95633-27-5
Chemical Structure
7-Azido-4-methylcoumarin
- CAS No.: 95633-27-5
- Formula:C10H7N3O2
- Molecular Weight:201.18
IUPAC Name: 7-azido-4-methyl-2H-chromen-2-one
InChIKey: HEKDKVLIMUWRRZ-UHFFFAOYSA-N
SMILES: [N-]=[N+]=NC1=CC(OC(C=C2C)=O)=C2C=C1
Biological Activity: 7-Azido-4-methylcoumarin is a selective coumarin-based fluorescent probe for hydrogen sulfide (H2S). In the presence of H2S, the aromatic azido group of 7-Azido-4-methylcoumarin is selectively reduced to produce the fluorescently active 7-amino-4-methylcoumarin (AMC). 7-Azido-4-methylcoumarin binds to the coumarin/phenol-binding site of BSA, the aglycone-binding site of UGT1A6, and the substrate-binding site of SULT1A1, respectively. 7-Azido-4-methylcoumarin retains its fluorescent properties after covalent binding, acts as a fluorescent H2S probe, and does not react with cysteine, homocysteine or glutathione (Ex/Em = 340/445 nm)[1][2][3][4].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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7-Azido-4-methylcoumarin | 98.90% | 7-Azido-4-methylcoumarin is a selective coumarin-based fluorescent probe for hydrogen sulfide (H2S). In the presence of H2S, the aromatic azido group of 7-Azido-4-methylcoumarin is selectively reduced to produce the fluorescently active 7-amino-4-methylcoumarin (AMC). 7-Azido-4-methylcoumarin binds to the coumarin/phenol-binding site of BSA, the aglycone-binding site of UGT1A6, and the substrate-binding site of SULT1A1, respectively. 7-Azido-4-methylcoumarin retains its fluorescent properties after covalent binding, acts as a fluorescent H2S probe, and does not react with cysteine, homocysteine or glutathione (Ex/Em = 340/445 nm). | ||||||||||||||||||||
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References
- [1]. Senay C, et al. Photoaffinity labeling of the aglycon binding site of the recombinant human liver UDP-glucuronosyltransferase UGT1A6 with 7-azido-4-methylcoumarin. Arch Biochem Biophys. 1999;368(1):75-84. [Content Brief]
- [2]. Chen G, et al. Photoaffinity labeling probe for the substrate binding site of human phenol sulfotransferase (SULT1A1): 7-azido-4-methylcoumarin. Protein Sci. 1999 Oct;8(10):2151-7. [Content Brief]
- [3]. Thorson MK, et al. Identification of cystathionine β-synthase inhibitors using a hydrogen sulfide selective probe. Angew Chem Int Ed Engl. 2013;52(17):4641-4644. [Content Brief]
- [4]. Hu H, et al. H2S-mediated protein S-sulfhydration modulates infectivity and autophagy in the rice blast fungus. Nat Commun. 2025;16(1):6222. [Content Brief]
