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

Abstract

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.

Aromatic Thiol pKa Effects on the Folding Rate of a Disulfide Containing Protein

“…The thiol pK a value was determined using UV-vis spectrophotometry, as previously described (24,31,32); 1 H NMR (300 MHz, D 2 O) δ 7.54 (d, J ) 7.9 Hz, 2H), 7.31 (d, J ) 7.9 Hz, 2H); 13 N,N′-Dithiobis(p-phenylenesulfonyl)]diglycine, diethyl ester. To a mixture of 4,4′-dithiobisbenzenesulfonyl chloride (25,33,34) (383 mg, 0.923 mmol) and glycine ethyl ester hydrochloride (362 mg, 2.59 mmol) in chloroform (8 mL) was added triethylamine (0.54 g, 5.35 mmol). After stirring of the sample for 18 h, the reaction mixture was concentrated under reduced pressure.…”

Crystal structure of 9-aminoacridinium chlorideN,N-dimethylformamide monosolvate

“…Additionally, photochemical reactions for these compounds in different media have been reported (Machulek et al, 2003). AA derivatives are promising analytical agents, since they exhibit relatively high quantum yields of light emission and stability (Adamczyk et al, 1999;Dodeigne, 2000;Renotte et al, 2000;Smith et al, 2009). 9-AA is a fluorescent dye of the family of nitrogen heterocyclic bases.…”

9-(2,6-Dichlorophenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate and its precursor 2,6-dichlorophenyl acridine-9-carboxylate

“…Numerous acridine-based derivatives are important owing to their chemiluminogenic ability and their utility as chemiluminescent indicators or fragments of chemiluminescent labels, with applications in immunoassays, nucleic acid diagnostics and quantitative assays of biomolecules, such as antigens, antibodies, hormones and enzymes, as well as DNA±RNA structural analyses (Becker et al, 1999;Dodeigne et al, 2000;Zomer & Jacquemijns, 2001). Among acridine-based chemiluminogens, phenyl acridine-9-carboxylates are the most promising analytical agents, since they exhibit relatively high quantum yields of light emission and stability (Adamczyk et al, 1999;Dodeigne et al, 2000;Razawi & McCapra, 2000;Renotte et al, 2000;Smith et al, 2000;Zomer & Jacquemijns, 2001). Continuing the search for new analytically interesting acridine-based chemiluminogens, we synthesized phenyl acridine-9-carboxylate substituted with two Cl atoms, (II), and its tri¯uoromethanesulfonate salt, (I), methylated at the endocyclic N atom, in order to determine how the presence of heavy Cl atoms in the phenyl fragment affects the stability and chemiluminogenic ability of this group of compounds.…”