title: Regioselective synthesis of cyclodextrin mono-substituted conjugates of non-steroidal anti-inflammatory drugs at C-2 secondary hydroxyl by protease in non-aqueous media.
abstract: Three beta-cyclodextrin (beta-CD) conjugates of non-steroidal anti-inflammatory drugs were synthesized by enzymatic methods. Transesterification of beta-CD with vinyl ester of indomethacin, ketoprofen and etodolac was performed by the catalysis of alkaline protease from Bacillus subtilis in anhydrous DMF for 3 days. The drug molecules were selectively conjugated onto one of the secondary hydroxyl groups of beta-CD through ester-linkage to improve their poor water solubility and absorption characteristics. The products were characterized by ESI-MS, (1)H NMR and (13)C NMR. The structures of products with monoacylation occurring at the C-2 secondary hydroxyl groups of beta-CD were confirmed.
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
authors.forename: Na
authors.initials: N
authors.lastname: Wang
authors.forename: Qi
authors.initials: Q
authors.lastname: Wu
authors.forename: Yong Mei
authors.initials: YM
authors.lastname: Xiao
authors.forename: Chun Xiu
authors.initials: CX
authors.lastname: Chen
authors.forename: Xian Fu
authors.initials: XF
authors.lastname: Lin
mesh_terms: D000215:Acylation; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry; D003505:Cyclodextrins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010447:Peptide Hydrolases / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D003505:Cyclodextrins; D010447:Peptide Hydrolases