28705-46-6

Usage

Uses

Used in Biochemical Research:
7-(DIETHYLAMINO)COUMARIN-3-CARBOXYLIC ACID ETHYL ESTER is used as a fluorescent probe for cell labeling, protein labeling, and localization studies, enabling researchers to track and visualize biological processes with precision.
Used in the Development of Fluorescent Sensors:
7-(DIETHYLAMINO)COUMARIN-3-CARBOXYLIC ACID ETHYL ESTER is utilized in the creation of fluorescent sensors designed to detect and measure the presence of various biomolecules and chemical species, contributing to advancements in analytical chemistry and molecular diagnostics.
Used in Biotechnology Applications:
In the biotechnology industry, 7-(DIETHYLAMINO)COUMARIN-3-CARBOXYLIC ACID ETHYL ESTER serves as a component in assays and other diagnostic tools, facilitating the study of biological interactions and the development of new therapeutic strategies.

InChI:InChI=1/C16H19NO4/c1-4-17(5-2)12-8-7-11-9-13(15(18)20-6-3)16(19)21-14(11)10-12/h7-10H,4-6H2,1-3H3

Upstream product

• 17754-90-4 4-(Diethylamino)salicylaldehyde 
• 105-53-3 diethyl malonate 
• 105-56-6 ethyl 2-cyanoacetate 
• 2033-24-1 cycl-isopropylidene malonate 
• 64-17-5 ethanol 
• 141-97-9 ethyl acetoacetate 
• 120-21-8 4-Diethylaminobenzaldehyde 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 91-68-9 3-diethylaminophenol 
• 23050-90-0 4-(diethylamino)-2-hydroxybenzoic acid 
• 1071-46-1 hydrogen ethyl malonate 

Downstream Products

• 20571-42-0 7-diethylamino-2H-benzopyran-2-one 
• 50995-74-9 7-(diethylamino)coumarin-3-carboxylic acid 
• 100343-98-4 7-diethylaminocoumarin-3-carboxylic acid, hydrazide 
• 812653-61-5 N-[(3-benzoxy-6-methyl-4-oxo-4H-pyran-2-yl)methyl]-7-methoxy-2-oxo-2H-chromene-3-carboxamide 
• 812653-53-5 N-[2-(3-benzoxy-2-methyl-4-oxopyridin-1(4H)-yl)ethyl]-7-diethylamino-2-oxo-2H-chromen-3-carboxamide 
• 812653-65-9 N-[(3-benzoxy-1,6-dimethyl-4-oxo-1,4-dihydropyridin-2-yl)methyl]-7-diethylamino-2-oxo-2H-chromene-3-carboxamide 
• 812653-66-0 N-(2-{[2-(acetylamino)ethyl][2-(3-benzoxy-2-methyl-4-oxopyridin-1(4H)-yl)ethyl]amino}ethyl)-7-diethylamino-2-oxo-2H-chromene-3-carboxamide 
• 72404-28-5 3-(4-phenylthiazol-2-yl)-7-(N,N-diethylamino)-chromen-2-one 
• 62143-26-4 7-diethylamino-3-(5-phenyl-[1,3,4]thiadiazol-2-yl)-chromen-2-one 
• 30750-25-5 N-phenyl-7-diethylamino-2-oxo-2H-1-benzopyran-3-carboxamide 
• 1350315-28-4 C₂₇H₃₁BN₄O₅ 
• 74696-96-1 3-acetyl-7-diethylaminocoumarin 

Relevant academic research and scientific papers

Fluorescent 7-diethylaminocoumarin pyrrolobenzodiazepine conjugates: Synthesis, DNA interaction, cytotoxicity and differential cellular localization

The pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) are a class of DNA minor groove binding agents that react covalently with guanine bases, preferably at Pu-G-Pu sites. A series of three fluorescent PBD-coumarin conjugates with different linker architectures has been synthesized to probe correlations between DNA binding affinity, cellular localization and cytotoxicity. The results show that the linker structure plays a critical role for all three parameters.

Probing the Anticancer Action of Oridonin with Fluorescent Analogues: Visualizing Subcellular Localization to Mitochondria

Oridonin (1) is a complex ent-kaurane diterpenoid exhibiting remarkable antitumor activity. However, the detailed mechanism or cellular target that underlies this activity has not yet been identified. Herein, we report an efficient approach for exploring the anticancer mechanism of oridonin through development of the potent fluorescent analogues. A series of novel fluorescent oridonin probes linked with coumarin moieties were designed, synthesized, and characterized. Fluorescence microscopy and confocal imaging studies suggested that fluorescent oridonin probe 17d was rapidly taken up into tumor cells and the mitochondrion was the main site of its accumulation. Moreover, we confirmed that cytochrome c played an important role in oridonin induced mitochondrion-mediated apoptosis and α,β-unsaturated ketone is the active moiety of oridonin, which is crucial to its uptake, localization, and cytotoxicity. Our results provide new insights on the molecular mechanism of oridonin and would be useful for its further development into an antitumor agent.

Glycyrrhetinic acid as a hepatocyte targeting unit for an anticancer drug delivery system with enhanced cell type selectivity

Herein, we report the potential of glycyrrhetinic acid (GA) as an active targeting ligand for hepatocellular carcinoma (HCC) for the development of diagnosis/therapy using small-molecule based approaches. Our preliminary results demonstrated that GA-conjugation to diagnostic/therapeutic counterparts significantly enhanced their HCC targeting ability and excellent therapeutic efficacy.

Synthesis and photoluminescent properties of two novel tripodal compounds containing coumarin moieties

Two novel tripodal compounds, tris[2-(7-diethylamino-coumarin-3-carboxamide)ethyl]amine (Tren-C1) and tris[2-(benzo[5,6]coumarin-3-carboxamide)ethyl]amine (Tren-C2), were synthesized and characterized. The UV-vis and fluorescence properties of Tren-C1 and Tren-C2 in solutions were investigated. These two compounds exhibited strong blue emission under ultraviolet light excitation. The maximal fluorescence emission occurred at about the level of 10-5 mol/L. The chromophore units in the tripodal compounds shown a little interaction in the ground state, while the interactions in the excited state was notable and which leads to a broad and bathochromic shift of the emission bands.

Astemizole Derivatives as Fluorescent Probes for hERG Potassium Channel Imaging

The detection and imaging of hERG potassium channels in living cells can provide useful information for hERG-correlation studies. Herein, three small-molecule fluorescent probes, based on the potent hERG channel inhibitor astemizole, for the imaging of hERG channels in hERG-transfected HEK293 cells (hERG-HEK293) and human colorectal cancer cells (HT-29), are described. These probes are expected to be applied in the physiological and pathological studies of hERG channels.

Development of a coumarin-furan conjugate as Zn2 + ratiometric fluorescent probe in ethanol-water system

In this study, a novel coumarin-derived compound bearing the furan moiety called 7-diethylamino-3-formylcoumarin (2′-furan formyl) hydrazone (1) has been designed, synthesized and evaluated as a Zn2 + ratiometric fluorescent probe in ethanol-water system. This probe 1 showed good selectivity and high sensitivity towards Zn2 + over other metal ions investigated, and a decrease in fluorescence emission intensity at 511 nm accompanied by an enhancement in fluorescence emission intensity at 520 nm of this probe 1 was observed in the presence of Zn2 + in ethanol-water (V: V = 9: 1) solution, which provided ratiometric fluorescence detection of Zn2 +. Additionally, the ratiometric fluorescence response of 1 to Zn2 + was nearly completed within 0.5 min, which suggested that this probe 1 could be utilized for sensing and monitoring Zn2 + in environmental and biological systems for real-time detection.

Coumarin-Based Reversible Fluorescent Probe for Selective Detection of Cu2+ in Living Cells

Copper ion plays an important role in many biological processes in human body. H2S is considered as the third gasses transmitter after carbon monoxide and nitric oxide. Here a novel ICT-based fluorescent ON-OFF-ON probe for Cu2+ and H2S detection was developed. Selectivity and sensitivity of probe was confirmed in aqueous Tris-HCl buffer (10?mM, pH?7.4, containing 90percent acetonitrile). Probe DF-CU shows high selectivity over other analytes. The degree of fluorescence quenching is linearly associated with the concentration of Cu2+ (R2?= 0.9919). The limit of detection (LOD, calculated according to the 3σ/slope) for Cu2+ was 6.4?μM. Probe can work in almost all pH. The probe shows a very fast response to Cu2+ (within 10?s). Its response to copper ion could be reversed by H2S. The complex of probe with Cu2+ could be used for H2S detection. Furthermore, this ON-OFF-ON fluorescent probe successfully applied in the living cells for the detection of Cu2+ and H2S.

Coumarin-derived cu2+-selective fluorescence sensor: Synthesis, mechanisms, and applications in living cells

A novel coumarin-based fluorogenic probe bearing the 2-picoIyI unit (1) was developed as a fluorescent chemosensor with high selectivity and suitable affinity in biological systems toward Cu2+ over other cations tested. The fluorescence on-off mechanism was studied by femtosecond time-resolved fluorescence (TRF) upconversion technique and ab initio calculations. The receptor can be applied to the monitoring of Cu2+ ion in aqueous solution with a pH span 4-10. To confirm the suitability of 1 for biological applications, we also employed it for the fluorescence detection of the changes of intracellular Cu2+ in cultured cells. The results indicate that 1 should be useful for the fluorescence microscopic imaging and the study on the biological functions of Cu2+.

A facile strategy for new organic white LED hybrid devices: Design, features and engineering

A facile and ecofriendly strategy to design and engineer new organic white LEDs is tested. The hybrid system was implemented by combining a commercial blue LED, with emission at 405 nm, with a hybrid transparent organic film (polycarbonate, PMMA, PVC) containing two selected organic dyes. The emitting molecules, a home-designed push-pull based coumarin and DCM ([2-[2-[4-(dimethylamino)phenyl]ethenyl]-6-methyl-4H-pyran-4-ylidene]-propanedinitrile), were selected for their optical features and appropriately mixed to obtain white light, perceptible by the naked eye, through the metamerism effect. The proposed strategy shows the critical parameters to account for in the selection of organic dyes, bearing in mind the preservation of the dye emission properties from the solution to the solid state. To this purpose, the contributions of dynamic and static quenching effects were analyzed in detail, to single out the optimum concentrations to assure the compliance with the respective sphere of interaction and guarantee high optical performances. Different new hybrid white-emitting LEDs, with tunable color rendering index (from warm to cold CCT), high energy efficiency (quantum yield larger than 90%), and high photostability, were produced to prove the proposed strategy.

FRET-Created Traffic Light Immunoassay Based on Polymer Dots for PSA Detection

There have been enormous efforts for developing the next generations of fluorometric lateral flow immunochromatographic strip (ICTS) owing to the great advances in fluorescent materials in these years. Here we developed one type of fluorometric ICTS based on ultrabright semiconducting polymer dots (Pdots) in which the traffic light-like signals were created by energy transfer depending on the target concentration. This platform was successfully applied for qualitatively rapid screening and quantitatively precise analysis of prostate-specific antigen (PSA) in 10 min from merely one drop of the whole blood sample. This FRET-created traffic light ICTS possesses excellent specificity and an outstanding detection sensitivity of 0.32 ng/mL for PSA. Moreover, we conducted proof-of-concept experiments to demonstrate its potential for multiplexed detection of cancer biomarkers at the same time in an individual test strip by taking advantage of the traffic light signals. To the best of our knowledge, it is the first model of a traffic light-like immunoassay test strip based on Pdots with multiplexing ability. These results would pave an avenue for designing the next generation of point-of-care diagnostics.