Synthesis and properties of novel chemiluminescent biological probes: substituted 4-(2-succinimidyloxycarbonylethyl)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulphonate

Substituted aryl acridinium esters, 2,6-dimethyl-4-(2-succinimidyloxycarbonylethyl)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulphonate (3), 2,6-dimethoxy-4-(2-succinimidyloxycarbonylethyl)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulphonate (4), 2-methoxy-4-(2-succinimidyloxycarbonylethyl)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulphonate (5) and 2,6-dibromo-4-(2-succinimidyloxycarbonylethyl)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulphonate (6), have been synthesised and coupled to immunoglobulin G (IgG). The chemiluminescent properties and hydrolytic stabilities of the conjugates have also been examined. The different substituents on the phenoxy ring affected the chemiluminescent efficiency and kinetics. All the human IgG conjugates of these substituted acridinium esters demonstrated much higher stability than the conjugate of the corresponding unsubstituted acridinium ester. (C) 2000 Elsevier Science S.A. All rights reserved.