Steroid-based Head to Tail Amphiphiles as Effective Iono- and Protonophores
| Autor: | Paolo Tecilla, Irene Izzo, Elena Cressina, Francesco De Riccardis, Elvira Avallone, Massimo Fregonese |
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| Přispěvatelé: | Avallone, E., Cressina, E., Fregonese, M., Tecilla, Paolo, Izzo, I., DE RICCARDIS, F. |
| Jazyk: | angličtina |
| Rok vydání: | 2005 |
| Předmět: |
Stereochemistry
medicine.medical_treatment Sodium trasporto Organic Chemistry chemistry.chemical_element Polyene Biochemistry Fluorescence spectroscopy Steroid ionofori chemistry.chemical_compound Membrane chimica supramolecolare chemistry Drug Discovery medicine Side chain Stereoselectivity Conjugate |
| Popis: | The synthesis of five steroid-oligo(ethyleneglycol) conjugates ( 1 – 5 ) has been accomplished starting from commercially available epi -androsterone ( 8 ) and known 3β-[( tert -butyldiphenylsilyl)oxy]-5α-23,24-bisnorchol-16-en-6α,7β,22-triol ( 27 ). The synthetic strategy was based on a convergent approach including stereoselective C-17 side chains construction and standard coupling reactions. The activities of the head-to-tail amphiphiles, once incorporated in 95:5 egg PC/PG vesicular membranes, have been assessed by direct determination of transported species by NMR techniques ( 23 Na + ) and fluorescence spectroscopy (H + ). The sodium and proton transmembrane transport was compared to those evaluated for the polyene macrolide antibiotic amphotericin B and those shown by the known related C 2 -symmetric sterol-polyether conjugates 6 and 7 . |
| Databáze: | OpenAIRE |
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