High stability and high efficiency chemiluminescent acridinium compounds obtained from 9-acridine carboxylic esters of hydroxamic and sulphohydroxamic acids

A series of hydroxamic acids and sulphohydroxamic acids were prepared and l inked to 9-acridinecarboxylic acid through a pseudo-ester function. After N -methylation of the heterocyclic ring, the different compounds were tested for their chemiluminescent properties. Substituents on the hydroxamic funct ions have shown various effects (steric or electronic) on the luminescence yield or stability of the molecule. The most interesting derivatives were selected in terms of chemical stabili ty and chemiluminescence efficiency. 9-[(N- hydroxysuccinimidyl-4-oxo-4-N-p henylaminobutanoate)N-carboxylate]-10-methyl-acridinium (FA6), 9-(N-phenylp ivalamide-N-carboxylate)-N 10-methylacridinium (FA17) and 9-(N-phenylpivala mide N-carboxylate)-10-carboxymethyl-acridinium (FA18) iodomercurates are v ery promising as chemiluminescent labels. These compounds can be detected a t very low levels (10(-16) 10(-17) mol/L) and in our stability evaluation, FA6, FA17 and FA18 showed similar results to the acridinium ester DMAE, The ir half-lives at 20 degreesC are greater than 2 weeks. Copyright (C) 2000 J ohn Wiley & Sons, Ltd.