NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins
| Autor: | Inmaculada Fernández, Noureddine Khiar, Rocío Recio, Juan Andrés Benito, Eleonora Elhalem |
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| Přispěvatelé: | Ministerio de Economía y Competitividad (España), Evgen Pharma, Junta de Andalucía, Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica, Ministerio de Economía y Competitividad (MINECO). España |
| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Polymers and Plastics Stereochemistry Sulforaphane stabilty 010402 general chemistry 01 natural sciences 03 medical and health sciences chemistry.chemical_compound Materials Chemistry chemistry.chemical_classification Cyclodextrins Chiral discrimination Cyclodextrin Organic Chemistry Ciencias Químicas Absolute configuration Affinity constant Nuclear magnetic resonance spectroscopy 0104 chemical sciences Chemical instability Química Orgánica 030104 developmental biology chemistry Affinity constants Isothiocyanate Sulforaphane analogues Enantiomer Sulforaphane CIENCIAS NATURALES Y EXACTAS |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname idUS. Depósito de Investigación de la Universidad de Sevilla |
| ISSN: | 1879-1344 |
| Popis: | Sulforaphane (SFN), a phytochemical isolated from broccoli, is an important antitumoral compound with additional beneficial effect on other important diseases. However, the chemical instability of SFN has hampered its clinical use. In order to circumvent this problem, we report the first comparative study on the inclusion complexes of SFN and SFN homologues with different cyclodextrins by NMR spectroscopy. From this study it has been shown that α-CD is the most indicated cyclodextrin for the stabilization of SFN and SFN homologues, and that the highest affinity constant is that of the isothiocyanate obtained from the wasabi. Furthermore, the study of the inclusion complexes of α-CD and the non-natural SFN and analogues with S absolute configuration at sulfur shows for the first time that α-CD is able to discriminate between the two enantiomers, with the natural R enantiomers forming the inclusion complexes with higher affinity. This work was supported by the Ministerio de Economía y Competitividad (grants No. CTQ2016-78580-C2-1-R, and CTQ2016-78580-C2-2-R), the Junta de Andalucía (P11-FQM-8046), and Evgen Pharma. |
| Databáze: | OpenAIRE |
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