Synthesis, structure elucidation, and chemiluminescent activity of new 9-substituted 10-(ω-(succinimidyloxycarbonyl)alkyl)acridinium esters

Smith, Keith, Mu, Xiaojing, Li, Zhaoqiang, Holland, Andy M., Woodhead, J. Stuart and El-Hiti, Gamal A. 2023. Synthesis, structure elucidation, and chemiluminescent activity of new 9-substituted 10-(ω-(succinimidyloxycarbonyl)alkyl)acridinium esters. Luminescence 38 (4) , pp. 487-496. 10.1002/bio.4474

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Abstract

Several new acridinium esters 2–9 having their central acridinium ring bearing a 9-(2,5-dimethylphenoxycarbonyl), 9-(2,6-bis(trifluoromethyl)phenoxycarbonyl) or 9-(2,6-dinitrophenoxycarbonyl) group, and a 10-methyl, 10-(3-(succinimidyloxycarbonyl)propyl), 10-(5-(succinimidyloxycarbonyl)pentyl), or 10-(10-(succinimidyloxycarbonyl)decyl) group, have been synthesized and their chemiluminescent properties have been tested. The 2,5-dimethylphenyl acridinium esters emit light slowly (glow) when treated with alkaline hydrogen peroxide, while the 2,6-dinitrophenyl and 2,6-bis(trifluoromethyl)phenyl esters emit light rapidly (flash). The substituent at the 10 position affects the hydrolytic stabilities of the compounds.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	1522-7235
Date of First Compliant Deposit:	11 October 2023
Date of Acceptance:	2 March 2023
Last Modified:	11 Nov 2024 13:00
URI:	https://orca.cardiff.ac.uk/id/eprint/158495

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