53518-15-3

Usage

Uses

Used in Biochemical Research:
Coumarin 151 is used as a key component in the preparation of peptidase substrates, which are essential for studying the activity and function of peptidases, a group of enzymes that break down peptides and proteins. Its role in this application is crucial for understanding the mechanisms of proteolysis and the regulation of protein function in biological systems.
Used in Fluorometric Assays:
In the field of molecular biology, Coumarin 151 is utilized in the synthesis of substrates for the fluorometric assay of proteolytic enzymes in biological fluids. This application allows researchers to measure the activity of these enzymes in samples, providing valuable insights into their roles in various biological processes and potential involvement in disease pathways.
Used as a Laser Dye:
Beyond its applications in biochemistry and molecular biology, Coumarin 151 also finds use as a laser dye due to its unique optical properties. This application takes advantage of its ability to absorb and emit light at specific wavelengths, making it a valuable tool in the development of laser technologies and other optical devices.

Purification Methods

Purify the coumarin by column chromatography on a C18 column, elute with acetonitrile/0.01M H2O/HCl (1:1), and recrystallise it from isopropanol. Alternatively, it is eluted from a silica gel column with CH2Cl2, or by extracting a CH2Cl2 solution (4g/L) with 1M aqueous NaOH (3 x 0.1L), followed by drying (MgSO4), filtration and evaporation. [Bissell J Org Chem 45 2283 1980, Zimmermann et al. Anal Biochem 70 258 1976.]

InChI:InChI=1/C10H6F3NO2/c11-10(12,13)7-4-9(15)16-8-3-5(14)1-2-6(7)8/h1-4H,14H2

Upstream product

• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 591-27-5 m-Hydroxyaniline 
• 211990-57-7 C₃₁H₃₈F₃N₅O₁₂ 
• 63450-46-4 7-(Carbethoxyamido)-4-(trifluoromethylcoumarin) 
• 7159-96-8 ethyl N-(3-hydroxyphenyl)carbamate 
• 309734-26-7 7-(2-hydroxybenzylideneamino)-4-(trifluoromethyl)-2H-chromen-2-one 
• 1398531-34-4 C₂₁H₁₂F₃NO₃ 
• 201608-14-2 ac-DEVD-AFC 
• 1574594-90-3 7-isocyanato-4-(trifluoromethyl)-2H-chromen-2-one 
• 1609986-36-8 C₂₇H₂₁F₃N₂O₉ 
• 1453905-09-3 C₂₈H₂₃F₃N₂O₉ 
• 1609986-40-4 C₂₅H₁₉F₃N₄O₉ 
• 1609986-41-5 C₂₆H₂₁F₃N₄O₉ 
• 1609986-38-0 C₂₆H₂₀F₃N₃O₉ 

Downstream Products

• 73496-34-1 7-(N^α-Boc-N^ε-Z-L-lysinamido)-4-(trifluoromethyl)-coumarin 
• 73496-38-5 7-(N^α-Z-L-Argininamido)-4-(trifluoromethyl)-coumarin Hydrochloride 
• 73496-39-6 7-(N^α-Z-L-Argininamido)-4-(trifluoromethyl)coumarin Hydrobromide 
• 73496-37-4 7-(N^α-Z-N^ε-Boc-L-Lysinamido)-4-(trifluoromethyl)-coumarin 
• 78277-39-1 7-Benzamido-4-(trifluoromethyl)coumarin 
• 427880-47-5 7-[N-(p-toluenesulfonyl)amino]-4-trifluoromethylcoumarin 
• 787549-23-9 (S)-[5-acetylamino-1-(2-oxo-4-trifluoromethyl-2H-chromen-7-ylcarbamoyl)pentyl]carbamic acid tert-butyl ester 
• 571193-65-2 4'-(4-(3,5-bis(N-(4-trifluoromethyl-7-aminocoumarin)methyl)phenoxymethyl)phenyl)-2,2':6',2-terpyridine 
• 73496-35-2 7-(N^α-Boc-L-Leucyl-N^ε-Z-L-lysinamido)-4-(trifluoromethyl)coumarin 
• 73496-36-3 7-(N^α-Z-D-Alanyl-L-leucyl-N^ε-Z-L-lysinamido)-4-(trifluoromethyl)coumarin 
• 200554-30-9 7-amino-4-trifluoromethylcoumarin-6-sulfonic acid, sodium salt 
• 859175-95-4 C₂₃H₂₁BF₃NO₅ 
• 1159794-22-5 (SP-4-3)-ammine(7-amino-4-(trifluoromethyl)coumarine)dichloroplatinum(II) 
• 1380328-60-8 4-((2-oxo-4-(trifluoromethyl)-2H-chromen-7-ylcarbamoyloxy)methyl)phenyl 2-(2-(2-phenylacetamido)acetamido)-3-(tritylthio)propanoate 

Relevant academic research and scientific papers

A Cyanine Photooxidation/β-Elimination Sequence Enables Near-infrared Uncaging of Aryl Amine Payloads

Uncaging strategies that use near-infrared wavelengths can enable the highly targeted delivery of biomolecules in complex settings. Many methods, including an approach we developed using cyanine photooxidation, are limited to phenol-containing payloads. Given the critical role of amines in diverse biological processes, we sought to use cyanine photooxidation to initiate the release of aryl amines. Heptamethine cyanines substituted with an aryl amine at the C4′ position undergo only inefficient release, likely due electronic factors. We then pursued the hypothesis that the carbonyl products derived from cyanine photooxidation could undergo efficient β-elimination. After examining both symmetrical and unsymmetrical scaffolds, we identify a merocyanine substituted with indolenine and coumarin heterocycles that undergoes efficient photooxidation and aniline uncaging. In total, these studies provide a new scheme—cyanine photooxidation followed by β-elimination—through which to design photocages with efficient uncaging properties.

Illuminating the Function of the Hydroxyl Radical in the Brains of Mice with Depression Phenotypes by Two-Photon Fluorescence Imaging

Depression is intimately linked with oxidative stress. As one of the most reactive and oxidative reactive oxygen species that is overproduced during oxidative stress, the hydroxyl radical (.OH) can cause macromolecular damage and subsequent neurological diseases. However, due to the high reactivity and low concentration of .OH, precise exploration of .OH in brains remains a challenge. The two-photon fluorescence probe MD-B was developed for in situ .OH imaging in living systems. This probe achieves exceptional selectivity towards .OH through the one-electron oxidation of 3-methyl-pyrazolone as a new specific recognition site. MD-B can be used to map .OH in mouse brain, thereby revealing that increased .OH is positively correlated with the severity of depression phenotypes. Furthermore, .OH has been shown to inactivate deacetylase SIRT1, thereby leading to the occurrence and development of depression phenotypes. This work provides a new strategy for the future treatment of depression.

Multi-Fluorinated Azido Coumarins for Rapid and Selective Detection of Biological H2S in Living Cells

Hydrogen sulfide (H2S) is an endogenously produced gaseous signaling molecule with multiple biological functions. In order to visualize the endogenous in situ production of H2S in living cells in real time, here we developed multi-fluorinated azido coumarins as fluorescent probes for the rapid and selective detection of biological H2S. Kinetic studies indicated that an increase in fluorine substitution leads to an increased rate of H2S-mediated reduction reaction, which is also supported by our theoretical calculations. To our delight, tetra-fluorinated coumarin 1 could react with H2S fast (t1/2≈1 min) and selectively, which could be further used for continuous enzymatic assays and for visualization of intracellular H2S. Bioimaging results obtained with 1 revealed that d-Cys could induce a higher level of endogenous H2S production than l-Cys in a time-dependent manner in living cell.

Benzopyrone or quinolinone compound and application thereof

The invention discloses a benzopyrone or quinolinone compound and application thereof in preparation of a medicine for treating prostatic cancer, and belongs to the field of medicines. The benzopyroneand quinolinone compound with the structural formula as shown in the formula (I) has obvious antagonistic activity on androgen receptors and also has inhibitory activity on prostate cancer cells which do not express the androgen receptors. Therefore, the compound can be used as an androgen receptor antagonist to be applied to treatment of diseases related to androgen receptors or treatment of various metastatic prostate cancers, and a new choice is provided for development of drugs for treating prostate cancers.

Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents

To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G0/G1 phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis.

IS100- A Highly Effective Enzyme Principle For Use In Dermal Therapeutics, And For Health And Beauty

A aqueous preparation called IS 100 consisting of at least a hundred of proteins prepared from wheat germ lysate is provided. The preparation shows protease activity and is considerably stable. None of the constituent proteins in IS 100 can permeate synthetic or biological membranes and therefore IS 100 has a variety of in vitro or external applications that require cleaving and cleansing of unwanted or dead tissues on dermal surface.

Disassembly kinetics of quinone-methide-based self-immolative spacers that contain aromatic nitrogen heterocycles

We prepared several pyridine- and pyrimidine-based self-immolative spacer groups to evaluate the significance of the resonance energy of the spacer aromatic ring on the kinetics of 1,4- and 1,6-elimination reactions, which govern spacer disassembly. Subsequently, we relied on a photoactivation procedure to accurately analyze the disassembly kinetics. Beyond providing new results that are relevant for deriving quantitative structure-property relationships, herein, we demonstrate that pH value can be used as an efficient parameter to finely control the disassembly time of a self-immolative spacer after an initial activation. Burn rubber: Kinetic analysis of the pH-dependent disassembly of self-immolative spacers that contain aromatic nitrogen heterocycles was performed. Electron-poor pyrimidine cores exhibited the longest disassembly times. This study confirms the trend that electron-rich aryl cores accelerate self-immolation.

Magnesium bis(trifluoromethane)sulfonimide: An efficient catalyst for the synthesis of coumarins under solvent-free conditions

Magnesium bis(trifluoromethane)sulfonimide [Mg(NTf2) 2] is an efficient catalyst for the synthesis of coumarins via the Pechmann condensation reaction of phenols and β-ketoesters under solvent-free conditions.

Development of a new enzyme-responsive self-immolative spacer conjugate applicable to the controlled drug release

A new self-immolative spacer conjugate based on a chemical adaptor unit aiming at controlled releasing drugs was designed and synthesized. It releases a fluorophore which was used as a model drug via a spontaneous cyclization mechanism after cleavage of an enzyme substrate. This system was proved to be stable under physiological conditions and only decomposed triggered by enzyme. It provides a generic linkage allowing connection of a variety of drugs and targeted devices to the chemical adaptor.

Uncovering the true mechanism of optical detection of HSO4 - in water by Schiff-base receptors - Hydrolysis vs. hydrogen bonding

The mechanism of optical detection of HSO4- in aqueous medium by Schiff-base receptors has previously been proposed to depend on selective hydrogen-bond interactions. Here, we clearly demonstrate for the first time that the acidic na