Characterization of Acridancarboxylic Acid Derivatives as Chemiluminescent Peroxidase Substrates

Akhavan-Tafti, Hashem; DeSilva, Renuka; Arghavani, Zahra; Eickholt, Robert A.; Handley, R.; Schoenfelner, B. A.; Sugioka, Katsuaki; Sugioka, and Yumiko; Schaap, A. Paul

doi:10.1021/jo970202m

Cited by 34 publications

(38 citation statements)

References 13 publications

(14 reference statements)

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“…Tris(2,2 0 -bipyridyl)dichlororuthenium(II) hexahydrate ðRuðbpyÞ 2þ 3 Þ and tripropylamine (TPA) were from Aldrich; stock solutions were prepared in 0.15 M phosphate buffer, pH 7.0, which contained 0.05 % Tween-20. 2 0 ,3 0 ,6 0 -Trifluorophenyl 10-methylacridan-9-carboxylate (TMC) was synthesized as described previously [31]; stock solutions were prepared in 1:1 ethanol: 1,4-dioxane.…”

Section: Methodsmentioning

confidence: 99%

“…Inevitably this double dilution protocol decreases the sensitivity of the assay, but attomoles of these compounds can be detected, which makes them suitable as labels for the majority of immunoassays [1]. 2 0 ,3 0 ,6 0 -Trifluorophenyl 10-methylacridan-9-carboxylate (TMC) is one of a class of compounds known as acridans that can be prepared by reducing the corresponding acridinium ester with a reducing agent such as powdered zinc in acetic acid [31]. Unlike acridinium esters they are relatively stable in the presence of hydrogen peroxide and are not converted to an inactive pseudobase under the conditions necessary for enzyme and immunochemical reactions.…”

Section: Introductionmentioning

confidence: 99%

“…Unlike acridinium esters they are relatively stable in the presence of hydrogen peroxide and are not converted to an inactive pseudobase under the conditions necessary for enzyme and immunochemical reactions. They can, however, be reconverted to the acridinium ester by oxidizing agents such as horseradish peroxidase (HRP) [31], and therefore they can be used as substrates for this enzyme when it is used as a label in DNA assays [32,33]. In the presence of an enhancer such as p-iodophenol it is possible to detect less than an amol of HRP with an acridan as the substrate [31].…”

Section: Introductionmentioning

confidence: 99%

“…They can, however, be reconverted to the acridinium ester by oxidizing agents such as horseradish peroxidase (HRP) [31], and therefore they can be used as substrates for this enzyme when it is used as a label in DNA assays [32,33]. In the presence of an enhancer such as p-iodophenol it is possible to detect less than an amol of HRP with an acridan as the substrate [31]. Recently it was shown that acridans can also be converted to the corresponding acridinium ester by electrochemical oxidation [34].…”

Section: Introductionmentioning

confidence: 99%

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Comparison Between Acridan Ester, Luminol, and Ruthenium Chelate Electrochemiluminescence

Wilson

Akhavan-Tafti²,

DeSilva³

et al. 2001

Electroanalysis

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Comparison Between Acridan Ester, Luminol, and Ruthenium Chelate Electrochemiluminescence

Wilson

Akhavan-Tafti²,

DeSilva³

et al. 2001

Electroanalysis

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“…Up to now, various analytical methods have been developed for the determination of nucleic acids, such as fluorometry, 1,2 chemiluminescence, 3 and electrochemistry. 4 Recently, fluorescent probes including organic dyes, such as yellow orange dyes, 5,6 metal ions, such as Tb(III), 7 and a metal complex 8 are frequently employed to investigate nucleic acids.…”

mentioning

confidence: 99%

Nucleic Acids Analysis with Nano-Ag-Tb(III) by a Resonance Light Scattering Technique

Zhao

Jin

et al. 2006

ANAL. SCI.

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The quantitative analysis of nucleic acids is very important because it can be used as a reference for measurements of other components in biological fluids and genetic diagnosis. Up to now, various analytical methods have been developed for the determination of nucleic acids, such as fluorometry, 1,2 chemiluminescence, 3 and electrochemistry. 4 Recently, fluorescent probes including organic dyes, such as yellow orange dyes, 5,6 metal ions, such as Tb(III), 7 and a metal complex 8 are frequently employed to investigate nucleic acids.Rayleigh scattering is a light-scattering phenomenon where electromagnetic radiation and a material interact with each other and generate elastic collisions.Based on macroscopic fluctuation theory, the intensity of scattered Rayleigh light is in proportion to λ0 -4 , 9 since the light scattering of molecular particles is 20-fold smaller than the wavelength of the incident beam. If the wavelength of the incident beam is close to that of the absorption band of the molecular particles, Rayleigh scattering will deviate from the ordinary law, and the intensity of some wavelengths will rapidly increase. This phenomenon is called resonance light scattering (RLS investigated the enhancing and quenching functions of nano-Ag on the luminescent properties of an europium complex, in which the effects of particles upon aggregation were considered.In this paper, the RLS of nano-Ag-Tb(III)-nucleic acids system is reported for the first time. The results show that with a common spectrofluorometer and inexpensive reagents, nucleic acids can be detected by this method with satisfactory results. Experimental ApparatusA transmission electron microscopy (TEM) image of the nano-Ag was acquired using a Hitachi H-600 (Japan) transmission electron microscope. The RLS spectrum and the intensity of RLS were measured with a Hitachi 850 spectrofluorometer (Japan).All absorption spectra were recorded with a Cintra 10e UV-Vis spectrophotometer (GBC). A 420A plus pH meter (Orion Research Inc.) was used to measure the pH of the solutions. ReagentsStock solutions of nucleic acids (100 µg ml -1 ) were prepared by dissolving purchased fish sperm DNA (fsDNA), calf thymus DNA (ctDNA) or yeast RNA (yRNA) (Sigma) in water. These stocks were stored at 0 -4˚C. The concentrations of nucleic acids, where necessary, were calculated according to the absorbance at 260 nm by using the molar extinction coefficients, εDNA (6600 l mol -1 cm -1 ) and εRNA (7800 l mol -1 cm -1 ), after establishing that the absorbance ratio, A260/A280, was 1.8 for DNA and 2.0 for RNA, respectively. A standard stock solution of the Tb(III) ion (0.01 mol l -1 ) was prepared by dissolving 934.5 mg of Tb4O7 in 15 ml of HCl (12 mol l -1 ) at 100˚C, and evaporating the solution to be almost dry; it was then diluted to 500 ml with doubly distilled water. The nano-Ag-terbium(III)-nucleic acids system was observed by a resonance light scattering (RLS) technique for the first time, and the quantitative analysis of nucleic acids at nanogram levels was establishe...

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Comparative studies of the chemiluminescent horseradish peroxidase-catalysed peroxidation of acridan (GZ-11) and luminol reactions: effect of pH and scavengers of reactive oxygen species on the light intensity of these systems

et al. 2000

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In this study, the chemiluminescent horseradish peroxidase/H(2)O(2)-catalysed oxidation of acridan (GZ-11) substrate was compared with the well-characterized light-producing luminol reaction. p-Iodophenol and p-phenylphenol were used as enhancers, respectively, for the luminol and acridan reactions. These two light-producing systems showed significant differences in relation to the effect of pH, as well as the effect of scavengers of reactive oxygen species, on the light intensity. Light production measured could be as low as pH 2.6 in the acridan reaction, whereas light emission was not detected in the luminol system below pH 5.6. In contrast with the luminol system, it was found that superoxide dismutase does not inhibit the light intensity of the acridan system. This suggests that superoxide anion does not participate in the mechanism of the light-emitting steps of the acridan reaction. Addition of hydroxyl radical scavengers, mannitol and benzoate, to the acridan reaction medium had no appreciable effect on the chemiluminescent intensity, indicating that hydroxyl radicals do not interfere in light-emitting steps. In addition, the peroxidation of the acridan substrate was found to be very slow at pH 5.6 in the absence of the enhancer, p-phenylphenol, whereas in its presence a rapid degradation of the acridan substrate was observed. Therefore, it is suggested that the enhancer might be initially oxidized by the HRP/H(2)O(2) system, resulting in the formation of the enhancer radical, which could be the actual oxidizing agent of the acridan substrate. Together, the data presented in this paper indicate that the chemiluminescent horseradish peroxidase-catalysed peroxidation of acridan (GZ-11) is more specific than the luminol reaction for the reactive oxygen species involved in the light-emitting steps, i. e, H(2)O(2).

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Characterization of Acridancarboxylic Acid Derivatives as Chemiluminescent Peroxidase Substrates

Cited by 34 publications

References 13 publications

Comparison Between Acridan Ester, Luminol, and Ruthenium Chelate Electrochemiluminescence

Comparison Between Acridan Ester, Luminol, and Ruthenium Chelate Electrochemiluminescence

Nucleic Acids Analysis with Nano-Ag-Tb(III) by a Resonance Light Scattering Technique

Comparative studies of the chemiluminescent horseradish peroxidase-catalysed peroxidation of acridan (GZ-11) and luminol reactions: effect of pH and scavengers of reactive oxygen species on the light intensity of these systems

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