Gabriel Navarrete-Vázquez
Universidad Autónoma del Estado de Morelos
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Featured researches published by Gabriel Navarrete-Vázquez.
Bioorganic & Medicinal Chemistry Letters | 2002
Juan Valdez; Roberto Cedillo; Alicia Hernández-Campos; Lilián Yépez; Francisco Hernández-Luis; Gabriel Navarrete-Vázquez; Amparo Tapia; Rafael Cortés; Manuel Hernández; Rafael Castillo
Compounds 1-18 have been synthesized and tested in vitro against the protozoa Giardia lamblia, Entamoeba histolytica and the helminth Trichinella spiralis. Inhibition of rat brain tubulin polymerization was also measured and compared for each compound. Results indicate that most of the compounds tested were more active as antiprotozoal agents than Metronidazole and Albendazole. None of the compounds was as active as Albendazole against T. spiralis. Although only compounds 3, 9 and 15 (2-methoxycarbonylamino derivatives) inhibited tubulin polymerization, these were not the most potent antiparasitic compounds.
Bioorganic & Medicinal Chemistry Letters | 2001
Gabriel Navarrete-Vázquez; Roberto Cedillo; Alicia Hernández-Campos; Lilián Yépez; Francisco Hernández-Luis; Juan Valdez; Raúl G. E. Morales; Rafael Cortés; Manuel Hernández; Rafael Castillo
2-(Trifluoromethyl)benzimidazole derivatives substituted at the 1-, 5-, and 6-positions have been synthesized and in vitro tested against the protozoa Giardia lamblia, Entamnoeha histolytica. and the helminth Trichinella spiralis. Results indicate that all the compounds tested are more active as antiprotozoal agents than Albendazole and Metronidazole. One compound (20) was as active as Albendazole against T. spiralis. These compounds were also tested for their effect on tubulin polymerization and none inhibited tubulin polymerization.
Bioorganic & Medicinal Chemistry | 2003
Gabriel Navarrete-Vázquez; Lilián Yépez; Alicia Hernández-Campos; Amparo Tapia; Francisco Hernández-Luis; Roberto Cedillo; José A. González; Antonio R. Martínez-Fernández; Mercedes Martı́nez-Grueiro; Rafael Castillo
Albendazole (Abz) and Mebendazole (Mbz) analogues have been synthesized and in vitro tested against the protozoa Giardia lamblia, Trichomonas vaginalis and the helminths Trichinella spiralis and Caenorhabditis elegans. Results indicate that compounds 4a, 4b (Abz analogues), 12b and 20 (Mbz analogues) are as active as antiprotozoal agents as Metronidazole against G. lamblia. Compound 9 was 58 times more active than Abz against T. vaginalis. Compounds 8 and 4a also shown high activity against this protozoan. Compounds 4b and 5a were as active as Abz. None of the Mbz analogues showed activity against T. vaginalis. The anthelmintic activity presented by these compounds was poor.
Diabetes, Obesity and Metabolism | 2008
Rolffy Ortiz-Andrade; Juan Carlos Sánchez-Salgado; Gabriel Navarrete-Vázquez; Scott P. Webster; Margareth Binnie; Sara García-Jiménez; Ismael León-Rivera; P. Cigarroa-Vazquez; Rafael Villalobos-Molina; Samuel Estrada-Soto
Aim: The present investigation was designed to determine the in vivo antidiabetic effect of naringenin (NG) in normoglycaemic and diabetic rat models through blood glucose (GLU) measurements following acute and subchronic time periods. Possible modes of action of NG were investigated and its acute toxicity determined.
European Journal of Medicinal Chemistry | 2011
Juan José Ramírez-Espinosa; María Yolanda Rios; Sugey López-Martínez; José L. Medina-Franco; Paolo Paoli; Guido Camici; Gabriel Navarrete-Vázquez; Rolffy Ortiz-Andrade; Samuel Estrada-Soto
The aim of the current study was to investigate the oral antidiabetic activity of four structurally-related triterpenic acids: ursolic (RE-01), oleanolic (RE-02), moronic (RE-03) and morolic (RE-04) acids. STZ-nicotinamide diabetic rats were treated with these triterpenes (50 mg/kg) and the antidiabetic effects in acute experiment were determined. All compounds showed significant antidiabetic activity in comparison with control group (p<0.05). The in vitro inhibitory activity of compounds against protein tyrosine phosphatase 1B (PTP-1B) was also evaluated. At 50 μM, the enzymatic activity was almost completely inhibited. All compounds were docked with a crystal structure of PTP-1B. Docking results suggested the potential binding of the triterpenic acids in a binding pocket next to the catalytic site. An extensive hydrogen bond network with the carboxyl group and Van der Waals interactions stabilize the protein-ligand complexes.
European Journal of Medicinal Chemistry | 2010
Mariana Torres-Piedra; Rolffy Ortiz-Andrade; Rafael Villalobos-Molina; Narender Singh; José L. Medina-Franco; Scott P. Webster; Margaret Binnie; Gabriel Navarrete-Vázquez; Samuel Estrada-Soto
The aim of the current study was to investigate the oral antidiabetic activity of six structurally related flavonoids: flavone (1), 3-hydroxyflavone (2), 6-hydroxyflavone (3), 7-hydroxyflavone (4), chrysin (5) and quercetin (6). Normoglycemic and STZ-nicotinamide diabetic rats were treated with these flavonoids (50 mg/kg) and the hypoglycemic and antidiabetic effects in acute and sub acute (five days of treatment) experiments were determined. Compounds 1, 5 and 6 were found most active in both experiments in comparison with control group (p<0.05). After five days of administration to STZ-nicotinamide diabetic rats, flavonoids induced a significantly diminishing of total cholesterol, TG and LDL and an augment of HDL compared with the control group (p<0.05). The in vitro inhibitory activity of the compounds against 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) was also evaluated. Quercetin, the most active compound, was docked into the crystal structure of 11beta-HSD1. Docking results indicate potential hydrogen bond interactions with hydroxyl groups of catalytic amino acid residues.
European Journal of Medicinal Chemistry | 2010
Francisco Hernández-Luis; Alicia Hernández-Campos; Rafael Castillo; Gabriel Navarrete-Vázquez; Olivia Soria-Arteche; Manuel Hernández-Hernández; Lilián Yépez-Mulia
A series of 2-(trifluoromethyl)-1H-benzimidazole derivatives (1a-1i) were synthesized via Phillips cyclocondensation of a substituted 1,2-phenylenediamine and trifluoroacetic acid. The synthesized compounds were evaluated in vitro against various protozoan parasites: Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis and Leishmania mexicana, and they showed nanomolar activities against the first three protozoa tested. The compounds were also tested in vitro and in vivo against the nematode Trichinella spiralis. Compounds 1b, 1c and 1e had the most desirable in vitro antiparasitic profile against all parasites studied. In the in vivo model against T. spiralis, compounds 1b and 1e showed good activity against the adult phase at 75 mg/Kg. However, against the muscle larvae stage, only compound 1f exhibited in vivo antiparasitic efficacy.
Bioorganic & Medicinal Chemistry Letters | 2008
Héctor Torres-Gómez; Emanuel Hernández-Núñez; Ismael León-Rivera; Jorge Guerrero-Álvarez; Roberto Cedillo-Rivera; Rosa Moo-Puc; Rocío Argotte-Ramos; María del Carmen Rodríguez-Gutiérrez; Manuel Jesús Chan-Bacab; Gabriel Navarrete-Vázquez
A series of ten novel hybrids from benzimidazole and pentamidine were prepared using a short synthetic route. Each compound was tested in vitro against the protozoa Trichomonas vaginalis, Giardia lamblia, Entamoeba histolytica, Leishmania mexicana, and Plasmodium berghei, in comparison with pentamidine and metronidazole. Some analogues showed high bioactivity in the low micromolar range (IC(50)<1 microM) against the first four protozoa, which make them significantly more potent than either standard. 1,5-bis[4-(5-methoxy-1H-benzimidazole-2-yl)phenoxy]pentane (2) was 3- and 9-fold more potent againstG. lamblia than metronidazole and pentamidine, respectively. This compound was 23-, 108-, and 13-fold more active than pentamidine against T. vaginalis, E. histolytica and L. mexicana, respectively. Studying further structure-activity relationships through the use of bioisosteric substitution in these hybrids should provide new leads against protozoal diseases.
Bioorganic & Medicinal Chemistry Letters | 2008
Hermenegilda Moreno-Diaz; Rafael Villalobos-Molina; Rolffy Ortiz-Andrade; Daniel Díaz-Coutiño; José L. Medina-Franco; Scott P. Webster; Margaret Binnie; Samuel Estrada-Soto; Maximiliano Ibarra-Barajas; Ismael León-Rivera; Gabriel Navarrete-Vázquez
N-(6-Substituted-1,3-benzothiazol-2-yl)benzenesulfonamide derivatives 1-8 were synthesized and evaluated for their in vivo antidiabetic activity in a non-insulin-dependent diabetes mellitus rat model. Several compounds synthesized showed significant lowering of plasma glucose level in this model. As a possible mode of action, the compounds were in vitro evaluated as 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) inhibitors. The most active compounds (3 and 4) were docked into the crystal structure of 11beta-HSD1. Docking results indicate potential hydrogen bond interactions with catalytic amino acid residues.
European Journal of Medicinal Chemistry | 2009
Emanuel Hernández-Núñez; Hugo Tlahuext; Rosa Moo-Puc; Héctor Torres-Gómez; Reyna Reyes-Martínez; Roberto Cedillo-Rivera; Carlos Nava-Zuazo; Gabriel Navarrete-Vázquez
Two new series of imidazole derivatives (acetamides: 1-8 and sulfonamides: 9-15) were synthesized using a short synthetic route. Compound 1 as well as the intermediate 16g were characterized by X-ray crystallography. Imidazole derivatives 1-15 were tested in vitro against three unicellular parasites (Giardia intestinalis, Trichomonas vaginalis and Entamoeba histolytica) in comparison with benznidazole (Bzn) and metronidazole. Compound 1 [N-benzyl-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetamide] was 2 times more active than Bzn against T. vaginalis and G. intestinalis and it was as active as Bzn against E. histolytica. Sulfonamides showed selective toxicity against E. histolytica over the other parasites. Toxicity assay showed that all compounds are non-cytotoxic against MDCK cell line. The results revealed that compounds 1-15 have antiparasitic bioactivity in the micromolar range against the parasites tested, and could be considered as benznidazole bioisosteres.