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 | Acesso ao texto completo restrito à biblioteca da Embrapa Instrumentação. Para informações adicionais entre em contato com cnpdia.biblioteca@embrapa.br. |
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Registro Completo |
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Biblioteca(s): |
Embrapa Instrumentação. |
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Data corrente: |
26/04/2021 |
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Data da última atualização: |
10/06/2022 |
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Tipo da produção científica: |
Artigo em Periódico Indexado |
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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. |
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Afiliação: |
CAUE RIBEIRO DE OLIVEIRA, CNPDIA. |
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Título: |
Amino - imino tautomerism in the salt formation of Albendazole: Hydrobromide and nitrate salts. |
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Ano de publicação: |
2021 |
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Fonte/Imprenta: |
Crystal Growth & Design, v. 21, 2021. |
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Páginas: |
1122?1135 |
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ISSN: |
1528-7843 |
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DOI: |
https://dx.doi.org/10.1021/acs.cgd.0c01444 |
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Idioma: |
Inglês |
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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 |
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Palavras-Chave: |
Anthelmintic; Crystal structures; Crystallization process. |
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Categoria do assunto: |
-- |
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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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| Registros recuperados : 6 | |
| 1. |  | CANDIDO, L. A.; SOUZA, A. C. de; MOTA, M. C.; CUADRA, S. V.; FIGUEIREDO, R. C. de; MENDONZA, R. A. M. Adaptação do modelo Noah-MP-Crop para representar a cultura da soja em Rondônia, Brasil. In: CONGRESSO BRASILEIRO DE AGROMETEOROLOGIA, 22., 2023, Natal. A agrometeorologia e a agropecuária: adaptação às mudanças climáticas: anais. Natal: Sociedade Brasileira de Agrometeorologia, 2023. p. 1150-1159. CBAGRO 2023.| Tipo: Artigo em Anais de Congresso |
| Biblioteca(s): Embrapa Agricultura Digital. |
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| 2. | | ASSUNÇÃO, L. M. F. de; MANZI, A. O.; HIGUCHI, N.; CANDIDO, L. A.; RANDOW, C. von; KUBOTA, P.; ARAUJO, A.; AMARAL, I.; LUIZÃO, F. Aplicação do modelo de vegetação dinâmica IBIS às condições de floresta de terra firme na região central da Amazônia. In: CONGRESSO BRASILEIRO DE METEOROLOGIA, 17.; ENCONTRO DE METEOROLOGIA DOS PAÍSES DO MERCOSUL E ASSOCIADOS, 1.; ENCONTRO SUL AMERICANO DE APLICAÇÕES DO SISTEMA EUMETCast PARA O MONITORAMENTO METEOROLÓGICO E AMBIENTAL, 4.; ENCONTRO DE METEOROLOGIA OPERACIONAL, 2., 2012, Gramado. Anais... Gramado: UFRGS, 2012.| Tipo: Artigo em Anais de Congresso |
| Biblioteca(s): Embrapa Amazônia Oriental. |
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| 3. | | CRESTANI, M.; CANDIDO, L. A.; CUADRA, S. V.; TOMÉ, A. M.; LOPES, A. B. de A.; LIMA, F. L. de; REIS, J.; BRIZOLLA, R. M. Validação do IAF estimado a partir do coeficiente de extinção da radiação PAR. In: CONGRESSO BRASILEIRO DE AGROMETEOROLOGIA, 22., 2023, Natal. A agrometeorologia e a agropecuária: adaptação às mudanças climáticas: anais. Natal: Sociedade Brasileira de Agrometeorologia, 2023. p. 1058-1072. CBAGRO 2023.| Tipo: Artigo em Anais de Congresso |
| Biblioteca(s): Embrapa Agricultura Digital. |
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| 4. | | MOTA, M. C.; CANDIDO, L. A.; CUADRA, S. V.; MARENCO, R. A.; SOUZA, R. V. A. de; TOMÉ, A. M.; LOPES, A. B. de A.; LIMA, F. L. de; REIS, J.; BRIZOLLA, R. M. CROPGRO-soybean model – Validation and application for the southern Amazon, Brazil. Computers and Electronics in Agriculture, v. 216, 108478, Jan. 2024.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Agricultura Digital. |
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| 5. | | MOTA, M. C.; CANDIDO, L. A.; CUADRA, S. V.; MARENCO, R. A.; TOMÉ, A. M.; LOPES, A. B. de A.; LIMA, F. L. de; REIS, J.; BRIZOLLA, R. M. Validation of the leaf area index estimated using the extinction coefficient of photosynthetically active radiation in soybean. Italian Journal of Agrometeorology, v. 1, p. 19-29, 2025| Tipo: Artigo em Periódico Indexado | Circulação/Nível: B - 1 |
| Biblioteca(s): Embrapa Agricultura Digital. |
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| 6. | | SOLANDER, K. C.; NEWMAN, B. D.; ARAUJO, A. C. de; BARNARD, H. R.; BERRY, Z. C.; BONAL, D.; BRETFELD, M.; BURBAN, B.; CANDIDO, L. A.; CÉLLERI, R.; CHAMBERS, J. Q.; CHRISTOFFERSEN, B. O.; DETTO, M.; DORIGO, W. A.; EWERS, B. E.; FERREIRA, S. J. F.; KNOHL, A.; LEUNG, L. R.; McDOWELL, N. G.; MILLER, G. R.; MONTEIRO, M. T. F.; MOORE, G. W.; NEGRON-JUAREZ, R.; SALESKA, S. R.; STIEGLER, C.; TOMASELLA, J.; XU, C. The pantropical response of soil moisture to El Niño. Hydrology and Earth System Sciences, v. 24, n. 5, p. 2303-2322, 2020.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Amazônia Oriental. |
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| Registros recuperados : 6 | |
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