New types of steroid-porphyrin conjugates derived from 20-hydroxyecdysone (20E) and 24-epibrassinolide (EBl) were synthesized. An exceptional regioselectivity in the reaction of both steroids with porphyrin boronic acids was found to give side-chain-conjugated boronic esters as sole products. UV–Vis-, fluorescence and NMR spectroscopy yielded similar data for all the studied compounds confirming the solvent driven supramolecular assembly with formation of J-aggregates. CD measurements of water diluted solutions showed a clear difference between 20E and EBl conjugates. The latter showed a strong supramolecular chirality, whereas 20E J-aggregates did not.
Zhylitskaya, H., Zhabinskii, V., Litvinovskaya, R., Lettieri, R., Monti, D., Venanzi, M., et al. (2012). Design and studies of novel polyoxysterol-based porphyrin conjugates. STEROIDS, 77, 1169-1175 [10.1016/j.steroids.2012.07.005].
Design and studies of novel polyoxysterol-based porphyrin conjugates
Lettieri, R;MONTI, DONATO;VENANZI, MARIANO;
2012-01-01
Abstract
New types of steroid-porphyrin conjugates derived from 20-hydroxyecdysone (20E) and 24-epibrassinolide (EBl) were synthesized. An exceptional regioselectivity in the reaction of both steroids with porphyrin boronic acids was found to give side-chain-conjugated boronic esters as sole products. UV–Vis-, fluorescence and NMR spectroscopy yielded similar data for all the studied compounds confirming the solvent driven supramolecular assembly with formation of J-aggregates. CD measurements of water diluted solutions showed a clear difference between 20E and EBl conjugates. The latter showed a strong supramolecular chirality, whereas 20E J-aggregates did not.| File | Dimensione | Formato | |
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