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Carbonyl-reactive chemiluminescent labels: acridinium hydroxylamines (AHA) Maciej Adamczyk*; J Grote; PG Mattingly; JA Moore; Y Pan Abbott Laboratories, 100 Abbott Park RD, D09NM, BLDG AP20, Abbott Park, IL, 60064-6016, USA      *(maciej.adamczyk@abbott.com) Typically chemiluminescent conjugates are prepared by amide formation with the chemiluminophore of interest. In complex molecules, multistep transformations are needed to achieve specificity. Oxo-groups are often underutilized as a convenient reactive functionalization site for many low molecular weight haptens as well as complex proteins and nucleic acids. In this work a carbonyl reactive acridinium salt was conveniently prepared by acylating ethyl N-(3-aminobutoxy)acetimidate with the N-hydoxysuccinimide active ester of N10-(3-sulfopropyl)-N-tosyl-N-(3-carboxypropyl)acridinium-9-carboxamide then hydrolyzing the acetimidate in aqueous acid to free the O-substituted acridinium hydroxylamine (AHA). AHA was used to label a variety of aldehyde and ketone containing substrates. Oxo-steroids (cortisol, estrone, norethindrone, 6-oxoestradiol, progesterone, digitoxin dialdehyde and digoxin dialdehyde) reacted with AHA (methanol/sodium acetate) to give the corresponding acridinium oxime conjugates in one step and good yield. DNA containing abasic sites generated by acid catalyzed depurination/depyrimidation also reacted readily with AHA (pH 6.8, phosphate buffer) indicating sensitivity approaching 1 abasic site per 107 nucleotides. [Poster: adamczyk.maciej.50661]

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