the ruthenium– and osmium–arene families of anticancer agents. The key to successful design of...
Published on Jun 1, 2009in Journal of Organometallic Chemistry2.07
Santiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University),
Beatriz Gallego6
Estimated H-index: 6
(Leipzig University)
+ 4 AuthorsGoran N. Kaluđerović19
Estimated H-index: 19
(University of Belgrade)
Abstract 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,...
Published on May 25, 2009in Chemistry: A European Journal5.16
Damián Pérez-Quintanilla19
Estimated H-index: 19
(URJC: King Juan Carlos University),
Santiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University)
+ 6 AuthorsGoran N. Kaluđerović19
Estimated H-index: 19
(University of Belgrade)
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...
Published on Jan 1, 2009in Coordination Chemistry Reviews13.48
Sotiris K. Hadjikakou34
Estimated H-index: 34
(UoI: University of Ioannina),
Nick Hadjiliadis36
Estimated H-index: 36
(UoI: University of Ioannina)
Tin compounds and their therapeutic potentials are under consideration from many research groups, while a number of early reviews recording advances in the screening for antiproliferative potential of organotins are also available. This review focuses upon results obtained on the antiproliferative activity of tin compounds in the past 5 years.
Published on Dec 1, 2008in Journal of Inorganic Biochemistry3.22
Santiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University),
Goran N. Kaluđerović8
Estimated H-index: 8
+ 4 AuthorsZorica D. Juranić25
Estimated H-index: 25
Abstract The reaction of 3-methoxyphenylacetic acid (3-MPAH), 4-methoxyphenylacetic acid (4-MPAH), 2,5-dimethyl-3-furoic acid (DMFUH) or 1,4-benzodioxane-6-carboxylic acid (BZDOH) with triphenyltin(IV) chloride (1:1) or diphenyltin(IV) dichloride (2:1) in the presence of triethylamine yielded the compounds [SnPh 3 (3-MPA)] ( 1 ), [SnPh 3 (4-MPA)] ( 2 ), [SnPh 3 (DMFU)] ( 3 ), [SnPh 3 (BZDO)] ( 4 ), [SnPh 2 (3-MPA) 2 ] ( 5 ), [SnPh 2 (4-MPA) 2 ] ( 6 ), [SnPh 2 (DMFU) 2 ] ( 7 ) and [SnPh 2 (BZDO) ...
Cited By25
Newest
Published on Jan 17, 2018in Zeitschrift für anorganische und allgemeine Chemie1.34
Xiao Xiao , Wenliang Li1
Estimated H-index: 1
+ 2 AuthorsBo Feng3
Estimated H-index: 3
Self-assembly of dibutyltin oxide with 3-(1,3-dioxo-2,3-dihydro-1H-phenalen-2-yl)benzoic acid (HL) produces (n-Bu)2SnL2 (complex 1) when benzene is used as solvent, while the reaction generates {[(n-Bu)2SnO]2L}2·C7H8 (complex 2) when toluene is reactive solvent. The novel organotin carboxylate (n-Bu)2SnL2 (complex 1) was characterized by elemental analysis, IR, 1H, 13C, 119Sn NMR spectroscopy. Single crystal X-ray study reveals that 1 is a dialkyltin carboxylate monomer possessing crystallograph...
Published on Jan 1, 2018in Dalton Transactions4.05
Diana Díaz-García2
Estimated H-index: 2
(URJC: King Juan Carlos University),
Diana Cenariu1
Estimated H-index: 1
+ 5 AuthorsSantiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University)
The mesoporous silica-based material SBA-15 (Santa Barbara Amorphous-15) has been modified with the aminodiol ligand 3-[bis(2-hydroxyethyl)amino]propyltriethoxysilane (PADOH) to give the corresponding material SBA-PADOH. Subsequent functionalization with a diorganotin(IV) compound, SnPh2Cl2 (1), and with two titanocene derivatives, TiCp2Cl2 ([Ti(η5-C5H5)2Cl2] (2)) and TiCpCpPhNfCl2 ([Ti(η5-C5H5)(η5-C5H4CHPhNf)Cl2] (3) (Ph = C6H5; Nf = C10H7)), gave the materials SBA-PADO-SnPh2 (M1), SBA-PADO-TiC...
Published on Dec 1, 2017in DARU2.70
Durdana Waseem3
Estimated H-index: 3
(QAU: Quaid-i-Azam University),
Arshad Farooq Butt1
Estimated H-index: 1
(Allama Iqbal Open University)
+ 2 AuthorsGul Majid Khan14
Estimated H-index: 14
(QAU: Quaid-i-Azam University)
Background Tributyltin (IV) compounds are promising candidates for drug development. In the current study, we evaluated in-vitro and in-silico profile of carboxylate derivatives of tributyltin (IV) complexes.
Published on Jun 1, 2017in Applied Organometallic Chemistry3.26
David Edeler2
Estimated H-index: 2
(MLU: Martin Luther University of Halle-Wittenberg),
Christian Bensing2
Estimated H-index: 2
(MLU: Martin Luther University of Halle-Wittenberg)
+ 1 AuthorsGoran N. Kaluđerović5
Estimated H-index: 5
(Leibniz Association)
The reaction of SnPh3Li with X(CH2)nO–THP (THP = tetrahydro-2H-pyran-2-yl; n = 3, 4, 6, 8, 11; X = Cl, Br) afforded organotin(IV) compounds with the general formula Ph3Sn(CH2)nO–THP (1–5). The tetraorganotin(IV) compounds were characterized using multinuclear NMR and infrared spectroscopies and high-resolution mass spectrometry. Anticancer activity of the synthesized compounds was tested in vitro against the A2780 (ovarian), A549 (lung), HeLa (adenocarcinoma) and SW480 (colon) tumour cell lines ...
Published on Apr 1, 2017in Chemical Biology & Drug Design2.26
Denise Hübner1
Estimated H-index: 1
(Leipzig University),
Milena R. Kaluđerović8
Estimated H-index: 8
+ 1 AuthorsGoran N. Kaluđerović8
Estimated H-index: 8
(Leibniz Association)
Two ionic triphenyltin(IV) chloride carboxylato compounds of the formula [NHEt3][Ph3SnCl(L)] (LH = N-phthaloylglycine (P-GlyH), 1; 1,2,4-benzenetricarboxylic 1,2-anhydride (BTCH), 2) were tested for the in vitro activity against 518A2 (melanoma), FaDu (head and neck carcinoma), HT-29 (colon cancer), MCF-7 (breast carcinoma) and SW1736 (thyroid cancer) cell lines. The ammonium salts of carboxylic acids are found to be not active, while anionic [Ph3SnCl(L)]– exhibited high cytotoxicity in nM range...
Published on Jan 12, 2017
Younes Ellahioui3
Estimated H-index: 3
,
Sanjiv Prashar21
Estimated H-index: 21
,
Santiago Gómez-Ruiz24
Estimated H-index: 24
For more than 100 years metal complexes have been extensively used in therapy and since the discovery of cisplatin the research in this field has expanded exponentially. The scientific community is always in search of new alternatives to platinum compounds and a wide variety of metallodrugs based on other metals have been reported with excellent therapeutic results. This short review focuses on the work that our research group has carried out since 2007 in collaboration with others and centers o...
Published on Jan 1, 2017in Journal of Inorganic Biochemistry3.22
Tushar S. Basu Baul23
Estimated H-index: 23
(NEHU: North Eastern Hill University),
Dhrubajyoti Dutta3
Estimated H-index: 3
(NEHU: North Eastern Hill University)
+ 6 AuthorsSunil K. Manna17
Estimated H-index: 17
(Centre for DNA Fingerprinting and Diagnostics)
Abstract Synthesis and spectroscopic properties of seven new dibutyltin(IV) compounds of 2-{( E )-4-hydroxy-3-[( E )-4-(aryl)iminomethyl]phenyldiazenyl}benzoic acids (L n HH′; n = 2–8) with general formula {[Bu 2 Sn(L n H)] 2 O} 2 ( 1 – 7 ) are reported. The compounds were characterized by elemental analysis and by UV–Visible, fluorescence, IR, 1 H, 13 C and 119 Sn NMR spectroscopies. Solid state structures of dibutyltin(IV) compounds 1 – 3 , 6 and 7 were accomplished from single crystal X-ray c...
Published on Apr 1, 2016in Coordination Chemistry Reviews13.48
Waseem A. Wani17
Estimated H-index: 17
(UTM: Universiti Teknologi Malaysia),
Sanjiv Prashar21
Estimated H-index: 21
(URJC: King Juan Carlos University)
+ 1 AuthorsSantiago Gómez-Ruiz24
Estimated H-index: 24
(URJC: King Juan Carlos University)
Abstract Nanotechnology has shown great promise in unraveling several important issues of conventional anticancer chemotherapy. Expectations project that a new generation of effective cancer therapies will be developed with enormous potential to overcome the biological, biophysical and biomedical obstacles that the human body enacts against standard chemotherapeutic treatments. Generally, nanostructures protect the entombed drug molecules from degradation in blood, allowing their safe and unimpa...
Published on Feb 1, 2016in Structural Chemistry1.62
Alexander A. Korlyukov23
Estimated H-index: 23
(RSMU: Russian National Research Medical University),
N. V. Shmatkova1
Estimated H-index: 1
(ODESSA)
+ 1 AuthorsAnna V. Vologzhanina19
Estimated H-index: 19
(A. N. Nesmeyanov Institute of Organoelement Compounds)
The results of detailed experimental and theoretical study of chemical intra- and intermolecular bonding of salicyl hydrazone complex with SnCl3 are described. The chemical bonding pattern in the crystal and isolated molecule is described in terms of Bader’s “Atoms in Molecules” (AIM) theory. Analysis of AIM charges has revealed that amount of charge transferred from ligand to SnCl3 moiety is equal to ≈ 0.3 e that leads to significant redistribution of bond lengths as compared to other tin(IV) s...
Published on Nov 1, 2014in Inorganica Chimica Acta2.43
Lin Niu3
Estimated H-index: 3
(Shanxi Medical University),
Yunlan Li3
Estimated H-index: 3
(Shanxi Medical University),
Qingshan Li9
Estimated H-index: 9
(Shanxi Medical University)
Abstract Organotin(IV) compounds are used globally as stabilizers, catalyzers and biocidal agents. However, due to the increased focus on the application of organotin(IV) compounds in health care, their use will no longer be limited to industry and agriculture. Bioactivities of organotins including anti-cancer, antiviral, antiparasitic, antimicrobial, antihypertensive activities and anti-hyperbilirubinemia have been widely discussed and their anti-cancer abilities have been studied most extensiv...
View next paperAntiproliferative and anti-tumor activity of organotin compounds