Thermal characterization and stability evaluation of leishmanicidal selenocyanate and diselenide derivatives

Etxebeste, Mikel; Durán, A.; Sanmartín, Carmen; González-Peñas, Elena; Plano, Daniel; Lizarraga, Elena

doi:10.1007/s10973-020-10544-x

J Therm Anal Calorim

2021

DOI: 10.1007/s10973-020-10544-x

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Thermal characterization and stability evaluation of leishmanicidal selenocyanate and diselenide derivatives

Mikel Etxebeste

A. Durán

Carmen Sanmartín

et al.

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Cited by 3 publications

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Organoselenium Compounds in Medicinal Chemistry

Gallo‐Rodriguez,

Rodriguez

2024

ChemMedChem

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The chemical and biological interest in this element and the molecules bearing selenium has been exponentially growing over the years. Selenium, formerly designated as a toxin, becomes a vital trace element for life that appears as selenocysteine and its dimeric form, selenocystine, in the active sites of selenoproteins, which catalyze a wide variety of reactions, including the detoxification of reactive oxygen species and modulation of redox activities. From the point of view of drug developments, organoselenium drugs are isosteres of sulfur‐containing and oxygen—containing drugs with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. This statement is the paramount relevance considering the big number of clinically employed compounds bearing sulfur or oxygen atoms if their structures including nucleosides and carbohydrates. Thus, in this article we have focused on the relevant features of the application of selenium in medicinal chemistry. With the increasing interest in selenium chemistry, we have attempted to highlight the most significant published data on this subject, mainly concentrating the analysis on the last years. In consequence, the recent advances of relevant pharmacological organoselenium compounds are discussed.

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Organoselenium Compounds in Medicinal Chemistry

Gallo‐Rodriguez,

Rodriguez

2024

ChemMedChem

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Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity

Ramos-Inza,

Almagro,

Font

et al. 2023

J Therm Anal Calorim

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Stability, thermal characterization, and identification of possible polymorphism are relevant in the development of novel therapeutic drugs. In this context, thirty new nonsteroidal anti-inflammatory drug (NSAID) derivatives containing selenium (Se) as selenoesters or diacyl diselenides with demonstrated anticancer activity were thermally characterized in order to establish thermal stability criteria and detect possible polymorphic forms. Compounds were analyzed by a combination of thermogravimetry, differential scanning calorimetry, and X-ray diffraction techniques, and five different calorimetric behaviors were identified. Two compounds based on naproxen (I.3d and I.3e) and an indomethacin-containing derivative (II.2) presented two crystalline forms. The stability under acid, alkaline and oxidative conditions of selected polymorphs was also assessed using high-performance liquid chromatography. In addition, the cytotoxic activity of Se-NSAID crystalline polymorphs was studied in several cancer cell lines in vitro. Remarkably, no significant differences were found among the polymorphic forms tested, thus proving that these compounds are thermally qualified for further drug development. Graphical abstract

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Thermal behavior and determination of physicochemical properties of novel candidates for antipsychotic drugs

Stępnicki,

Gwarda,

Bartyzel

et al. 2024

J Therm Anal Calorim

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Treatment of schizophrenia with currently available drugs is often ineffective or results in several adverse reactions. In previous studies focusing on the search for new antipsychotic drugs, we designed and obtained a series of dopamine D2 and serotonin 5-HT1A and 5-HT2A receptor ligands that were pharmacologically evaluated and showed promising antipsychotic activity. Evaluation of ADMET parameters is an important issue in drug development and should be performed at its early stage to avoid developing molecules with poor pharmacokinetics, that are unlikely to enter the market. For this reason, in this work we focused on the assessment of physicochemical parameters of selected compounds from the series we obtained to assess their drug-like potential. The results of thermal analysis showed that most of the tested compounds are thermally stable above 200 °C, with one compound stable up to 190 °C. Permeability through biological membranes assessed in the parallel artificial membrane permeability assay indicated that all tested compounds effectively migrate through biological membranes by means of passive diffusion. The solubility of the tested compounds was determined in PBS, reflecting physiological pH, and 0.01 M HCl, indicating their low to moderate solubility in PBS, which was significantly improved in acidic environment. The lipophilicity of the studied compounds expressed as LogD falls within the range of 1.84–2.80, what suggest that they would show good oral absorption and the ability to cross lipid barriers. The studies were supplemented with in silico prediction of ADMET parameters, which also indicate the probable high drug-likeness of the tested compounds.

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Thermal characterization and stability evaluation of leishmanicidal selenocyanate and diselenide derivatives

Cited by 3 publications

References 54 publications

Organoselenium Compounds in Medicinal Chemistry

Organoselenium Compounds in Medicinal Chemistry

Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity

Thermal behavior and determination of physicochemical properties of novel candidates for antipsychotic drugs

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