85157-21-7

Usage

Uses

Used in Biological Research:
7-Amino-4-carboxymethylcoumarin is used as a fluorescent marker for tracking and visualizing biological processes. Its application is particularly beneficial in studies that involve protein activity, enzymatic reactions, or the tracing of cell structures, providing a means to observe these processes in real-time.
Used in Medical Research:
In the medical field, 7-Amino-4-carboxymethylcoumarin is employed as a tracer in diagnostic procedures and therapeutic monitoring. Its fluorescent properties allow for the detection and visualization of biological molecules, which can be crucial in understanding disease mechanisms and evaluating the effectiveness of treatments.
Used in Chemical Research:
7-Amino-4-carboxymethylcoumarin is utilized as a fluorescent probe in chemical research, where it aids in the identification and analysis of chemical compounds. Its ability to fluoresce under UV or blue light makes it an effective tool for studying molecular interactions and chemical reactions.
Used in Drug Delivery Systems:
7-Amino-4-carboxymethylcoumarin is also used in the development of drug delivery systems, where it can serve as a marker to monitor the distribution and release of therapeutic agents within the body. This can help in optimizing drug delivery and ensuring that the medication reaches its intended target.

InChI:InChI=1/C11H9NO4/c12-7-1-2-8-6(3-10(13)14)4-11(15)16-9(8)5-7/h1-2,4-5H,3,12H2,(H,13,14)

Upstream product

• 85157-20-6 ethyl 7-N-(carbethoxy)aminocoumarin-4-acetate 
• 542-05-2 acetonedicarboxylic acid 
• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 77-92-9 citric acid 
• 7159-96-8 ethyl N-(3-hydroxyphenyl)carbamate 
• 591-27-5 m-Hydroxyaniline 
• 343310-64-5 ethyl 2-(7-(ethoxycarbonylamino)-2-oxo-2H-chromen-4-yl)acetic acid 
• 141692-64-0 methyl 7-ethoxycarbonylaminocoumarin-4-acetate 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 

Downstream Products

• 141692-66-2 benzyl 7-aminocoumarin-4-acetamidoacetate 
• 141692-73-1 benzyl 2-(7-aminocoumarin-4-yl)acetate 
• 378247-75-7 2-(7-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-oxo-2H-chromen-4-yl)acetic acid 
• 525579-01-5 N-{4-[(benzyloxycarbonylmethyl-carbamoyl)-methyl]-2-oxo-2H-chromen-7-yl}-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester 
• 525579-02-6 (2-{7-[6-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoylamino]-2-oxo-2H-chromen-4-yl}-acetylamino)-acetic acid benzyl ester 
• 1135458-88-6 Z-Gly-Gly-Leu-ACA-β-Ala-OH 
• 1201896-27-6 Z-Gly-Gly-Leu-ACA-Lys(Nε-pentynoyl)-NH2 

Relevant academic research and scientific papers

A Suite of Activity-Based Probes to Dissect the KLK Activome in Drug-Resistant Prostate Cancer

Kallikrein-related peptidases (KLKs) are a family of secreted serine proteases, which form a network (the KLK activome) with an important role in proteolysis and signaling. In prostate cancer (PCa), increased KLK activity promotes tumor growth and metastasis through multiple biochemical pathways, and specific quantification and tracking of changes in the KLK activome could contribute to validation of KLKs as potential drug targets. Herein we report a technology platform based on novel activity-based probes (ABPs) and inhibitors enabling simultaneous orthogonal analysis of KLK2, KLK3, and KLK14 activity in hormone-responsive PCa cell lines and tumor homogenates. Importantly, we identifed a significant decoupling of KLK activity and abundance and suggest that KLK proteolysis should be considered as an additional parameter, along with the PSA blood test, for accurate PCa diagnosis and monitoring. Using selective inhibitors and multiplexed fluorescent activity-based protein profiling (ABPP), we dissect the KLK activome in PCa cells and show that increased KLK14 activity leads to a migratory phenotype. Furthermore, using biotinylated ABPs, we show that active KLK molecules are secreted into the bone microenvironment by PCa cells following stimulation by osteoblasts suggesting KLK-mediated signaling mechanisms could contribute to PCa metastasis to bone. Together our findings show that ABPP is a powerful approach to dissect dysregulation of the KLK activome as a promising and previously underappreciated therapeutic target in advanced PCa.

Dual-Reactable Fluorescent Probes for Highly Selective and Sensitive Detection of Biological H2S

Hydrogen sulfide (H2S) is an important endogenous signaling molecule with a variety of biological functions. Development of fluorescent probes for highly selective and sensitive detection of H2S is necessary. We show here that dual-reactable fluorescent H2S probes could react with higher selectivity than single-reactable probes. One of the dual-reactable probes gives more than 4000-fold turn-on response when reacting with H2S, the largest response among fluorescent H2S probes reported thus far. In addition, the probe could be used for high-throughput enzymatic assays and for the detection of Cys-induced H2S in cells and in zebrafish. These dual-reactable probes hold potential for highly selective and sensitive detection of H2S in biological systems. Two heads are better than one: Fluorescent probes with two types of reactive heads (R1 and R2) for H2S can lead to a higher selectivity than that of single-reactable probes (See Figure). The probe was used for highly selective and sensitive detection of biological H2S.

Ubiquitin 7-amino-4-carbamoylmethylcoumarin as an improved fluorogenic substrate for deubiquitinating enzymes

A new fluorogenic substrate Ub-ACC (ubiquitin C-terminal 7-amino-4-carbamoylmethyl-coumarin) was developed for DUB (deubiquitinating enzyme) activity assays. This substrate can be synthesized with higher efficiency than the classical DUB substrate, Ub-AMC (ubiquitin C-terminal 7-amino-4-methylcoumarin). DUB assays using UCH-L3, OTUD2 and USP30 demonstrated that Ub-ACC shows nearly 2-fold higher sensitivity than Ub-AMC.

Marine natural products as inhibitors of cystathionine beta-synthase activity

A library consisting of characterized marine natural products as well as synthetic derivatives was screened for compounds capable of inhibiting the production of hydrogen sulfide (H2S) by cystathionine beta-synthase (CBS). Eight hits were valid

O-fluorination of aromatic azides yields improved azido-based fluorescent probes for hydrogen sulfide: Synthesis, spectra, and bioimaging

Hydrogen sulfide (H2S) is an endogenously produced gaseous signaling molecule with multiple biological functions. To visualize the endogenous in situ production of H2S in real time, new coumarin- and boron-dipyrromethene- based fluorescent turn-on probes were developed for fast sensing of H2S in aqueous buffer and in living cells. Introduction of a fluoro group in the ortho position of the aromatic azide can lead to a greater than twofold increase in the rate of reaction with H2S. On the basis of o-fluorinated aromatic azides, fluorescent probes with high sensitivity and selectivity toward H2S over other biologically relevant species were designed and synthesized. The probes can be used to in situ to visualize exogenous H2S and d-cysteine-dependent endogenously produced H2S in living cells, which makes them promising tools for potential applications in H2S biology.

A versatile access to new halogenated 7-azidocoumarins for photoaffinity labeling: Synthesis and photophysical properties

A versatile methodology for the synthesis of 6/8-halogenated 7-aminocoumarins from the corresponding 7-hydroxy analogs using Pd-catalyzed amination reaction as the key step is presented. Further readily conversion into 7-azidocoumarins was performed and the resulting aryl azides proved higher stability and reactivity than the corresponding non-halogenated parent compound. These new compounds may thus constitute attractive scaffolds for designing novel photoaffinity reagents for various challenging bio-labeling applications.

Fluorescence-based detection of single nucleotide permutation in DNA via catalytically templated reaction

Templated reduction of low fluorescence azidocoumarin-PNA conjugate to high fluorescence aminocoumarin was achieved using a catalytic amount of DNA with single nucleotide resolution. The Royal Society of Chemistry.

Expedient solid-phase synthesis of fluorogenic protease substrates using the 7-amino-4-carbamoylmethylcoumarin (ACC) fluorophore

A highly efficient solid-phase synthesis method for the preparation of fluorogenic protease substrates based upon the bifunctional leaving group 7-amino-4-carbamoylmethylcoumarin (ACC) is reported. Methods for the large-scale preparation of the novel fluorogenic leaving-group ACC are provided (Scheme 1). Detailed procedures are also provided for loading a diverse set of amino acids to support-bound ACC in good yields and with minimal racemization. Finally, procedures are included for the preparative synthesis of optimized ACC substrates for HIV-1 protease and plasmin.

Bifunctional coumarin derivatives in solution and solid phase synthesis of fluorogenic enzyme substrates

The use of the fluorescent bifunctional compounds 7-amino-4-coumarinyl-acetic acid 1, 7-hydroxy-4-coumarinyl-acetic acid 2 and ethyl 7-amino-4-coumarinyl-acetate 3 in solution and solid phase synthesis of fluorogenic enzyme substrates was examined. The in

SYNTHESIS AND FLUORESCENT PROPERTIES OF NAW HETEROBIFUNCTIONAL FLUORESCENT PROBES

Heterobifunctional fluorescent molecules possessing the same fluorescent properties as their monofunctional parent compounds are investigated.Two different functions of these probes do not alter their lasing properties and allow many potential applications in cellular biochemistry.This paper investigates two families of compouds derived from carbazole and coumarin.The synthesis and spectral properties of these probes are described.