817638-68-9

Basic information

• Product Name: 3-azido-7-hydroxycoumarin
• Synonyms: 3-azido-7-hydroxycoumarin;3-Azido-7-hydroxy-2H-chroMen-2-one;3-Azido-7-hydroxy-chroMan-2-one;3-azido-7-hydroxy-chroMen-2-one;3-Azido-7-hydroxy-2H-1-benzopyran-2-one
• CAS NO: 817638-68-9
• Molecular Formula: C9H5N3O3
• Molecular Weight: 203.156
• EINECS: -0
• Mol File: 817638-68-9.mol

Chemical Properties

• Melting Point: 118-120℃
• Appearance: /
• Storage Temp.: -20°C
• Solubility: DMSO (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: 3-azido-7-hydroxycoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-azido-7-hydroxycoumarin(817638-68-9)
• EPA Substance Registry System: 3-azido-7-hydroxycoumarin(817638-68-9)

Safety Data

• Hazardous Substances Data: 817638-68-9(Hazardous Substances Data)

Usage

Uses

Used in Imaging Applications:
3-Azido-7-hydroxycoumarin is used as a fluorescent dye for imaging purposes due to its ability to emit fluorescence only after the click reaction. This minimizes background signal and allows for clear visualization of the target biomolecules.
Used in Protein Labeling:
3-Azido-7-hydroxycoumarin is used as a protein labeling agent in bicarbonate buffered solutions. It has a high absorption and emission wavelength (404/477 nm), which enables quick and efficient labeling of proteins, making it a valuable tool in various research and diagnostic applications.

InChI:InChI=1/C9H5N3O3/c10-12-11-7-3-5-1-2-6(13)4-8(5)15-9(7)14/h1-4,13H

Upstream product

• 69019-75-6 3-acetamido-2-oxo-2H-chromen-7-yl acetate 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 543-24-8 N-acetylglycine 
• 79418-41-0 3-amino-7-hydroxy-2H-chromen-2-one 
• 79418-42-1 3-acetylamino-7-hydroxy-2H-1-benzopyran-2-one 

Relevant articles and documents

Bichromophoric dyes for wavelength shifting of dye-protein fluoromodules

Dye-protein fluoromodules consist of fluorogenic dyes and single chain antibody fragments that form brightly fluorescent noncovalent complexes. This report describes two new bichromophoric dyes that extend the range of wavelengths of excitation or emission of existing fluoromodules. In one case, a fluorogenic thiazole orange (TO) was attached to an energy acceptor dye, Cy5. Upon binding to a protein that recognizes TO, red emission due to efficient energy transfer from TO to Cy5 replaces the green emission observed for monochromophoric TO bound to the same protein. Separately, TO was attached to a coumarin that serves as an energy donor. The same green emission is observed for coumarin-TO and TO bound to a protein, but efficient energy transfer allows violet excitation of coumarin-TO, versus longer wavelength, blue excitation of monochromophoric TO. Both bichromophores exhibit low nanomolar KD values for their respective proteins, >95% energy transfer efficiency and high fluorescence quantum yields.

Fluorescent mannosides serve as acceptor substrates for glycosyltransferase and sugar-1-phosphate transferase activities in Euglena gracilis membranes

Synthetic hexynyl α-D-mannopyranoside and its α-1,6-linked disaccharide counterpart were fluorescently labelled through CuAAC click chemistry with 3-azido-7-hydroxycoumarin. The resulting triazolyl-coumarin adducts, which were amenable to analysis by TLC,

Clickable degradable aliphatic polyesters via copolymerization with alkyne epoxy esters: Synthesis and postfunctionalization with organic dyes

Degradable aliphatic polyesters are the cornerstones of nanoparticle (NP)-based therapeutics. In this paradigm, covalent modification of the NP with cell-targeting motifs and dyes can aid in guiding the NP to its destination and gaining visual confirmation. Therefore, strategies to impart chemistries along the polymer backbone that are amenable to easy modification, such as 1,3-dipolar cycloaddition of an azide to an alkyne (the click reaction ), could be significant. Here we present a simple and efficient way to introduce alkyne groups at high density in aliphatic polyesters without compromising their crystallinity via the copolymerization of cyclic lactones with propargyl 3-methylpentenoate oxide (PMPO). Copolymers of lactic acid and ε-caprolactone with PMPO were synthesized with up to 9 mol % alkyne content, and accessibility of the alkyne groups to the click reaction was demonstrated using several dyes commonly employed in fluorescence microscopy and imaging (Cy3, ATTO-740, and coumarin 343). In order to establish the suitability of these copolymers as nanocarriers, copolymers were formulated into NPs, and cytocompatibility, cellular uptake, and visualization studies undertaken in HeLa cells. Dye-modified NPs exhibited no quenching, remained stable in solution for at least 10 days, showed no cytotoxicity, and were readily taken up by HeLa cells. Furthermore, in addition to enabling the incorporation of multiple fluorophores within the same NP through blending of individual dye-modified copolymers, dye-modified polyesters offer advantages over physical entrapment of dye, including improved signal to noise ratio and localization of the fluorescence signal within cells, and possess the necessary prerequisites for drug delivery and imaging.

CuAAC click chemistry for the enhanced detection of novel alkyne-based natural product toxins

In the context of discovering and quantifying terminal alkyne-based natural products, here we report the combination of CuAAC click chemistry with LC-MS for the detection of polyether toxins (prymnesins) associated with harmful algal blooms. The added-val

A Biocompatible Heterogeneous MOF–Cu Catalyst for In Vivo Drug Synthesis in Targeted Subcellular Organelles

As a typical bioorthogonal reaction, the copper-catalyzed azide–alkyne cycloaddition (CuAAC) has been used for drug design and synthesis. However, for localized drug synthesis, it is important to be able to determine where the CuAAC reaction occurs in living cells. In this study, we constructed a heterogeneous copper catalyst on a metal–organic framework that could preferentially accumulate in the mitochondria of living cells. Our system enabled the localized synthesis of drugs through a site-specific CuAAC reaction in mitochondria with good biocompatibility. Importantly, the subcellular catalytic process for localized drug synthesis avoided the problems of the delivery and distribution of toxic molecules. In vivo tumor therapy experiments indicated that the localized synthesis of resveratrol-derived drugs led to greater antitumor efficacy and minimized side effects usually associated with drug delivery and distribution.

Synthesis of fluorescent poly(coumarin-triazoles) via a CuAAC 'click' reaction

We describe a new fluorescent polymer system based on a coumarin-triazole functionality. The non-fluorescent 3-azidocoumarin-alkyne monomers are polymerized in a step-growth manner via a Cu (I)-catalyzed 1,3-dipolar cycloaddition (CuAAC) reaction. The process involves the conversion of a quenching azide group to 1,2,3-triazole in the monomer that leads to an increase in the intensity of fluorescence in the new polymer. The solubility and photophysical properties of the polymer were enhanced through co-polymerization with an aliphatic co-monomer.

Development of an ‘OFF-ON-OFF’ fluorescent pH sensor suitable for the study of intracellular pH

Changes of pH in living organisms are closely related to various physiological functions, so fluorescent sensors of pH would be useful as experimental tools and possibly also for medical diagnosis. We previously reported a pH sensor with ‘OFF-ON-OFF’ -type fluorescence change, which would be potentially more useful than conventional sensors with ‘OFF-ON’ type change. It can be utilized as a sensor for a specific range of pH, however, the range with strong fluorescence is relatively wide, around pH 7–10, which renders it impractical for use in biological studies. So in the present work, we adjusted the pH detection range by the introduction of chloro groups at the ortho-positions to the phenolic hydroxyl groups, whose deprotonation could control fluorescence change, and obtained a sensor specifically responsive to pH around 6. This sensor was confirmed to be suitable for fluorescence imaging of changes of intracellular pH in living cells.

Synthesis and cytotoxicity study of novel 3-(triazolyl)coumarins based fluorescent scaffolds

Recently a choice of fluorescent bioimaging probes have been developed as medical diagnostic tools. Herein, we have introduced a series of coumarin-based target specific probes for cancer theranostic application which play a dual role in the field of both diagnosis and therapy. A fluorogenic version of 1,3-dipolar cycloaddition between azides and alkynes (DBCO) has been introduced to develop the triazolylcoumarin based fluorescent scaffolds. These scaffolds were screened for their anticancer activity against breast cancer (MCF7) and human epitheloid cervix carcinoma (HeLa) cell line. It was established that triazolylcoumarins (5c and 5d) are having electronegative substitution in the benzene ring displayed most effective anticancer profile in both the cell lines. Compounds 5a and 5d exhibited maximum quantum yield and strong cellular uptake in the MCF-7 cell line.

Tetravalent platinum complex with bioactive group and preparation method of tetravalent platinum complex

The invention discloses a tetravalent platinum complex with a bioactive group and a preparation method of the tetravalent platinum complex. The tetravalent platinum complex is a platinum (IV) complex and has the structure shown in the formula II (please see the formula in the description), wherein in the formula II, Y is OH or Cl, and Bio represents the bioactive group. The platinum (IV) complex is prepared according to the equation in the formula III (please see the formula in the description), wherein in the formula III, Y is OH or Cl, Bio-OH represents a compound with bioactivity, TBTU represents a coupling agent O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, TEA represents a catalyst triethylamine, DMF represents solvent N,N-dimethyl formamide, and DMSO represents solvent dimethylsulfoxide. Cis-platinum is adopted for the bottom face of an octahedron, a small-molecular targeted or medicine active group is introduced to one axial position, a hydroxyl group or helium atom is introduced into another axial position, and the anti-tumor tetravalent platinum complex overcoming cisplatin resistance is provided, so the high-efficiency and low-toxin platinum (IV) complex is obtained.

Development of surface immobilized 3-azidocoumarin-based fluorogenic probe via strain promoted click chemistry

A new class of imaging probe, a fluorogenic version of 1, 3-dipolar cycloaddition of azides and alkynes has been developed. 3-azidocoumarin scaffolds were selectively immobilized on the DBCO modified bead surface via SPAAC and provide direct and strong fluorescence in fluorescence microscopy. This developed click-on beads could be applied to label various biomolecules, such as nucleic acids, proteins and other molecules. To this end, 5′(7-hydroxy 3-azido coumarin) labelled DNA primer also displayed strong fluorescence upon successful immobilization on the bead surface.