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802409

Sigma-Aldrich

7-Azido-4-Methylcoumarin

97%

Synonyme(s) :

4-Methyl-7-azidocoumarin, 7-Azido-4-methyl-2H-1-benzopyran-2-one

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About This Item

Formule empirique (notation de Hill):
C10H7N3O2
Numéro CAS:
95633-27-5
Poids moléculaire :
201.18
Numéro MDL:
MFCD16652405
Code UNSPSC :
12352125
ID de substance PubChem :
329768736
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

97%

Forme

powder

Pf

117.8 °C

Chaîne SMILES 

CC1=CC(=O)Oc2cc(ccc12)N=[N+]=[N-]

InChI

1S/C10H7N3O2/c1-6-4-10(14)15-9-5-7(12-13-11)2-3-8(6)9/h2-5H,1H3

Clé InChI

HEKDKVLIMUWRRZ-UHFFFAOYSA-N

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Application

7-Azido-4-methylcoumarin (AzMC) is a fluorogenic probe useful for the detection of hydrogen sulfide (H2S). The aromatic azide moiety is selectively reduced in the presence of H2S, producing the fluorescent 7-amino-4-methylcoumarin (AMC) with a concomitant increase in fluorescence with λex = 365nm and λem = 450nm. The probe can be used both to monitor enzymatic production of H2S in vitro and also to visualize H2S in cells. The probe is highly sensitive and selective for H2S, providing a linear detection range in vitro between 200nm – 100μM H2S with 10μM probe, and reacting selectively with H2S in the presence of mM concentrations of cysteine, homocysteine, glutathionine and many other common biological analytes.

Caution: Use of this product with DTT, TCEP and/or biological thiols >25mM should be avoided for maximum efficiency.

AzMC is readily soluble in DMSO.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Megan K Thorson et al.
Angewandte Chemie (International ed. in English), 52(17), 4641-4644 (2013-03-21)
Buzzing with activity: A hydrogen sulfide selective fluorogenic probe, 7-azido-4-methylcoumarin (AzMC), serves as a highly sensitive assay for cystathionine β-synthase activity, and is suitable for the high-throughput discovery of novel enzyme inhibitors.
Rebecca A Ellwood et al.
Proceedings of the National Academy of Sciences of the United States of America, 118(9) (2021-02-26)
Duchenne muscular dystrophy (DMD) is an X-linked recessive disorder characterized by progressive muscle degeneration and weakness due to mutations in the dystrophin gene. The symptoms of DMD share similarities with those of accelerated aging. Recently, hydrogen sulfide (H2S) supplementation has
Bifeng Chen et al.
The Analyst, 138(3), 946-951 (2012-12-18)
A coumarin-based fluorescence chemoprobe was developed and evaluated for the selective and sensitive detection of hydrogen sulfide in degassed PBS buffers and fetal bovine serum. Fluorescence detection of hydrogen sulfide in living cells was also successfully achieved using two-photon confocal
Ghulam Mohammad et al.
Investigative ophthalmology & visual science, 61(14), 35-35 (2020-12-30)
Hyperglycemia damages the retinal mitochondria, and the mitochondrial damage plays a central role in the development of diabetic retinopathy. Patients with diabetes also have higher homocysteine levels, and abnormalities in homocysteine metabolism result in decreased levels of hydrogen sulfide (H2S)
Karim Zuhra et al.
Cells, 8(8) (2019-08-07)
Hydrogen sulfide (H2S) is an endogenously produced signaling molecule. The enzymes 3-mercaptopyruvate sulfurtransferase (MST), partly localized in mitochondria, and the inner mitochondrial membrane-associated sulfide:quinone oxidoreductase (SQR), besides being respectively involved in the synthesis and catabolism of H2S, generate sulfane sulfur

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