10-Methyl-9-acridinium carboxylate

An HPLC-CL determination of environmentally important chlorophenols was reported by using 10-methyl-9-acridinium carboxylate as a CL label. A two-step derivatization was used to produce the CL derivatives (Fig. 10). Following the separation under reversed-phase conditions, the CL reaction was performed by the base-catalyzed postcolumn oxidation. The quantum efficiency was dependent on the species of analytes. The detection limit of chlorophenols (S/N = 3) ranged from 300 amol to 1.25 fmol per injection (Fig. 11) [52],... 

Methyl-8-hydroxyquinoline, 7 588 10-Methyl-9-acridinium carboxylate, chemiluminescence reagent, 5 846 Methyl abietate, 24 553 Methyl acetate... 

While luminol and isoluminol require an oxidant plus a catalyst for initiation of the chemiluminescent reaction, esters derived from A -methyl acridinium carboxylic acid require only alkaline hydrogen peroxide (W4). Acridinium esters were first introduced by McCapra s group (M23, M25, S32), based on earlier work on the bioluminescence of the lucigenin/luciferase system (G18), and reviewed in McCapra and Beheshti (M21). From Fig. 19, one can see the structural similarity between lucigenin and a typical acridinium ester. 

Only one acridinium phenyl carboxylate has found significant use as a chemiluminescent label. 4-(2-succinimidyloxycarbonylethyl)-phenyl-10-methyl-acridinium-9-carboxylate fluorosulphonate has been employed for the determination of albumin and thyroxine and a-fetoprotein. 

A NOVEL CHEMILUMINESCENT IMMUNOASSAY OF TOTAL THYROXINE USING THE ACRIDINIUM ESTER 2 ,6,-DIMETHYL-4 -(N-SUCCINIMIDYLOXYCARBONYL) PHENYL-10-METHYL-ACRIDINIUM -9-CARBOXYLATE METHOSULFATE AS LABEL... 

Fig. 27. Two acridinium esters with increased stability for covalent labeling of (a) lysine groups, viz., 2, 6 -dimethyl-4 -(N-succinimidyloxycarbonyl)phenyl-10-methylacridinium-9-carboxylafe meth-osulfate (b) carboxyl groups, viz., 2, 6 -dimethyl-4 -[iV-(2-aminoethyl)carbanioyl]phenyl-10-methyl-acridinium-9-carboxylate bromide. Taken from Law et al. (L2).

Lin JM, Yamada M (1998) Electrogenerated chemiluminescence of methyl-9-(p-formylphenyl) acridinium carboxylate fluorosulfonate and its applications to immunoassay. Microchem J 58(1) 105-116. doi 10.1006/mchj.1997.1539... 

Abbreviations SPQ 6-methoxy-N -(sulfopropyl)quinolinium SPA N-(sulfopropyl)acridinium lucigenin bis-N-methylacridinium nitrate MACA 10-methylacridinium-9-carboxamide MAMC N-methylacridinium-9-methyl carboxylate. 

Fig. 26. An activated acridinium ester for covalent labeling, viz., 4-(2-succinimidyloxycarbonyl-methyl)phenyl-IO-methylacridinium-9-carboxylate fluorosulfonate. After Weeks et al. (W4,W5).

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