New fluorogenic reagent having halogenobenzofurazan structure for thiols:  4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole

Toyo’oka, Toshimasa; Imai, Kazuhiro

doi:10.1021/ac00277a044

Cited by 154 publications

(64 citation statements)

References 16 publications

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“…We have already reported the fluorescent derivatization reagents with benzofurazan structure (Uchiyama et al, 2001a) such as 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F; Imai and Watanabe, 1981) for amines, (4-aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole (ABD-F; Toyo'oka and Imai, 1984) for thiols, and 4-mercapto-7-methylthio-2,1,3-benzoxadiazole (MTBD-SH; Uchiyama et al, 2001b) for carboxylic acids. The benzofurazan structure is rather small and thus these reagents are much more reactive compared with the derivatization reagents with polymethine structures.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of a hydrophilic fluorescent derivatization reagent for carboxylic acids, 4‐N‐(4‐N‐aminoethyl)piperazino‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐PZ‐NH₂), and its application to capillary electrophoresis with laser‐induced fluorescence detection

Santa

Matsumura

Huang

et al. 2002

Biomedical Chromatography

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A hydrophilic fluorescent derivatization reagent for fatty acids, 4-N-(4-N-aminoethyl)piperazino-7-nitro-2,1,3-benzoxadiazole (NBD-PZ-NH 2 ), was designed and synthesized. NBD-PZ-NH 2 possesses not only a fluorophore and a reacting group but also a positive charge group and, thus, was hydrophilic and suitable for application to capillary electrophoresis. NBD-PZ-NH 2 reacted with fatty acids in the presence of triphenylphosphine (TPP) and 2,2'-dipyridyl disulfide (DPDS) at room temperature within 10 min. The derivatives were strongly fluoresced and were positively charged at pH below 3. The derivatives of C4-C20 fatty acids were separated within 10 min in 50% acetonitrile in water containing 30 mM ammonium acetate and 1.0 M acetic acid by capillary electrophoresis with laser-induced fluorescence (CE-LIF) detection. The detection limits attained were 6.5 nM (signal-to-noise ratio of 3). It is proposed that NBD-PZ-NH 2 is a prominent derivatization reagent for fatty acids which is suitable for CE-LIF application.

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Section: Introductionmentioning

confidence: 99%

Design and synthesis of a hydrophilic fluorescent derivatization reagent for carboxylic acids, 4‐N‐(4‐N‐aminoethyl)piperazino‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐PZ‐NH₂), and its application to capillary electrophoresis with laser‐induced fluorescence detection

Santa

Matsumura

Huang

et al. 2002

Biomedical Chromatography

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“…SBD −F was first synthesized from the reaction of fuming sulfuric acid with 4−fluorobenzofurazan which is obtained from 2,6− difluoroaniline in two steps [16]. ABD−F and DBD−F was also obtained from the reaction of ammonia and dimethylamine, respectively, with 4−fluoro−7−chlorosulfonylbenzofurazan, derived from the reaction of 4−fluorobenzofurazan with thionylchloride (SO2 Cl2) [15,17]. and in organic solvents rather than in water [18].…”

Section: Benzofurazan−bearing Reagents For the Analysis Of Achiral Momentioning

confidence: 99%

Development of Benzofurazan−bearing Fluorescence Labeling Reagents for Separation and Detection in High−performance Liquid Chromatography

Toyo’oka

2012

Chromatography

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IntroductionHigh−performance liquid chromatography (HPLC) coupled with various detection systems has been widely adopted for the analyses of various molecules in many research fields, such as biological, pharmaceutical, food, and environmental [1,2]. The widening use of HPLC in the last four decades seems to be due to the advances in instrumentation, column resins, detection systems, and data AbstractThis review summarizes the synthesis, features and application of benzofurazan (i.e., 2,1,3−benzoxadiazole)−bearing fluorescence labeling re-

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“…In addition, NAM has been used to determine cysteine content in commercial yeast extracts (Kuroda et al, 1997). In contrast, ABD-F, a reagent with a halogenobenzofurazan structure, has been used to determine cysteine content (Toyo'oka et al, 1984;Reddy et al, 1993), but cysteine labeling by ABD-F was reported to be unstable under certain conditions (Treuheit et al, 1993). Although these two fluorescent reagents are often used, their performance has not been compared.…”

Section: Introductionmentioning

confidence: 99%

A Rapid and Precise Method to Determine Cysteine Content in Food Materials using 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole

Nishiuchi

Kohmura

Wakabayashi

2011

FSTR

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A method to determine cysteine content in food materials using 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxidiazole (ABD-F) was compared to a method using N-acridinyl maleimide (NAM). Cysteine in samples was derivatized with two fluorogenic reagents and analyzed using HPLC. The cysteine derivative with ABD-F gave a single peak while the cysteine derivative with NAM produced three peaks in standard. The cysteine content in model samples determined with ABD-F was nearly identical to the content determined with NAM. However, when the cysteine content of six types of food materials was measured, four samples were identical in each method, but two samples produced different results because the separation of cysteine derivatives with NAM was influenced by other compounds in the food samples. Since the ABD-F method gave the better separation, it can be useful for the determination of cysteine content in food materials.Keywords: 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxidiazole (ABD-F), N-acridinylmaleimide (NAM), cysteine *To whom correspondence should be addressed. E-mail: hiroaki_nishiuchi@ajinomoto.com IntroductionL-Cysteine, one of the 20 natural amino acids, is an important sulfur-containing compound because it is the only source of sulfur for cell metabolism in most organisms. Cysteine is indispensable for protein folding, protein assembly, and protein stability through disulfide bond formation with the reactive thiol residue. In addition to this metabolic importance, cysteine also plays an important industrial role. Cysteine has been used for industrial applications such as pharmaceuticals, cosmetics, bakery, and flavorings, resulting in consumption of approximately 4000 tons/y globally (Wada et al., 2006). For example, cysteine was reported to be effective as a reducing agent in production of French bread, crackers, and cookies (Grandvoinnet et al., 1979). In the beverage industry, cysteine was effective in preventing browning of fruit juice, such as grape juice or pear juice, during concentration (Skalski and Sistrunk, 1974; Montgomery, 1983.) In addition, cysteine prevented the development of off-flavor in stored orange juice . In flavor chemistry, cysteine is an important source of sulfur in a variety of aromas (Strakenmann et al., 2008). Thus, cysteine will continue to play an important role in the food industry. Therefore, a reliable method to determine the cysteine content in food materials is necessary.Several methods have been developed to determine cysteine content. Previously, mercaptide-forming reactions using metal ions were used. However, more recent methods use fluorescent reagents to react with thiol residues. For example, NAM, a maleimide reagent, provides blue fluorescence by reaction with thiol compounds and has been used for analysis of thiol compounds such as cysteine or glutathione (Nara et al., 1978;Takahashi et al., 1979;Meguro et al., 1996). In addition, NAM has been used to determine cysteine content in commercial yeast extracts (Kuroda et al., 1997). In contrast, ABD-F, a reagent with a halo...

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New fluorogenic reagent having halogenobenzofurazan structure for thiols: 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole

Cited by 154 publications

References 16 publications

Design and synthesis of a hydrophilic fluorescent derivatization reagent for carboxylic acids, 4‐N‐(4‐N‐aminoethyl)piperazino‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐PZ‐NH₂), and its application to capillary electrophoresis with laser‐induced fluorescence detection

Design and synthesis of a hydrophilic fluorescent derivatization reagent for carboxylic acids, 4‐N‐(4‐N‐aminoethyl)piperazino‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐PZ‐NH₂), and its application to capillary electrophoresis with laser‐induced fluorescence detection

Development of Benzofurazan−bearing Fluorescence Labeling Reagents for Separation and Detection in High−performance Liquid Chromatography

A Rapid and Precise Method to Determine Cysteine Content in Food Materials using 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole

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New fluorogenic reagent having halogenobenzofurazan structure for thiols: 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole

Cited by 154 publications

References 16 publications

Design and synthesis of a hydrophilic fluorescent derivatization reagent for carboxylic acids, 4‐N‐(4‐N‐aminoethyl)piperazino‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐PZ‐NH2), and its application to capillary electrophoresis with laser‐induced fluorescence detection

Design and synthesis of a hydrophilic fluorescent derivatization reagent for carboxylic acids, 4‐N‐(4‐N‐aminoethyl)piperazino‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐PZ‐NH2), and its application to capillary electrophoresis with laser‐induced fluorescence detection

Development of Benzofurazan−bearing Fluorescence Labeling Reagents for Separation and Detection in High−performance Liquid Chromatography

A Rapid and Precise Method to Determine Cysteine Content in Food Materials using 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole

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Design and synthesis of a hydrophilic fluorescent derivatization reagent for carboxylic acids, 4‐N‐(4‐N‐aminoethyl)piperazino‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐PZ‐NH₂), and its application to capillary electrophoresis with laser‐induced fluorescence detection

Design and synthesis of a hydrophilic fluorescent derivatization reagent for carboxylic acids, 4‐N‐(4‐N‐aminoethyl)piperazino‐7‐nitro‐2,1,3‐benzoxadiazole (NBD‐PZ‐NH₂), and its application to capillary electrophoresis with laser‐induced fluorescence detection