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Registro Completo |
Biblioteca(s): |
Embrapa Instrumentação. |
Data corrente: |
26/04/2021 |
Data da última atualização: |
10/06/2022 |
Tipo da produção científica: |
Artigo em Periódico Indexado |
Autoria: |
CARVALHO JUNIOR, P. S.; DINIZ, L. F.; SILVA, G. T. S. T. da; COUTINHO, N. D.; SANTOS, P. G. dos; CARVALHO-SILVA, V. H.; RIBEIRO, C.; ELLENA, J. |
Afiliação: |
CAUE RIBEIRO DE OLIVEIRA, CNPDIA. |
Título: |
Amino - imino tautomerism in the salt formation of Albendazole: Hydrobromide and nitrate salts. |
Ano de publicação: |
2021 |
Fonte/Imprenta: |
Crystal Growth & Design, v. 21, 2021. |
Páginas: |
1122?1135 |
ISSN: |
1528-7843 |
DOI: |
https://dx.doi.org/10.1021/acs.cgd.0c01444 |
Idioma: |
Inglês |
Conteúdo: |
Albendazole (ABZ) is a poorly soluble anthelmintic drug that can exist in amine and imine desmotropic forms. These facts can affect the solubility and bioavailability of the drug product. Here, we investigate the salt formation of ABZ with the acids HCl, HBr, and HNO3 associated with the tautomerism of the ABZ molecule. The reaction of ABZ with an excess of the acids HCl, HBr, and HNO3 results in the protonation of the imidazole ring, hiding the occurrence of tautomeric states. Thus, the ABZ HCl, ABZ HBr, and ABZ HNO3 salts were obtained and characterized by single-crystal X-ray diffraction, powder X-ray diffraction, FT-infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), and aqueous solubility measurements. Furthermore, static and dynamic DFT calculations were carried out to understand how the albendazolium cation (ABZ-H+ ) is obtained from ABZ in amine and imine forms. An analysis of crystal structures reveals that cations and anions aggregate in 1D chains stabilized by NH···X (X = Cl−, Br−, O−) interactions, generating layered structures. In solution, the intramolecular amine ↔ imine conversion (ΔG⧧ ≈ 50 kcal mol−1 ) and the solvent-mediated deprotonation of the ABZ-H+ cation (ΔG⧧ ≈ 20 kcal mol−1 ) requires a higher energy barrier to occur, allowing the independence between tautomers to propitiate the crystallization process. Consequently, the process is dependent on the tautomer population in the starting material. All salts were demonstrated to be more soluble than pure ABZ. Given the good physical−chemical profile of these salts, our results show a notable effect on the multicomponent crystal design, manufacturability, and processing of the drug ABZ. MenosAlbendazole (ABZ) is a poorly soluble anthelmintic drug that can exist in amine and imine desmotropic forms. These facts can affect the solubility and bioavailability of the drug product. Here, we investigate the salt formation of ABZ with the acids HCl, HBr, and HNO3 associated with the tautomerism of the ABZ molecule. The reaction of ABZ with an excess of the acids HCl, HBr, and HNO3 results in the protonation of the imidazole ring, hiding the occurrence of tautomeric states. Thus, the ABZ HCl, ABZ HBr, and ABZ HNO3 salts were obtained and characterized by single-crystal X-ray diffraction, powder X-ray diffraction, FT-infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), and aqueous solubility measurements. Furthermore, static and dynamic DFT calculations were carried out to understand how the albendazolium cation (ABZ-H+ ) is obtained from ABZ in amine and imine forms. An analysis of crystal structures reveals that cations and anions aggregate in 1D chains stabilized by NH···X (X = Cl−, Br−, O−) interactions, generating layered structures. In solution, the intramolecular amine ↔ imine conversion (ΔG⧧ ≈ 50 kcal mol−1 ) and the solvent-mediated deprotonation of the ABZ-H+ cation (ΔG⧧ ≈ 20 kcal mol−1 ) requires a higher energy barrier to occur, allowing the independence between tautomers to propitiate the crystallization process. Consequently, the process is dependent on the tautomer population in the starting material. Al... Mostrar Tudo |
Palavras-Chave: |
Anthelmintic; Crystal structures; Crystallization process. |
Categoria do assunto: |
-- |
Marc: |
LEADER 02599naa a2200277 a 4500 001 2131514 005 2022-06-10 008 2021 bl uuuu u00u1 u #d 022 $a1528-7843 024 7 $ahttps://dx.doi.org/10.1021/acs.cgd.0c01444$2DOI 100 1 $aCARVALHO JUNIOR, P. S. 245 $aAmino - imino tautomerism in the salt formation of Albendazole$bHydrobromide and nitrate salts.$h[electronic resource] 260 $c2021 300 $a1122?1135 520 $aAlbendazole (ABZ) is a poorly soluble anthelmintic drug that can exist in amine and imine desmotropic forms. These facts can affect the solubility and bioavailability of the drug product. Here, we investigate the salt formation of ABZ with the acids HCl, HBr, and HNO3 associated with the tautomerism of the ABZ molecule. The reaction of ABZ with an excess of the acids HCl, HBr, and HNO3 results in the protonation of the imidazole ring, hiding the occurrence of tautomeric states. Thus, the ABZ HCl, ABZ HBr, and ABZ HNO3 salts were obtained and characterized by single-crystal X-ray diffraction, powder X-ray diffraction, FT-infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), and aqueous solubility measurements. Furthermore, static and dynamic DFT calculations were carried out to understand how the albendazolium cation (ABZ-H+ ) is obtained from ABZ in amine and imine forms. An analysis of crystal structures reveals that cations and anions aggregate in 1D chains stabilized by NH···X (X = Cl−, Br−, O−) interactions, generating layered structures. In solution, the intramolecular amine ↔ imine conversion (ΔG⧧ ≈ 50 kcal mol−1 ) and the solvent-mediated deprotonation of the ABZ-H+ cation (ΔG⧧ ≈ 20 kcal mol−1 ) requires a higher energy barrier to occur, allowing the independence between tautomers to propitiate the crystallization process. Consequently, the process is dependent on the tautomer population in the starting material. All salts were demonstrated to be more soluble than pure ABZ. Given the good physical−chemical profile of these salts, our results show a notable effect on the multicomponent crystal design, manufacturability, and processing of the drug ABZ. 653 $aAnthelmintic 653 $aCrystal structures 653 $aCrystallization process 700 1 $aDINIZ, L. F. 700 1 $aSILVA, G. T. S. T. da 700 1 $aCOUTINHO, N. D. 700 1 $aSANTOS, P. G. dos 700 1 $aCARVALHO-SILVA, V. H. 700 1 $aRIBEIRO, C. 700 1 $aELLENA, J. 773 $tCrystal Growth & Design$gv. 21, 2021.
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Embrapa Instrumentação (CNPDIA) |
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Biblioteca(s): |
Embrapa Uva e Vinho. |
Data corrente: |
10/04/2024 |
Data da última atualização: |
10/04/2024 |
Tipo da produção científica: |
Resumo em Anais de Congresso |
Autoria: |
BORTOLINI, F.; SILVA, G. A. da. |
Afiliação: |
F. BORTOLINI, UNIVERSIDADE DO CONTESTADO; GILDO ALMEIDA DA SILVA, CNPUV. |
Título: |
Influência da concentração inicial de so2 sobre a evolução da acidez volátil no vinho. |
Ano de publicação: |
2005 |
Fonte/Imprenta: |
In: SIMPÓSIO LATINO AMERICANO DE CIÊNCIA DE ALIMENTOS, 6., 2005, Campinas. Ciência de alimentos: abrindo caminhos para o desenvolvimento científico, tecnológico e industrial. [S.l.]: Sociedade Brasileira de Ciência e Tecnologia de Alimentos, 2005. Resumo. |
Páginas: |
1 |
Idioma: |
Português |
Conteúdo: |
O vinho é um produto final da fermentação do mosto de uvas. É o resultado não só do notável trabalho de Saccharomyces cerevisiae, mas também das interações entre leveduras e bactérias. Além de produzir substâncias inibitórias (bacteriocinas) para leveduras e causar parada ou retardamento da fermentação, bactérias lácticas podem aumentar a acidez volátil no vinho. |
Palavras-Chave: |
Levedura. |
Thesagro: |
Saccharomyces Cerevisiae; Vinho. |
Categoria do assunto: |
-- |
URL: |
https://ainfo.cnptia.embrapa.br/digital/bitstream/doc/1163420/1/Bortolini-2005-0433-SLACA.pdf
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Marc: |
LEADER 01107nam a2200169 a 4500 001 2163420 005 2024-04-10 008 2005 bl uuuu u00u1 u #d 100 1 $aBORTOLINI, F. 245 $aInfluência da concentração inicial de so2 sobre a evolução da acidez volátil no vinho.$h[electronic resource] 260 $aIn: SIMPÓSIO LATINO AMERICANO DE CIÊNCIA DE ALIMENTOS, 6., 2005, Campinas. Ciência de alimentos: abrindo caminhos para o desenvolvimento científico, tecnológico e industrial. [S.l.]: Sociedade Brasileira de Ciência e Tecnologia de Alimentos, 2005. Resumo.$c2005 300 $a1 520 $aO vinho é um produto final da fermentação do mosto de uvas. É o resultado não só do notável trabalho de Saccharomyces cerevisiae, mas também das interações entre leveduras e bactérias. Além de produzir substâncias inibitórias (bacteriocinas) para leveduras e causar parada ou retardamento da fermentação, bactérias lácticas podem aumentar a acidez volátil no vinho. 650 $aSaccharomyces Cerevisiae 650 $aVinho 653 $aLevedura 700 1 $aSILVA, G. A. da
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