3-Azido-7-hydroxycoumarin
Switch-on dye to label DNA/RNA
| Size | Catalog No. | Price |
|---|---|---|
| 5 mg | BCFA-047-5 | € 135,00 |
| 10 mg | BCFA-047-10 | € 200,00 |
Chemical Properties
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Molecular Formula
C9H5N3O3
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Shelf Life
12 months unopened after receipt
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Storage Conditions
-20 °C, dark
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Molecular Weight
203.15 g/mol
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Purity
≥ 98% (HPLC)
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Physical State
amber to brown crystalline solid
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CAS Number
817638-68-9
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Additional name
3-Azido-7-hydroxy-chromen-2-on; 3-Azido-7-
hydroxy-chroman-2-one -
Excitation (max)
before click reaction: 260 nm
after click reaction: 404 nm -
Emission (max)
before click reaction: 391 nm
after click reaction: 480 nm -
Solubility
DMSO, DMF, MeOH, MeCN
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Preparation/Handling
For a 10 mM solution add 492 μL to 1 mg.
Product Information
3-Azido-7-hydroxycoumarin has the special property to become fluorescent only when it is click ligated. The formed triazole expands the electron system of the dye and enables fluorescence. Therefore, there is no background signal of the click unligated leftover dye. This dye is a valuable tool for nucleic acid labeling.
LITERATURE
Imaging the glycome, Laughlin et al, 2009, Sci USA, Vol. 106, p. (1):12
https://doi.org/10.1073/pnas.0811481106
Fluorogenic “click” reaction for labeling and detection of DNA in proliferating cells, Li et al, 2010, Biotechniques, Vol. 49, p. (1):525
https://doi.org/10.2144/000113463
A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes, Sivakumar et al, 2004, Org. Lett., Vol. 6, p. (24):4603
https://doi.org/10.1021/ol047955x
Site-Directed Immobilization of Bone Morphogenetic Protein 2 to Solid Surfaces by Click Chemistry, C. Siverino et al., 2018, Journal of Visualized Experiments, Vol. 133, e56616.
Characterization and Scaled-Up Production of Azido-Functionalized Silk Fiber Produced by Transgenic Silkworms with an Expanded Genetic Code, H. Teramoto et al., 2019, International Journal of Molecular Sciences, Vol. 20(3), p. 616.
https://doi.org/10.3390/ijms20030616
A lipid transfer protein knockout library reveals ORP9-ORP11 dimer mediating PS/PI(4)P exchange at the ER-trans Golgi contact site to promote sphingomyelin synthesis, B. Cabukusta et al., 2023, bioRxiv.
https://doi.org/10.1101/2023.06.02.543249
Trifunctional lipid probes for comprehensive studies of single lipid species in living cells, D. Höglinger, 2017, Proceedings of the National Academy of Sciences, Vol. 114(7), p. 1566-1571.