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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 Unidades Centrais. |
Data corrente: |
29/12/2016 |
Data da última atualização: |
16/06/2017 |
Autoria: |
BUAINAIN, A. M.; JARDIM, A.; ALVES, E. R. de A.; BARROS, J. R. M. de; NETO, O.; NAVARRO, Z. S. de. |
Afiliação: |
ANTÔNIO MÁRCIO BUAINAIN, INSTITUTO DE ECONOMIA DA UNICAMP; ARNALDO JARDIM, SECRETÁRIO DA AGRICULTURA DE SÃO PAULO; ELISEU ROBERTO DE ANDRADE ALVES, DE/PR; JOSÉ ROBERTO MENDONÇA DE BARROS, DIRETOR PRESIDENTE DA MB ASSOCIADOS; OCTACIANO NETO, SECRETÁRIO DA AGRICULTURA DO ESPÍRITO SANTO; ZANDER SOARES DE NAVARRO, SIM. |
Título: |
A economia agropecuária brasileira. O que fazer? |
Ano de publicação: |
2016 |
Fonte/Imprenta: |
O Estado de São Paulo, São Paulo, 15 maio 2016. Caderno de Economia, p. B8. |
Idioma: |
Português |
Palavras-Chave: |
Agropecuária. |
Thesagro: |
Economia. |
Categoria do assunto: |
-- |
URL: |
https://ainfo.cnptia.embrapa.br/digital/bitstream/item/152546/1/A-economia-agropecuaria-brasileira..pdf
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Marc: |
LEADER 00570naa a2200193 a 4500 001 2059614 005 2017-06-16 008 2016 bl uuuu u00u1 u #d 100 1 $aBUAINAIN, A. M. 245 $aA economia agropecuária brasileira. O que fazer?$h[electronic resource] 260 $c2016 650 $aEconomia 653 $aAgropecuária 700 1 $aJARDIM, A. 700 1 $aALVES, E. R. de A. 700 1 $aBARROS, J. R. M. de 700 1 $aNETO, O. 700 1 $aNAVARRO, Z. S. de 773 $tO Estado de São Paulo, São Paulo, 15 maio 2016. Caderno de Economia, p. B8.
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