Encapsulation of the Antioxidant R-(+)-α-Lipoic Acid in Permethylated α- and β-Cyclodextrins: Thermal and X-ray Structural Characterization of the 1:1 Inclusion Complexes
| العنوان: | Encapsulation of the Antioxidant R-(+)-α-Lipoic Acid in Permethylated α- and β-Cyclodextrins: Thermal and X-ray Structural Characterization of the 1:1 Inclusion Complexes |
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| المؤلفون: | Mino R. Caira, Buntubonke Mzondo, Susan A. Bourne |
| المصدر: | Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry Molecules; Volume 22; Issue 6; Pages: 866 |
| بيانات النشر: | MDPI, 2017. |
| سنة النشر: | 2017 |
| مصطلحات موضوعية: | crystal structure, Antioxidant, antioxidant, Stereochemistry, medicine.medical_treatment, Pharmaceutical Science, Crystal structure, 010402 general chemistry, Crystallography, X-Ray, 01 natural sciences, Article, Antioxidants, Analytical Chemistry, chemistry.chemical_compound, X-Ray Diffraction, Drug Discovery, medicine, Molecule, Thermal stability, R-(+)-α-lipoic acid, cyclodextrins, thermal analysis, X-ray diffraction, stability, Physical and Theoretical Chemistry, Thermal analysis, 010405 organic chemistry, Chemistry, Organic Chemistry, beta-Cyclodextrins, RALA, 0104 chemical sciences, Lipoic acid, Chemistry (miscellaneous), X-ray crystallography, Molecular Medicine |
| الوصف: | The naturally occurring compound α-lipoic acid (ALA) is implicated in manifold critical biological roles and its potent antioxidant properties and potential for treatment of various diseases have led to its widespread use as a dietary supplement. However, shortcomings of poor aqueous solubility and low thermal stability have hampered its development as a medicinal agent, prompting the use of cyclodextrins (CDs) to address these problems. The paucity of published structural data on the nature of the interactions between ALA and CDs motivated the present study, which describes the synthesis and X-ray structural elucidation of crystalline inclusion complexes between the biologically relevant R-(+)-α-lipoic acid (RALA) and the host molecules permethylated α-CD (TMA) and permethylated β-CD (TMB). Single crystal X-ray diffraction of TMA·RALA·6H2O and TMB·RALA revealed significantly different orientations of the RALA molecule within the TMA and TMB cavities, but in both cases the guest molecule is fully encapsulated by the respective parent host molecules and residues of CD molecules of neighboring complex units. While pure RALA melted at 46–48 °C, combined thermal analysis techniques indicated that on heating the respective complexes, the release of RALA occurred at significantly higher onset temperatures, in the range 150–170 °C. |
| وصف الملف: | application/pdf |
| اللغة: | English |
| تدمد: | 1420-3049 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::3976dd2732919fefa5fd64c75bf994cfTest http://europepmc.org/articles/PMC6152681Test |
| حقوق: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....3976dd2732919fefa5fd64c75bf994cf |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 14203049 |
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