A new class of peroxidase substrates has been developed which
produces chemiluminescence upon
enzymatic oxidation. A wide variety of
N-alkylacridancarboxylic acid derivatives including
esters,
thioesters, and sulfonamides are efficiently oxidized by a peroxidase
and a peroxide to enzymatically
produce the corresponding chemiluminescent acridinium compound. In
conjunction with a
peroxidase enhancer, continuous light emission with high light
intensities and an extended duration
are produced. Alternately, an appropriately designed acridan
substrate produces a stable acridinium
ester intermediate which can be accumulated and the chemiluminescence
elicited as a burst of
light by raising the pH. The effects of leaving groups and
substitution on the acridan ring on the
mechanism of light production are discussed. Peroxidase-catalyzed
oxidation in the presence of a
peroxide permits the detection of enzyme with subattomolar sensitivity
and a broad linear dynamic
range.
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