High stability and high efficiency chemiluminescent acridinium compounds obtained from 9‐acridine carboxylic esters of hydroxamic and sulphohydroxamic acids

Renotte, R.; Sarlet, G.; Thunus, L.; Lejeune, R.

doi:10.1002/1522-7243(200009/10)15:5<311::aid-bio600>3.3.co;2-v

Cited by 2 publications

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“…Chemiluminescence (CL) assays have been utilized for determining various kinds of compounds qualitatively and quantitatively. − CL compounds have been developed as useful luminescent reagents. In particular, luminol (3-aminophthalhydrazide) derivatives, − acridinium ester derivatives, − and dioxetane derivatives − are essential compounds in highly sensitive CL assays. Recently, luminol was applied to CL imaging in vivo by CL resonance energy transfer (CRET) .…”

Section: Introductionmentioning

confidence: 99%

“…10-Carboxymethylacridinium derivatives were synthesized when a methyl group (an electron-donating group) was introduced at the 2- and 6-positions of the phenyl moiety, resulting in strong CL intensity . 9-Acridinecarboxylic esters of hydroxamic and sulfohydroxamic acids had strong CL intensity at picomolar levels . Acridinium dimethylphenyl esters containing N -sulfopropyl groups in the acridinium ring were highly sensitive CL compounds .…”

Section: Introductionmentioning

confidence: 99%

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Strongly Chemiluminescent Acridinium Esters under Neutral Conditions: Synthesis, Properties, Determination, and Theoretical Study

et al. 2017

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Various novel acridinium ester derivatives having phenyl and biphenyl moieties were synthesized, and their optimal chemiluminescence conditions were investigated. Several strongly chemiluminescent acridinium esters under neutral conditions were found, and then these derivatives were used to detect hydrogen peroxide and glucose. Acridinium esters having strong electron-withdrawing groups such as cyano, methoxycarbonyl, and nitro at the 4-position of the phenyl moiety in phenyl 10-methyl-10λ-acridine-9-carboxylate trifluoromethanesulfonate salt showed strong chemiluminescence intensities. The chemiluminescence intensity of 3,4-dicyanophenyl 10-methyl-10λ-acridine-9-carboxylate trifluoromethanesulfonate salt was approximately 100 times stronger than that of phenyl 10-methyl-10λ-acridine-9-carboxylate trifluoromethanesulfonate salt at pH 7. The linear calibration ranges of hydrogen peroxide and glucose were 0.05-10 mM and 10-2000 μM using 3,4-(dimethoxycarbonyl)phenyl 10-methyl-10λ-acridine-9-carboxylate trifluoromethanesulfonate salt at pH 7 and pH 7.5, respectively. The proposed chemiluminescence reaction mechanism of acridinium ester via a dioxetanone structure was evaluated via quantum chemical calculation on density functional theory. The proposed mechanism was composed of the nucleophilic addition reaction of hydroperoxide anion, dioxetanone ring formation, and nonadiabatic transition due to spin-orbit coupling around the transition state (TS) to the triplet state (T) following the decomposition pathway. The TS which appeared in the thermal decomposition would be a rate-determining step for all three processes.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Strongly Chemiluminescent Acridinium Esters under Neutral Conditions: Synthesis, Properties, Determination, and Theoretical Study

et al. 2017

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“…Various representative chemiluminescent compounds such as luminol, indole, acridinium ester and lophine derivatives were developed and the chemiluminescence (CL) properties of each were studied. However, these representative chemiluminescent compounds require strongly alkaline conditions to obtain strong CL intensity.…”

Section: Introductionmentioning

confidence: 99%

Enhancement effect on the chemiluminescence of acridinium esters under neutral conditions

Nakazono

Nanbu

2017

Luminescence

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Enhancement effect on the chemiluminescence of acridinium ester derivatives under neutral conditions was investigated. Additions of phenols did not enhance the chemiluminescence intensities of acridinium ester derivatives in the presence of horseradish peroxidase and hydrogen peroxide. Additions of cetyltrimethylammonium bromide apparently enhanced the chemiluminescence intensities of phenyl 10-methyl-10λ -acridine-9-carboxylate derivatives with electron-withdrawing groups at the 4-position of the phenyl group. In particular, the chemiluminescence intensity of 4-(trifluoromethyl)phenyl 10-methyl-10λ -acridine-9-carboxylate trifluoromethanesulfonate salt was 5.5 times stronger in the presence of cetyltrimethylammonium bromide than in its absence at pH 7. The chemiluminescence intensity of 3,4-dicyano-phenyl 10-methyl-10λ -acridine-9-carboxylate trifluoromethanesulfonate salt was 46 times stronger in the presence of cetyltrimethylammonium bromide at pH 7 than in its absence at pH 10.

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High stability and high efficiency chemiluminescent acridinium compounds obtained from 9‐acridine carboxylic esters of hydroxamic and sulphohydroxamic acids

Cited by 2 publications

References 0 publications

Strongly Chemiluminescent Acridinium Esters under Neutral Conditions: Synthesis, Properties, Determination, and Theoretical Study

Strongly Chemiluminescent Acridinium Esters under Neutral Conditions: Synthesis, Properties, Determination, and Theoretical Study

Enhancement effect on the chemiluminescence of acridinium esters under neutral conditions

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