Teruel Puche, José Antonio

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Teruel Puche, José Antonio

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Teruel Puche, José Antonio

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Universidad de Murcia. Departamento de Bioquímica y Biología MolecularA

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Kinetic characterization of the oxidation of catecolamines and related compounds by laccase
(Elsevier, 2020-07-25) Taboada Rodriguez, Amaury; Manzano Nicolás, Jesús; Teruel Puche, José Antonio; Marín Iniesta, Fulgencio; García Cánovas, Francisco; García Molina, Francisco; Tudela Serrano, José; Muñoz Muñoz, José Luis; Bioquímica y Biología Molecular A
The pathways of melanization and sclerotization of the cuticle in insects are carried out by the action of laccases on dopamine and related compounds. In this work, the laccase action of Trametes versicolor (TvL) on catecholamines and related compounds has been kinetically characterized. Among them, dopamine, l-dopa, l-epinephrine, l-norepinephrine, dl-isoprenaline, l-isoprenaline, dl-α-methyldopa, l-α-methyldopa and l-dopa methylester. A chronometric method has been used, which is based on measuring the lag period necessary to consume a small amount of ascorbic acid, added to the reaction medium. The use of TvL has allowed docking studies of these molecules to be carried out at the active site of this enzyme. The hydrogen bridge interaction between the hydroxyl oxygen at C-4 with His-458, and with the acid group of Asp-206, would make it possible to transfer the electron to the T1 Cu-(II) copper centre of the enzyme. Furthermore, Phe-265 would facilitate the adaptation of the substrate to the enzyme through Π-Π interactions. To kinetically characterize these compounds, we need to take into consideration that, excluding l-dopa, l-α-methyldopa and dl-α-methyldopa, all compounds are in hydrochloride form. Because of this, first we need to kinetically characterize the inhibition by chloride and, after that, calculate the kinetic parameters KM and VmaxS. From the kinetic data obtained, it appears that the best substrate is dopamine. The presence of an isopropyl group bound to nitrogen (isoprenaline) makes it especially difficult to catalyse. The formation of the ester (l-dopa methyl ester) practically does not affect catalysis. The addition of a methyl group (α-methyl dopa) increases the rate but decreases the affinity for catalysis. l-Epinephrine and l-norepinephrine have an affinity similar to isoprenaline, but faster catalysis, probably due to the greater nucleophilic power of their phenolic hydroxyl.
Open Access
Influencia de la fluidez de la membrana sobre la ATPasa dependiente de Ca2+ del retículo sarcoplásmico de músculo esquelético
(Murcia: Universidad de Murcia, Servicio de Publicaciones, 1985) García Delicado, Esmerilda; García Cánovas, Francisco; Gómez Fernández, Juan Carmelo; Teruel Puche, José Antonio; García Carmona, Francisco; Facultad de Veterinaria
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A comparison of the location in membranes of curcumin and curcumin-derived bivalent compounds with potential neuroprotective capacity for Alzheimer’s disease
(Elsevier, 2021-03) Ausili, Alessio; Gómez Murcia, Victoria; Candel, Adela M.; Beltrán, Andrea; Torrecillas, Alejandro; He, Liu; Jiang, Yuqi; Zhang, Shijun; Teruel Puche, José Antonio; Gómez Fernández, Juan C.; Bioquímica y Biología Molecular A
Curcumin and two bivalent compounds, namely 17MD and 21MO, both obtained by conjugation of curcumin with a steroid molecule that acts as a membrane anchor, were comparatively studied. When incorporated into 1,2-dipalmitoyl-sn-glycero-3-phosphocholine the compounds showed a very limited solubility in the model membranes. Curcumin and the two bivalent compounds were also incorporated in membranes of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine and quenching the fluorescence of pure curcumin or of the curcumin moiety in the bivalent compounds by acrylamide it was seen that curcumin was accessible to this water soluble quencher but the molecule was somehow located in a hydrophobic environment. This was confirmed by quenching with doxyl-phosphatidylcholines, indicating that the curcumin moieties of 17MD and 21MO were in a more polar environment than pure curcumin itself. 1H NOESY MAS-NMR analysis supports this notion by showing that the orientation of curcumin was parallel to the plane of the membrane surface close to C2 and C3 of the fatty acyl chains, while the curcumin moiety of 17MD and 21MO positioned close to the polar part of the membrane with the steroid moiety in the centre of the membrane. Molecular dynamics studies were in close agreement with the experimental results with respect to the likely proximity of the protons studied by NMR and show that 17MD and 21MO have a clear tendency to aggregate in a fluid membrane. The anchorage of the bivalent compounds to the membrane leaving the curcumin moiety near the polar part may be very important to facilitate the bioactivity of the curcumin moiety when used as anti-Alzheimer drugs.
Open Access
Considerations about the inhibition of monophenolase and diphenolase activities of tyrosinase. Characterization of the inhibitor concentration which generates 50 % of inhibition, type and inhibition constants. A review
(Elsevier, 2024-04-10) García Molina, Pablo; Saura Sanmartín, Adrián; Berná Cánovas, José; Muñoz Muñoz, Jose Luis; García Cánovas, Francisco; García Molina, Francisco; Rodríguez López, José Neptuno; Teruel Puche, José Antonio; Saura Sanmartín, Adrián; García Molina, Francisco; Química Orgánica
Tyrosinase is a copper oxidase enzyme which catalyzes the first two steps in the melanogenesis pathway, L tyrosine to L-dopa conversion and, then, to o-dopaquinone and dopachrome. Hypopigmentation and, above all, hyperpigmentation issues can be originated depending on their activity. This enzyme also promotes the browning of fruits and vegetables. Therefore, control of their activity by regulators is research topic of great relevance. In this work, we consider the use of inhibitors of monophenolase and diphenolase activities of the enzyme in order to accomplish such control. An experimental design and data analysis which allow the accurate calculation of the degree of inhibition of monophenolase activity (iM) and diphenolase activity (iD) are proposed. The IC50 values (amount of inhibitor that causes 50 % inhibition at a fixed substrate concentration) can be calculated for the two activities and from the values of ICM 50 (monophenolase) and ICD 50(diphenolase). Addi tionally, the strength and type of inhibition can be deduced from these values. The data analysis from these ICD 50 values allows to obtain the values of Kapp I1 or Kapp I2 , or Kapp I1 and Kapp I3 from the values of ICM 50. In all cases, the values of the different Kapp I must satisfy their relationship with ICM 50 and ICD 50.
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Membrane vesicles for nanoencapsulated sulforaphane increased their anti-inflammatory role on an In vitro human macrophage model.
(MDPI, 2022-02-09) Yepes-Molina, Lucía; Pérez-Jiménez, María Isabel; Martínez-Esparza Alvargonzález, María Concepción; Teruel Puche, José Antonio; Ruiz Alcaraz, Antonio José; García Peñarrubia, María del Pilar; Carvajal, Micaela; Bioquímica y Biología Molecular B e Inmunología
At present, there is a growing interest in finding new non‐toxic anti‐inflammatory drugs to treat inflammation, which is a key pathology in the development of several diseases with considerable mortality. Sulforaphane (SFN), a bioactive compound derived from Brassica plants, was shown to be promising due to its anti‐inflammatory properties and great potential, though its actual clinical use is limited due to its poor stability and bioavailability. In this sense, the use of nanocarriers could solve stability‐related problems. In the current study, sulforaphane loaded into membrane vesicles derived from broccoli plants was studied to determine the anti‐inflammatory potential in a human‐macrophage‐like in vitro cell model under both normal and inflammatory conditions. On the one hand, the release of SFN from membrane vesicles was modeled in vitro, and two release phases were stabilized, one faster and the other slower due to the interaction between SFN and membrane proteins, such as aquaporins. Furthermore, the anti‐inflammatory action of sulforaphane‐loaded membrane vesicles was demonstrated, as a decrease in interleukins crucial for the development of nflammation, such as TNF‐α, IL‐1β and IL‐6, was observed. Furthermore, these results also showed that membrane vesicles by themselves had anti‐inflammatory properties, opening the possibility of new lines of research to study these vesicles, not only as carriers but also as active compounds.
Open Access
Anticarcinogenic trimethoxybenzoate of catechin stabilizes the liquid crystalline bilayer phase in phosphatidylethanolamine membranes
(Elsevier, 2022-11-11) Aranda, Elisa; Teruel Puche, José Antonio; Ortiz López, Antonio; Pérez Cárceles, María Dolores; Rodríguez López, José Neptuno; Aranda Martínez, Francisco José; Bioquímica y Biología Molecular A
The anticarcinogenic properties of catechins stand out among the great variety of biological actions attributed to these compounds. The capacity of catechins to interact with lipids and their participation in membrane related processes points out to the membrane as their potential site of action. Phosphatidylethanolamine is an abundant phospholipid in mammalian membranes that has tendency to form non lamellar phases, it is associated with important cellular processes, and it has been related to cancer. In order to shed light into the molecular effect of the anticarcinogenic 3,4,5- trimethoxybenzoate of catechin (TMBC) on lipid polymorphism and membrane structure and dynamics, we present a combined experimental and computational study of the interaction between this semisyn thetic catechin and biomimetic membranes composed of unsaturated phosphatidylethanolamine. Our experimental evidence reveals that TMBC is readily incorporated into unsaturated phos phatidylethanolamine system where it is able to shift the gel to liquid crystalline phase transition tem perature to lower values, decreasing the cooperativity and the enthalpy change of the transition. The presence of TMBC is able to promote the formation of gel phase immiscibility and to block the formation of the inverted hexagonal pha se. In the bilayer liquid crystalline phase, the catechin decreases the inter lamellar repeat distance, it increases the fluidity of the membrane, and it alters the hydrogen bond pat tern of the interfacial region of the bilayer. Our molecular dynamics results concur with the experimental data and locate TMBC forming different domains near the interfacial region of the bilayer where it mod ifies the lateral pressure profile of the membrane leading to a stabilization of the bilayer in the liquid crystalline phase and to a potential alteration of the function of the membrane
Open Access
Molecular docking studies of ortho-substituted phenols to tyrosinase helps discern if a molecule can be an enzyme substrate
(MDPI, 2024-06-23) García-Molina, Pablo; García-Cánovas, Francisco; García-Molina, Francisco; Montenegro Arce, María Fernanda; Rodríguez López, José Neptuno; Teruel Puche, José Antonio; Tudela Serrano, José; Bioquímica y Biología Molecular A
Phenolic compounds with a position ortho to the free phenolic hydroxyl group occupied can be tyrosinase substrates. However, ortho-substituted compounds are usually described as inhibitors. The mechanism of action of tyrosinase on monophenols is complex, and if they are ortho-substituted, it is more complicated. It can be shown that many of these molecules can become substrates of the enzyme in the presence of catalytic o-diphenol, MBTH, or in the presence of hydrogen peroxide. Docking studies can help discern whether a molecule can behave as a substrate or inhibitor of the enzyme. Specifically, phenols such as thymol, carvacrol, guaiacol, eugenol, isoeugenol, and ferulic acid are substrates of tyrosinase, and docking simulations to the active center of the enzyme predict this since the distance of the peroxide oxygen from the oxy-tyrosinase form to the ortho position of the phenolic hydroxyl is adequate for the electrophilic attack reaction that gives rise to hydroxylation occurring.
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Estudios estructurales y cinéticos de la ATPasa de retículo sarcoplásmico / Jose Antonio Teruel Puche ; Dirección Juan Carmelo Gómez Fernández.
(Murcia : Universidad, Facultad de Ciencias Químicas y Matemáticas,, 1986) Teruel Puche, José Antonio
Open Access
3,4,5-Trimethoxybenzoate of Catechin, an Anticarcinogenic Semisynthetic Catechin, Modulates the Physical Properties of Anionic Phospholipid Membranes
(MDPI, 2022-05-03) Aranda, Elisa; Aranda Martínez, Francisco José; Ortiz López, Antonio; Rodríguez López, José Neptuno; Teruel Puche, José Antonio; Pérez Cárceles, María Dolores; Bioquímica y Biología Molecular A
3,4,5-Trimethoxybenzoate of catechin (TMBC) is a semisynthetic catechin which shows strong antiproliferative activity against malignant melanoma cells. The amphiphilic nature of the molecule suggests that the membrane could be a potential site of action, hence the study of its inter action with lipid bilayers is mandatory in order to gain information on the effect of the catechin on the membrane properties and dynamics. Anionic phospholipids, though being minor components of the membrane, possess singular physical and biochemical properties that make them physiologically essential. Utilizing phosphatidylserine biomimetic membranes, we study the interaction between the catechin and anionic bilayers, bringing together a variety of experimental techniques and molecular dynamics simulation. The experimental data suggest that the molecule is embedded into the phos phatidylserine bilayers, where it perturbs the thermotropic gel to liquid crystalline phase transition. In the gel phase, the catechin promotes the formation of interdigitation, and in the liquid crystalline phase, it decreases the bilayer thickness and increases the hydrogen bonding pattern of the interfacial region of the bilayer. The simulation data agree with the experimental ones and indicate that the molecule is located in the interior of the anionic bilayer as monomer and small clusters reaching the carbonyl region of the phospholipid, where it also disturbs the intermolecular hydrogen bonding between neighboring lipids. Our observations suggest that the catechin incorporates well into phos phatidylserine bilayers, where it produces structural changes that could affect the functioning of the membrane
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Effect of pH and temperature on the aggregation behaviour of dirhamnolipid biosurfactant. An experimental and molecular dynamics study
(Elsevier, 2021-04-05) Ortiz, Julia; Oliva, Alfonso; Teruel Puche, José Antonio; Aranda Martínez, Francisco José; Ortiz López, Antonio; Bioquímica y Biología Molecular A
Hypothesis: Pseudomonas aeruginosa dirhamnolipid (diRL) has been shown to form aggregates of different size and structure, under various conditions. Due to the presence of a carboxyl group in the molecule, it is expected that pH would strongly affect this aggregation behaviour. In addition, preliminary observations of temperature-induced changes in the states of aggregation of diRL supported the need of further investigation. Experiments: A systematic experimental study, using differential scanning calorimetry (DSC), small-angle Xray diffraction (SAXD), and Fourier-transform infrared pectroscopy (FTIR), has been carried out to charac terize pH and temperature driven changes in the aggregation behavior of diRL biosurfactant. Molecular dynamics (MD) simulations, supported by the experimental results, allowed depicting molecular details on formation of diRL membranes and other aggregated structures under various physicochemical conditions. Findings: DiRL could adopt fairly organizedmultilayered structures (membranes) at low pH and temperature, which became highly disordered upon increasing either of these parameters. The effect of pH on the gauche/ all-trans conformer ratio of the diRL acyl chains was not of significance, whereas temperature-induced effects were observed. For the first time it is described that diRL underwent an endothermic thermotropic transition with Tc = 34 C as observed by DSC, at pH 4.5 (protonated diRL), but not at pH 7.4 (unprotonated diRL). FTIR confirmed these findings, showing a significant additional disordering of the all-trans acyl chains upon increasing temperature around that same value in the protonated form, an effect not observed for the disso ciated form of the biosurfactant. In addition, at pH 7.4, changing temperature did not modify the hydration state of the polar moiety of diRL, whereas at pH 4.5 a significant decrease in the hydration state around 34 C took place. SAXD data showed that protonated diRL formed multilayered structures at 20 C, which con verted into poorly correlated layers at 50 C. MD simulations supported these findings, showing that the membrane-like structures formed by protonated diRL at 20 C became unstable at higher temperatures, tend ing to form other structures, which could be micelles or other type of layered structures, whereas the nega tively charged form of diRL organized in micelle-type aggregates in the whole range of temperature under study.