title: Design and studies of novel polyoxysterol-based porphyrin conjugates.
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.
authors: Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk, Belarus.
authors: Halina A
authors: HA
authors: Zhylitskaya
authors: Vladimir N
authors: VN
authors: Zhabinskii
authors: Raisa P
authors: RP
authors: Litvinovskaya
authors: Raffaella
authors: R
authors: Lettieri
authors: Donato
authors: D
authors: Monti
authors: Mariano
authors: M
authors: Venanzi
authors: Vladimir A
authors: VA
authors: Khripach
authors: Pavel
authors: P
authors: Drašar
mesh_terms: D001897:Boronic Acids / Q000737:chemistry; D060406:Brassinosteroids / Q000737:chemistry*; D002942:Circular Dichroism; D004441:Ecdysterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis*; D012997:Solvents; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D013260:Steroids, Heterocyclic / Q000737:chemistry*; D014867:Water
chemical_list: D001897:Boronic Acids; D060406:Brassinosteroids; D004952:Esters; D011166:Porphyrins; D012997:Solvents; D013260:Steroids, Heterocyclic; D014867:Water; D004441:Ecdysterone; C023623:brassinolide