Karina Mondragón-Vásquez

Universidad Veracruzana

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Hugo Morales‐Rojas

Universidad Autónoma del Estado de Morelos

Dea Herrera‐Ruiz

Universidad Autónoma del Estado de Morelos

J.I. Arenas-Garcia

Universidad Autónoma del Estado de Morelos

H. Hopfl

University of Newcastle Australia

Herbert Höpfl

Universidad Autónoma del Estado de Morelos

Jorge Guillermo Domínguez-Chávez

Universidad Veracruzana

Guillermo Ordáz

Instituto Nacional de Ciencias Médicas y Nutrición Salvador Zubirán

Paulina Barrera-Gómez

Instituto Nacional de Ciencias Médicas y Nutrición Salvador Zubirán

Armando R. Tovar

Instituto Nacional de Ciencias Médicas y Nutrición Salvador Zubirán

Miranda Bernal-Gámez

Instituto Nacional de Ciencias Médicas y Nutrición Salvador Zubirán

Cooperative Institutions

Universidad Veracruzana

Instituto Politécnico Nacional

Universidad Autónoma del Estado de Morelos

Instituto Nacional de Ciencias Médicas y Nutrición Salvador Zubirán

Center for Research and Advanced Studies of the National Polytechnic Institute

Universidad Nacional Autónoma de México

Centro de Investigación en Materiales Avanzados

Instituto Nacional de Enfermedades Respiratorias

Secretaria de Salud

Mexican Institute of Petroleum

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Characterization, stability and solubility of co-amorphous systems of glibenclamide and L-arginine at different pH

Tropical Journal of Pharmaceutical Research (2022)

Salma O Aragón-Aburto Karina Mondragón-Vásquez Gerardo Valerio- Alfaro Jorge G Domínguez-Chávez

Purpose: To investigate the stability and solubility of co-amorphous systems of glibenclamide (GBC) with L-arginine (L-Arg) at different pH values. Methods: Three co-amorphous solids of GBC and L-Arg were obtained by fast solvent evaporation using 2:1, 1:1 and 1:2 stoichiometries. All co-amorphous systems were characterized by XRPD, FTIR, RAMAN and NMR-solid state as well as thermal techniques such as DSC and TGA. The stability of coamorphous systems was evaluated by indicative stability and stability in relevant physiological media was measured at different pH values. Results: The chemical characterization suggest that there was no proton transference between L-Arg and GBC indicative of co-amorphous solids. Stability studies showed that all the co-amorphous solids are unstable under humid conditions and only the co-amorphous system of GBC: L-Arg 1:2 was stable in all the pH values tested. Solubility studies at different pH values showed that the co-amorphous GBC: L-Arg 1:1 and 1:2, showed increasing solubility values even at pH < 7 (0.6468 mg/mL at pH 1.2 for coamorphous GBC: L-Arg 1:2 at the first hour) where free GBC was not soluble. Conclusion: Co-amorphous systems of GBC and L-Arg, is an interesting strategy to increase the solubility of poorly-soluble drugs at acidic pH values Keywords: Co-amorphous; Glibenclamide; L-Arginine; Solubility; Stability

Thermal Stability

Chemical Stability

10.4314/tjpr.v21i7.1

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CCDC 773418: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

J.I. Arenas-Garcia Dea Herrera‐Ruiz Karina Mondragón-Vásquez Hugo Morales‐Rojas H. Hopfl

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/cctyszh

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Chemical modification of sesame protein by acylation reactions: characterisation and evaluation of functional properties

International Journal of Food Science & Technology (2024)

M.A. Castillo‐Ortega Oscar García‐Barradas Ma. Remedios Mendoza-López Karina Mondragón-Vásquez Maribel Jiménez‐Fernández

Summary Proteins are commonly used ingredients to impart certain non‐nutritional properties to foods. Consequently, the industry is constantly seeking to enhance proteins that provide these attributes to food products. Therefore, the aim of this research was to extract the protein from sesame seeds and evaluate the effect of chemical modification through acylation with lauroyl chloride and acetic anhydride on functional properties (solubility index, emulsifying, foaming, swelling and water‐holding and oil‐holding capacity). Chemical modification was successfully demonstrated using FTIR spectroscopy and X‐rays. It was found that acylation with lauroyl chloride or acetic anhydride altered the physicochemical and functional properties, particularly at pH 10. Both reactions exhibited substitution degrees exceeding 20%. Chemical modification via acylation resulted in significant improvements in water and oil retention capacity, emulsifying activity and foaming activity. Thermal analysis revealed significant changes in the modified samples, altering their denaturation temperature, leading to the conclusion that chemical modifications through acylation with lauroyl chloride or acetic anhydride offer benefits in certain functional properties relevant to the food industry. They also represent an opportunity to diversify the application of a by‐product obtained from sesame oil extraction.

Chemical modification

Chemical structure

10.1111/ijfs.17244

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Citations (2)

Co-Crystals of Active Pharmaceutical Ingredients - Acetazolamide

Crystal Growth & Design (2010)

J.I. Arenas-Garcia Dea Herrera‐Ruiz Karina Mondragón-Vásquez Hugo Morales‐Rojas Herbert Höpfl

A total of 20 co-crystal formers have been combined with acetazolamide (ACZ) via solvent drop grinding in acetone, acetonitrile, and water. The screening experiments provided co-crystals with 4-hydroxybenzoic acid (4HBA) and nicotinamide (NA) (ACZ-4HBA and ACZ-NA-H2O), which were identified by X-ray powder diffraction (XRPD) and further characterized by IR spectroscopy and differential scanning calorimetry-thermogravimetric analysis (DSC-TGA). Both co-crystals could be prepared also by neat grinding (NG) and reaction crystallization (RC). Single-crystal X-ray diffraction analyses allowed for an examination of the dominant hydrogen bonding patterns in the co-crystals, showing that 4HBA binds to the thiadiazole acetamide fragment of ACZ via C(N)NH···HOOC and O−H···N interactions, while NA is linked through N−H···N and N−H···O contacts. In ACZ-NA-H2O, the components are connected further by crystal lattice water molecules through N−H···Ow and Ow−H···N hydrogen bonds. Phase stability assays in water at physiological pH values ranging from 1.2 to 6.8 showed that for ACZ-4HBA the crystalline solid phase did not transform to ACZ within 72 h, while for ACZ-NA-H2O a gradual transformation occurred. Thermal treatment of ACZ-NA-H2O and reaction crystallization experiments in methanol and anhydrous ethanol gave the dehydrated crystalline phase ACZ-NA, which is stable at ambient conditions for at least four months but transforms to the corresponding co-crystal monohydrate when stirred with deionized water.

Thermogravimetric analysis

Powder Diffraction

10.1021/cg1005693

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Citations (68)

Molecular recognition of cationic phenothiazinium and phenoxazinium dyes with π-extended 2′-deoxyadenosine nucleotides

Chemical Communications (2009)

Karina Mondragón-Vásquez Hugo Morales‐Rojas

N 6-(N′-Arylcarbamoyl)-2′-deoxyadenosine-H-phosphonates displayed molecular recognition towards cationic phenothiazinium and phenoxazinium dyes in aqueous solutions; studies have shown that binding is driven mainly by aromatic interactions and that size and shape-complementarity of the aromatic rings in host and guest provides selectivity.

Cationic polymerization

Deoxyadenosine

Molecular Recognition

Complementarity (molecular biology)

10.1039/b913315a

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Citations (3)

CCDC 773416: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

J.I. Arenas-Garcia Dea Herrera‐Ruiz Karina Mondragón-Vásquez Hugo Morales‐Rojas H. Hopfl

10.5517/cctysxf

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CCDC 773415: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

J.I. Arenas-Garcia Dea Herrera‐Ruiz Karina Mondragón-Vásquez Hugo Morales‐Rojas H. Hopfl

10.5517/cctyswd

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Modification of the Supramolecular Hydrogen-Bonding Patterns of Acetazolamide in the Presence of Different Cocrystal Formers: 3:1, 2:1, 1:1, and 1:2 Cocrystals from Screening with the Structural Isomers of Hydroxybenzoic Acids, Aminobenzoic Acids, Hydroxybenzamides, Aminobenzamides, Nicotinic Acids, Nicotinamides, and 2,3-Dihydroxybenzoic Acids

Crystal Growth & Design (2011)

J.I. Arenas-Garcia Dea Herrera‐Ruiz Karina Mondragón-Vásquez Hugo Morales‐Rojas Herbert Höpfl

Acetazolamide (ACZ) has been combined via liquid-assisted grinding in water with a library of cocrystal formers derived from benzoic and nicotinic acid, which provided novel cocrystals with 2-hydroxybenzamide, 2-aminobenzamide, picolinamide, and 2,3-dihydroxybenzoic acid. The cocrystalline phases were identified first by XRPD analysis and then structurally characterized by IR spectroscopy and single-crystal X-ray diffraction analysis. These cocrystals and the previously reported cocrystalline phases obtained from 4-hydroxybenzoic acid and nicotinamide constitute a series of six cocrystals of varied stoichiometric ratios (3:1, 2:1, 1:1, and 1:2), which allowed for a profound analysis of the structural and chemical factors that govern their formation. The structural analysis has shown that the ACZ molecules participate in the dominant hydrogen-bonding patterns within the crystal structures: three cocrystal structures exhibit extended supramolecular aggregates of ACZ having channels, pores, or semispherical voids, in which the cocrystal formers are included as guest molecules, and can, therefore, be described as inclusion or clathrate complexes. One cocrystal can be considered as a pillared or intercalation compound, and the remaining two cocrystals are true two-component 2D or 3D networks. In addition, a variety of alternative preparative methods (liquid-assisted grinding, neat grinding, reaction crystallization, solution-mediated phase transformation, and solution crystallization) have been employed, showing that four of the six cocrystals required the presence of water for successful cocrystal formation.

Cocrystal

Benzoic acid

Powder Diffraction

Crystal Engineering

10.1021/cg201140g

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Citations (46)

CCDC 773417: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

J.I. Arenas-Garcia Dea Herrera‐Ruiz Karina Mondragón-Vásquez Hugo Morales‐Rojas H. Hopfl

10.5517/cctysyg

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Non-Conjugated Chitosan-Based Nanoparticles to Proteic Antigens Elicit Similar Humoral Immune Responses to Those Obtained with Alum

Journal of Nanoscience and Nanotechnology (2017)

Irma Yadira Izaguirre-Hernández Gabriela Mellado‐Sánchez Karina Mondragón-Vásquez Pablo Thomas-Dupont Luis A. Sánchez-Vargas

Biodegradables Chitosan-based Nanoparticles (CS NPs) have been extensively studied as delivery system for therapeutic molecules and as efficient carriers or adjuvants in experimental vaccination. Physicochemical association between CS NPs and antigens is a key step for the biological function as carrier devices. However, for the adjuvant CS NPs property, it is not well known if coupling with vaccine antigens is required or not to potentiate the immune response. To address this issue, in this work, we evaluated the potential adjuvant effect of CS NPs by simply mixing with two different antigens such as Bovine Serum Albumin (BSA) or E protein from Dengue Virus serotype 2 (E protein DENV2). Thus the CS NPs were prepared by ionic gelation with sodium tripolyphosphate, resulting particles among 68 and 188 nm of size. Immunization of 6–8 week old female BALB/c mice, were carried out by intraperitoneal route with a simple combination of CS NPs either with BSA (CS NPs-BSA) at 10 μg or with E protein DENV2 (CS NPs-Protein E) at 5 μg. Combinations with the above antigens with CS NPs elicited robust specific primary and secondary humoral responses comparable to alum, a well-known adjuvant. BSA-specific IgG titers were detectable by day 14 after priming with the CS NPs-BSA formulation, with titers that ranged from 102 to 103 EU ml-. After a second immunization, the anti-BSA titers ranged around 104 EU ml-. In contrast, in the group of mice immunized with the protein alone, BSA-specific serum IgG titers were undetectable at day 14 and 28. For the immunizations with the CS NPs-E protein formulation, we observed also a remarkable specific-antibody production in the primary response, with titers reaching 103 EU ml-. After the booster immunization the anti-E protein DENV2 antibodies titers reached peak values around 104 EU ml-. Interestingly, for both antigens, the combination with CS NPs polarized the immune response to a Th2-like profile, which is characterized mainly by the production of the IgG1 Isotype, confirming that CS NPs can enhance and modulate the humoral immune responses against different antigens independently of physicochemical conjugation. This could represent a simplification in the use of CS NPs as adjuvants in vaccination.

Bovine serum albumin

Alum

Humoral immunity

Antibody titer

10.1166/jnn.2017.13067

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Citations (12)