Novel 5-aminosalicylic derivatives as anti-inflammatories and myeloperoxidase inhibitors evaluated in silico, in vitro and ex vivo

Pérez, Laura Cristina Cabrera; Gutiérrez-Sánchez, Mara; Wejebe, Jessica Elena Mendieta; Rgodríguez, Maricarmen Hernández; Vázquez, Manuel Jonathan Fragoso; Salazar, Juan Rodrigo; Correa-Basurto, José; Martinez, Itzia Irene Padilla; Rosales‐Hernández, Martha Cecilia

doi:10.1016/j.arabjc.2016.12.026

Cited by 9 publications

(5 citation statements)

References 55 publications

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“…Stronger antioxidant activity was observed along with the lower content of impurities, which was especially evident in the case of the Dye2B sample. Antioxidant properties were also demonstrated by 5-ASA derivatives obtained in the studies of Perez et al [30]. These 5-ASA amide derivatives showed an increased ability to scavenge free radicals compared to the control 5-ASA preparation, which was examined using two research methods (DPPH and ABTS assays).…”

Section: Antioxidative Propertiesmentioning

confidence: 92%

Synthesis and Bioactive Properties of the Novel Coloured Compound Obtained via the Laccase-Mediated Transformation of 5-Aminosalicylic Acid

Polak,

Grąz,

Szałapata

et al. 2024

Molecules

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Biocatalysis processes based on oxidoreductases, such as fungal laccase, are important for discovering new organic compounds with broad structures and potential applications. They include bioactive compounds, which can be obtained through laccase-mediated oxidation of organic substrates having hydroxyl and/or amino groups especially, e.g., 5-aminosalicylic acid (5-ASA) is characterised for its potential for oxidation by a fungal laccase obtained from a Cerrena unicolor strain. The biotransformation process was optimised in terms of the buffer and co-solvent concentration, buffer pH value, and laccase activity. Selected crude dyes were analysed for their bioactive properties, toxicity, and suitability for the dyeing of wool fibres. The data obtained clearly indicated that a low concentration of the reaction buffer in the pH range from 5 to 6 and in the presence of 10% acetonitrile increased the rate of substrate oxidation and the amount of the product formed. The red-brown compound obtained via laccase-mediated oxidation of 5-aminosalicylic acid showed antioxidant properties and unique antimicrobial activity against Staphylococcus aureus and Staphylococcus epidermidis strains with the MIC value of 0.125 mg/mL detected for the purest dye. In addition, it was reported to have good wool fibre dyeing properties and no irritant effect after patch tests on a selected group with increased skin sensitivity.

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Section: Antioxidative Propertiesmentioning

confidence: 92%

Synthesis and Bioactive Properties of the Novel Coloured Compound Obtained via the Laccase-Mediated Transformation of 5-Aminosalicylic Acid

Polak,

Grąz,

Szałapata

et al. 2024

Molecules

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“…A molecule capable of decreasing the amount of ROS can protect against cell damage and apoptosis [50]. Many researchers have suggested that the presence of conjugated double bonds throughout a molecule (as in the case of C40) can give intrinsic antioxidant properties through free radical scavenging [54,56,57].…”

Section: Ppar Researchmentioning

confidence: 99%

In Vivo and Ex Vivo Evaluation of 1,3-Thiazolidine-2,4-Dione Derivatives as Euglycemic Agents

Alemán-González-Duhart

Álvarez-Almazán

Valdés

et al. 2021

PPAR Research

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Thiazolidinediones (TZDs), used to treat type 2 diabetes mellitus, act as full agonists of the peroxisome proliferator-activated receptor gamma. Unfortunately, they produce adverse effects, including weight gain, hepatic toxicity, and heart failure. Our group previously reported the design, synthesis, in silico evaluation, and acute oral toxicity test of two TZD derivatives, compounds 40 (C40) and 81 (C81), characterized as category 5 and 4, respectively, under the Globally Harmonized System. The aim of this study was to determine whether C40, C81, and a new compound, C4, act as euglycemic and antioxidant agents in male Wistar rats with streptozotocin-induced diabetes. The animals were randomly divided into six groups ( n = 7 ): the control, those with diabetes and untreated, and those with diabetes and treated with pioglitazone, C40, C81, or C4 (daily for 21 days). At the end of the experiment, tissue samples were collected to quantify the level of glucose, insulin, triglycerides, total cholesterol, and liver enzymes, as well as enzymatic and nonenzymatic antioxidant activity. C4, without a hypoglycemic effect, displayed the best antioxidant activity. Whereas C81 could only attenuate the elevated level of blood glucose, C40 generated euglycemia by the end of the treatment. All compounds produced a significant decrease in triglycerides.

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“…57 Studies on 5aminosalicylic derivatives indicated their binding to myeloperoxidase (MPO), which involves π−cation interactions with Arg239. 58 Succinate-coenzyme Q reductase (SQR) is a central enzyme in the respiratory chain and Krebs cycle, which is a target protein for pharmaceuticals and agricultural fungicides. Virtual screening and structure-based design led to discovery of many pyrazole-4-carboxamides as potent SQR inhibitors, where the pyrazole ring forms π−cation interactions with Arg46 of the C chain.…”

Section: ■ Inhibitor−enzyme Interactionsmentioning

confidence: 99%

“…The MIF inhibitor NVS-2 containing an anisyl group shows a π–cation interaction with Lys32 that leads to a striking increase of binding affinity . Studies on 5-aminosalicylic derivatives indicated their binding to myeloperoxidase (MPO), which involves π–cation interactions with Arg239 . Succinate-coenzyme Q reductase (SQR) is a central enzyme in the respiratory chain and Krebs cycle, which is a target protein for pharmaceuticals and agricultural fungicides.…”

Section: Inhibitor–enzyme Interactionsmentioning

confidence: 99%

π–Cation Interactions in Molecular Recognition: Perspectives on Pharmaceuticals and Pesticides

Liang

2018

J. Agric. Food Chem.

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The π-cation interaction that differs from the cation-π interaction is a valuable concept in molecular design of pharmaceuticals and pesticides. In this Perspective we present an up-to-date review (from 1995 to 2017) on bioactive molecules involving π-cation interactions with the recognition site, and categorize into systems of inhibitor-enzyme, ligand-receptor, ligand-transporter, and hapten-antibody. The concept of π-cation interactions offers use of π systems in a small molecule to enhance the binding affinity, specificity, selectivity, lipophilicity, bioavailability, and metabolic stability, which are physiochemical features desired for drugs and pesticides.

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Novel 5-aminosalicylic derivatives as anti-inflammatories and myeloperoxidase inhibitors evaluated in silico, in vitro and ex vivo

Cited by 9 publications

References 55 publications

Synthesis and Bioactive Properties of the Novel Coloured Compound Obtained via the Laccase-Mediated Transformation of 5-Aminosalicylic Acid

Synthesis and Bioactive Properties of the Novel Coloured Compound Obtained via the Laccase-Mediated Transformation of 5-Aminosalicylic Acid

In Vivo and Ex Vivo Evaluation of 1,3-Thiazolidine-2,4-Dione Derivatives as Euglycemic Agents

π–Cation Interactions in Molecular Recognition: Perspectives on Pharmaceuticals and Pesticides

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