91366-64-2

Usage

InChI:InChI=1/C6H2ClFN2O3S/c7-14(11,12)4-2-1-3(8)5-6(4)10-13-9-5/h1-2H

Upstream product

• 29270-55-1 4-fluoro-2,1,3-benzoxadiazole 

Downstream Products

• 1449371-77-0 C₁₃H₁₀FN₃O₃S 
• 1449371-69-0 C₂₁H₂₀N₆O₃S 
• 1449371-78-1 C₂₀H₁₉N₅O₅S₂ 
• 1449371-76-9 C₂₆H₂₄N₁₀O₆S₂ 
• 1449371-68-9 C₂₇H₂₅N₁₁O₄S 
• 215818-28-3 4-Phenylaminosulfonyl-7-fluoro-2,1,3-benzoxadiazole 
• 91366-65-3 4-Aminosulfonyl-7-fluoro-2,1,3-benzoxadiazole 

Relevant academic research and scientific papers

Design, synthesis, and evaluation of positron emission tomography/fluorescence dual imaging probes for targeting facilitated glucose transporter 1 (GLUT1)

Increased energy metabolism followed by enhanced glucose consumption is a hallmark of cancer. Most cancer cells show overexpression of facilitated hexose transporter GLUT1, including breast cancer. GLUT1 is the main transporter for 2-deoxy-2-[18F]fluoro-d-glucose (2-[18F]FDG), the gold standard of positron emission tomography (PET) imaging in oncology. The present study's goal was to develop novel glucose-based dual imaging probes for their use in tandem PET and fluorescence (Fl) imaging. A glucosamine scaffold tagged with a fluorophore and an18F-label should confer selectivity to GLUT1. Out of five different compounds, 2-deoxy-2-((7-sulfonylfluoro-2,1,3-benzoxadiazol-4-yl)amino)-d-glucose (2-FBDG) possessed favorable fluorescent properties and a similar potency as 2-deoxy-2-((7-nitro-2,1,3-benzoxadiazol-4-yl)amino)-d-glucose (2-NBDG) in competing for GLUT1 transport against2-[18F]FDGin breast cancer cells. Radiolabeling with18F was achieved through the synthesis of prosthetic group 7-fluoro-2,1,3-benzoxadiazole-4-sulfonyl [18F]fluoride ([18F]FBDF) followed by the reaction with glucosamine. The radiotracer was finally analyzedin vivoin a breast cancer xenograft model and compared to2-[18F]FDG. Despite favourablein vitrofluorescence imaging properties,2-[18F]FBDGwas found to lack metabolic stabilityin vivo, resulting in radiodefluorination. Glucose-based2-[18F]FBDGrepresents a novel dual-probe for GLUT1 imaging using FI and PET with the potential for further structural optimization for improved metabolic stabilityin vivo.

Fluorogenic 2,1,3-benzoxadiazoles and fluorometric amine/thiol assays therewith

Fluorogenic compounds are disclosed which are reactive with biologically important analytes including primary amines, secondary amines, and/or thiols and are of the general formula: STR1 wherein X is a group such as STR2 --CN, --CO2 CH3, or SO2 R, and wherein R is OR3, or Cl; R1 and R2 are hydrogen atoms or alkyl groups having 1 to 3 carbon atoms and R3 is a phenyl or benzyl group. The inventive compounds form a fluorescent adduct with the above analytes at the number 7 position of the benzoxadiazole ring. The fluorescent adduct thereby formed enables detection of very minute amounts of analyte (picomoles) using conventional fluorescent analytical methods.

New Fluorogenic Reagent Having Halogenobenzofurazan Structure for Thiols: 4-(Aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole

4-(Aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole (ABD-F) has been synthesized as a new fluorogenic reagent for thiols.Its reaction rate to homocysteine is over 30 times faster than that with ammonium 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate (SBD-F).The fluorogenic reaction to thiol was completed quantitatively in 5 min at 50 deg C and pH 8.0.Alanine, proline, and cystine did not react under the same conditions.The fluorescence intensity of the fluorophor was pH dependent with the highest at pH 2.The ABD-thiols obtained by the prelabeling technique were separated and detected by reversed-phase HPLC.The detection limits (S/N = 3) for cysteine, glutathione, N-acetylcysteine, homocysteine, and cysteamine were 0.6, 0.4, 1.9, 0.5, and 0.5 pmol, respectively.