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| 7. |  | PLOTEGHER, F.; RIBEIRO, C. Moagem e caracterização de uma rocha fosfática natural (bayovar) com potencial uso para fertilização direta. In: WORKSHOP DA REDE DE NANOTECNOLOGIA APLICADA AO AGRONEGÓCIO, 8, 2014, Juiz de fora. Anais... São Carlos: Embrapa Instrumentação; Campo Grande: Embrapa Gado de Corte; Juiz de Fora: Embrapa Gado de Leite, 2014. p. 403-407. Editores: Maria Alice Martins, Humberto de Mello Brandão, Marlene de Barros Coelho, Daniel Souza Corrêa, Caue Ribeiro, Luiz Henrique Capparelli Mattoso.| Biblioteca(s): Embrapa Instrumentação. |
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| 18. | | PLOTEGHER, F.; RIBEIRO, C. Avaliação do potencial uso direto de rochas fosfáticas para a fertilização de solos: um estudo inicial. In: WORKSHOP DA REDE DE NANOTECNOLOGIA APLICADA AO AGRONEGÓCIO, 7.; ESCOLA DE NANOTECNOLOGIA, 3., 2013, São Carlos, SP. Anais... São Carlos, SP: Embrapa Instrumentação, 2013. p. 439-441 Editores: Maria Alice Martins, Odílio Benedito Garrido de Assis, Caue Ribeiro, Luiz Henrique Capparelli Mattoso. CD-ROM. Editores: Maria Alice Martins, Odílio Benedito Garrido de Assis, Caue Ribeiro, Luiz Henrique Capparelli Mattoso.| Biblioteca(s): Embrapa Instrumentação. |
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| 20. | | PLOTEGHER, F.; RIBEIRO, C. Caracterização do fertilizante superfosfato simples - um estudo sobre o efeito da moagem sobre a cinética de solubilidade. In: WORKSHOP DA REDE DE NANOTECNOLOGIA APLICADA AO AGRONEGÓCIO, 8, 2014, Juiz de fora. Anais... São Carlos: Embrapa Instrumentação; Campo Grande: Embrapa Gado de Corte; Juiz de Fora: Embrapa Gado de Leite, 2014. p. 395-399. Editores: Maria Alice Martins, Humberto de Mello Brandão, Marlene de Barros Coelho, Daniel Souza Corrêa, Caue Ribeiro, Luiz Henrique Capparelli Mattoso.| Biblioteca(s): Embrapa Instrumentação. |
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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. |
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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Circulação/Nível: |
A - 1 |
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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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