57620-22-1

Usage

Biochem/physiol Actions

N-benzyl-2,4-dinitrobenzenesulfonamide reacts with cysteine to release SO2.

Upstream product

• 1441410-01-0 (E)-ethyl 2-cyano-2-(2,4-dinitrophenylsulfonyloxyimino)acetate 
• 100-46-9 benzylamine 
• 1656-44-6 2,4-dinitrobenzenesulfonyl chloride 

Downstream Products

• 1154040-96-6 N-benzyl-N'-(β-D-glucopyranosyl)succinamide 

Relevant academic research and scientific papers

Construction of a novel near-infrared fluorescent probe with multiple fluorescence emission and its application for SO2 derivative detection in cells and living zebrafish

Sulfur dioxide (SO2) in biological systems is an important gaseous signal molecule and plays important roles in physiological activities. It can be endogenously produced by enzymes in mitochondria during oxidation of sulphur-containing molecules. Thus, the development of probes for sulfur dioxide detection in biological environment is necessary. Here, a new near-infrared fluorescent probe (Rh-TPA) with multiple fluorescence emission was constructed and applied for SO2 derivative detection. Rh-TPA was constructed via conjugation of a rhodamine analogue with a triphenylamine group. Rh-TPA exhibited a major emission peak at 740 nm and a shoulder peak at 810 nm. After interacting with SO2 derivatives, the conjugated system dissociated into two smaller chromophores with two emission peaks (520 nm and 570 nm) in the visible region. The probe showed negligible cytotoxicity, as demonstrated by the MTT results. Biological imaging application experiments indicated that the probe can be used to image SO2 derivatives in HeLa cells and living zebrafish.

A two-photon ratiometric fluorescent probe for the synergistic detection of the mitochondrial SO2/HClO crosstalk in cells and: In vivo

Known as a new member of the reactive sulphur species (RSS), endogenous sulfur dioxide (SO2) plays potentially reductive roles such as antioxidation, anti-aging, anti-inflammation, and cytoprotection; however, SO2 is also a metabolite of antioxidation. Hypochlorous acid (HClO) has powerful bio-effects on the innate immune system, and its uncontrolled production leads to adverse damage in cells. To illuminate the potential crosstalk between SO2 and HClO in redox homeostasis, we designed a two-photon ratiometric fluorescent probe for dual-response to mitochondrial SO2/HClO crosstalk in cells and in vivo. Our probe can effectively achieve ratio-type fluorescence dual-response to SO2 and HClO with desirable properties such as large two-photon absorption cross sections, rapid response times (SO2 2 and 15.2 nM for HClO), and favorable selectivity. The probe has been successfully applied to quantitatively detect endogenous SO2 and HClO in HeLa and Raw 264.7 cells. We have verified that there exists a crosstalk between SO2 and HClO during the process of oxidative stress in mitochondria. We have also detected that SO2 can be endogenously produced through oxidation of intracellular sulfur-containing amino acids by HClO in zebrafish in real-time.

Sulfonamide synthesis via oxyma-O-sulfonates - Compatibility to acid sensitive groups and solid-phase peptide synthesis

A milder and more efficient procedure for the synthesis of sulfonamides by activating sulfonic acid groups as the corresponding sulfonate esters of ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) is reported. This method is greener than all other existing protocols for the purpose. Other important advantages lie in (a) its applicability to less nucleophilic anilines under ambient and milder conditions and (b) its compatibility with solid phase peptide synthesis and acid-labile groups such as trityl (Trt) and tBu, which empowers the solid phase synthesis of sulfonamides of various peptides. To illustrate this, the syntheses of three sulfonamide derivatives of the peptide GAILG-NH2, which is relevant in the context of drug design against type 2 diabetes, are demonstrated by using Fmoc-based solid-phase peptide synthesis (SPPS). The activation of sulfonic acids as their corresponding O-sulfonate esters facilitates sulfonamide synthesis, which can be applied to those substrates that possess acid-labile functional groups and is compatible with solid phase synthesis. Copyright

Design, synthesis, and evaluation of thiol-activated sources of sulfur dioxide (SO2) as antimycobacterial agents

Here, 2,4-dinitrophenylsulfonamides with tunable cysteine-activated SO 2 release profiles with half-lives of SO2 release varying from 2 to 63 min are reported. N-Benzyl-2,4-dinitrobenzenesulfonamide (6), which is prepared in one step

One-pot syntheses of dissymmetric diamides based on the chemistry of cyclic monothioanhydrides. Scope and limitations and application to the synthesis of glycodipeptides

(Chemical Equation Presented) Opening cyclic monothioanhydrides by amines provides a convenient entry into amido thioacids that can be trapped in situ by 2,4-dinitrobenzenesulfonamides, by electron-deficient azides, or by amines in the presence of Sanger's reagent leading, in each case, to dissymmetric diamides in what can be considered a one-pot, three-component coupling sequence. The use of monothiomaleic anhydride and bifunctional nucleophiles such as amino thiols provides access to heterocyclic amides. The low reactivity of cyclic monothioanhydrides toward alcohols enables the use of methanol as solvent and obviates the need for the protection of alcohols in the various reaction components. Reaction of N-benzyloxycarbonyl-L-aspartic monothioanhydride with unprotected glycosyl amines, followed by capture of the thioacid intermediate with N-sulfonyl amino acid derivatives results in a three-component convergent synthesis of glycosylated peptides.