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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 : 45 | |
| 4. |  | MENDONÇA, V. R.; LOPES, O. F.; NOGUEIRA, A. E.; SILVA, G. T. S. T.; RIBEIRO, C. Challenges of synthesis and environmental applications of metal-free nano-heterojunctions. In: INAMUDDIN, G. S.; KUMAR, A.; LICHITFOUSE, E.; ASIRI, A. M. (Eds.). Nanophotocatalysis and Environmental Applications: Spinger, Cham, 2019. 108-130 Chapter 4| Tipo: Capítulo em Livro Técnico-Científico |
| Biblioteca(s): Embrapa Instrumentação. |
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| 9. | | SILVA, G. T. S. T. da; CARVALHO, K. T.; LOPES, O. F.; OLIVEIRA, C. R. de. Photocatalytic degradation of organic compounds over g-C3N4/Nb2O5 heterostructures. In: INTERNATIONAL CONGRESS ON CERAMICS, 7., CONGRESSO BRASILEIRO DE CERÂMICA, 62., 2018, Foz do Iguaçu. Resumos... Foz do Iguaçu: Metallum, 2018. p. 379.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Instrumentação. |
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| 11. | | SILVA, G. T. S. T.; CARVALHO, K. T. G.; LOPES, O. F.; OLIVEIRA, C. R. de. Síntese sonoquímica de heteroestruturas g-C3N4/Nb2O5: avaliação da perfomance fotocatalítica para degradação de poluentes orgânicos. In: WORKSHOP DA REDE DE NANOTECNOLOGIA APLICADA AO AGRONEGÓCIO, 9., 2017, São Carlos. Anais ... São Carlos: Embrapa Instrumentação, 2017. p.487-490. Editores: Caue Ribeiro de Oliveira, Elaine Cristina Paris, Luiz Henrique Capparelli Mattoso, Marcelo Porto Bemquerer, Maria Alice Martins, Odílio Benedito Garrido de Assis.| Tipo: Artigo em Anais de Congresso |
| Biblioteca(s): Embrapa Instrumentação. |
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| 12. | | TORRES, J. A.; NOGUEIRA, A. E.; SILVA, G. T. S. T.; OLIVEIRA, C. R. de. Redução fotocatalítica de CO2: influência do caráter básico do MgO. In: WORKSHOP DA REDE DE NANOTECNOLOGIA APLICADA AO AGRONEGÓCIO, 9., 2017, São Carlos. Anais ... São Carlos: Embrapa Instrumentação, 2017. p.414-417. Editores: Caue Ribeiro de Oliveira, Elaine Cristina Paris, Luiz Henrique Capparelli Mattoso, Marcelo Porto Bemquerer, Maria Alice Martins, Odílio Benedito Garrido de Assis.| Tipo: Artigo em Anais de Congresso |
| Biblioteca(s): Embrapa Instrumentação. |
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| 13. | | BOLFE, E. L.; PENA JUNIOR, M. A. G.; CONTINI, E.; D'OLIVEIRA, F. M.; SILVA, G. T. S. da. Base de dados da agropecuária brasileira: planejamento estratégico e desenvolvimento. Brazilian Journal of Development, Curitiba, v. 5, n. 1, p. 201-214, jan. 2019.| Tipo: Artigo em Periódico Indexado |
| Biblioteca(s): Embrapa Unidades Centrais. |
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| 15. | | NOGUEIRA, A. E.; SILVA, G. T. S. T.; OLIVEIRA, J. A.; TORRES, J. A.; SILVA, M.; CARMO, M.; RIBEIRO, C. Unveiling copper oxide role in CO2 photoreduction process - catalyst or reactant? In: SPRING MEETING OF THE EUROPEAN MATERIALS RESEARCH SOCIETY, 37. 2019, Nice, França, 2019.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Instrumentação. |
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| 17. | | MENDES, J. O. S.; CARVALHO, K. T. G.; SILVA, G. T. S. T. da; OLIVEIRA, C. R. de. Studies of photocatalytic reduction of carbon dioxide for renewable fuel production using niobium oxide. In: INTERNATIONAL CONGRESS ON CERAMICS, 7., CONGRESSO BRASILEIRO DE CERÂMICA, 62., 2018, Foz do Iguaçu. Resumos... Foz do Iguaçu: Metallum, 2018. p. 381.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Instrumentação. |
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| 18. | | 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. Amino - imino tautomerism in the salt formation of Albendazole: Hydrobromide and nitrate salts. Crystal Growth & Design, v. 21, 2021. 1122?1135| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Instrumentação. |
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| 19. | | OLIVEIRA, J. A.; SILVA, R. R. M.; SILVA, G. T. S. T. da; TORRES, J. A.; VALI, A.; RIBEIRO, C.; KRISHNAN, R.; RUOTOLO, L. A. M. Copper vanadates: Targeted synthesis of two pure phases and use in a photoanode/cathode setup for selective photoelectrochemical conversion .of carbon dioxide to liquid fuel. Materials Research Bulletin, v 149, 111716, 2022.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Instrumentação. |
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| 20. | | RIBEIRO, C.; SILVA, G. T. S. T.; NOGUEIRA, A. E.; TORRES, J. A.; OLIVEIRA, J. A.; LOPES, O. F.; CARMO, M. From environmental applications to renewable energy production: an overview about Nb2O5 and related materials. In: SPRING MEETING OF THE EUROPEAN MATERIALS RESEARCH SOCIETY, 37. 2019, Nice, França, 2019.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Instrumentação. |
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| Registros recuperados : 45 | |
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