Chemiluminogenic labels, old and new

Zomer, G.; Stavenuiter, J. F. C.

doi:10.1016/s0003-2670(00)82640-9

Cited by 43 publications

(25 citation statements)

References 11 publications

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“…Only FA 18 (9-(N-phenylpivalamide N-carboxylate)-10-carboxymethyl acridinium iodomercurate) was obtained using a different procedure. Although halogenoalkanoic esters have been proposed for the N-alkylation of various luminescent acridinium derivatives (5,6), this procedure was inefficient for the present compound, even using HgCl 2 catalysis. N-Alkylation has thus been carried out earlier in the synthesis process (on the methyl ester of 9-acridinecarboxylic acid) and the leaving group (Nhydroxy-N-phenylpivalamide) introduced into the molecule using N-N-carbonyldiimidazole (CDI) in the presence of allylbromide.…”

Section: Discussionmentioning

confidence: 93%

“…Since McCapra (1,2) explained the chemiluminescence mechanism of acridinium esters and correlated the chemiluminescence activity to the acidity of a leaving group linked to the 9-carboxylic function of the acridinium ring, several classes of chemiluminescent acridinium derivatives using phenols, thiols, sulphonamides and fluoroalcohols as leaving groups have been described (3)(4)(5)(6)(7). Most of these compounds exhibited the expected properties but no significant differences were observed in efficiency.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2000

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A series of hydroxamic acids and sulphohydroxamic acids were prepared and linked to 9-acridinecarboxylic acid through a pseudo-ester function. After N-methylation of the heterocyclic ring, the different compounds were tested for their chemiluminescent properties. Substituents on the hydroxamic functions have shown various effects (steric or electronic) on the luminescence yield or stability of the molecule. The most interesting derivatives were selected in terms of chemical stability and chemiluminescence efficiency. 9-[(N-hydroxysuccinimidyl-4-oxo-4-N-phenylaminobutanoate)N-carb oxylat e]-10-methyl-acridinium (FA6), 9-(N-phenylpivalamide-N-carboxylate)-10-methylacridinium (FA17) and 9-(N-phenylpivalamide N-carboxylate)-10-carboxymethyl-acridinium (FA18) iodomercurates are very promising as chemiluminescent labels. These compounds can be detected at very low levels (10(-16)-10(-17) mol/L) and in our stability evaluation, FA6, FA17 and FA18 showed similar results to the acridinium ester DMAE. Their half-lives at 20 degrees C are greater than 2 weeks.

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Section: Discussionmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

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

et al. 2000

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“…Diphenyl oxalates are commonly used for commercial glow sticks and belong to the general class of “peroxyoxalate CL” (PO‐CL) . They constitute the most efficient substances with quantum efficiencies of—in cases such as sulfonamide substituted diphenyl oxalates—above 30% compared to below 5% for luminol or 7% for acridinium derivatives . Biologists furthermore identified an interesting way to utilize PO‐CL in conjunction with a photosensitizer to induce local toxicity and oxidative cellular damage in photodynamic therapy (PDT).…”

Section: Methodsmentioning

confidence: 99%

Making and Breaking Chemical Bonds by Chemiluminescence

Kockler

Frisch

Barner‐Kowollik

2018

Macromol. Rapid Commun.

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Chemiluminescent (CL) reactions are powerful analytical tools and are present in commercially available everyday objects such as glow sticks. Herein, the photons generated by chemiluminescence are exploited to induce covalent bond breakage and formation, using a chemically generated photonic field at ambient temperature through space as energy transducer. Remarkably, the generated photons enable both the cleavage of species generating radicals as well as the execution of [2 + 2] cycloadditions, demonstrating that disparate types of reactions can be triggered. The herein-presented photochemical concept establishes the field of CL-induced photochemistry, which is poised to enable photochemical transformations in situations where physical light sources, such as lamps, LEDs, and lasers cannot be employed, including in biological environments.

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“…The theoretically predicted thermodynamic data indicated that these two pathways are possible for most compounds [ 12 , 17 ]. The relaxation of electronically excited product is accompanied by the emission of light, i.e., chemiluminescence [ 4 , 42 ].…”

Section: Introductionmentioning

confidence: 99%

Computational Insights on the Mechanism of the Chemiluminescence Reaction of New Group of Chemiluminogens—10-Methyl-9-thiophenoxycarbonylacridinium Cations

Pieńkos

Zadykowicz

2020

IJMS

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Immunodiagnostics, in which one of the promising procedures is the chemiluminescent labelling, is essential to facilitate the detection of infections in a human organism. One of the standards commonly used in luminometric assays is luminol, which characterized by low quantum yield in aqueous environments. Acridinium esters have better characteristics in this topic. Therefore, the search for new derivatives, especially those characterized by the higher quantum yield of chemiluminescence, is one of the aims of the research undertaken. Using the proposed mechanism of chemiluminescence, we examined the effect of replacing a single atom within a center of reaction on the efficient transformation of substrates into electronically excited products. The density functional theory (DFT) and time dependent (TD) DFT calculated thermodynamic and kinetic data concerning the chemiluminescence and competitive dark pathways suggests that some of the scrutinized derivatives have better characteristics than the chemiluminogens used so far. Synthesis of these candidates for efficient chemiluminogens, followed by studies of their chemiluminescent properties, and ultimately in chemiluminescent labelling, are further steps to confirm their potential applicability in immunodiagnostics.

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Chemiluminogenic labels, old and new

Cited by 43 publications

References 11 publications

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

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

Making and Breaking Chemical Bonds by Chemiluminescence

Computational Insights on the Mechanism of the Chemiluminescence Reaction of New Group of Chemiluminogens—10-Methyl-9-thiophenoxycarbonylacridinium Cations

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