7-Azido-4-methylcoumarin
Based on 2 publication(s) in Google Scholar
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).
For research use only. We do not sell to patients.
- Purity: 98.90%
- CAS No.: 95633-27-5
- Formula: C10H7N3O2
- Molecular Weight:201.18
-
Storage:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
Publications Citing Use of MedChemExpress (MCE) 7-Azido-4-methylcoumarin
More
Biological Activity
Guide (The following is our recommended protocol. This protocol is only a guide and should be modified according to your specific needs).
1. Dye Preparation
1.1 Preparation of Stock Solution
Prepare a 10-50 mM stock solution using anhydrous DMSO.
Note: It is recommended to aliquot the stock solution and store it at -20 °C or -80 °C, protected from light.
1.2 Preparation of Working Solution
Dilute the stock solution with pre-warmed, serum-free cell culture medium or PBS to prepare a 10-50 μM working solution.
Note: Please adjust the working solution concentration according to your specific requirements, and prepare it immediately before use.
2. Staining of Magnaporthe oryzae
2.1 Obtain Magnaporthe oryzae samples at various developmental stages.
2.2 Add 50 μM of the dye working solution, gently agitate to ensure the solution completely covers the cells, and incubate at room temperature for 30 minutes, protected from light.
2.3 Aspirate the dye working solution, wash with culture medium 2–3 times (5 minutes per wash), and observe using a fluorescence microscope (Ex/Em = 340/445 nm).
7-Azido-4-methylcoumarin (0.25-4.0 mM; 1 min pre-incubation, 0-30 min UV irradiation) irreversibly inactivates UGT1A6 from V79 cells expressing recombinant human liver UGT1A6 in a time- and concentration-dependent manner, with a Kd of 2.89 mM and k2 of 0.113 min-1, decreasing the Vmax of pNP glucuronidation without altering the enzyme's affinity for pNP[1].
7-Azido-4-methylcoumarin (0.1-2 mM; 1-5 min pre-incubation, 20 min UV irradiation) specifically binds to the aglycon (substrate) binding site of UGT1A6 from V79 cells expressing recombinant human liver UGT1A6, as demonstrated by protective effects of aglycon site ligands and lack of interference with co-substrate site binding, and also binds specifically to phenol/coumarin sites on BSA[1].
7-Azido-4-methylcoumarin (15.6 μM-2 mM; 30 min UV exposure) covalently labels purified human SULT1A1 in a concentration- and light-dependent manner[2].
7-Azido-4-methylcoumarin (AzMC) (10 μM; 100 nM-100 μM; 1 mM-10 mM) functions as a selective fluorogenic probe for H2S, producing a linear fluorescent signal across NaHS concentrations from 100 nM to 100 μM and showing no significant reactivity with cysteine, homocysteine, PLP, or AdoMet[3].
7-Azido-4-methylcoumarin (50 μM; 30 min) reliably detects intracellular H2S levels in Magnaporthe oryzae mycelium, appressoria, and conidia, revealing significantly higher H2S levels in CSE1 overexpression mutants and H2S level changes with NaHS or hypotaurine treatment[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
-
CAS No. 95633-27-5
-
Appearance Solid
-
Molecular Weight 201.18
-
Formula C10H7N3O2
-
Color Off-white to light yellow
-
SMILES
[N-]=[N+]=NC1=CC(OC(C=C2C)=O)=C2C=C1
-
Shipping
Room temperature in continental US; may vary elsewhere.
-
Storage
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Publications (2)
-
Journal Impact Factor
-
Most Recent
-
Nat Commun
H2S-mediated protein S-sulfhydration modulates infectivity and autophagy in the rice blast fungus. [Abstract]2025 Jul 5;16(1):6222. PMID: 40617858 -
Acta Pharmacol Sin
ADT-OH promotes mitophagy and suppresses the cytosolic mtDNA-cGAS-STING inflammatory cascade in microglia. [Abstract]2026 Apr 9. PMID: 41951774
Solvent & Solubility
DMSO : 50 mg/mL (248.53 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
-
Data Sheet (275 KB)
-
SDS (251 KB)
- English - EN (251 KB)
- Français - FR (251 KB)
- Deutsch - DE (251 KB)
- Norwegian - NO (251 KB)
- Español - ES (251 KB)
- Swedish - SV (251 KB)
- Italian - IT (251 KB)
- Korean - KR (251 KB)
- Portuguese - PT (251 KB)
-
Handling Instructions (2659 KB)
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]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 4.9707 mL | 24.8534 mL | 49.7067 mL | 124.2668 mL |
| 5 mM | 0.9941 mL | 4.9707 mL | 9.9413 mL | 24.8534 mL | |
| 10 mM | 0.4971 mL | 2.4853 mL | 4.9707 mL | 12.4267 mL | |
| 15 mM | 0.3314 mL | 1.6569 mL | 3.3138 mL | 8.2845 mL | |
| 20 mM | 0.2485 mL | 1.2427 mL | 2.4853 mL | 6.2133 mL | |
| 25 mM | 0.1988 mL | 0.9941 mL | 1.9883 mL | 4.9707 mL | |
| 30 mM | 0.1657 mL | 0.8284 mL | 1.6569 mL | 4.1422 mL | |
| 40 mM | 0.1243 mL | 0.6213 mL | 1.2427 mL | 3.1067 mL | |
| 50 mM | 0.0994 mL | 0.4971 mL | 0.9941 mL | 2.4853 mL | |
| 60 mM | 0.0828 mL | 0.4142 mL | 0.8284 mL | 2.0711 mL | |
| 80 mM | 0.0621 mL | 0.3107 mL | 0.6213 mL | 1.5533 mL | |
| 100 mM | 0.0497 mL | 0.2485 mL | 0.4971 mL | 1.2427 mL |