Joan Estelrich

University of Barcelona, Barcino, Catalonia, Spain

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Publications (83)232.5 Total impact

  • Colloids and Surfaces A Physicochemical and Engineering Aspects 05/2014; 450:121–129. · 2.11 Impact Factor
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    ABSTRACT: Nanotechnology is an exciting and promising scientific discipline. At the nanoscale, a material displays novel physical properties that offer many new and beneficial products and applications. In particular, magnetic nanoparticles - a core/shell nanoparticle - present considerable diagnostic and therapeutic potentials, and superparamagnetic iron oxide nanoparticles (SPIONs) are considered promising theranostic tools. Alzheimer's disease (AD) is a neurodegenerative disorder that predominantly affects people over 65 years of age. The disease is characterized by the presence of extracellular plaques in the brain which are formed by interwoven fibrils composed of variants of the β-amyloid peptide. Medication can temporarily retard worsening of symptoms, but only in the first stages of the disease; early detection is thus of crucial importance. This minireview covers the progress made in research on the use of magnetic nanoparticles for ex vivo and/or in vivo detection and diagnosis of AD by means of magnetic resonance imaging (MRI), or to label peptides and fibrils. Of particular importance is the use of these nanoparticles to detect AD biomarkers in biological fluids. A description is given of the bio-barcode amplification assay using functionalized magnetic particles, as well as the use of such nanoparticles as a system for inhibiting or delaying the assembly of peptide monomers into oligomers and fibrils. Lastly, a brief overview is given of possible future lines of research in this.
    Nanoscale Research Letters 01/2014; 9(1):538. · 2.52 Impact Factor
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    ABSTRACT: We have studied the effect of head group and alkyl chain length on β-phase formation in poly(9,9-dioctylfluorene) (PFO) solubilized in phospholilpid liposomes. Systems studied have three different alkyl chain lengths (1,2-dimyristoyl-sn-glycero-3-phosphatidylcholine (DMPC), 1,2-didodecanoyl-sn-glycero-3-phosphatidylcholine (DLPC), 1,2-dipalmitoyl-sn-glycero-3- phosphatidylcholine (DPPC)) and head groups (1,2-dimyristoyl-sn-glycero-3-phosphate monosodium salt (DMPA), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (DMPE) and 1,2-dimyristoyl-sn-glycero-3-phospho-L-serine sodium salt (DMPS)). Changes in liposome size upon addition of PFO are followed by dynamic light scattering. All the phospolipids induce the formation of PFO β-phase, which is followed by the emission intensity and deconvolution of the absorption spectra. Both the head group and alkyl chain length affect the yield of β-phase. The photophysics of PFO incorporated in liposomes is characterized by stationary and time-resolved fluorescence, while the polymer-phospholipid interactions have been studied by the effect of the PFO concentration on the phospholipid phase transitions (differential scanning calorimetry). This article is protected by copyright. All rights reserved.
    Photochemistry and Photobiology 07/2013; · 2.29 Impact Factor
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    ABSTRACT: This study looked at the effect of an external magnet on the biodistribution of magnetoliposomes intravenously administrated in mice (8 mg iron/kg) with and without induced acute inflammation. Our results showed that due to enhanced vascular permeability, magnetoliposomes accumulated at the site of inflammation in the absence of an external magnetic field, but the amount of iron present increased under the effect of a magnet located at the inflammation zone. This increase was dependent on the time (20 or 60 min) of exposure of the external magnetic field. It was also observed that the presence of the magnet was associated with lower amounts of iron in the liver, spleen, and plasma than was found in mice in which a magnet had not been applied. The results of this study confirm that it is possible to target drugs encapsulated in magnetic particles by means of an external magnet.
    Nanoscale Research Letters 08/2012; 7(1):452. · 2.52 Impact Factor
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    ABSTRACT: The effect of adding charged nonadsorbing polymers to electrostatically structured suspensions of charged liposomes has been experimentally studied by means of light scattering techniques. The static structure factor of the mixtures is analyzed using two polymers of different sizes. As the polymer concentration increases, the main peak of the structure factor decreases and shows an important shift to larger values of the scattering vector. Such displacement is the consequence of the electrostatic-enhanced depletion attraction induced by the polymers that counteracts the electrostatic repulsion. For the shorter polymer, the system remains stable for all studied polymer concentrations. However, for the long polymer chains, the effective attraction induced at the highest polymer density studied is strong enough to destabilize the mixture. In this case, the aggregation of the liposomes leads to clusters of nearly linear morphology. The PRISM theory is employed to calculate the effective pair potential between liposomes. The theoretical predictions are able to support the experimental observations, and provide an explanation of the interplay between the electrostatic repulsive interaction and the depletion attraction. In particular, they show that the depletion attraction is especially long ranged, and is dominated by electrostatic effects rather than entropic.
    Physical review. E, Statistical physics, plasmas, fluids, and related interdisciplinary topics 05/2012; 85(5).
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    ABSTRACT: The neurotoxicity effect of the β-amyloid (Aβ) peptide, the primary constituent of senile plaques in Alzheimer's disease, occurs through interactions with neuronal membranes. Here, we attempt to clarify the mechanisms and consequences of the interaction of Aβ with lipid membranes. We have used liposomes as a model of biological membrane, and have devoted particular attention to the bilayer charge effect. Our results show that insertion and surface association of peptide with membrane, increased in a membrane charge-dependent manner, lead to a reduction of Aβ soluble species, lag time elongation and an increase in the inter-molecular β-sheet ratio of amyloid fibrils. In addition, our findings suggest that the fine balance between peptide insertion and surface association modulates Aβ aggregation, influencing the amyloid fibrils concentration as well as their morphology.
    Biochimie 04/2012; 94(8):1730-8. · 3.14 Impact Factor
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    ABSTRACT: Bicellar systems are lipid nanostructures formed by long-and short-chained phospholipids dispersed in aqueous solution. Because of their attractive combination of lipid composition, small size and morphological versatility, bicelles became new targets for skin research. Bicelles modify the skin biophysical parameters and modulate the skin barrier function acting as enhancers for drug penetration. Moreover, these aggregates have the ability to penetrate through the narrow intercellular spaces of the skin stratum corneum and to reinforce its lipid lamellae. Their structures allows for the incorporation of different molecules that can be carried through the skin layers. The remarkable versatility of bicelles is their most important characteristic, which makes it possible their use in different fields. These aggregates represent new nanosystems for skin applications. In this work we provide an overview of the main properties of bicelles and their effects on the skin. Correspondence/Reprint request: Dr.
    01/2012: pages 135-149; , ISBN: 978-81-7895-569-8
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    ABSTRACT: The contribution of fibrinogen (FBN) to hemostasis acting on platelet aggregation and clot formation is well established. It has been suggested that FBN-coated liposomes could be useful in restoring hemostasis. In the present study, we evaluated the modifications induced by multilamellar raw liposomes (MLV) or fibrinogen-coated liposomes (MLV-FBN) on hemostatic parameters. Different experimental settings using whole blood or thrombocytopenic blood were used. Thromboelastometry, aggregation studies, platelet function analyzer (PFA-100(®)) tests and studies under flow conditions were applied to detect the effect of MLV-FBN on hemostatic parameters. The presence of MLV-FBN in whole blood modified its viscoelastic properties, prolonging clot formation time (CFT) (226.5 ± 26.1 mm versus 124.1 ± 9.4 mm; P < 0.01) but reducing clot firmness (45.4 ± 1.8 mm versus 35.5 ± 2.3 mm; P < 0.05). Under thrombocytopenic conditions, FIBTEM analysis revealed that MLV-FBN shortened clotting time (CT) compared to MLV (153.3 ± 2.8 s versus 128.0 ± 4.6 s; P < 0.05). Addition of either liposome decreased fibrin formation on the subendothelium (MLV 8.1% ± 4.7% and MLV-FBN 0.8% ± 0.5% versus control 36.4% ± 6.7%; P < 0.01), whereas only MLV-FBN significantly reduced fibrin deposition in thrombocytopenic blood (14.4% ± 6.3% versus control 34.5% ± 5.2%; P < 0.05). MLV-FBN inhibited aggregation induced by arachidonic acid (52.1% ± 8.1% versus 88.0% ± 2.1% in control; P < 0.01) and ristocetin (40.3% ± 8.8% versus 94.3% ± 1.1%; P < 0.005), but it did not modify closure times in PFA-100(®) studies. In perfusion experiments using whole blood, MLV and MLV-FBN decreased the covered surface (13.25% ± 2.4% and 9.85% ± 2.41%, respectively, versus control 22.0% ± 2.0%; P < 0.01) and the percentage of large aggregates (8.4% ± 2.3% and 3.3% ± 1.01%, respectively, versus control 14.6% ± 1.8%; P < 0.01). Our results reveal that, in addition to the main contribution of fibrinogen to hemostasis, MLV-FBN inhibits platelet-mediated hemostasis and coagulation mechanisms.
    International Journal of Nanomedicine 01/2012; 7:2339-47. · 4.20 Impact Factor
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    ABSTRACT: Paul Ehrlich's dream of a 'magic bullet' that would specifically destroy invading microbes is now a major aspect of clinical medicine. However, a century later, the implementation of this medical holy grail continues being a challenge in three main fronts: identifying the right molecular or cellular targets for a particular disease, having a drug that is effective against it, and finding a strategy for the efficient delivery of sufficient amounts of the drug in an active state exclusively to the selected targets. In a previous work, we engineered an immunoliposomal nanovector for the targeted delivery of its contents exclusively to Plasmodium falciparum-infected red blood cells [pRBCs]. In preliminary assays, the antimalarial drug chloroquine showed improved efficacy when delivered inside immunoliposomes targeted with the pRBC-specific monoclonal antibody BM1234. Because difficulties in determining the exact concentration of the drug due to its low amounts prevented an accurate estimation of the nanovector performance, here, we have developed an HPLC-based method for the precise determination of the concentrations in the liposomal preparations of chloroquine and of a second antimalarial drug, fosmidomycin. The results obtained indicate that immunoliposome encapsulation of chloroquine and fosmidomycin improves by tenfold the efficacy of antimalarial drugs. The targeting antibody used binds preferentially to pRBCs containing late maturation stages of the parasite. In accordance with this observation, the best performing immunoliposomes are those added to Plasmodium cultures having a larger number of late form-containing pRBCs. An average of five antibody molecules per liposome significantly improves in cell cultures the performance of immunoliposomes over non-functionalized liposomes as drug delivery vessels. Increasing the number of antibodies on the liposome surface correspondingly increases performance, with a reduction of 50% parasitemia achieved with immunoliposomes encapsulating 4 nM chloroquine and bearing an estimated 250 BM1234 units. The nanovector prototype described here can be a valuable platform amenable to modification and improvement with the objective of designing a nanostructure adequate to enter the preclinical pipeline as a new antimalarial therapy.
    Nanoscale Research Letters 12/2011; 6:620. · 2.52 Impact Factor
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    ABSTRACT: Bicelles emerge as promising membrane models, and because of their attractive combination of lipid composition, small size and morphological versatility, they become new targets in skin research. Bicelles are able to modify skin biophysical parameters and modulate the skin's barrier function, acting to enhance drug penetration. Because of their nanostructured assemblies, bicelles have the ability to penetrate through the narrow intercellular spaces of the stratum corneum of the skin to reinforce its lipid lamellae. The bicelle structure also allows for the incorporation of different molecules that can be carried through the skin layers. All of these characteristics can be modulated by varying the lipid composition and experimental conditions. The remarkable versatility of bicelles is their most important characteristic, which makes their use possible in various fields. This system represents a platform for dermal applications. In this review, an overview of the main properties of bicelles and their effects on the skin are presented.
    Small 11/2011; 8(6):807-18. · 7.82 Impact Factor
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    ABSTRACT: The use of nanotechnology in biotechnological applications has attracted tremendous attention from researchers. Currently many nanomaterials, such as soft nanoparticles, are under investigation and development for their use in biomedicine. Among soft nanoparticles, polymeric gels in the nanometre range, known as nanogel particles, have received considerable attention. Nanogel particles, which are formed by polymeric chains loosely cross-linked to form a three-dimensional network, swell by a thermodynamically good solvent but do not dissolve in it. Nanogels are composed of hydrophilic polymers capable of undergoing reversible volume-phase transitions in response to environmental stimuli. Among them, temperature-sensitive nanogels showing a volume phase transition temperature (VPTT) near physiological temperature have been investigated in detail. Nanogels based on biocompatible and temperature-sensitive polymers having a lower critical solution temperature (LCST) around 32 °C in aqueous solutions swell at low temperatures and collapse at high ones. This unique behavior makes these nanogels attractive for pharmaceutical, therapeutical, and biomedical applications. In this review, different synthesis strategies to produce this type of nanogels in dispersed media are revised. Special attention is paid to poly(N-vinylcaprolactam) (PVCL)-based nanogels due to their proven biocompatibility. On the other hand, an extensive review on the characteristics, preparation, and physicochemical properties of another type of soft nanoparticles, which are the bicelles, is presented. The different morphologies obtained depending on experimental conditions such as temperature, lipid concentration, and long- and short-chain phospholipids molar ratio are revised, emphasizing on an important property of bicelles: their alignment in the presence of a magnetic field, and presenting the most important applications of bicelles as membrane models in diverse conformational studies of proteins and membrane peptides, together with the possibilities of administration of such vesicles by systemic routes. A key challenge for the characterization of both soft nanoparticles (nanogels and bicelles) involves the elucidation of their colloidal properties. In this work, some colloidal features of these nanoparticles such as their size, electric double layer or the internal structure and motions of their chains are analyzed. In addition, an overview on the previous and current understanding of the methods and techniques employed in this colloidal characterization is presented, mainly from an experimental point of view. Finally, the most recent results on polyelectrolyte gels and bicelles obtained from computer simulations are also briefly commented. Concerning polyelectrolyte gels, this review is mainly focused on the most important feature of these systems, their large capacity of swelling, which has been explored by simulation in the last decade.
    Soft Matter 06/2011; 7(11):5067. · 4.15 Impact Factor
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    ABSTRACT: The well-structured β-phase emission of the neutral poly(9,9-dioctylfluorene) (PFO) is observed in 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) bilayers, either as polydisperse aqueous liposomes or as the lamellar phase in thin films, and has been characterized by absorption, fluorescence (steady-state and time-resolved), and fluorescence anisotropy spectroscopy. Inclusion of PFO in DMPC liposomes provides a way of obtaining the ordered structure of this neutral polymer in aqueous suspensions. Quantification of the increase of the PFO β-phase in DMPC liposomes with the increase in polymer concentration is followed by deconvolution of the absorption spectra. In solid films, the presence of the phospholipids enhances the β-phase formation. In addition, the effect of the PFO concentration on the phospholipid phase transitions has been studied by differential scanning calorimetry (in liposome) and polarized light thermal microscopy (in solid film), confirming PFO/DMPC interactions in both liposome and films. The liposome size and structure in the presence and absence of polymer were characterized by dynamic light scattering and transmission electron microscopy, which showed relatively modest changes in liposome shape but a decrease in size upon incorporation of PFO.
    The Journal of Physical Chemistry B 05/2011; 115(19):5794-800. · 3.61 Impact Factor
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    ABSTRACT: Anionic ferrofluid was encapsulated in 200nm-diameter liposomes. The process involved phase-reverse evaporation followed by sequential extrusion. Magnetoliposomes were characterized by transmission electron microscopy, Doppler laser electrophoresis, SQUID magnetometry, dynamic light scattering and iron content by atomic absorption spectrophotometry. The absence of hysteresis of the magnetic power of particles at room temperature is characteristic of a material with superparamagnetic properties. The encapsulation efficiency was determined for several iron/phospholipid ratios, and this parameter ranged from 0.016 to 0.024mg iron per mmole of phospholipids, depending on the initial magnetite concentration. In comparison with magnetoliposomes that were obtained solely by extrusion, this method afforded significantly better encapsulation (P=0.0002). Magnetic particles were intravenously administered to healthy or inflammation-induced mice. After 1h, the content of iron was determined in exudates, liver, spleen and plasma. Magnetoliposomes accumulated in the exudates collected from the inflammation site, which suggests that these particles could be loaded with the drugs needed to treat some inflammatory processes.
    International Journal of Pharmaceutics 02/2011; 405(1-2):181-7. · 3.99 Impact Factor
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    ABSTRACT: This study examines the inactivation of the enzyme glucose 6-phosphate dehydrogenase (G6PD) by methylglyoxal (MG) and the eventual protection exerted by endogenous amines. To determine the protective effect of amines, the rate constant of the reaction of MG with the amino group of N-α-acetyl-lysine, carnosine, spermine and spermidine was measured at pH 7.4, and the behavior of endogenous amines was analyzed on the basis of quantum chemical reactivity descriptors. A 63% reduction in the enzyme activity was found upon incubation of G6PD with MG at pH 7.4. The inactivation of G6PD was even larger when the pH was increased to 9.4, revealing a weak protective effect by the amines. The results suggest that some basic residues of G6PD exhibit an anomalous reactivity, which likely reflects a shift in the standard pK(a) value due to the local environment in the enzyme. Under the experimental conditions used in the assays, this hypothesis was corroborated by mass spectrometry analysis, which points out that modification of Lys182 in the binding site is responsible for the inactivation of G6PD by MG. These results emphasize the need to search for more effective antiglycating agents, which can compete with basic amino acid residues possessing enhanced reactivity in proteins.
    Bioorganic & medicinal chemistry 01/2011; 19(5):1613-22. · 2.82 Impact Factor
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    ABSTRACT: Current administration methods of antimalarial drugs deliver the free compound in the blood stream, where it can be unspecifically taken up by all cells, and not only by Plasmodium-infected red blood cells (pRBCs). Nanosized carriers have been receiving special attention with the aim of minimizing the side effects of malaria therapy by increasing drug bioavailability and selectivity. Liposome encapsulation has been assayed for the delivery of compounds against murine malaria, but there is a lack of cellular studies on the performance of targeted liposomes in specific cell recognition and on the efficacy of cargo delivery, and very little data on liposome-driven antimalarial drug targeting to human-infecting parasites. We have used fluorescence microscopy to assess in vitro the efficiency of liposomal nanocarriers for the targeted delivery of their contents to pRBCs. 200-nm liposomes loaded with quantum dots were covalently functionalized with oriented, specific half-antibodies against P. falciparum late form-infected pRBCs. In less than 90min, liposomes dock to pRBC plasma membranes and release their cargo to the cell. 100.0% of late form-containing pRBCs and 0.0% of non-infected RBCs in P. falciparum cultures are recognized and permeated by the content of targeted immunoliposomes. Liposomes not functionalized with antibodies are also specifically directed to pRBCs, although with less affinity than immunoliposomes. In preliminary assays, the antimalarial drug chloroquine at a concentration of 2nM, ≥10 times below its IC(50) in solution, cleared 26.7±1.8% of pRBCs when delivered inside targeted immunoliposomes.
    Journal of Controlled Release 01/2011; 151(2):202-11. · 7.63 Impact Factor
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    ABSTRACT: Differential Scanning Calorimetry (DSC) was used to study the effect of the incorporation of a series of semifluorinated diblocks F(n)H(m) (F(6)H(10), F(6)H(16), F(8)H(14), F(8)H(16), F(8)H(18) and F(8)H(20)) on the gel and liquid states of the bilayer of large multilamellar DMPC and DPPC liposomes. The presence of the F(n)H(m) diblocks affects slightly the T(m) of the main gel-liquid transitions of DMPC and DPPC, but is accompanied by the appearance of a second transition in the calorimetric traces whose T(m) is mainly determined by the length of the F(n) segment. The DSC results are consistent with the previously established conclusion that the F(n) segments of the diblocks form a central layer in the core of the lipid bilayer, with the H(m) segments being interdigitated with the lipid chains. The DSC traces suggest that the structure of the fluorinated liposomes is a double bilayer at 3:4 and 1:2 and a trilayer at 2:1 lipid/F(n)H(m) molar ratios. At temperatures between the two phase transitions T(m)'s, the fluorinated liposomes are neither in a gel-like or a liquid-like state but rather possess both characteristics.
    Journal of Colloid and Interface Science 08/2010; 348(2):388-392. · 3.55 Impact Factor
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    ABSTRACT: We study the relaxation of both spontaneous and shear-induced fluctuations in suspensions of charged-stabilized colloidal particles near the glass transition by dynamic light scattering and rheology. Both observations are here understood in terms of a common structural relaxation process under a hard-sphere mode-coupling formalism. For ergodic systems, we show that the descriptions of the relaxation dynamics in time and frequency domains are governed by a common set of dynamic parameters. It is further shown that the microscopic ergodicity break-up induces the emergence of the macroscopic glass elasticity.
    Physical Review E 08/2010; 82(2 Pt 1):021406. · 2.31 Impact Factor
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    ABSTRACT: Bicelles are discoidal phospholipid nanostructures at high lipid concentrations. Under dilute conditions, bicelles become larger and adopt a variety of morphologies. This work proposes a strategy to preserve the discoidal morphology of bicelles in environments with high water content. Bicelles were formed in concentrated conditions and subsequently encapsulated in liposomes. Later dilution of these new structures, called bicosomes, demonstrated that lipid vesicles were able to isolate and protect bicelles entrapped inside them from the medium. Characterization of systems before and after dilution by dynamic light-scattering spectroscopy and cryo-transmission electron microscopy showed that free bicelles changed in size and morphology, whereas encapsulated bicelles remained unaltered by the effect of dilution. Free and entrapped bicelles (containing the paramagnetic contrast agent gadodiamide) were injected into rat brain lateral ventricles. Coronal and sagittal visualization was performed by magnetic resonance imaging. Whereas rats injected with free bicelles did not survive the surgery, those injected with bicosomes did, and a hyperintensity effect due to gadodiamide was observed in the cerebrospinal fluid. These results indicate that bicosomes are a good means of preserving the morphology of bicelles under dilution conditions.
    Biophysical Journal 07/2010; 99(2):480-8. · 3.67 Impact Factor
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    ABSTRACT: The effect of bicelles formed by dipalmitoylphosphatidylcholine (DPPC)/dihexanoylphosphatidylcholine (DHPC) on stratum corneum (SC) lipids was studied by attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopy at different temperatures. Analysis of the lipid organization in terms of chain conformational order and lateral packing shows that the use of bicelles hampers the fluidification of SC lipids with temperature and leads to a lateral packing corresponding to a stable hexagonal phase. Grazing incidence small- and wide-angle X-ray scattering (GISAXS and GIWAXS) techniques confirm these results and give evidence of higher lamellar order after treatment with these bicelles. Additionally, the effects of DPPC/DHPC and dimyristoylphosphatidylcholine (DMPC)/DHPC bicelles at different SC depths were compared. The combination of ATR-FTIR spectroscopy and the tape-stripping method was very useful for this purpose.
    Langmuir 04/2010; 26(13):10578-84. · 4.38 Impact Factor
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    ABSTRACT: a b s t r a c t This study examines the inactivation of the enzyme glucose 6-phosphate dehydrogenase (G6PD) by methylglyoxal (MG) and the eventual protection exerted by endogenous amines. To determine the pro-tective effect of amines, the rate constant of the reaction of MG with the amino group of N-a-acetyl-lysine, carnosine, spermine and spermidine was measured at pH 7.4, and the behavior of endogenous amines was analyzed on the basis of quantum chemical reactivity descriptors. A 63% reduction in the enzyme activity was found upon incubation of G6PD with MG at pH 7.4. The inactivation of G6PD was even larger when the pH was increased to 9.4, revealing a weak protective effect by the amines. The results suggest that some basic residues of G6PD exhibit an anomalous reactivity, which likely reflects a shift in the standard pK a value due to the local environment in the enzyme. Under the experimental conditions used in the assays, this hypothesis was corroborated by mass spectrometry analysis, which points out that modification of Lys182 in the binding site is responsible for the inactivation of G6PD by MG. These results emphasize the need to search for more effective antiglycating agents, which can compete with basic amino acid residues possessing enhanced reactivity in proteins.

Publication Stats

615 Citations
232.50 Total Impact Points

Institutions

  • 1996–2014
    • University of Barcelona
      • Department of Physicochemistry
      Barcino, Catalonia, Spain
  • 2011–2013
    • Universidad de Burgos
      • Department of Chemistry
      Burgos, Castile and Leon, Spain
  • 2012
    • Autonomous University of Barcelona
      Cerdanyola del Vallès, Catalonia, Spain
  • 2000–2011
    • Spanish National Research Council
      • Department of Chemical and Surfactants Technology
      Madrid, Madrid, Spain
  • 2007–2010
    • University of Granada
      • Departamento de Física Aplicada
      Granada, Andalusia, Spain
  • 2008
    • French National Centre for Scientific Research
      Lutetia Parisorum, Île-de-France, France