Regiodependent Luminescence Quenching of Biotinylated N-Sulfonyl-acridinium-9-carboxamides by Avidin

Biotin was conjugated to chemiluminescent N-sulfonylacridinium-9-carboxamides at the N-10 or 9-position carboxamide. Upon binding to avidin, the light output of the N-10 derivative (8) was quenched up to 92% upon triggering with basic peroxide, while the 9-position carboxamide conjugate (9) was quen...

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Bibliographic Details
Published in:Organic letters 2003-10, Vol.5 (21), p.3779-3782
Main Authors: Adamczyk, Maciej, Mattingly, Phillip G, Moore, Jeffrey A, Pan, You
Format: Article
Language:English
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Summary:Biotin was conjugated to chemiluminescent N-sulfonylacridinium-9-carboxamides at the N-10 or 9-position carboxamide. Upon binding to avidin, the light output of the N-10 derivative (8) was quenched up to 92% upon triggering with basic peroxide, while the 9-position carboxamide conjugate (9) was quenched only 33%. The utility of this effect was demonstrated in a model homogeneous chemiluminescence assay.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035323p