3-Azido-7-hydroxycoumarin

Product ID: M2814



Unit SizePriceQuantity 
10mg
$60.24
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Description

A new fluorogenic "click" labeling dye for conjugation to alkyne-containing biomolecules. The probe is non-fluorescent until triazole reaction occurs providing improved detection limits.

The widely used "Click" chemistry technique for bioorthogonal reporting in living systems has been used for the analysis of an increasing variety of intracellular biomolecules. This system typically utilizes the reaction of azide derivatives of biological molecules (sugars, lipids, etc.) with a fluorescent alkyne or cyclooctene derivative. Since azides are rare in biological systems, this reporting method can be used to trace the linked biological compounds inside living cells.

In a corollary to the common CLICK technique, this detection agent employs a quenched azide dye that becomes highly fluorescent after the Click reaction when it forms triazoles at the site of alkyne modified biomolecules. The new probe is highly permeable to cell membranes and tissues. The uses of these new fluorogenic click dyes can range from intracellular probes for thiols and H2S, to tracing alkyne modified DNA or alkyne modified Methionine or Phenylalanine (unnatural amino acids) in mutated proteins. For more applications, please see the references and citations link above.


Technical Data
SKU M2814
CAS Number 817638-68-9
Unit Size 10mg
Alternative Names 3-Azido-7-hydroxy-chroman-2-one, 3-azido umbelliferone
Absorption 325
Emission Wavelength 441
Detection Method Fluorescence
Molecular Formula C9H5N3O3
Molecular Weight 203.15
Storage Conditions -20C, Protect From Light

References and Citations

References:

  • Zhu, Z, Li Y, Wei C, Wen X, Xi Z, Yi L (2016) "Multi-Fluorinated Azido Coumarins for Rapid and Selective Detection of Biological H2S in Living Cells." Chemistry - An Asian Journal, 11(1): 68-71.
  • Nocentini A, Carta F, Ceruso M, Bartolucci G, Supuran CT (2015) " Click-tailed coumarins with potent and selective inhibitory action against the tumor-associated carbonic anhydrases IX and XII Bioorganic & Medicinal Chemistry, 23(21): 6955-6966.
  • Organophosphorus-catalyzed Staudinger reduction Quick ViewOther Sources By van Kalkeren, Henri A. et al From Advanced Synthesis & Catalysis, 354(8), 1417-1421; 2012
  • Xinghua Wu X, Yu Chen Y, Herve Aloysius H, and Longqin Hu L (2011) "A novel high-yield synthesis of aminoacyl p-nitroanilines and aminoacyl 7-amino-4-methylcoumarins: important synthons for the synthesis of chromogenic/fluorogenic protease substrates." Beil. J. Org. Chem., 117: 1030-1035.
  • Droumaguet CL, Wang C, Wang Q (2009) "Fluorgenic click reaction." Chem. Soc. Reviews 39: 1233-1239.
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