1155356-49-2

Usage

Synthesis

Reaction of a diazonium salt with a pyrrole derivative

Potential applications

Organic chemistry, materials science, development of organic dyes, pigments, and materials with photochromic or fluorescent properties
Further research and testing needed to understand potential applications.

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 201858-51-7 p-methyl red 
• 114143-63-4 4-[4-(dimethylamino)phenylazo]benzoic acid 

Downstream Products

• 1561749-40-3 C₂₀H₂₃N₇O₃ 
• 1431163-78-8 C₇₁H₁₁₂N₂₀O₁₃S 
• 1431163-79-9 C₁₀₉H₁₈₂N₃₀O₂₁S 
• 1431163-77-7 C₂₂H₂₃N₅OS₂ 
• 4238-39-5 N-[4-[(1E)-2-[4-(dimethylamino)phenyl]diazenyl]benzoyl]-glycine 

Relevant academic research and scientific papers

Resin bead micro-UV-visible absorption spectroscopy

The construction and design of a microscope coupled with a miniature UV-vis spectrometer is described. This was applied to the study of dyes linked to solid supports and displayed good correlation in spectral shape and λmax values when compared

Synthesis and evaluation of fluorogenic substrates for phospholipase D and phospholipase C

Fluorogenic analogues of phosphatidylcholine and lysophosphatidylcholine, DDPB and lysoDDPB, were synthesized by an enzyme-assisted strategy. The analogues were evaluated as substrates for phospholipases C and D and lysophospholipase D. DDPB was cleaved b

Synthetic Fluorogenic Peptides Reveal Dynamic Substrate Specificity of Depalmitoylases

Palmitoylation is a post-translational modification involving the thioesterification of cysteine residues with a 16-carbon-saturated fatty acid. Little is known about rates of depalmitoylation or the parameters that dictate these rates. Here we report a modular strategy to synthesize quenched fluorogenic substrates for the specific detection of depalmitoylase activity and for mapping the substrate specificity of individual depalmitoylases. We demonstrate that human depalmitoylases APT1 and APT2, and TgPPT1 from the parasite Toxoplasma gondii, have distinct specificities that depend on amino acid residues distal to the palmitoyl cysteine. This information informs the design of optimal and non-optimal substrates as well as isoform-selective substrates to detect the activity of a specific depalmitoylase in complex proteomes. In addition to providing tools for studying depalmitoylases, our findings identify a previously unrecognized mechanism for regulating steady-state levels of distinct palmitoylation sites by sequence-dependent control of depalmitoylation rates. Amara et al. describe a method for preparing positional scanning libraries of fluorogenic palmitoylated peptide substrates. This allowed identification of residues that are distal to the palmitoylation site that impact turnover. This information allowed the design of substrates that are selective for a specific depalmitoylating enzyme.

Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics

The inverse electron demand Diels–Alder pyridazine elimination reaction between tetrazines and allylic substituted trans-cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we report a fluorogenic tool consisting of a TCO-linked EDANS fluorophore and a DABCYL quencher for accurate determination of both the click and release rate constants for any tetrazine at physiologically relevant concentrations.

ENZYME DETECTION COMPOUND AND MANUFACTURING METHOD OF THE COMPOUND

PROBLEM TO BE SOLVED: To obtain a noel compound for detecting enzyme and a detection method of enzyme using the same and a compound having following structure, R1 and R2 are each independently H, an alkyl group having 1 to 2 carbon atoms, an alkenyl group having 2 carbon atoms or an alkynyl group or a phenyl group having 2 carbon atoms, n is 2 to 12 and X is an amino acid residue. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2018,JPOandINPIT

TUNABLE FLUORESCENCE USING CLEAVABLE LINKERS

The invention relates to cleavable chemistry in general, and in particular, to tunable fluoresence using cleavable linkers present in fluorochrome-quencher conjugates.

FRET-based imaging of transbilayer movement of pepducin in living cells by novel intracellular bioreductively activatable fluorescent probes

To elucidate the mechanisms of direct transmembrane penetration of pepducins, which are artificial lipopeptide G protein-coupled receptor (GPCR) modulators, we developed two types of FRET-based probes, Pep13-FL-SS-Dab (13) targeting the inner leaflet of the lipid bilayer and Pep13-Dab-SS-FL (14) targeting the cytosol, respectively. They are composed of a pepducin moiety and a fluorescent switch component consisting of 5(6)-carboxyfluorescein (FAM) as a fluorophore and dabcyl as a quencher connected through disulfide bond linkage. When they are internalized into the cytosol, intracellular glutathione can cleave the disulfide bond to release the quencher, which results in a turn-on fluorescence signal. Using these probes, we performed live cell imaging of transbilayer movements of pepducins on MCF-7 cells for the first time. The results suggested that the lipid moiety of the probes facilitated pepducin flipping across and tethering to the membrane. The present study raises the possibility of applying the probe architecture for direct intracellular drug delivery. The Royal Society of Chemistry 2013.

A specific molecular beacon probe for the detection of human prostate cancer cells

The small-molecule, water-soluble molecular beacon probe 1 is hydrolyzed by the lysate and living cells of human prostate cancer cell lines (LNCaP), resulting in strong green fluorescence. In contrast, probe 1 does not undergo significant hydrolysis in ei

Multicolor, one- and two-photon imaging of enzymatic activities in live cells with fluorescently quenched activity-based probes (qABPs)

Fluorescence imaging provides an indispensable way to locate and monitor biological targets within complex and dynamic intracellular environments. Of the various imaging agents currently available, small molecule-based probes provide a powerful tool for live cell imaging, primarily due to their desirable properties, including cell permeability (as a result of their smaller sizes), chemical tractability (e.g., different molecular structures/designs can be installed), and amenability to imaging a wide variety of biological events. With a few exceptions, most existing small molecule probes are however not suitable for in vivo bioimaging experiments in which high-resolution studies of enzyme activity and localization are necessary. In this article, we reported a new class of fluorescently Quenched Activity-Based Probes (qABPs) which are highly modular, and can sensitively image (through multiple enzyme turnovers leading to fluorescence signal amplification) different types of enzyme activities in live mammalian cells with good spatial and temporal resolution. We have also incorporated two-photon dyes into our modular probe design, enabling for the first time activity-based, fluorogenic two-photon imaging of enzyme activities. This, hence, expands the repertoire of smart, responsive probes currently available for live cell bioimaging experiments.

Efficient functional molecule incorporation method to functionalized peptide nucleic acid (PNA): use in synthesis of labeled PNA oligomers

A novel efficient synthetic method for a functionalized PNA (peptide nucleic acid) is described, in which a functional molecule is incorporated in place of a nucleobase. Novel ω-AA-BocPNA-OH (20-24, AA=amino acid) were designed as PNA precursor monomer units into which functional molecules could be incorporated efficiently. Compounds 20-24 reacted quantitatively with OSu (N-hydroxysuccinimidyl) active ester derivatives and isothiocyanate derivatives of commercial functional molecules to give target functionalized PNA monomer units 25-53. Various types of functionalized PNA monomer units could be efficiently incorporated into multiple predetermined positions in a PNA oligomer by SPPS (solid phase peptide synthesis) in the same way as for the four A(Cbz), G(Cbz), C(Cbz), and T PNA monomer units.