Fluorescent reaction between ascorbic acid and DAN and its analytical application

Yang, Jinghe; Tong, Changlun; Jie, Nianqin; Zhang, Guiling; Ren, Xuezhen; Hu, Jingtian

doi:10.1016/s0039-9140(96)02129-7

Cited by 16 publications

(7 citation statements)

References 5 publications

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“…The proposed reaction and reaction products are further supported by an earlier study that reported the use of 2,3-diaminonaphthalene to detect AA (35). Yang et al (35) proposed a similar reaction scheme in which the two primary amine groups from 2,3-diaminonaphthalene reacted with the carbonyl moiety on ascorbate to form a quinoxaline structure. Interestingly, 2,3-diaminonaphthalene, a previously defined fluorescent indicator for NO, reacts with NO in the presence of oxygen to generate a triazole structure; this is the reaction upon which the development of DAFs and diamino-rhodamines as fluorescent NO indicators was based (12).…”

Section: Discussionmentioning

confidence: 99%

Interfering with Nitric Oxide Measurements

Zhang¹,

Kim²,

Hatcher³

et al. 2002

Journal of Biological Chemistry

184

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4,5-Diaminofluorescein (DAF-2) is widely used for detection and imaging of NO based on its sensitivity, noncytotoxicity, and specificity. In the presence of oxygen, NO and NO-related reactive nitrogen species nitrosate 4,5-diaminofluorescein to yield the highly fluorescent DAF-2 triazole (DAF-2T). However, as reported here, the DAF-2 reaction to form a fluorescent product is not specific to NO because it reacts with dehydroascorbic acid (DHA) and ascorbic acid (AA) to generate new compounds that have fluorescence emission profiles similar to that of DAF-2T. When DHA is present, the formation of DAF-2T is attenuated because the DHA competes for DAF-2, whereas AA decreases the nitrosation of DAF-2 to a larger extent, possibly because of additional reducing activity that affects the amount of available N 2 O 3 from the NO. The reaction products of DAF-2 with DHA and AA have been characterized using capillary electrophoresis with laser-induced fluorescence detection and electrospray mass spectrometry. The reactions of DAF-2 with DHA and AA are particularly significant because DHA and AA often colocalize with nitric-oxide synthase in the central nervous, cardiovascular, and immune systems, indicating the importance of understanding this chemistry.NO is involved in a variety of important biological functions in the cardiovascular system, the central and peripheral nervous system, the reproductive system, and the immune system (1-6). NO is normally generated via an enzymatically regulated pathway with the conversion of L-arginine to citrulline by a family of at least three distinct nitric-oxide synthase (NOS) 1 enzymes, the neuronal, inducible, and endothelial NOS forms (or NOS-I, -II, and -III) (7-9). Endothelial and neuronal NOS, also named constitutive NOS, are calcium-dependent. Although cells expressing constitutive NOS generally produce small amounts of NO (submicromolar at the cellular level), inducible NOS, which is synthesized in immune-competent cells when stimulated by cytokines, endotoxins, and other biologically active compounds, is calcium-independent and produces NO at higher levels (1-10 M in microphages) (10). Although in situ and immunohistochemical techniques allow one to determine whether NOS is present in a particular tissue, whether the NOS is actively producing NO under specific conditions and the amount of NO produced are important questions to answer to understand the physiological roles of NOS.Direct detection (or imaging) of NO production in a biological system was unsatisfactory until the development of a series of fluorescent indicators for NO, the diaminofluoresceins (DAFs) in 1998 by the Nagano group (11). In the presence of oxygen, NO nitrosates DAFs to produce the highly fluorescent triazofluoresceins. DAFs provide the advantages of sensitivity (detection limits of 5 nM), simple protocols, and noncytotoxicity, and they are also believed to offer high specificity to NO. Since then, an increasing number of researchers have used them for NO detection and NO imaging (10, 12).The specificity...

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Section: Discussionmentioning

confidence: 99%

Interfering with Nitric Oxide Measurements

Zhang¹,

Kim²,

Hatcher³

et al. 2002

Journal of Biological Chemistry

184

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“…According to the paper reported (10), in this experiment AA can react with DAN and from a condensation product that can emit strong fluorescence.…”

Section: Mechanismmentioning

confidence: 93%

Β-Cyclodextrin ENHANCED FLUORIMETRY FOR a DETERMINATION OF ASCORBIC ACID

Yang

Sun

et al. 2001

Analytical Letters

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A simple, sensitive and selected fluorimetry for determination of ascorbic acid (AA) is described. The method is based on the reaction of ascorbic acid in alkaline medium with 2,3-diaminonaphthalene without oxidant. The addition of bcyclodextrin(b-CD) greatly enhance the fluorescence of the system. Under optimum conditions, a linear relationship was obtained between the fluorescence intensity and the concentration of ascorbic acid in the range of 0.05-600 mg/ml, the detection limit is 8 ng/ml. In AA-DAN-b-CD system, the inclusion complex is formed. Its inclusion constant is 1.1 Â 10 6 L 2 /mol 2 .

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“…Fluorimetric determinations of AA have also been developed using the condensation reactions of AA with o-phenylenediamine (OPDA) (18) and 2,3-diaminonaphthalene (DAN) (19).…”

Section: Introductionmentioning

confidence: 99%

Optical ascorbic acid sensor based on the fluorescence quenching of silver nanoparticles

Park¹,

Alam²,

Lee³

et al. 2009

Luminescence

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A sensitive and selective fluorimetric sensor for the assay of ascorbic acid (AA) using silver nanoparticles as emission reagent was investigated. In this study, silver nanoparticles were prepared based on aqueous-gaseous phase reaction of silver nitrate solution and ammonia gas. The nanoparticles were water-soluble, stable and had a narrow emission band. They were used as a fluorescence probe for the assay of ascorbic acid on its quenching effect on the emission of silver nanoparticles. The principal reason for quenching is likely to be a complexation between ascorbic acid and silver nanoparticles. The quenching mechanism was established by Stern-Volmer law. Under the optimum conditions, the quenched fluorescence intensity was linear with the concentration of ascorbic acid in the range of 4.1 x 10(-6) to 1.0 x 10(-4) m (r = 0.9985) with a detection limit of 1.0 x 10(-7) m. The RSD for repeatability of the sensor for the assay of ascorbic acid concentration of 3.0 x 10(-5) and 4.0 x 10(-6) m was found to be 1.5 and 1.3%, respectively. The proposed method was applied to the determination of ascorbic acid in vegetables and vitamin C tablets.

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Fluorescent reaction between ascorbic acid and DAN and its analytical application

Cited by 16 publications

References 5 publications

Interfering with Nitric Oxide Measurements

Interfering with Nitric Oxide Measurements

Β-Cyclodextrin ENHANCED FLUORIMETRY FOR a DETERMINATION OF ASCORBIC ACID

Optical ascorbic acid sensor based on the fluorescence quenching of silver nanoparticles

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