Molecular structure of 7-Azido-4-methylcoumarin, CAS Number: 95633-27-5
7-Azido-4-methylcoumarin (CAS 95633-27-5)
See product citations (2)
Alternate Names:
AzMC
Application:
7-Azido-4-methylcoumarin is A highly sensitive and selective fluorogenic H2S probe
CAS Number:
95633-27-5
Purity:
≥98%
Molecular Weight:
201.18
Molecular Formula:
C10H7N3O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
QUICK LINKS
Ordering Information
Product Citations
Description
Technical Information
Safety Information
SDS & Certificate of Analysis
7-Azido-4-methylcoumarin is a highly sensitive and selective fluorogenic H2S probe. The aromatic azide moiety of AzMC is selectively reduced in the presence of H2S, producing the fluorescent 7-amino-4-methylcoumarin (AMC) with a concomitant increase in fluorescence with lambdaex = 365 nm and lambdaem = 450 nm. It is a photoaffinity labeling probe for the substrate binding site of human sulfotransferase 1A1 (SULT1A1). 7-Azido-4-methylcoumarin is a tool for monitoring the activity of pyridoxal-5′-phosphate (PLP)-dependent enzymes (e.g. cystathionine beta-synthase (CBS), cystathionine gamma-lyase (CGL) and tryptophan synthase (TS)) and to identify novel cystathionine beta-synthase (CBS) inhibitors and activators.
7-Azido-4-methylcoumarin (CAS 95633-27-5) References
- Photoaffinity labeling of the aglycon binding site of the recombinant human liver UDP-glucuronosyltransferase UGT1A6 with 7-azido-4-methylcoumarin. | Senay, C., et al. 1999. Arch Biochem Biophys. 368: 75-84. PMID: 10415114
- Photoaffinity labeling probe for the substrate binding site of human phenol sulfotransferase (SULT1A1): 7-azido-4-methylcoumarin. | Chen, G., et al. 1999. Protein Sci. 8: 2151-7. PMID: 10548061
- CYP2E1 active site residues in substrate recognition sequence 5 identified by photoaffinity labeling and homology modeling. | Collom, SL., et al. 2007. Arch Biochem Biophys. 459: 59-69. PMID: 17222385
- 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. | Wu, X., et al. 2011. Beilstein J Org Chem. 7: 1030-5. PMID: 21915204
- Identification of cystathionine β-synthase inhibitors using a hydrogen sulfide selective probe. | Thorson, MK., et al. 2013. Angew Chem Int Ed Engl. 52: 4641-4. PMID: 23512751
- AP39, a novel mitochondria-targeted hydrogen sulfide donor, stimulates cellular bioenergetics, exerts cytoprotective effects and protects against the loss of mitochondrial DNA integrity in oxidatively stressed endothelial cells in vitro. | Szczesny, B., et al. 2014. Nitric Oxide. 41: 120-30. PMID: 24755204
- Marine natural products as inhibitors of cystathionine beta-synthase activity. | Thorson, MK., et al. 2015. Bioorg Med Chem Lett. 25: 1064-6. PMID: 25666819
- Garlic oil polysulfides: H2S- and O2-independent prooxidants in buffer and antioxidants in cells. | DeLeon, ER., et al. 2016. Am J Physiol Regul Integr Comp Physiol. 310: R1212-25. PMID: 27101293
- Fluorescence quenching by metal centered porphyrins and poryphyrin enzymes. | Olson, KR., et al. 2017. Am J Physiol Regul Integr Comp Physiol. 313: R340-R346. PMID: 28835449
- Manganese Porphyrin-Based SOD Mimetics Produce Polysulfides from Hydrogen Sulfide. | Olson, KR., et al. 2019. Antioxidants (Basel). 8: PMID: 31842297
- Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives. | Pršir, K., et al. 2022. Molecules. 27: PMID: 35163905
- SKF38393 prevents high glucose (HG)-induced endothelial dysfunction by inhibiting the effects of HG on cystathionine γ-lyase/hydrogen sulfide activity and via a RhoA/ROCK1 pathway. | Chang, GQ., et al. 2022. Front Biosci (Landmark Ed). 27: 49. PMID: 35226992
- Cystathionine-beta-synthase (CBS)-derived hydrogen sulfide (H2S) supports proliferation, migration and bioenergetics in colon cancer-associated fibroblasts (CAFs). | Modis, K., Maskey, M., Johnson, P., Szabo, C., Hellmich, M. R., & Chao, C. 2017. Cancer Research. 77(13_Supplement): 2980-2980.
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
7-Azido-4-methylcoumarin, 1 mg | sc-396668 | 1 mg | $62.00 | |||
7-Azido-4-methylcoumarin, 5 mg | sc-396668A | 5 mg | $141.00 |