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Thiol-specific acridinium reagents for labeling proteins and nucleic acids Maciej Adamczyk*; PG Mattingly; JA Moore; SD Rege Abbott Laboratories, 100 Abbott Park Rd, D09NM, BLDG AP20, Abbott Park, IL, 60064-6016, USA      *(maciej.adamczyk@abbott.com) Previously we have reported the synthesis of a variety of N-sulfonylacridinium-9-carboxamides critical for the development of immunassays (HIV, HCV, HbsAg, HBc, etc) on the Abbott Prism and Architect platforms. Maleimide derivatives of acridinium labels have not been reported and offer the advantage of site-specific conjugation. Thus, NHS esters of three N-sulfonylacridinium-9-carboxamides were reacted with a series of maleimide-containing amino-terminal spacer arms to give the title compounds. Studies with N-acetyl-L-cysteine showed that thiols add exclusively at the maleimide when equimolar concentrations of the reactants are present. Addition of the thiol to the 9-position of the N-sulfonylacridinium-9-carboxamide can result when a large excess of the thiol reagent is present, but this is reversible and does not interfere with the desired alkylation reaction. The acridinium labels are extremely stable and compatible even with the conditions used during nucleic acid hybridizations (65 °C, 14 h). Our results indicate maleimide-derivatized acridinium labels can be utilized for the site-specific conjugation of thiolated proteins and nucleic acids, providing sensitive chemiluminescent conjugates. [Poster: adamczyk.maciej.50662]

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