Synthesis of 2-substituted beta-cyclodextrin derivatives with a hydrolytic activity against the organophosphorylester paraoxon.
Beta-cyclodextrin was substituted by an iodosobenzoic acid derivative to create a catalytic hydrolytic activity against neurotoxic organophosphorus agents. The catalytic moiety was introduced on a secondary hydroxy group at the position 2 of a glucose unit. Several beta-cyclodextrin derivatives were obtained. In these derivatives, the methylene linker occupied all potential positions on the aromatic ring. Kinetic assays were carried out with paraoxon as organophosphate model. Three regioisomers hydrolyzed paraoxon, although the paraoxon-leaving group, para-nitrophenol, was not released from the beta-cyclodextrin torus.
Masurier
Nicolas
N
Laboratoire de Pharmacochimie, Département de Chimie Organique Pharmaceutique, Faculté de Médecine et de Pharmacie de Rouen, 22 Boulevard Gambetta, 76183 Rouen cedex 1, France.
Estour
François
F
Froment
Marie-Thérèse
MT
Lefèvre
Bertrand
B
Debouzy
Jean-Claude
JC
Brasme
Bernard
B
Masson
Patrick
P
Lafont
Olivier
O
D002384:Catalysis; D002800:Cholinesterase Inhibitors / Q000737:chemistry; D006868:Hydrolysis; D007306:Insecticides / Q000737:chemistry; D007700:Kinetics; D010261:Paraoxon / Q000737:chemistry*; D020011:Protective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry
D002800:Cholinesterase Inhibitors; D007306:Insecticides; D020011:Protective Agents; D047392:beta-Cyclodextrins; D010261:Paraoxon