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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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Registro original: |
Embrapa Instrumentação (CNPDIA) |
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| Registros recuperados : 17 | |
| 3. |  | MOREIRA, G. C. M.; PÉRTILLE, F.; GODOY, T. F.; BRASSOLOTI, R.; BOSCHIERO, C.; LEDUR, M. C.; COUTINHO, L. L. Discovery of candidate genes for fatness in chickens based on genotyping with 600K SNP chip in a QTL region. In: CONGRESSO BRASILEIRO DE GENÉTICA, 60., 2014, Guarujá. Resumos? Ribeirão Preto: Sociedade Brasileira de Genética, 2014. p. 64| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 4. | | SOUZA, M. A. de; SILVA, M. V. G. B.; COSTA, C. N.; ATTÍLIO, D. B.; PÉRTILLE, F.; COUTINHO, L. L. Frequências de variantes alélicas dos genes LGB, OPN, BLAD, DGAT1, CVM e DUMPS. In: REUNIÃO ANUAL DA SOCIEDADE BRASILEIRA DE ZOOTECNIA, 48., 2011, Belém, PA. O desenvolvimento da produção animal e a responsabilidade frente a novos desafios: anais. Viçosa, MG: Sociedade Brasileira de Zootecnia, 2011.| Tipo: Artigo em Anais de Congresso |
| Biblioteca(s): Embrapa Gado de Leite. |
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| 5. | | PÉRTILLE, F.; ZANELLA, R.; FELÍCIO, A. M.; LEDUR, M. C.; PEIXOTO, J. de O.; COUTINHO, L. L. Identification of polymorphisms associated with production traits on chicken (Gallus gallus) chromosome 4. Genetics and Molecular Research, v. 14, n. 3, p. 10717-10728, 2015.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 6. | | SILVA, V. H. da; REGITANO, L. C. de A.; GEISTLINGER, L.; PÉRTILLE, F.; GIACHETTO, P. F.; BRASSALOTI, R. A.; MOROSINI, N. S.; ZIMMER, R.; COUTINHO, L. L. Genome-wide detection of CNVs and their association with meat tenderness in Nelore cattle. Plos One, june 2016.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Pecuária Sudeste. |
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| 7. | | PÉRTILLE, F.; BOSAGNA, C. G.; SILVA, V. H. da; BOSCHIERO, C.; NUNES, J. de R. da S.; LEDUR, M. C.; JENSEN, P.; COUTINHO, L. L. High-throughput and cost-effective chicken genotyping using next-generation sequencing. Scientific Reports, v. 6, n. 26929, 2016.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 8. | | PÉRTILLE, F.; TESSMANN, A. L.; COUTINHO, L. L.; AVILA, V. S. de; PEIXOTO, J. de O.; COLDEBELLA, A.; LEDUR, M. C. Investigation of the LEPR1 A>G polymorphism in the leptin receptor gene in a commercial broiler population. In: CONGRESSO BRASILEIRO DE GENÉTICA, 57., 2011, Águas de Lindóia. Resumos. Águas de Lindóia: SBG, 2011. p.103. Projeto/Plano de Ação: 01.06.10602-03.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 9. | | PÉRTILLE, F.; FELÍCIO, A. M.; ROSÁRIO, M. F. do; SILVA, V. H.; MANGUETTI, T.; SILVA, N. A.; LEDUR, M. C.; COUTINHO, L. L. PPARGC1A indel polymorphism is associated with performance and carcass traits in chickens. In: CONGRESSO BRASILEIRO DE GENÉTICA, 58., 2012, Foz do Iguaçu. Resumos... Foz do Iguaçú: SBG, 2012. p. 72| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 10. | | PÉRTILLE, F.; IBELLI, A. M. G.; SHARIF, M. E.; POLETI, M. D.; FRÖHLICH, A. S.; REZAEI, S.; LEDUR, M. C.; JENSEN, P.; GUERRERO-BOSAGNA, C.; COUTINHO. L. L. Putative epigenetic biomarkers of stress in red blood cells of chickens reared across different biomes. Frontiers in Genetics, 20 Nov 2020.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 11. | | MOREIRA, G. C. M.; POLETI, M. D.; PÉRTILLE, F.; BOSCHIERO, C.; CESAR, A. S. M.; GODOY, T. F.; LEDUR, M. C.; REECY, J. M.; GARRICK, D. J.; COUTINHO, L. L. Unraveling genomic associations with feed efficiency and body weight traits in chickens through an integrative approach. BMC Genetics, v. 20, n. 83, 2019.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 2 |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 12. | | PERTILLE, F.; MOREIRA, G. C. M. M.; ZANELLA, R.; NUNES, J. de R. da S.; BOSCHIERO, C.; ROVADOSCKI, G. A.; MOURÃO, G. B.; LEDUR, M. C.; COUTINHO, L. L. Genome-wide association study for performance traits in chickens using genotype by sequencing approach. Scientific Reports, v. 7, n. 41748, 2017.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 13. | | ZANELLA, R.; LAGO, L. V.; SILVA, A. N. da; PÉRTILLE, F.; CARVALHO, N. S. de; PANETTO, J. C. do C.; ZANELLA, G. C.; FACIOLI, F. L.; SILVA, M. V. G. B. Genetic characterization of Indubrasil cattle breed population. Veterinary Sciences, v. 5, n. 4, 2018. 10 p.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: B - 5 |
| Biblioteca(s): Embrapa Gado de Leite. |
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| 14. | | MOREIRA, G. C. M.; BOSCHIERO, C.; CESAR, A. S. M.; REECY, J. M.; GODOY, T. F.; PÉRTILLE, F.; LEDUR, M. C.; MOURA, A. S. A. M. T. M.; GARRICK, D. J.; COUTINHO, L. L. Integration of genome wide association studies and whole genome sequencing provides novel insights into fat deposition in chicken. Scientific Reports, v. 8, n. 16222, 2018.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 15. | | DAL PIZZOL, M. S.; IBELLI, A. M. G.; MORÉS, N.; MORES, M. A. Z.; PEIXOTO, J. de O.; SAVOLDI, I. R.; PERTILLE, F.; MARIANI, P. D. S. C.; COUTINHO, L. L.; LEDUR, M. C. Perfil de metilação diferencial no cromossomo 6 de suínos normais e afetados com osteocondrose latens. In: JORNADA DE INICIAÇÃO CIENTÍFICA, 13., 2019, Concórdia. Anais... Concórdia: Embrapa Suínos e Aves: UNC, 2019. p. 36-37. JINC 2019.| Tipo: Artigo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 16. | | DAL PIZZOL, M. S.; IBELLI, A. M. G.; SALMÓRIA, L. A.; MORES, M. A. Z.; PEIXOTO, J. de O.; SAVOLDI, I. R.; PERTILLE, F.; MARIANI, P. D. S. C.; COUTINHO, L. L.; LEDUR, M. C. Perfil de metilação diferencial em suínos normais e afetados com osteocondrose latens. In: SIMPÓSIO BRASILEIRO DE MELHORAMENTO ANIMAL ON-LINE, 14., 2021. Anais... Chapecó: UDESC: Concórdia: Embrapa Suínos e Aves, 2022.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 17. | | POLETI, M. D.; REGITANO, L. C. de A.; SOUZA, G. H. M. F.; CESAR, A. S. M.; SIMAS, R. C.; VIGNATTO, B. S.; MONTENEGRO, H.; PÉRTILLE, F.; BALIEIRO, J. C. C.; CAMERON, L. C.; ELER, J. P.; COUTINHO, L. L. Proteome alterations associated with the oleic acid and cis-9, trans-11 conjugated linoleic acid content in bovine skeletal muscle. Journal of Proteomics, v. 222, p. 1-14, e103792, jun. 2020.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Pecuária Sudeste. |
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| Registros recuperados : 17 | |
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