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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 | |
| 2. |  | SILVA, V. H.; GIACHETTO, P. F.; TIZIOTO, P. L.; GONÇALVES, T. M.; REGITANO, L. C. A.; COUTINHO, L. L. A network landscape from CNVs to Nellore cattle beef tenderness. In: INTERNATIONAL SYMPOSIUM ON ANIMAL FUNCTIONAL GENOMICS, 5., 2013, Guarujá. Programme and abstract book... [S.l.: s.n.], 2013. p. 8. ISAFG 2013. AB.01.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Agricultura Digital; Embrapa Pecuária Sudeste. |
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| 3. | | GODOY, T. F.; SILVA, V. H.; TESSMANN, A. L.; PANDOLFI, J. R. C.; PEIXOTO, J. de O.; COUTINHO, L. L.; LEDUR, M. C. Adiponectin receptor 2 gene associated with bone traits in broiler chickens. In: CONGRESSO BRASILEIRO DE GENÉTICA, 60., 2014, Guarujá. Resumos... Ribeirão Preto: Sociedade Brasileira de Genética, 2014. p. 39.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 4. | | 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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| 5. | | GONÇALVES, T. M.; ANDRADE, S. C. S.; GASPARIN, G.; SILVA, V. H. da; REGITANO, L. C. de A.; COUTINHO, L. L. Glutathione pathway could be associated with meat tenderness in Nellore. In: INTERNATIONAL SYMPOSIUM ON ANIMAL FUNCTIONAL GENOMICS, 5., 2013, Guarujá. Abstract... Guarujá:[ s.n.], 2013. AB.40.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Pecuária Sudeste. |
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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. | | GODOY, T. F.; SILVA, V. H. da; MOREIRA, G. C. M.; BOSCHIERO, C.; LEDUR, M. C.; CROOIJAMANS, R. P.; GROENEN, M. A. M.; COUTINHO, L. L. Inherited CNVs in regions related to breast muscle development in a broiler population. In: PLANT AND ANIMAL GENOME CONFERENCE, 26., 2018, San Diego. Abstracts... [S.l. : s.n.], 2018. Paper 29816. Organizers: Sébastien Praud and Kellye Eversole. PAG XXVI.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 9. | | SILVA, V. H.; PANDOLFI, J. R. C.; GODOY, T. F.; PEIXOTO, J. de O.; TESSMANN, A. L.; CANTAO, M. E.; LEDUR, M. C. Hepatocyte nuclear factor 4 gene associated with bone traits and birth weight in male chickens. In: CONGRESSO BRASILEIRO DE GENÉTICA, 59., 2013, Águas de Lindóia. Resumos... Ribeirão Preto: SBG, 2013. p. 27.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 10. | | GODOY, T. F.; MOREIRA, G. C. M.; SILVA, V. H.; BOSCHIERO, C.; LEDUR, M. C.; MOURA, A. S. A. M. T.; COUTINHO, L. L. Identification of CNVs on the genome of Brazilian chicken lines. In: PLANT & ANIMAL GENOME CONFERENCE, 24., 2016, San Diego, CA. [Abstracts...]. San Diego: [s.n.], 2016. Pôster P0646.| Tipo: Resumo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 11. | | 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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| 12. | | FERNANDES, L. T.; GODOY, T. F.; SILVA, V. H.; PANDOLFI, J. R. C.; CANTAO, M. E.; PEIXOTO, J. de O.; COUTINHO, L. L.; LEDUR, M. C. Sex-specific association of a SNP in the ADIPOR2 gene with carcass traits in a paternal broiler line. In: WORLD CONGRESS OF GENETICS APPLIED TO LIVESTOCK PRODUCTION, 10., 2014, Vancouver. Proceedings... Vancouver: WCGALP: American Society of Animal Science, 2014.| Tipo: Artigo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 13. | | GEISTLINGER, L.; SILVA, V. H. da; CESAR, A. S. M.; TIZIOTO, P. C.; WALDRON, L.; ZIMMER, R.; REGITANO, L. C. de A.; COUTINHO, L. L. Widespread modulation of gene expression by copy number variation in skeletal muscle. Scientific Reports, v. 8, n. 1399, p. 1-11, jan. 2018.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Pecuária Sudeste. |
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| 14. | | FERNANDES, A. C.; SILVA, V. H. da; GOES, C. P.; MOREIRA, G. C. M.; GODOY, T. F.; IBELLI, A. M. G.; PEIXOTO, J. de O.; CANTAO, M. E.; LEDUR, M. C.; REZENDE, F. M. de; COUTINHO, L. L. Genome-wide detection of CNVs and their association with performance traits in broilers. BMC Genomics, v. 22, n. 354, 2021.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 15. | | MOREIRA, G. C. M.; GODOY, T. F.; BOSCHIERO, C.; CESAR, A. S. M.; REECY, J. M.; LEDUR, M. C.; GARRICK, D.; SILVA, V. H. da; CROOIJAMANS, R. P.; GROENEN, M. A. M.; COUTINHO, L. L. Integration of GWAS, CNV and sele ction signature reveals candidate genes for abdominal fat regulation in chickens. In: WORLD CONGRESS ON GENETICS APPLIED TO LIVESTOCK PRODUCTION, 11., 2018, Auckland, New Zealand. Proceedings... Massey University, 2018. Digital Archive.| Tipo: Artigo em Anais de Congresso |
| Biblioteca(s): Embrapa Suínos e Aves. |
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| 16. | | RAMOS, B.; VAZ, W. F.; DINIZ, L. F.; SANCHES NETO, F. O.; RIBEIRO, J. C. O.; CARVALHO-SILVA, V. H.; TEIXEIRA, A. C. S. C.; RIBEIRO, C.; NAPOLITANO, H. B.; CARVALHO JR, P. S. Kinetics, mechanism, and tautomerism in ametryn acid hydrolysis: From molecular structure to environmental impacts. Chemosphere, v. 324, 138278, 2023. 1 - 10| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Instrumentação. |
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| 17. | | BRUSCADIN, J. J.; CARDOSO, T. F.; DINIZ, W. J. da S.; AFONSO, J.; SOUZA, M. M. de; PETRINI, J.; ANDRADE, B. G. N.; SILVA, V. H. da; FERRAZ, J. B. S.; ZERLOTINI NETO, A.; MOURÃO, G. B.; COUTINHO, L. L.; REGITANO, L. C. de A. Allele-specific expression reveals functional SNPs affecting muscle-related genes in bovine. Biochimica et Biophysica Acta. Gene Regulatory Mechanisms, v. 1865, n. 8, 194886, Nov. 2022.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Agricultura Digital; Embrapa Pecuária Sudeste. |
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| Registros recuperados : 17 | |
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| Nenhum registro encontrado para a expressão de busca informada. |
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