Matencio Durán, Adrián

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Matencio Durán, Adrián

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Bioquímica y Biología Molecular A

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Nanoparticles of betalamic acid derivatives with cyclodextrins. Physicochemistry, production characterization and stability
(Elsevier, 2020-07-14) Guerrero Rubio, Alejandra; Matencio Durán, Adrián; Gandía Herrero, Fernando; López Nicolás, José Manuel; García Carmona, Francisco; Bioquímica y Biología Molecular A
The use of betalains as bioactive compounds has been widely investigated. However, their use as a functional food requires a more exhaustive study because of their photosensitivity and poor stability. For this reason, this works studies the stabilization of two highly bioactive betalain derivatives, phenylethylamine-betaxanthin (Ph- Bx) and indoline-betacyanin (In-Bc) by nanoencapsulation in natural a modified cyclodextrins (CDs). Methyl- β-CD (Mβ-CD) showed the best results for Ph-Bx while Hydroxypropyl-β-CD (HPβ-CD) was better in the case of In- Bc. In addition, the effect of pH and temperature on encapsulation was studied finding that the encapsulation constant (KF) value increased as the pH decreased in the case of Ph-Bx but not in the case of In-Bc. The KF decreased as the temperatures increased. The thermodynamic parameters, ΔH◦, ΔS◦ and ΔG◦, were also calculated. Molecular docking provided further insight into how the different interactions influenced the encapsulation constant. The results show that the presence of CDs during the biotechnological synthesis of Ph-Bx and In- Bc increased production by 51 and 26%, respectively, and also increased the stability of both derivatives. This study represents a first step towards increasing the production of this type of compound for introduction into functional foods.
Open Access
Encapsulación molecular de diferentes compuestos bioactivos con ciclodextrinas: aplicaciones in vitro e in vivo
(Universidad de Murcia, 2020-01-20) Matencio Durán, Adrián; García Carmona, Francisco; López Nicolás, José Manuel; García Carmona, Francisco; Escuela Internacional de Doctorado
Introducción El desarrollo de nuevos productos está en auge. La sociedad cada día demanda nuevas cualidades y la industria intenta satisfacer esta demanda con el estudio y adicción de nuevas sustancias bioactivas. No obstante, muchas de estas sustancias necesitan ser añadidas con una molécula matriz que mejore sus propiedades. En este punto, unas moléculas conocidas como ciclodextrinas (CDs) adquirieron hace unos años un protagonismo que a día de hoy aun mantienen. Debido a su interior hidrofóbico y exterior hidrofílico, presentan la propiedad de incluir una amplia variedad de moléculas orgánicas e inorgánicas, comúnmente denominadas moléculas huésped (complejo de inclusión), aumentando así la solubilidad aparente de distintas moléculas hidrofóbicas y parcialmente hidrofóbicas; de esta propiedad, se derivan muchas otras propiedades secundarias. Por ello, es intención de esta tesis doctoral mostrar su potencial in vitro e in vivo en diversas aplicaciones. Objetivos 1. Demostrar el potencial de las ciclodextrinas en distintos campos, para ello se dividará el trabajo en 3 grandes bloques: a. Bloque 1: caracterización de diversos complejos de inclusión de inclusión con ciclodextrinas comerciales. b. Bloque 2: Estudiar distintas aplicaciones de las ciclodextrinas en química analítica, industria alimentaria y farmacológica. c. Bloque 3: Estudiar la síntesis, caracterización y aplicación del polímero denominado nanoesponja de ciclodextrinas. Metodología Para el bloque 1, distintas técnicas de cómo HPLC, fluorescencia, RMN, DSC o modelado molecular fueron usadas para caracerizar los complejos. Para el bloque 2, metodologías de digestión in vitro, extracción de compuestos o el uso de modelos de alimentos fueron puestos a punto y utilizados. Para el bloque 3, se sintetizaron los polímeros y se caracterizaron los complejos de inclusión mediante técnicas del apartado 1. Se utilizó en nematodo Caenorhabditis elegans para estudiar el efecto sobre la extensión de la vida media de compuestos bioactivos encapsulados. Conclusiones En el bloque 1, hemos visto el potencial para encapsular distintos compuestos bioactivos con ciclodextrinas. En el bloque 2, vimos como efectivamente las ciclodextrinas pudieron separar isómeros (química analítica), estabilizar compuestos alimentarios (industria alimentaria) o usarse en enfermedades raras (farmacología). En el bloque 3, pudimos ver como el polímero ofrece una liberación suave del compuesto bioactivo por su características poliméricas así como su efecto en la vida media de C.elegans. En definitiva, esta tesis en su conjunto representa un importante avance en el conocimiento relacionado con ciclodextrinas en distintos campos: nuevos métodos de separación de moléculas, de estabilización de alimentos y fármacos… Además, establece nuevas metodologías para trabajar con ellas en distintos campos como química analítica, ciencia alimentaria y farmacéutica.
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A physicochemical, thermodynamical, structural and computational evaluation of kynurenic acid/cyclodextrin complexes
(Elsevier, 2021-03-23) Matencio Durán, Adrián; Caldera, Fabrizio; Rubin Pedrazzo, Alberto; Monfared, Yousef Khazaei; Dhakar, Nilesh K.; Trotta, Francesco; Bioquímica y Biología Molecular A; Facultad de Biología
In this work, the interaction between Kynurenic acid (KYNA) and several natural and modified cyclodextrins (CDs) is carried out. Among all the CD tested, HPβ-CD showed the strongest complexation constant (KF), with a value of 270.94 ± 29.80 M−1. Between natural (α- and β-) CDs, the complex of KYNA with β-CD was the most efficient. The inclusion complex of KYNA with CDs showed a strong influence of pH and temperature. The KF value decreased at high pH values, when the pKa was passed. Moreover, an increase of the temperature caused a decrease in the KF values. The thermodynamic parameters of the complexation (ΔH°, ΔS° and ΔG°) were studied with negative entropy, enthalpy and spontaneity of the process at 25 °C. Moreover, the inclusion complex was also characterized using FTIR and TGA. Finally, molecular docking calculations provided different interactions and their influence in the complexation constant.
Open Access
A way to increase the bioaccesibility and photostability of roflumilast, a COPD treatment, by cyclodextrin monomers
(MDPI, 2019-05-04) Matencio Durán, Adrián; Hernández-García, Samanta; López Nicolás, José Manuel; García Carmona, Francisco; Bioquímica y Biología Molecular A; Facultad de Biología
Roflumilast is an orally available inhibitor of phosphodiesterase (PDE) type 4, which is widely used in chronic obstructive pulmonary diseases. However, it has low solubility and adverse effects include diarrhea and nausea. Since its solubilization may improve treatment and, dismissing any adverse effects, its interaction with cyclodextrins (CDs) was studied. The Higuchi-Connors method was used to determine the complexation constant with different CDs, pH values and temperatures. Molecular docking was used to predict interaction between the complexes. An in vitro digestion experiment was carried out to test roflumilast protection. Finally, the photostability of the complex was evaluated. The complex formed with β-CD had the highest K11 value (646 ± 34 M−1), although this value decreased with increasing temperature. Similarly, K11 decreased as the pH increased. In vitro digestion showed that CDs protect the drug during digestion and even improve its bioaccessibility. Finally, CDs reduced the drug’s extreme photosensitivity, originating a fluorescence signal, which is described for first time. The kinetic parameters of the reaction were obtained. This study not only completes the complexation study of roflumilast-CD, but also points to the need to protect roflumilast from light, suggesting that tablets containing the drug might be reformulated.
Open Access
Stilbenes: Characterization, bioactivity, encapsulation and structural modifications. A review of their current limitations and promising approaches
(Taylor and Francis Group, 2022-03-02) Navarro Orcajada, Silvia; Vidal Sánchez, Francisco José; Albadelejo Maricó, Lorena; Matencio Durán, Adrián; Conesa Valverde, Irene; López Nicolás, José Manuel; Vidal Sánchez, Francisco José; García Carmona, Francisco; Bioquímica y Biología Molecular A
Stilbenes are phenolic compounds naturally synthesized as secondary metabolites by the shikimate pathway in plants. Research on them has increased in recent years due to their therapeutic potential as antioxidant, antimicrobial, anti-inflammatory, anticancer, cardioprotective and anti-obesity agents. Amongst them, resveratrol has attracted the most attention, although there are other natural and synthesized stilbenes with enhanced properties. However, stilbenes have some physicochemical and pharmacokinetic problems that need to be overcome before considering their applications. Human clinical evidence of their bioactivity is still controversial due to this fact and hence, exhaustive basis science on stilbenes is needed before applied science. This review gathers the main physicochemical and biological properties of natural stilbenes, establishes structure-activity relationships among them, emphasizing the current problems that limit their applications and presenting some promising approaches to overcome these issues: the encapsulation in different agents and the structural modification to obtain novel stilbenes with better features. The bioactivity of stilbenes should move from promising to evident.
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Applications of cyclodextrins in food science. A Review
(Elsevier, 2020-08-25) Matencio Durán, Adrián; Navarro Orcajada, Silvia; López Nicolás, José Manuel; García Carmona, Francisco; Bioquímica y Biología Molecular A; Facultad de Biología
Background: The food industry is constantly attempting to develop better products that will have a positive effect on health (commonly known as functional foods). In this respect, cyclodextrins (CDs) could be of interest because they are tasteless, non-caloric and odourless molecules with several valuable characteristics, such as a capacity to separate chiral compounds and solubilize or stabilize bioactive compounds (BaC). Scope and approach: This review represents a revision of the state-of-the-art of CDs and their uses in the food industry. Key findings and conclusions: We analysed their metabolism and regulatory aspects of current applications of CDs: as carriers, for removing components, to produce or extract BaC, their use as nanosensors or in food packaging. We study how inclusion complexed are formed referring to the most common techniques and parameters Moreover, how inclusion complexes are formed will be studied with reference to the most common techniques and parameters. In conclusion, their applications in the food and other industries will increase in the coming years without a doubt.
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Study of oxyresveratrol complexes with insoluble cyclodextrin based nanosponges: Developing a novel way to obtain their complexation constants and application in an anticancer study
(Elsevier, 2019-12-17) Kumar Dhakarb, Nilesh; Bessonec, Federica; Musso, Giorgia; Cavallic, Roberta; Dianzanic, Chiara; Matencio Durán, Adrián; López Nicolás, José Manuel; García Carmona, Francisco; Bioquímica y Biología Molecular A
The complexation of the bioactive compound oxyresveratrol (OXY) with a polymer called cyclodextrin-based nanosponge (CD-NS) and its application was studied.A new methodology is used to calculate, an apparent inclusion complex constant (KFapp) between a ligand and CD-NSs. Moreover, the KFapp of resveratrol was also evaluated and compared. The complex of OXY with the nanosponge β-CDI 1:4, was studied in vitro using DSC, TGA and FTIR techniques and its drug loading and release behavior were studied. An in vitro digestion showed higher protection of OXY complexed than free OXY. The bioactivity enhancing capacity of OXY was also studied against prostate (PC-3) and colon (HT-29 and HCT-116) cancer cell lines, where it showed stronger cell viability inhibition than the free drug. The findings as a whole represent a new opportunity for studying the complexation of drugs in CD-NSs and the use of oxyresveratrol as an ingredient in nutraceutical products.
Open Access
Ellagic acid–borax fluorescence interaction: application for novel cyclodextrin-borax nanosensors for analyzing ellagic acid in food samples
(Royal Society of Chemistry, 2018-06-18) Matencio Durán, Adrián; Navarro Orcajada, Silvia; López Nicolás, José Manuel; García Carmona, Francisco; Bioquímica y Biología Molecular A; Facultad de Biología
The food industry needs cheap, fast and sensitive methods to increase the number of analyses that are routinely carried out; for this reason, new methods are constantly being sought. This paper describes a novel fluorescent nanosensor based on cyclodextrin (CD) to determine ellagic acid (EA). The encapsulation of EA in the presence of borax was studied. Firstly, the complexation of EA–borax was tested. The stoichiometry of the EA–borax complex showed a 1 : 2 complex, with KF1 = 2548 ± 127 M−1 and KF2 = 302 ± 15 M−1. Different CDs were used to obtain a 1 : 1 : 1 CD–EA–borax complex with γ-CD providing the best complexation constant (KF3 = 364 ± 18 M−1). Furthermore, when the accuracy and sensitivity of the nanosensor were tested using a crude blueberry extract, the CD/borax mixture provided an 18 times stronger signal than with the crude extract alone and 7 times stronger than that obtained using borax alone.
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Comparative study of the antioxidant capacity of four stilbenes using ORAC, ABTS+, and FRAP Techniques
(Springer, 2017-03-17) Rodríguez-Bonilla, Pilar; Matencio Durán, Adrián; Gandía Herrero, Fernando; López Nicolás, José Manuel; García Carmona, Francisco; Bioquímica y Biología Molecular "A"
Researchers use several different analytical techniques, such as ORAC, ABTS·+, or FRAP, for measuring the antioxidant capacity of bioactive compounds. However, many authors do not take into account that these three techniques have different objectives. This contribution reports on the use of two types of tests to evaluate the antioxidant activity of four stilbene tests based first on the hydrogen atom transfer reaction (ORAC method) and the second on the single electron transfer reaction (ABTS·+ and FRAP assays). For the ORAC assay, the greatest antioxidant activity was shown by resveratrol, followed by oxyresveratrol, pterostilbene, and pinosylvin, while in the ABTS.+ assay, the highest antioxidant capacity was presented by oxyresveratrol, followed by resveratrol, pinosylvin, and finally pterostilbene. In the FRAP assay, the reducing activity shown by all the stilbenes was below that obtained for trolox. The role of phenolic hydroxyl groups was studied. The technique used should be selected taking into account the objectives and the conditions of the medium.
Open Access
The inclusion complex of oxyresveratrol in modified cyclodextrins: a thermodynamic, structural, physicochemical, fluorescent and computational study
(Elsevier, 2017-04-06) Matencio Durán, Adrián; López Nicolás, José Manuel; García Carmona, Francisco; Bioquímica y Biología Molecular A; Facultad de Biología
The interaction between oxyresveratrol (a type of stilbene with high biological activity) and modified cyclodextrins (CDs) was studied. Using HPLC-RP, was seen to form a 1:1 complex with all the CDs tested. The best CD in this respect was MβCD (KF = 606.65 ± 30.18 M−1), the complexation showing a strong dependence on pH and temperature: The complexation constant (KF) decreased as the pH and temperature increased. The thermodynamic parameters studied (ΔH°, ΔS° and ΔG°) showed negative entropy, enthalpy and Gibbs free energy change at 25 °C. In addition, fluorescence signal of oxyresveratrol increased when MβCD was added. The oxyresveratrol emission and excitation spectra were obtained for first time. A 1H NMR was carried out to study the structure of the complex and, DSC studied demonstrated the complexation. A computational study by molecular docking was made to complement the structural study.