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 linked 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 functions 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 stability and chemiluminescence efficiency. 9-[(N-hydroxysuccinimidyl-4-oxo-4-N-phenylaminobutanoate)N-carb oxylat e]-10-methyl-acridinium (FA6), 9-(N-phenylpivalamide-N-carboxylate)-10-methylacridinium (FA17) and 9-(N-phenylpivalamide N-carboxylate)-10-carboxymethyl-acridinium (FA18) iodomercurates are very promising as chemiluminescent labels. These compounds can be detected at 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. Their half-lives at 20 degrees C are greater than 2 weeks.
Renotte
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Biocode Biotechnology, rue Ernest Solvay, 101, B-4000 Liège, Belgique.
Sarlet
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Thunus
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Lejeune
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D000166:Acridines / Q000138:chemical synthesis / Q000737:chemistry*; D015195:Drug Design; D004355:Drug Stability; D006877:Hydroxamic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D007202:Indicators and Reagents; D008163:Luminescent Measurements; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D000166:Acridines; D006877:Hydroxamic Acids; D007202:Indicators and Reagents