Leitat Tecnological Center

Barcelona, Spain

Leitat Tecnological Center

Barcelona, Spain

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Quirante J.,University of Barcelona | Ruiz D.,University of Barcelona | Gonzalez A.,University of Barcelona | Lopez C.,University of Barcelona | And 13 more authors.
Journal of Inorganic Biochemistry | Year: 2011

The study of the reactivity of three 1-(2-dimethylaminoethyl)-1H-pyrazole derivatives of general formula [1-(CH 2) 2NMe 2}-3,5-R 2-pzol] {where pzol represents pyrazole and RH (1a), Me (1b) or Ph (1c)} with [MCl 2(DMSO) 2] (MPt or Pd) under different experimental conditions allowed us to isolate and characterize cis-[M{κ 2-N,N′-{[1-(CH 2) 2NMe 2}-3,5-R 2-pzol])}Cl 2] {MMPtPt (2a-2c) or Pd (3a-3c)} and two cyclometallated complexes [M{κ 3-C,N,N′- {[1-(CH 2) 2NMe 2}-3-(C 5H 4)-5-Ph-pzol])}Cl] {MPt(II) (4c) or Pd(II) (5c)}. Compounds 4c and 5c arise from the orthometallation of the 3-phenyl ring of ligand 1c. Complex 2a has been further characterized by X-ray crystallography. Ligands and complexes were evaluated for their in vitro antimalarial against Plasmodium falciparum and cytotoxic activities against lung (A549) and breast (MDA MB231 and MCF7) cancer cellular lines. Complexes 2a-2c and 5c exhibited only moderate antimalarial activities against two P. falciparum strains (3D7 and W2). Interestingly, cytotoxicity assays revealed that the platinacycle 4c exhibits a higher toxicity than cisplatin in the three human cell lines and that the complex 2a presents a remarkable cytotoxicity and selectivity in lung (IC 50 = 3 μM) versus breast cancer cell lines (IC 50 > 20 μM). Thus, complexes 2c and 4c appear to be promising leads, creating a novel family of anticancer agents. Electrophoretic DNA migration studies in presence of the synthesized compounds have been performed, in order to get further insights into their mechanism of action. © 2011 Elsevier Inc. All rights reserved.


Chukwu J.U.,University of Barcelona | Lopez C.,University of Barcelona | Gonzalez A.,University of Barcelona | Font-Bardia M.,University of Barcelona | And 3 more authors.
Journal of Organometallic Chemistry | Year: 2014

The study of the reactivity of the novel pyrazole derivative [1-{MeO-(CH2)2-}-3,5-Ph2-(C3HN 2)] (1) with Na2[PdCl4] or Pd(OAc)2 under different experimental conditions has allowed us to isolate and characterize the trans-isomers of [Pd{[1-{MeO-(CH2) 2-}-3,5-Ph2-(C3HN2)]} 2(X)2] [X = Cl (2) or OAc (3)] and the di-μ-ligand bridged cyclopalladated complexes [Pd{κ2,C,N[1-{MeO-(CH 2)2-}-3-(C6H4),5-Ph-(C 3HN2)]}(μ-X)]2 [X = OAc (4) or Cl (5)]. Further treatment of compounds 4 or 5 with PPh3 in CH 2Cl2 produced the bridge splitting and the formation of [Pd{κ2,C,N[1-{MeO-(CH2)2-}-3-(C 6H4),5-Ph-(C3HN2)]}X(PPh 3)] [X = OAc (6) or Cl (7)]. The cytotoxic assessment of the free ligand (1) and the Pd(II) complexes on the two breast cancer cell lines MCF7 and MDA-MB231 reveals that: a) compound 1 is less active than its analogue [1-{Me2N-(CH2)2-}-3,5-Ph2-(C 3HN2)] (Ic) and b) palladacycles 4-7 showed a remarkable cytotoxic activity in the MDA-MB231 cell line (with IC50 values in the range 9.1-14.4 μM). © 2014 Elsevier B.V. All rights reserved.


Talancon D.,University of Barcelona | Lopez C.,University of Barcelona | Font-Bardia M.,University of Barcelona | Calvet T.,University of Barcelona | And 7 more authors.
Journal of Inorganic Biochemistry | Year: 2013

The study of the reactivity of (1S,2R) [(η5-C 5H5)Fe{[(η5-C5H4) CHNCH(Me)CH(OH)C6H5}] (1a) with cis-[PtCl 2(DMSO)2] under different experimental conditions has allowed to isolate and characterize three pairs of isomeric and diastereomerically pure platinum(II) complexes. Two of the pairs are the trans- and cis- isomers of (1S,2R)[Pt{(η5-C5H 5)Fe[(η5-C5H4)CHNCH(Me)CH(OH) C6H5]}Cl2(DMSO)] [trans-(2a) and cis-(3a), respectively], and of (1S,2R) [Pt{(κ2-N,O)(η5- C5H5)Fe[(η5-C5H 4)CHNCH(Me)CH(O)C6H5]}Cl(DMSO)], {trans-(Cl, N) in (4a)} or a cis-(Cl, N) {in (5a)}; while the third one is formed by platinacycles: [Pt{(κ2-C,N[(η5-C 5H3)]CHN-CH(Me)CH(OH)C6H5] Fe(η5-C5H5)}Cl(DMSO)] with different planar chirality [Sp (in 6a) or Rp (in 7a)]. The crystal structures of compounds 2a, 3a, 5a and 6a are also reported. The cytotoxic assessment of 1a-7a on lung (A549), breast (MDA-MB-231) and colon (HCT-116) cancer cell lines is also reported and reveals that the potency of the complexes is strongly dependent on the mode of binding of the iminoalcohol {(N) in 2a and 3a, (N,O)- in 4a and 5a or (C,N)- in 6a and 7a}, the relative arrangement of the monodentate ligands (in 2a-5a), and the planar chirality of the 1,2-ferrocenylunit in (6a and 7a). Among the new products (2a-7a), compounds 4a and 5a exhibit the highest potency with IC50 values smaller than cisplatin in the three cancer cell lines assayed. Electrophoretic DNA migration studies in the presence of 2a-7a have been performed in order to get further insights into their mechanism of action. A comparative study of the solution behaviour of all the complexes in DMSO-d 6 or in DMSO-d6:D2O (1:1) mixtures at 298 K is also reported. © 2012 Elsevier Inc. All rights reserved.


Tome M.,University of Barcelona | Lopez C.,University of Barcelona | Gonzalez A.,Institute Of Biomedicina Ibub | Ozay B.,Institute Of Biomedicina Ibub | And 8 more authors.
Journal of Molecular Structure | Year: 2013

The synthesis and characterization of the new 2-phenylindole derivative: C8H3N-2-C6H5-3NOMe-5OMe (3c) and the trans- and cis-isomers of [Pt(3c)Cl2(DMSO)] complexes (4c and 5c, respectively) are described. The crystal structures of 4c·CH 2Cl2 and 5c confirm: (a) the existence of a Pt-N indole bond, (b) the relative arrangement of the Cl- ligands [trans- (in 4c) or cis- (in 5c)] and (c) the anti-(E) configuration of the oxime. The cytotoxic assessment of C8H3N-2-(C 6H4-4'R1)-3NOMe-5R2 [with R 1 = R2 = H (3a); R1 = Cl, R2 = H (3b) and R1 = H, R2 = OMe (3c)] and the geometrical isomers of [Pt(L)Cl2(DMSO)] with L = 3a-3c [trans- (4a-4c) and cis- (5a-5c), respectively] against human breast adenocarcinoma cell lines (MDA-MB231 and MCF-7) is also reported and reveals that all the platinum(II) complexes (except 4a) are more cytotoxic than cisplatin in front of the MCF7 cell line. Electrophoretic DNA migration studies of the synthesized compounds in the absence and in the presence of topoisomerase-I have been performed, in order to get further insights into their mechanism of action. © 2013 Elsevier B.V. All rights reserved.

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