55804-67-6

Usage

Uses

Used in Laser Applications:
Coumarin 334 is used as a laser dye for its ability to efficiently convert light into specific wavelengths, making it suitable for various laser applications. Its absorption maximum of 452 nm allows for precise control and manipulation of light, which is crucial in fields such as scientific research, medical applications, and industrial processes.
Used in Dye and Metabolite Analysis:
In addition to its laser applications, Coumarin 334 is also utilized in the analysis of dyes and metabolites. Its distinctive chemical properties make it a valuable tool for studying and identifying various compounds, contributing to the advancement of chemical research and understanding of biological processes.

InChI:InChI=1/C17H17NO3/c1-10(19)14-9-12-8-11-4-2-6-18-7-3-5-13(15(11)18)16(12)21-17(14)20/h8-9H,2-7H2,1H3

Upstream product

• 536-90-3 m-Anisidine 
• 63468-83-7 8-methoxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline 
• 41175-50-2 8-hydroxyjulolidine 
• 63149-33-7 9-formyl-8-hydroxyjulolidine 
• 141-97-9 ethyl acetoacetate 
• 591-27-5 m-Hydroxyaniline 
• 6290-50-2 1-methoxypentane-2,4-dione 

Downstream Products

• 55804-65-4 coumarin-343 

Relevant academic research and scientific papers

Development of an ultrafast fluorescent probe for specific recognition of hypochlorous acid and its application in live cells

Hypochlorous acid (HOCl), a highly potent oxidant of reactive oxygen species, plays critical roles in many physiological and pathological processes. In this work, a novel coumarin-based fluorescent probe, Cou-HOCl, was prepared for the detection of HOCl. The probe exhibited good selectivity over other analytes, excellent sensitivity with a detection limit of 16 nM, and fast response within 5 s. And further study demonstrated that the probe could be used not only to image exogenous HOCl in various cells, but also to determine the fluctuating levels of HOCl in macrophage cells during inflammation.

A novel fluorescent probe with dual-sites for simultaneously monitoring metabolisms of cysteine in living cells and zebrafishes

Understanding cellular metabolism holds immense potential for developing new drugs that regulate metabolic pathways. Two gas signal molecules, SO2 and H2S, are the main metabolites from cysteine (Cys) via oxidation and desulfurization pathways, respectively. However, a few fluorescent probes for real-time monitor of the metabolic pathways of cysteine have been reported. To understand metabolic alterations of cysteine, we have rationally designed and prepared a dual-signal fluorescent probe HN, which could differentiate SO2 and H2S through two different fluorescence channels simultaneously, along with similar reaction kinetics and both “off-on” fluorescence responses. Probe HN exhibits the potential to monitor the metabolism pathways of cysteine, and the distinguishment of cancer cells from normal cells could be realized. This methodology will promote further understanding of the physiological and pathological roles of cysteine.

Amplification-free detection of circulating microRNA biomarkers from body fluids based on fluorogenic oligonucleotide-templated reaction between engineered peptide nucleic acid probes: Application to prostate cancer diagnosis

Highly abundant in cells, microRNAs (or miRs) play a key role as regulators of gene expression. A proportion of them are also detectable in biofluids making them ideal noninvasive biomarkers for pathologies in which miR levels are aberrantly expressed, such as cancer. Peptide nucleic acids (PNAs) are engineered uncharged oligonucleotide analogues capable of hybridizing to complementary nucleic acids with high affinity and high specificity. Herein, novel PNA-based fluorogenic biosensors have been designed and synthesized that target miR biomarkers for prostate cancer (PCa). The sensing strategy is based on oligonucleotide-templated reactions where the only miR of interest serves as a matrix to catalyze an otherwise highly unfavorable fluorogenic reaction. Validated in vitro using synthetic RNAs, these newly developed biosensors were then shown to detect endogenous concentrations of miR in human blood samples without the need for any amplification step and with minimal sample processing. This low-cost, quantitative, and versatile sensing technology has been technically validated using gold-standard RT-qPCR. Compared to RT-qPCR however, this enzyme-free, isothermal blood test is amenable to incorporation into low-cost portable devices and could therefore be suitable for widespread public screening.

Synthesis of a NIR fluorescent dye and its application for rapid detection of HSO3? in living cells

SO2 and its derivatives (HSO3?, SO32?) play a significant important role in many industries and organisms. Based on coumarin and benzopyranose, a promising NIR ratiometric fluorescent probe BAOA (11-oxo-2,2′,3,3′,6,7,7′,8′-octahydro -1H,1′H,5H,6′H,11H- [10,12′-bipyrano [2,3-f] pyrido [3,2,1-ij] quinolin]-13′-ium perchlorate) was designed and developed to detect HSO3? rapidly and sensitively. The sensing mechanism was Michael addition reaction, in which, strongly nucleophilic HSO3? attacked carbon-carbon double bonds and BAOA-HSO3 was formed. A superior linear calibration curve between the fluorescence ratio I490/I722 and concentrations of HSO3? was obtained in the range of 1.25–8.75 μmol/L and the LOD was figured out as 63.0 nmol/L. Cell experiments showed that BAOA could not only locate mitochondria, lysosomes, ER and Golgi but also detect exogenous HSO3? in living cells.

Micromolecular fluorescent probe for detecting hypochlorous acid, and preparation method and application thereof

The invention discloses a micromolecular fluorescent probe for detecting hypochlorous acid, and a preparation method and application thereof, and relates to the technical field of biological detection. The preparation method of the fluorescent probe comprises the following steps: reacting 8-hydroxy-nonalonidin-9-formaldehyde represented by formula (II) with ethyl acetate and piperidine in an alcohol to obtain a coumarin derivative represented by formula (III); and reacting the coumarin derivative of the formula (III) with methanesulfonic acid and 2-mercaptoethanol in an organic solution in aninert atmosphere to obtain a compound represented by formula (I), namely the fluorescent probe disclosed by the invention. The fluorescent probe provided by the invention has very high selectivity andsensitivity, and can be used for detecting the exogenous hypochlorous acid of living cells and fluorescence imaging of HOCl dynamic change in inflammatory cells as the micromolecular fluorescent probe for detecting the hypochlorous acid.

Preparation method and application of ratio type fluorescent probe for peroxynitrite

The invention relates to a preparation method and an application of a ratio type fluorescent probe for peroxynitrite (ONOO). The structural formula of the fluorescent probe is shown in the description. The invention provides the preparation method for synthesizing the fluorescent probe from 8-hydroxyjulolidine-9-carboxaldehyde, ethyl acetoacetate and 2-(4-diethylamino-2-hydroxybenzoyl)benzoicacid. The fluorescent probe is a near-infrared ratio type fluorescent probe for peroxynitrite. The fluorescent probe has a very high sensitivity to ONOO, and the fluorescence intensity ratio (F500/F720) is enhanced by 72 times; the fluorescent probe has a very high selectivity to the ONOO, and is not interfered by other active oxygen, active nitrogen, active sulfur and biological thiols; and the fluorescent probe rapidly interacts with the ONOO, and the response time is within 7 min; and additionally, the fluorescent probe is applied to the detection of the content of peroxynitrite in living cells.

A hepatocyte-targeting near-infrared ratiometric fluorescent probe for monitoring peroxynitrite during drug-induced hepatotoxicity and its remediation

A novel hepatocyte-targeting near-infrared fluorescent probe named Gal-NIR is developed. Gal-NIR shows ratiometric response to ONOO- with high sensitivity and selectivity. Moreover, the probe can accurately target the hepatocyte, and thus is used for assessing drug-induced hepatotoxicity and its remediation by using hepatoprotective medicines in living cells and mice.

(7-Dialkylamino-3-coumarinyl)pyrazolines – new effective push-pull photogenerators of acidity

(7-Dialkylamino-3-coumarinyl)pyrazolines and their julolidine analog have been synthesized and proved as new effective photogenerators of acidity. Having D-π-linker ?A conjugated system of push-pull type these compounds possess intensive absorption in visible region of electronic spectra, high photosensitivity and undergo photodehydrogenation with proton elimination in the presence of CCl4 or C2Cl6 with a high speed.

Tracking mitochondrial1O2-ROS production through a differential mitochondria-nucleoli fluorescent probe

The dual-emissive fluorescent probe described here enabled dynamic tracking of singlet oxygen (1O2)-ROS species production and localization dynamics between the mitochondria and nucleoli in the presence of agents perturbing the mitochondrial membrane potential and under a photodynamic (PDT) system. Local structural information during the probe-1O2 interaction was followed by spectrally resolved confocal microscopy.

Extensive reduction in back electron transfer in twisted intramolecular charge-transfer (TICT) coumarin-dye-sensitized TiO2 nanoparticles/film: A femtosecond transient absorption study

We report the synthesis, characterization, and optical and electrochemical properties of two structurally similar coumarin dyes (C1 and C2). These dyes have been deployed as sensitizers in TiO2 nanoparticles and thin films, and the effect of molecular structure on interfacial electron-transfer dynamics has been studied. Steady-state optical absorption, emission, and time-resolved emission studies on both C1 and C2, varying the polarity of the solvent and the solution pH, suggest that both photoexcited dyes exist in a locally excited (LE) state in solvents of low polarity. In highly polar solvents, however, C1 exists in an intramolecular charge-transfer (ICT) state, whereas C2 exists in both ICT and twisted intramolecular charge-transfer (TICT) states, their populations depending on the degree of polarity of the solvent and the pH of the solution. We have employed femtosecond transient absorption spectroscopy to monitor the charge-transfer dynamics in C1- and C2-sensitized TiO2 nanoparticles and thin films. Electron injection has been confirmed by direct detection of electrons in the conduction band of TiO 2 nanoparticles and of radical cations of the dyes in the visible and near-IR regions of the transient absorption spectra. Electron injection in both the C1/TiO2 and C2/TiO2 systems has been found to be pulse-width limited (2 system than in the C1/TiO2 system. The involvement of TICT states in C2 is solely responsible for the higher electron injection yield as well as the slower BET process compared to those in the C1/TiO2 system. Further pH-dependent experiments on C1- and C2-sensitized TiO2 thin films have corroborated the participation of the TICT state in the slower BET process in the C2/TiO2 system.