5354-61-0

Usage

Uses

Used in Fluorescent Labeling:
DANSYLAMIDOETHYL MERCAPTAN is used as a fluorescent label for biomolecules due to its distinct fluorescence properties. DANSYLAMIDOETHYL MERCAPTAN's ability to absorb and emit light at specific wavelengths makes it a valuable tool for various applications in the field of biochemistry and molecular biology.
Used in Chemical Synthesis:
DANSYLAMIDOETHYL MERCAPTAN serves as a versatile intermediate in the synthesis of various organic compounds. Its chemical properties allow it to be used in the production of a wide range of molecules, including pharmaceuticals, dyes, and other specialty chemicals.
Used in Analytical Chemistry:
DANSYLAMIDOETHYL MERCAPTAN's fluorescence characteristics make it useful in analytical chemistry for the detection and quantification of specific substances. It can be employed as a probe or indicator in various analytical techniques, such as high-performance liquid chromatography (HPLC) and capillary electrophoresis.
Used in Pharmaceutical Industry:
DANSYLAMIDOETHYL MERCAPTAN is used as a building block in the development of new drugs. Its unique chemical properties and reactivity make it a valuable component in the synthesis of novel pharmaceutical compounds with potential therapeutic applications.
Used in Research and Development:
DANSYLAMIDOETHYL MERCAPTAN's fluorescence properties and chemical reactivity make it an essential tool in research and development for various scientific applications. It can be used to study the structure, function, and interactions of biomolecules, as well as to develop new methods and techniques in the life sciences.

Upstream product

• 605-65-2 5-(dimethylamino)naphth-1-ylsulfonyl chloride 
• 56-17-7 cystamine dihydrochioride 
• 90120-75-5 monodansylcystamine 
• 64307-60-4 2-(5-(dimethylamino)naphthalene-1-sulfonamido)ethyl 4-methylbenzenesulfonate 
• 5282-89-3 5-dimethylamino-N-(2-hydroxyethyl)naphthalene-1-sulfonamide 
• 301523-01-3 5-(N,N-dimethylamino)naphthalene-1-sulfon(2-acetothioethyl)amide 
• 881013-37-2 N,N’-(disulfanediylbis(ethane-2,1-diyl))bis(5-(dimethylamino)naphthalene-1-sulfonamide) 

Downstream Products

• 97-54-1 2-methoxy-4-propenylphenol 

Relevant academic research and scientific papers

Emollient, humectant, and fluorescent α,β-unsaturated thiol esters for long-acting skin applications

We describe compounds in which an emollient or a humectant bears an α,β-unsaturated thiol ester capable of reacting with nucleophilic amino acids in stratum corneum proteins. These compounds should serve as long-lasting moisturizers for skin. The emollient derivatized was octadecyl propanoate, and the humectant was poly(ethylene glycol). These hydrophobic and hydrophilic compounds, as well as a fluorescent, dansyl-containing thiol ester, were found to react within minutes with the thiol N-acetylcysteamine upon addition of a catalytic amount of an organic base in chloroform. The structures of the products resulting from conjugate addition to the unsaturated thiol esters were determined by NMR spectroscopy. In the case of the α,β,γ,δ-unsaturated (sorboyl) thiol ester, both the 1,4-addition product and the β,γ-unsaturated-1,6-addition product formed, followed by diadduct. An in vivo test of the fluorescent α,β-unsaturated thiol ester showed that this compound persisted on skin for 3 weeks vs. 6 days for the non-bonding control compound.

Reduction with tris(2-carboxyethyl)phosphine (TCEP) enables the use of an S-sulphonate protecting group for thiol-mediated bioconjugation

Herein, we demonstrate the effectiveness of the water-friendly S-sulphonate group as an alternative to traditional thiol protecting groups for subsequent deprotection-bioconjugation reactions, under conditions that are compatible with the use of biochemic

The role of hydrophobicity in the antimicrobial and hemolytic activities of polymethacrylate derivatives

We synthesized cationic random amphiphilic copolymers by radical copolymerization of methacrylate monomers with cationic or hydrophobic groups and evaluated their antimicrobial and hemolytic activities. The nature of the hydrophobic groups, and polymer co

Pharmacological evaluation of disulfiram analogs as antimicrobial agents and their application as inhibitors of fosB-mediated fosfomycin resistance

Disulfide analogs of the alcohol sobriety medication disulfiram (Antabuse) were evaluated for antimicrobial activity. Structure-activity relationship analyses of MIC data obtained for methicillin-resistant Staphylococcus aureus (MRSA) and other pathogenic organisms revealed correlations between the lipophilicity and bulkiness of the substituents. Analogs conferring optimal anti-MRSA activity contained S-octyl disulfides and either N,N-dimethyl- or N-pyrrolidine dithiocarbamate substituents. Additional testing revealed that both disulfiram and its S-octyl derivative are capable of sensitizing?S. aureus to the bactericidal effects of fosfomycin. Mechanistic studies established that the compounds decrease intracellular levels of the fosB cofactor bacillithiol through a thiol-disulfide exchange reaction. The increased fosfomycin susceptibility?in S. aureus?was thereby attributed to a depleted cellular bacillithiol pool available for inactivation?by fosB.

Sulfydryl-containing fluorescent compound or thioester derivative thereof and preparation and application thereof

The invention provides a sulfydryl-containing fluorescent compound or a thioester derivative thereof and preparation and application thereof. The sulfydryl-containing fluorescent compound or the thioester derivative of the sulfydryl-containing fluorescent compound can emit strong fluorescence, the compund can directly react with nitric oxide or specifically and rapidly react with nitric oxide after the ester group is removed so as to generate the weak fluorescence product, and the quenched fluorescence can be gradually recovered to the initial level when the nitric oxide concentration is reduced so as to achieve the reversibility and the real-time dynamic detection on nitric oxide. The fluorescent probe is good in stability and can be stored and used for a long time; the detection signal-to-noise ratio is high, and the sensitivity is good; the compound has the advantages of good selectivity, good biofilm permeability, rapid detection reaction and reversibility of detection response andis suitable for real-time dynamic observation of endogenous nitric oxide in organisms such as solutions, intracellular organisms and living tissues. The structural formula of sulfydryl-containing fluorescent compound or the thioester derivative thereof is shown in the specification.

Aldehyde-mediated bioconjugation: Via in situ generated ylides

A technically simple approach for rapid, high-yielding and site-selective bioconjugation has been developed for both in vitro and cellular applications. This method involves the generation of maleimido-phosphonium ylides via 4-nitrophenol catalysis under physiological conditions followed by their Wittig reactions with aldehyde-appended biomolecules.

Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection

Siderophores, such as enterobactin (Ent), are small molecules that can be selectively imported into bacteria along with iron by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy-to-perform, one-pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB-Glc-Ent, it can selectively label Gram-negative bacteria that utilize Ent, including some E. coli strains and P. aeruginosa. V. cholerae, a bacterium that utilizes linearized Ent, can also be weakly targeted. Moreover, the targeting is effective under iron-limiting but not iron-rich conditions. Our results suggest that the RhB-Glc-Ent probe is sensitive not only to the bacterial strain but also to the iron condition in the environment.

METHODS FOR DETECTING AND CATEGORIZING SKIN SENSITIZERS

Methods for detecting skin sensitization chemical compounds using Nuclear Magnetic Resonance (NMR) spectroscopy and/or a microplate spectrophotometric assay or other spectroscopic methods.

Methods and Compounds for Detection of Medical Disorders

The invention provides methods for detection of medical disorders, associated with cellular oxidative stress, cell degeneration and/or cell death. The invention further relates to compounds comprising a thiol (—SH) group, for detecting cells undergoing ox

Fluorophore-labeled S-nitrosothiols

A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown-that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.