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About This Item
Empirical Formula (Hill Notation):
C10H7N3O2
CAS Number:
Molecular Weight:
201.18
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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reaction suitability
reaction type: click chemistry
SMILES string
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
InChI key
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 ?ex = 365 nm and ?em = 450 nm. The probe can be used both to monitor enzymatic production of H2S in vitro [1] and also to visualize H2S in cells [2]. The probe is highly sensitive and selective for H2S, providing a linear detection range in vitro between 200 nm – 100 μM H2S with 10 μM 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 >25 mM should be avoided for maximum efficiency.
AzMC is readily soluble in DMSO.
Caution: Use of this product with DTT, TCEP and/or biological thiols >25 mM should be avoided for maximum efficiency.
AzMC is readily soluble in DMSO.
Other Notes
Please note that Sigma-Aldrich provides this product to early discovery researchers as part of a collection of unique chemicals. Sigma-Aldrich does not collect analytical data for this product. Buyer assumes responsibility to confirm product identity and/or purity. All sales are final.
NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY; (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE; OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY; WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.
NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY; (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE; OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY; WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.
Storage Class
13 - Non Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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.
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
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
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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