Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Abstract

Fluorogenic and fluorescent labeling reagents having a benzofurazan (2,1,3-benzoxadiazole) skeleton such as 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F), 4-N,N-dimethylaminosulfonyl-7-fluoro-2,1,3-benzoxadiazole (DBD-F), 4-aminosulfonyl-7-fluoro-2,1,3-benzoxadiazole (ABD-F), ammonium 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate (SBD-F), 4-hydrazino-7-nitro-2,1,3-benzoxadiazole (NBD-H), 4-N,N-dimethylaminosulfonyl-7-hydrazino-2,1,3-benzoxadiazole (DBD-H), 4-nitro-7-N-piperazino-2,1,3-benzoxadiazole (NBD-PZ), 4-N,N-dimethylaminosulfonyl-7-N-piperazino-2,1,3-benzoxadiazole (DBD-PZ), 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole (DBD-COCl) and 7-N,N-dimethylaminosulfonyl-4-(2,1,3-benzoxadiazolyl) isothiocyanate (DBD-NCS) are reviewed in terms of synthetic method, reactivity, fluorescence characteristics, sensitivity and application to analytes.

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

“…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.…”

Labeling of alprenolol with fluorescent aryl iodide as a reagent based on Mizoroki–Heck coupling reaction

“…Many fluorescent labeling reagents have been developed for a various functional groups such as amine, phenol, thiol, aldehyde and carbonyl groups [1][2][3][4]. Although the fluorescent labeling reagents are frequently applied to the drug analysis in biological fluids, there are drawbacks as follows: (1) fluorescent labeling technique cannot be applied to compounds which do not possess derivatizable functional groups, (2) fluorescent labeling reagent reacts with co-existing biological substances and the resultant products can interfere with the detection of target analyte.…”

New Fluorescent Probes Applicable to Aggregates of Fluorocarbon Surfactants

“…4-Chloro-7-nitrobenzo-2-oxa-1,3-diazol (NBD-Cl) has been used for detecting small quantities of amines and amino acids 16,17) . NBD-Cl is non-fluorescent compound, while NBD labeled derivatives gave strong fluorescence resulting from the reaction of NBD-Cl and amino groups.…”

“…The NaBH 4 reduction of 6-methoxy-N-(3-sulfopropyl)quinorinium (SPQ) probes has been reported as a method to judge whether the inner aqueous phase is present or not 16,20) . The SPQ dissolved in micellar aqueous solution underwent instantaneous reduction with the addition of NaBH 4 , while SPQ in vesicles was hardly reduced owing to the solubilization into an inner aqueous phase 20) .…”