913689-08-4

Usage

Uses

Used in Fluorescence Probes:
2-(2,7-Difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic Acid is used as an intermediate for the synthesis of B431935, a fluorinated biarsenical derivative, which is used as a fluorescence probe in various applications.
Used in Chemical Synthesis:
2-(2,7-Difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic Acid is used as a key intermediate in the synthesis of complex organic compounds, particularly in the production of B431935, a fluorinated biarsenical derivative with potential applications in various fields.

Upstream product

• 85-44-9 phthalic anhydride 
• 103068-41-3 4-fluororesorcinol 
• 2105-61-5 1,2,4-trifluoro-5-nitrobenzene 
• 195136-62-0 1-Fluoro-2,4-dimethoxy-5-nitro-benzene 
• 195136-65-3 1-Amino-2,4-dimethoxy-5-fluorobenzene 
• 195136-58-4 2′,7′-difluorofluorescein 
• 827020-43-9 bis(2,4-dinitrobenzenesulfonyl)-2',7'-difluorofluorescein 

Downstream Products

• 861669-98-9 2-[3,6-bis-(2,2-dimethoxyethoxy)-2,7-difluoro-9H-xanthen-9-yl]benzoic acid 
• 861669-97-8 2-[3,6-bis-(2,2-dimethoxyethoxy)-2,7-difluoro-9H-xanthen-9-yl]benzoic acid 2,2-dimethoxyethyl ester 

Relevant academic research and scientific papers

Fat mass and obesity-associated protein (FTO) inhibitors prepared from 9-(2-carboxyphenyl) xanthene compounds and therapeutic effects thereof

The invention relates to usage of the following general formula I as a drug for diseases targeting fat mass and obesity-associated protein (FTO), and provides usage of 9-(2-carboxyphenyl) xanthene compounds in preparation of FTO inhibitors. Specifically, the invention discloses usage of the 9-(2-carboxyphenyl) xanthene compounds as shown in the formula (I), as well as derivatives and pharmaceutically acceptable salts thereof, in preparation of the FTO inhibitors or pharmaceutical compositions for treating FTO-related diseases.

Probing the target-specific inhibition of sensitized protein tyrosine phosphatases with biarsenical probes

Selective control of enzyme activity is critical for elucidating the roles of specific proteins in signaling pathways. One potential means for developing truly target-specific inhibitors involves the use of protein engineering to sensitize a target enzyme to inhibition by a small molecule that does not inhibit homologous wild-type enzymes. Previously, it has been shown that protein tyrosine phosphatases (PTPs) can be sensitized to inhibition by a biarsenical probe, FlAsH-EDT2, which inhibits PTP activity by specifically binding to cysteine residues that have been introduced into catalytically important regions. In the present study, we developed an array of biarsenical probes, some newly synthesized and some previously reported, to investigate for the first time the structure-activity relationships for PTP inhibition by biarsenicals. Our data show that biarsenical probes which contain substitutions at the 2′ and 7′ positions are more effective than FlAsH-EDT2 at inhibiting sensitized PTPs. The increased potency of 2′,7′-substituted probes was observed when PTPs were assayed with both para-nitrophenylphosphate and phosphopeptide PTP substrates and at multiple probe concentrations. The data further indicate that the enhanced inhibitory properties are the result of increased binding affinity between the 2′,7′-substituted biarsenical probes and sensitized PTPs. In addition we provide previously unknown physicochemical and stability data for various biarsenical probes.

Improved photostable FRET-competent biarsenical-tetracysteine probes based on fluorinated fluoresceins

We have developed fluoro-substituted versions of the biarsenical-tetracysteine label FlAsH, exhibiting significant improvements in important properties over the original fluorescein derivative. In complexes with tetracysteine targets, F2FlAsH exhibits 50 times improved photostability, lower pH sensitivity, higher absorbance and quantum yield than FlAsH, and F4FlAsH adds a new color to the palette of biarsenical dyes. The two probes also provide a new FRET pair with a larger Ro value (54 A) than any previously obtained with biarsenical dyes. Copyright

SULFONATE COMPOUND AND FLUORESCENT PROBE USING THE SAME

The present invention provides a sulfonate compound, including a structure represented by a general formula (I) below, where, in the formula (I), an atomic group A-O is an atomic group that forms a fluorescent compound upon cleavage of a covalent bond between the atomic group A-O and a sulfonyl group, one or a plurality of atomic groups B-SO3- are bonded to an atomic group A, B is a ring that is substituted by one or a plurality of electron-withdrawing groups, the electron-withdrawing group is at least one selected from the group consisting of an alkyl halide group, a nitro group and a cyano group, and B may be the same or different in kind in the case where the plurality of B exist.

A design of fluorescent probes for superoxide based on a nonredox mechanism

Fluorometric detection of O2-? is performed based on desulfonylation of 3 to the corresponding fluoresceins 4 through nucleophilic substitution, and this fluorescing process is quite specific toward O2-? over H

Fluorescent probes for hydrogen peroxide based on a non-oxidative mechanism

Highly selective detection of H2O2 through a non-oxidative mechanism has been achieved by desulfonylation of 1 to the corresponding fluorescein, This approach has been used for the intracellular formation of H2O2/sub

Novel fluorogenic substrates for acid phosphatase

Fluorinated versions of fluorescein diphosphate (FDP) can provide significantly enhanced fluorescence upon hydrolysis by acid phosphatase, as compared with FDP, when measured at the reaction pH.

Synthesis of fluorinated fluoresceins

Several novel fluorinated fluoresceins (Oregon Green dyes) were prepared by the reaction of fluororesorcinols with phthalic anhydride and its derivatives. A novel regiospecific synthesis of fluororesorcinols was key to the successful synthesis of these new fluorophores. (Polyfluoro)- nitrobenzenes were reacted with 2 equiv of sodium methoxide followed by reduction, hydrodediazoniation, and demethylation, giving the first straightforward synthesis of 2-fluororesorcinol, 4-fluororesorcinol, 2,4- difluororesorcinol, and 2,4,5-trifluororesorcinol. These fluorinated fluoresceins have higher photostability and ionize at a lower pH (pK(a) = 3.3-6.1) than fluorescein (pK(a) = 6.5). Some of the fluorinated fluoresceins have very high quantum yields (0.85-0.97), which, in combination with their lower pK(a)s and high photostability, makes them superior fluorescent dyes for use as reporter molecules in biological systems.