Publications by authors named "José L Serrano"

12 Publications

  • Page 1 of 1

Combination Chemotherapy with Cisplatin and Chloroquine: Effect of Encapsulation in Micelles Formed by Self-Assembling Hybrid Dendritic-Linear-Dendritic Block Copolymers.

Int J Mol Sci 2021 May 14;22(10). Epub 2021 May 14.

Grupo de Terapia Génica y Celular, Instituto Aragonés de Ciencias de la Salud (IACS/IIS-Aragon), 50009 Zaragoza, Spain.

Clinical outcomes of conventional drug combinations are not ideal due to high toxicity to healthy tissues. Cisplatin (CDDP) is the standard component for many cancer treatments, yet its principal dose-limiting side effect is nephrotoxicity. Thus, CDDP is commonly used in combination with other drugs, such as the autophagy inhibitor chloroquine (CQ), to enhance tumor cell killing efficacy and prevent the development of chemoresistance. In addition, nanocarrier-based drug delivery systems can overcome chemotherapy limitations, decreasing side effects and increasing tumor accumulation. The aim of this study was to evaluate the toxicity of CQ and CDDP against tumor and non-tumor cells when used in a combined treatment. For this purpose, two types of micelles based on Pluronic F127 hybrid dendritic-linear-dendritic block copolymers (HDLDBCs) modified with polyester or poly(esteramide) dendrons derived from 2,2'-bis(hydroxymethyl)propionic acid (HDLDBC-bMPA) or 2,2'-bis(glycyloxymethyl)propionic acid (HDLDBC-bGMPA) were explored as delivery nanocarriers. Our results indicated that the combined treatment with HDLDBC-bMPA(CQ) or HDLDBC-bGMPA(CQ) and CDDP increased cytotoxicity in tumor cells compared to the single treatment with CDDP. Encapsulations demonstrated less short-term cytotoxicity individually or when used in combination compared to the free drugs. However, and more importantly, a low degree of cytotoxicity against non-tumor cells was maintained, even when drugs were given simultaneously.
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http://dx.doi.org/10.3390/ijms22105223DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8156097PMC
May 2021

Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends.

ACS Appl Mater Interfaces 2020 Mar 21;12(9):10929-10937. Epub 2020 Feb 21.

Instituto de Ciencia de Materiales de Madrid, CSIC Cantoblanco, 28049 Madrid, Spain.

A new rod-shaped benzothiadiazole fluorophore, namely, 4,7-di-(4-nonylphenyl)benzo[][1,2,5]thiadiazole, which strongly emits fluorescence both in solution and in solid state has been synthesized, and its photophysical properties were rationalized with the help of density functional theory calculations. This molecule crystallizes in two distinct light-emitting crystalline phases, which can be interconverted in response to pressure, temperature, and solvent vapors. Powder X-ray diffraction indicates that in both polymorph, molecules adopt a lamellar packing, the different interlayer spacing being the main difference between the two structures. Single-crystal analysis of one of the polymorphs allows us to identify weak interaction planes, which presumably facilitates the polymorphic transformation through mechanically or thermally induced sliding processes. The polymorphic transformation and the origin of the switchable fluorescence have been rationalized through a spectroscopic and theoretical study. This study suggests that the different colors observed are due to different intermolecular aromatic interactions owing to the displacement of the molecules with respect to the layer normal. Interestingly, blending this molecule with a biodegradable polymer such as poly(vinyl alcohol) gives rise to a thermally activated reversible switchable fluorescent system, which entitles this material as an attractive candidate for technological applications, such as thermal sensors, security inks, or rewritable paper.
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http://dx.doi.org/10.1021/acsami.9b21209DOI Listing
March 2020

Fluorescent and Electroactive Monoalkyl BTD-Based Liquid Crystals with Tunable Self-Assembling and Electronic Properties.

ACS Omega 2018 Sep 25;3(9):11857-11864. Epub 2018 Sep 25.

Material Science Factory, Instituto de Ciencia de Materiales de Madrid, Cantoblanco, 20849 Madrid, Spain.

We report here on a series of redox active benzothiadiazole-based luminophores functionalized on one edge with a phenyl-nonyl substituent, which confers these molecules a rodlike shape and a tendency to self-assemble into layered superstructures. On the other edge, the molecules are endowed with different p-substituted phenyl rings, which allows the modulation of their redox and optical properties on the basis of the electronic nature of the terminal substituents. We have found that just one lateral alkyl chain is sufficient to induce mesomorphism in these molecules, which present nematic or smectic mesophases upon thermal treatment. Single-crystal analysis allows us to get an insight into the nature of the forces responsible for different supramolecular assemblies in these derivatives, and point to a strong contribution of the terminal groups in the different arrangements observed. The interesting redox and optical properties together with their self-assembling tendencies render these new materials interesting candidates for optoelectronics.
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http://dx.doi.org/10.1021/acsomega.8b01696DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644942PMC
September 2018

Unconventional Single-Molecule Conductance Behavior for a New Heterocyclic Anchoring Group: Pyrazolyl.

J Phys Chem Lett 2018 Sep 5;9(18):5364-5372. Epub 2018 Sep 5.

Departamento de Química Física, Facultad de Ciencias , Universidad de Zaragoza , 50009 Zaragoza , Spain.

Electrical conductance across a molecular junction is strongly determined by the anchoring group of the molecule. Here we highlight the unusual behavior of 1,4-bis(1H-pyrazol-4-ylethynyl)benzene that exhibits unconventional junction current versus junction-stretching distance curves, which are peak-shaped and feature two conducting states of 2.3 × 10 G and 3.4 × 10 G. A combination of theory and experiments is used to understand the conductance of single-molecule junctions featuring this new anchoring group, i.e., pyrazolyl. These results demonstrate that the pyrazolyl moiety changes its protonation state and contact binding during junction evolution and that it also binds in either end-on or facial geometries with gold contacts. The pyrazolyl moiety holds general interest as a contacting group, because this linkage leads to a strong double anchoring of the molecule to the gold electrode, resulting in enhanced conductance values.
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http://dx.doi.org/10.1021/acs.jpclett.8b02051DOI Listing
September 2018

Cationic poly(ester amide) dendrimers: alluring materials for biomedical applications.

J Mater Chem B 2018 Jun 31;6(23):3956-3968. Epub 2018 May 31.

Instituto de Nanociencia de Aragón (INA), Universidad de Zaragoza, Spain.

Novel cationic poly(ester amide) dendrimers have been synthesized by copper(i) azide-alkyne cycloaddition (CuAAC) of a tripropargylamine core and azide-terminated dendrons, in turn prepared by iterative amide coupling of the new monomer 2,2'-bis(glycyloxymethyl)propionic acid (bis-GMPA). The alternation of ester and amide groups provided a dendritic scaffold that was totally biocompatible and degradable in aqueous media at physiological and acidic pH. The tripodal dendrimers naturally formed rounded aggregates with a drug that exhibited low water solubility, camptothecin, thus improving its cell viability and anti-Hepatitis C virus (anti-HCV) activity. The presence of numerous peripheral cationic groups enabled these dendrimers to form dendriplexes with both pDNA and siRNA and they showed effective in vitro siRNA transfection in tumoral and non-tumoral cell lines.
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http://dx.doi.org/10.1039/c8tb00639cDOI Listing
June 2018

DNA Transfection to Mesenchymal Stem Cells Using a Novel Type of Pseudodendrimer Based on 2,2-Bis(hydroxymethyl)propionic Acid.

Bioconjug Chem 2017 04 13;28(4):1135-1150. Epub 2017 Mar 13.

Departamento de Quı́mica Orgánica, Facultad de Ciencias, Instituto de Nanociencia de Aragón, Universidad de Zaragoza , Zaragoza 50009, Spain.

In the search for effective vehicles to carry genetic material into cells, we present here new pseudodendrimers that consist of a hyperbranched polyester core surrounded by amino-terminated 2,2-bis(hydroxymethyl)propionic acid (bis-MPA) dendrons. The pseudodendrimers are readily synthesized from commercial hyperbranched bis-MPA polyesters of the second, third, and fourth generations and third-generation bis-MPA dendrons, bearing eight peripheral glycine moieties, coupled by the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). This approach provides globular macromolecular structures bearing 128, 256, and 512 terminal amino groups, and these can complex pDNA. The toxicity of the three pseudodendrimers was studied on two cell lines, mesenchymal stem cells, and HeLa, and it was demonstrated that these compounds do not affect negatively cell viability up to 72 h. The complexation with DNA was investigated in terms of N-to-P ratio and dendriplex stability. The three generations were found to promote internalizing of pDNA into mesenchymal stem cells (MSCs), and their transfection capacity was compared with two nonviral commercial transfection agents, Lipofectamine and TransIT-X2. The highest generations were able to transfect these cells at levels comparable to both commercial reagents.
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http://dx.doi.org/10.1021/acs.bioconjchem.7b00037DOI Listing
April 2017

A polymer network prepared by the thiol-yne photocrosslinking of a liquid crystalline dendrimer.

Macromol Rapid Commun 2013 Mar 16;34(6):498-503. Epub 2013 Jan 16.

Instituto de Ciencia de Materiales de Aragón, Departamento de Química Orgánica, Consejo Superior de Investigaciones Científicas-Universidad de Zaragoza, 50009 Zaragoza, Spain.

A polymer network is prepared by the thiol-yne photopolymerization of multifunctional dendrimer with a tetrathiol crosslinker. The network obtained shows a liquid crystalline phase at room temperature, which has been characterized by optical microscopy, differential scanning calorimetry, and X-ray diffraction. Photoinduced deformation of uniaxially aligned free-standing films of the photocrosslinked material has been demonstrated.
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http://dx.doi.org/10.1002/marc.201200730DOI Listing
March 2013

Synthesis and characterization of maltose-based amphiphiles as supramolecular hydrogelators.

Langmuir 2011 Dec 29;27(24):15236-47. Epub 2011 Nov 29.

Instituto de Ciencia de Materiales de Aragón (ICMA), Universidad de Zaragoza-CSIC, Dpt. Química Orgánica, Facultad de Ciencias, Pedro Cerbuna 12, 50009, Zaragoza, Spain.

Low molecular mass amphiphilic glycolipids have been prepared by linking a maltose polar head and a hydrophobic linear chain either by amidation or copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. The liquid crystalline properties of these amphiphilic materials have been characterized. The influence of the chemical structure of these glycolipids on the gelation properties in water has also been studied. Glycolipids obtained by the click coupling of the two components give rise to stable hydrogels at room temperature. The fibrillar structure of supramolecular hydrogels obtained by the self-assembly of these gelators have been characterized by electron microscopy. Fibers showed some torsion, which could be related with a chiral supramolecular arrangement of amphiphiles, as confirmed by circular dichroism (CD). The sol-gel transition temperature was also determined by differential scanning calorimetry (DSC) and NMR.
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http://dx.doi.org/10.1021/la203447eDOI Listing
December 2011

High charge mobility in discotic liquid-crystalline triindoles: just a core business?

Angew Chem Int Ed Engl 2011 Aug 24;50(32):7399-402. Epub 2011 Jun 24.

Instituto de Ciencia de Materiales de Madrid, Cantoblanco, Madrid, Spain.

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http://dx.doi.org/10.1002/anie.201005820DOI Listing
August 2011

Philic and phobic segregation in liquid-crystal ionic dendrimers: an enthalpy-entropy competition.

Angew Chem Int Ed Engl 2010 Mar;49(11):1990-4

Instituto de Ciencia de Materiales de Aragón-CSIC, Universidad de Zaragoza, Plaza San Francisco s/n, 50009-Zaragoza, Spain.

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http://dx.doi.org/10.1002/anie.200905654DOI Listing
March 2010

Ionic thermotropic liquid crystal dendrimers.

J Am Chem Soc 2005 May;127(20):7397-403

Dpto. de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-CSIC, Spain.

The synthesis and characterization of two families of ionic liquid crystal dendrimers consisting of the ammonium salts of the commercially available poly(amidoamine) (G = 0-5) and poly(propylene imine) (G = 1-5) dendrimers and three long-chain carboxylic acids are reported. The liquid crystalline behavior was investigated by means of differential scanning calorimetry, polarizing light optical microscopy, and X-ray diffractometry. The thermal stability of the ionic materials was further studied by NMR. Most of the dendrimers show lamellar mesomorphism, and two of them exhibit columnar mesomorphism. On the basis of the experimental results, we propose models both at the molecular level and in the mesophase for all the materials.
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http://dx.doi.org/10.1021/ja042264hDOI Listing
May 2005

Paraoxonase activity and genetic polymorphisms in greenhouse workers with long term pesticide exposure.

Hum Exp Toxicol 2003 Nov;22(11):565-74

Department of Legal Medicine and Toxicology, University of Granada School of Medicine, Spain.

Serum paraoxonase (PON1) is a high-density lipoprotein (HDL) associated protein, which plays a critical role in the pathogenesis of atherosclerosis, although it was primarily associated with the hydrolysis of organophosphorus compounds. PON1 was initially thought to be independent from physiological or pathological states, although recently some environmental factors have been reported to modulate its activity. In this study, we have investigated the promoter (PON1 -108C/T and -909 C/G) and coding region (PON1 192Q/R and 55L/M) polymorphisms, as well as PON1 activity towards different substrates (paraoxon, phenylacetate and diazoxon) in 102 individuals with long term low dose exposure to pesticides in a plastic greenhouse setting (sprayers), who are probably the group of agricultural workers with the highest exposure to pesticides. PON1 activity towards paraoxon was nonsignificantly decreased (up to 53.5%) in the sprayers subgroup exposed to organophosphates (n = 41) compared with nonsprayers acting as controls (n = 39). None of the genotypes studied was associated significantly with the subgroup of individuals exposed to organophosphates, although differences between sprayers and nonsprayers were observed in the PON1 -909 G/C polymorphism. Among the environmental factors that significantly predicted lower rates of PON1 activity towards paraoxon are, interestingly, the exposure to organophosphates and current smoking. By contrast, the utilization of protective clothing while spraying pesticides inside the greenhouses was positively associated with PON1 activity, very likely by preventing the pesticides from being absorbed. This study suggests that chronic exposure to pesticides might decrease PON1 activity and pinpoints the potential usefulness of monitoring PON1 activity in occupational settings where exposure to organophosphates occurs.
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http://dx.doi.org/10.1191/0960327103ht400oaDOI Listing
November 2003
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