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Article: Diversity of Solid Forms Promoted by Ball Milling: Characterization and Intrinsic Dissolution Studies of Pioglitazone Hydrochloride and Fluvastatin Sodium Drug-Drug Systems.

Villeda-Villegas, Marco / Páez-Franco, José C / Coyote-Dotor, Guadalupe / Núñez-Pineda, Alejandra / Dorazco-González, Alejandro / Fuentes-Noriega, Inés / Rubio-Carrasco, Kenneth / Toledo Jaldín, Helen P / Morales-Morales, David / Germán-Acacio, Juan Manuel

Pharmaceuticals (Basel, Switzerland)

2023 Volume 16, Issue 6

Abstract: Coamorphous salt in a 1:1 ratio prepared by ball milling from Fluvastatin sodium (FLV) and Pioglitazone hydrochloride (PGZ·HCl) can be selectively formed by neat grinding (NG). Furthermore, the salt-cocrystal continuum was preferably formed by employing ... ...

Abstract	Coamorphous salt in a 1:1 ratio prepared by ball milling from Fluvastatin sodium (FLV) and Pioglitazone hydrochloride (PGZ·HCl) can be selectively formed by neat grinding (NG). Furthermore, the salt-cocrystal continuum was preferably formed by employing liquid-assisted grinding (LAG) using ethanol (EtOH). Attempts to prepare the coamorphous salt starting from the salt-cocrystal continuum by NG were unsuccessful. Interestingly, through ball milling by NG or LAG, a great diversity of solid forms (PGZ·HCl-FLV 1:1) could be accessed: NG and hexane (coamorphous); ethyl acetate (physical mixture); EtOH (salt-cocrystal continuum); and water (which presents two T
Language	English
Publishing date	2023-05-24
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2193542-7
ISSN	1424-8247
ISSN	1424-8247
DOI	10.3390/ph16060781
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: Ball-Milling Preparation of the Drug-Drug Solid Form of Pioglitazone-Rosuvastatin at Different Molar Ratios: Characterization and Intrinsic Dissolution Rates Evaluation.

Muñoz Tecocoatzi, M Fernanda / Páez-Franco, José C / Rubio-Carrasco, Kenneth / Núñez-Pineda, Alejandra / Dorazco-González, Alejandro / Fuentes-Noriega, Inés / Vilchis-Néstor, Alfredo R / Olvera, Lilian I / Morales-Morales, David / Germán-Acacio, Juan Manuel

Pharmaceutics

2023 Volume 15, Issue 2

Abstract: Ball-milling using neat grinding (NG) or liquid-assisted grinding (LAG) by varying the polarity of the solvents allowed access to various drug-drug solid forms of pioglitazone hydrochloride (PGZ·HCl) and rosuvastatin calcium (RSV). Using NG, the ... ...

Abstract	Ball-milling using neat grinding (NG) or liquid-assisted grinding (LAG) by varying the polarity of the solvents allowed access to various drug-drug solid forms of pioglitazone hydrochloride (PGZ·HCl) and rosuvastatin calcium (RSV). Using NG, the coamorphous form was formed from the reaction of pioglitazone hydrochloride (PGZ·HCl) and rosuvastatin calcium (RSV) in a 2:1 molar ratio. The formation of the expected coamorphous salt could not be corroborated by FT-IR, but DSC data showed that it was indeed a single-phase amorphous mixture. By varying the molar ratios of the reactants, either keeping PGZ·HCl constant and varying RSV or vice versa, another coamorphous form was obtained when a 1:1 molar ratio was employed. In the case of the other outcomes, it was observed that they were a mixture of solid forms coexisting simultaneously with the coamorphous forms (1:1 or 2:1) together with the drug that was in excess. When RSV was in excess, it was in an amorphous form. In the case of PGZ·HCl, it was found in a semicrystalline form. The intrinsic dissolution rates (IDRs) of the solid forms of PGZ·HCl-RSV in stoichiometric ratios (1:1, 2:1, 1:4, 6:1, and 1:10) were evaluated. Interestingly, a synchronized release of both drugs in the dissolution medium was observed. In the case of the release of RSV, there were no improvements in the dissolution profiles, because the acidic media caused the formation of degradation products, limiting any probable modification in the dissolution processes. However, the coamorphous 2:1 form exhibited an improvement of 1.03 times with respect to pure PGZ·HCl. It is proposed that the modification of the dissolution process of the coamorphous 2:1 form was limited by changes in the pH of the media as RSV consumes protons from the media due to degradation processes.
Language	English
Publishing date	2023-02-13
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2527217-2
ISSN	1999-4923
ISSN	1999-4923
DOI	10.3390/pharmaceutics15020630
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Article: Relevance of Fluorinated Ligands to the Design of Metallodrugs for Their Potential Use in Cancer Treatment.

Páez-Franco, José C / Zermeño-Ortega, Miriam R / de la O-Contreras, Carmen Myriam / Canseco-González, Daniel / Parra-Unda, Jesus R / Avila-Sorrosa, Alcives / Enríquez, Raúl G / Germán-Acacio, Juan M / Morales-Morales, David

Pharmaceutics

2022 Volume 14, Issue 2

Abstract: Fluorination of pharmaceutical agents has afforded crucial modifications to their pharmacological profiles, leading to important advances in medicinal chemistry. On the other hand, metallodrugs are considered to be valuable candidates in the treatment of ...

Abstract	Fluorination of pharmaceutical agents has afforded crucial modifications to their pharmacological profiles, leading to important advances in medicinal chemistry. On the other hand, metallodrugs are considered to be valuable candidates in the treatment of several diseases, albeit with the caveat that they may exhibit pharmacological disadvantages, such as poor water solubility, low bioavailability and short circulating time. To surmount these limitations, two approaches have been developed: one based on the design of novel metallodrug-delivering carriers and the other based on optimizing the structure of the ligands bound to the metal center. In this context, fluorination of the ligands may bring beneficial changes (physicochemical and biological) that can help to elude the aforementioned drawbacks. Thus, in this review, we discuss the use of fluorinated ligands in the design of metallodrugs that may exhibit potential anticancer activity.
Language	English
Publishing date	2022-02-11
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	2527217-2
ISSN	1999-4923
ISSN	1999-4923
DOI	10.3390/pharmaceutics14020402
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Article ; Online: Metabolomics analysis identifies glutamic acid and cystine imbalances in COVID-19 patients without comorbid conditions. Implications on redox homeostasis and COVID-19 pathophysiology.

Páez-Franco, José C / Maravillas-Montero, José L / Mejía-Domínguez, Nancy R / Torres-Ruiz, Jiram / Tamez-Torres, Karla M / Pérez-Fragoso, Alfredo / Germán-Acacio, Juan Manuel / Ponce-de-León, Alfredo / Gómez-Martín, Diana / Ulloa-Aguirre, Alfredo

PloS one

2022 Volume 17, Issue 9, Page(s) e0274910

Abstract: It is well known that the presence of comorbidities and age-related health issues may hide biochemical and metabolic features triggered by SARS-CoV-2 infection and other diseases associated to hypoxia, as they are by themselves chronic inflammatory ... ...

Abstract	It is well known that the presence of comorbidities and age-related health issues may hide biochemical and metabolic features triggered by SARS-CoV-2 infection and other diseases associated to hypoxia, as they are by themselves chronic inflammatory conditions that may potentially disturb metabolic homeostasis and thereby negatively impact on COVID-19 progression. To unveil the metabolic abnormalities inherent to hypoxemia caused by COVID-19, we here applied gas chromatography coupled to mass spectrometry to analyze the main metabolic changes exhibited by a population of male patients less than 50 years of age with mild/moderate and severe COVID-19 without pre-existing comorbidities known to predispose to life-threatening complications from this infection. Several differences in serum levels of particular metabolites between normal controls and patients with COVID-19 as well as between mild/moderate and severe COVID-19 were identified. These included increased glutamic acid and reduced glutamine, cystine, threonic acid, and proline levels. In particular, using the entire metabolomic fingerprint obtained, we observed that glutamine/glutamate metabolism was associated with disease severity as patients in the severe COVID-19 group presented the lowest and higher serum levels of these amino acids, respectively. These data highlight the hypoxia-derived metabolic alterations provoked by SARS-CoV-2 infection in the absence of pre-existing co-morbidities as well as the value of amino acid metabolism in determining reactive oxygen species recycling pathways, which when impaired may lead to increased oxidation of proteins and cell damage. They also provide insights on new supportive therapies for COVID-19 and other disorders that involve altered redox homeostasis and lower oxygen levels that may lead to better outcomes of disease severity.
MeSH term(s)	Amino Acids/metabolism ; COVID-19 ; Cystine/metabolism ; Gas Chromatography-Mass Spectrometry ; Glutamic Acid/metabolism ; Glutamine/metabolism ; Homeostasis ; Humans ; Hypoxia ; Male ; Oxidation-Reduction ; Oxygen ; Proline/metabolism ; Reactive Oxygen Species ; SARS-CoV-2
Chemical Substances	Amino Acids ; Reactive Oxygen Species ; Glutamine (0RH81L854J) ; Glutamic Acid (3KX376GY7L) ; Cystine (48TCX9A1VT) ; Proline (9DLQ4CIU6V) ; Oxygen (S88TT14065)
Language	English
Publishing date	2022-09-20
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2267670-3
ISSN	1932-6203 ; 1932-6203
ISSN (online)	1932-6203
ISSN	1932-6203
DOI	10.1371/journal.pone.0274910
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: Synthesis, Characterization, and Intrinsic Dissolution Studies of Drug-Drug Eutectic Solid Forms of Metformin Hydrochloride and Thiazide Diuretics.

Coyote-Dotor, Guadalupe / Páez-Franco, José C / Canseco-González, Daniel / Núñez-Pineda, Alejandra / Dorazco-González, Alejandro / Fuentes-Noriega, Inés / Vilchis-Néstor, Alfredo R / Rodríguez-Hernández, Joelis / Morales-Morales, David / Germán-Acacio, Juan Manuel

Pharmaceutics

2021 Volume 13, Issue 11

Abstract: The mechanochemical synthesis of drug-drug solid forms containing metformin hydrochloride (MET·HCl) and thiazide diuretics hydrochlorothiazide (HTZ) or chlorothiazide (CTZ) is reported. Characterization of these new systems indicates formation of binary ... ...

Abstract	The mechanochemical synthesis of drug-drug solid forms containing metformin hydrochloride (MET·HCl) and thiazide diuretics hydrochlorothiazide (HTZ) or chlorothiazide (CTZ) is reported. Characterization of these new systems indicates formation of binary eutectic conglomerates, i.e., drug-drug eutectic solids (DDESs). Further analysis by construction of binary diagrams (DSC screening) exhibited the characteristic V-shaped form indicating formation of DDESs in both cases. These new DDESs were further characterized by different techniques, including thermal analysis (DSC), solid state NMR spectroscopy (SSNMR), powder X-ray diffraction (PXRD) and scanning electron microscopy-energy dispersive X-ray spectroscopy analysis (SEM-EDS). In addition, intrinsic dissolution rate experiments and solubility assays were performed. In the case of MET·HCl-HTZ (χ
Language	English
Publishing date	2021-11-14
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2527217-2
ISSN	1999-4923
ISSN	1999-4923
DOI	10.3390/pharmaceutics13111926
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Article: Mechanochemistry: A Green Approach in the Preparation of Pharmaceutical Cocrystals.

Solares-Briones, Mizraín / Coyote-Dotor, Guadalupe / Páez-Franco, José C / Zermeño-Ortega, Miriam R / de la O Contreras, Carmen Myriam / Canseco-González, Daniel / Avila-Sorrosa, Alcives / Morales-Morales, David / Germán-Acacio, Juan M

Pharmaceutics

2021 Volume 13, Issue 6

Abstract: Mechanochemistry is considered an alternative attractive greener approach to prepare diverse molecular compounds and has become an important synthetic tool in different fields (e.g., physics, chemistry, and material science) since is considered an ... ...

Abstract	Mechanochemistry is considered an alternative attractive greener approach to prepare diverse molecular compounds and has become an important synthetic tool in different fields (e.g., physics, chemistry, and material science) since is considered an ecofriendly procedure that can be carried out under solvent free conditions or in the presence of minimal quantities of solvent (catalytic amounts). Being able to substitute, in many cases, classical solution reactions often requiring significant amounts of solvents. These sustainable methods have had an enormous impact on a great variety of chemistry fields, including catalysis, organic synthesis, metal complexes formation, preparation of multicomponent pharmaceutical solid forms, etc. In this sense, we are interested in highlighting the advantages of mechanochemical methods on the obtaining of pharmaceutical cocrystals. Hence, in this review, we describe and discuss the relevance of mechanochemical procedures in the formation of multicomponent solid forms focusing on pharmaceutical cocrystals. Additionally, at the end of this paper, we collect a chronological survey of the most representative scientific papers reporting the mechanochemical synthesis of cocrystals.
Language	English
Publishing date	2021-05-25
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	2527217-2
ISSN	1999-4923
ISSN	1999-4923
DOI	10.3390/pharmaceutics13060790
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Diversity of Solid Forms Promoted by Ball Milling

Marco Villeda-Villegas / José C. Páez-Franco / Guadalupe Coyote-Dotor / Alejandra Núñez-Pineda / Alejandro Dorazco-González / Inés Fuentes-Noriega / Kenneth Rubio-Carrasco / Helen P. Toledo Jaldín / David Morales-Morales / Juan Manuel Germán-Acacio

Pharmaceuticals, Vol 16, Iss 781, p

Characterization and Intrinsic Dissolution Studies of Pioglitazone Hydrochloride and Fluvastatin Sodium Drug–Drug Systems

2023 Volume 781

Abstract: Coamorphous salt in a 1:1 ratio prepared by ball milling from Fluvastatin sodium (FLV) and Pioglitazone hydrochloride (PGZ·HCl) can be selectively formed by neat grinding (NG). Furthermore, the salt–cocrystal continuum was preferably formed by employing ... ...

Abstract	Coamorphous salt in a 1:1 ratio prepared by ball milling from Fluvastatin sodium (FLV) and Pioglitazone hydrochloride (PGZ·HCl) can be selectively formed by neat grinding (NG). Furthermore, the salt–cocrystal continuum was preferably formed by employing liquid-assisted grinding (LAG) using ethanol (EtOH). Attempts to prepare the coamorphous salt starting from the salt–cocrystal continuum by NG were unsuccessful. Interestingly, through ball milling by NG or LAG, a great diversity of solid forms (PGZ·HCl-FLV 1:1) could be accessed: NG and hexane (coamorphous); ethyl acetate (physical mixture); EtOH (salt–cocrystal continuum); and water (which presents two T g , indicating immiscibility of the components). An exploration was performed at different drug-to-drug ratios by NG. By differential scanning calorimetry (DSC), the presence of two endothermic events was observed in this screening: incongruous melting point (solidus) and excess of one of the components (liquidus), except in the 1:1 solid form. From these results, eutectic behavior was observed. Through the construction of a binary phase diagram, it was determined that the 1:1 molar ratio gives rise to the formation of the most stable coamorphous composition. Dissolution profile studies of these solid forms were carried out, specifically on pure FLV and the solid forms of PGZ⋅HCl-FLV (1:2; 1:4; and 1:6), together with the coamorphous 1:1 salt. By itself, pure FLV presented the highest K int (13.6270 ± 0.8127 mg/cm 2 ⋅min). On the other hand, the coamorphous 1:1 showed a very low K int (0.0220 ± 0.0014 mg/cm 2 ·min), indicating very fast recrystallization by the FLV, which avoids observing a sudden release of this drug in the solution. This same behavior was observed in the eutectic composition 1:2. In the other solid forms, the value of K int increases along with the %w of FLV. From the mechanochemical point of view, ball milling by NG or LAG became an important synthetic tool since it allows obtaining a great variety of solid forms to explore the solid-state ...
Keywords	drug–drug coamorphous ; drug–drug salt–cocrystal continuum ; mechanochemical reactions ; intrinsic dissolution experiments ; fluvastatin sodium ; pioglitazone hydrochloride ; Medicine ; R ; Pharmacy and materia medica ; RS1-441
Subject code	500
Language	English
Publishing date	2023-05-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Severity of SARS-CoV-2 infection is linked to double-negative (CD27

Cervantes-Díaz, Rodrigo / Sosa-Hernández, Víctor Andrés / Torres-Ruíz, Jiram / Romero-Ramírez, Sandra / Cañez-Hernández, Mariana / Pérez-Fragoso, Alfredo / Páez-Franco, José C / Meza-Sánchez, David E / Pescador-Rojas, Miriam / Sosa-Hernández, Víctor Adrián / Gómez-Martín, Diana / Maravillas-Montero, José L

Inflammation research : official journal of the European Histamine Research Society ... [et al.

2021 Volume 71, Issue 1, Page(s) 131–140

Abstract: Objectives: The role of B cells in COVID-19, beyond the production of specific antibodies against SARS-CoV-2, is still not well understood. Here, we describe the novel landscape of circulating double-negative (DN) CD27: Methods: Using multiparametric ...

Abstract	Objectives: The role of B cells in COVID-19, beyond the production of specific antibodies against SARS-CoV-2, is still not well understood. Here, we describe the novel landscape of circulating double-negative (DN) CD27 Methods: Using multiparametric flow cytometry, we determined DN B cell subset amounts from 91 COVID-19 patients, correlated those with cytokines, clinical and laboratory parameters, and segregated them by principal components analysis. Results: We detected significant increments in the DN2 and DN3 B cell subsets, while we found a relevant decrease in the DN1 B cell subpopulation, according to disease severity and patient outcomes. These DN cell numbers also appeared to correlate with pro- or anti-inflammatory signatures, respectively, and contributed to the segregation of the patients into disease severity groups. Conclusion: This study provides insights into DN B cell subsets' potential role in immune responses against SARS-CoV-2, particularly linked to the severity of COVID-19.
MeSH term(s)	Adult ; Aged ; Aged, 80 and over ; B-Lymphocytes/cytology ; COVID-19/blood ; COVID-19/diagnosis ; COVID-19/immunology ; COVID-19/virology ; Cell Lineage ; Computational Biology ; Disease Progression ; Female ; Humans ; Immunoglobulin D/blood ; Male ; Middle Aged ; Principal Component Analysis ; Prognosis ; Respiration, Artificial ; SARS-CoV-2 ; Severity of Illness Index ; Tumor Necrosis Factor Receptor Superfamily, Member 7/blood ; Young Adult
Chemical Substances	Immunoglobulin D ; Tumor Necrosis Factor Receptor Superfamily, Member 7
Language	English
Publishing date	2021-11-30
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1221794-3
ISSN	1420-908X ; 1023-3830
ISSN (online)	1420-908X
ISSN	1023-3830
DOI	10.1007/s00011-021-01525-3
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Indole- and Pyrazole-Glycyrrhetinic Acid Derivatives as PTP1B Inhibitors: Synthesis, In Vitro and In Silico Studies.

De-la-Cruz-Martínez, Ledy / Duran-Becerra, Constanza / González-Andrade, Martin / Páez-Franco, José C / Germán-Acacio, Juan Manuel / Espinosa-Chávez, Julio / Torres-Valencia, J Martin / Pérez-Villanueva, Jaime / Palacios-Espinosa, Juan Francisco / Soria-Arteche, Olivia / Cortés-Benítez, Francisco

Molecules (Basel, Switzerland)

2021 Volume 26, Issue 14

Abstract: Regulating insulin and leptin levels using a protein tyrosine phosphatase 1B (PTP1B) inhibitor is an attractive strategy to treat diabetes and obesity. Glycyrrhetinic acid (GA), a triterpenoid, may weakly inhibit this enzyme. Nonetheless, semisynthetic ... ...

Abstract	Regulating insulin and leptin levels using a protein tyrosine phosphatase 1B (PTP1B) inhibitor is an attractive strategy to treat diabetes and obesity. Glycyrrhetinic acid (GA), a triterpenoid, may weakly inhibit this enzyme. Nonetheless, semisynthetic derivatives of GA have not been developed as PTP1B inhibitors to date. Herein we describe the synthesis and evaluation of two series of indole- and
MeSH term(s)	Enzyme Inhibitors/chemical synthesis ; Enzyme Inhibitors/chemistry ; Glycyrrhetinic Acid/analogs & derivatives ; Glycyrrhetinic Acid/chemical synthesis ; Glycyrrhetinic Acid/chemistry ; Humans ; Indoles/chemical synthesis ; Indoles/chemistry ; Molecular Docking Simulation ; Molecular Dynamics Simulation ; Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors ; Protein Tyrosine Phosphatase, Non-Receptor Type 1/chemistry ; Pyrazoles/chemical synthesis ; Pyrazoles/chemistry ; Structure-Activity Relationship
Chemical Substances	Enzyme Inhibitors ; Indoles ; Pyrazoles ; PTPN1 protein, human (EC 3.1.3.48) ; Protein Tyrosine Phosphatase, Non-Receptor Type 1 (EC 3.1.3.48) ; Glycyrrhetinic Acid (P540XA09DR)
Language	English
Publishing date	2021-07-20
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules26144375
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Article ; Online: Metabolomics analysis reveals a modified amino acid metabolism that correlates with altered oxygen homeostasis in COVID-19 patients.

Páez-Franco, José C / Torres-Ruiz, Jiram / Sosa-Hernández, Víctor A / Cervantes-Díaz, Rodrigo / Romero-Ramírez, Sandra / Pérez-Fragoso, Alfredo / Meza-Sánchez, David E / Germán-Acacio, Juan Manuel / Maravillas-Montero, José L / Mejía-Domínguez, Nancy R / Ponce-de-León, Alfredo / Ulloa-Aguirre, Alfredo / Gómez-Martín, Diana / Llorente, Luis

Scientific reports

2021 Volume 11, Issue 1, Page(s) 6350

Abstract: We identified the main changes in serum metabolites associated with severe (n = 46) and mild (n = 19) COVID-19 patients by gas chromatography coupled to mass spectrometry. The modified metabolic profiles were associated to an altered amino acid ... ...

Abstract	We identified the main changes in serum metabolites associated with severe (n = 46) and mild (n = 19) COVID-19 patients by gas chromatography coupled to mass spectrometry. The modified metabolic profiles were associated to an altered amino acid catabolism in hypoxic conditions. Noteworthy, three α-hydroxyl acids of amino acid origin increased with disease severity and correlated with altered oxygen saturation levels and clinical markers of lung damage. We hypothesize that the enzymatic conversion of α-keto-acids to α- hydroxyl-acids helps to maintain NAD recycling in patients with altered oxygen levels, highlighting the potential relevance of amino acid supplementation during SARS-CoV-2 infection.
MeSH term(s)	Adult ; Amino Acids/metabolism ; COVID-19/metabolism ; Case-Control Studies ; Female ; Homeostasis ; Humans ; Male ; Metabolomics ; Middle Aged ; Mitochondria/metabolism ; Oxygen/metabolism
Chemical Substances	Amino Acids ; Oxygen (S88TT14065)
Language	English
Publishing date	2021-03-18
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2615211-3
ISSN	2045-2322 ; 2045-2322
ISSN (online)	2045-2322
ISSN	2045-2322
DOI	10.1038/s41598-021-85788-0
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