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D1946

Sigma-Aldrich

DAF-FM DA

≥98% (HPLC)

Synonym(s):

4-Amino-5-(N-methylamino)-3′,6′-bis(acetyloxy)-2′,7′-difluoro-spiro[isobenzofuran-1(3H),9′-[9H]xanthen]-3-one, Diaminofluorescein-FM diacetate

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About This Item

Empirical Formula (Hill Notation):
C25H18F2N2O7
CAS Number:
Molecular Weight:
496.42
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

film

storage condition

desiccated

color

colorless to yellow

fluorescence

λex 500 nm; λem 515 nm in DMSO

shipped in

wet ice

storage temp.

−20°C

SMILES string

CNc1ccc2c(c1N)C(=O)OC23c4cc(F)c(OC(C)=O)cc4Oc5cc(OC(C)=O)c(F)cc35

InChI

1S/C25H18F2N2O7/c1-10(30)33-20-8-18-13(6-15(20)26)25(12-4-5-17(29-3)23(28)22(12)24(32)36-25)14-7-16(27)21(34-11(2)31)9-19(14)35-18/h4-9,29H,28H2,1-3H3

InChI key

BEVHTVRRVVEMEF-UHFFFAOYSA-N

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Application

DAF-FM DA has been used to measure the nitric oxide (NO) levels in liver tissue homogenates. It has also been used in NO staining for detection of NO from human umbilical vein endothelial cells (HUVECs).

Biochem/physiol Actions

DAF-FM DA is a cell-permeable fluorescent probe for the detection of nitric oxide (NO). DAF-2 is the original compound and is widely used, but DAF-FM and DAF-FM DA are more sensitive to nitric oxide (NO) compared with DAF-2 and more photo-stable and less pH sensitive. DAF-FM DA permeates well into living cells and is rapidly transformed into water-soluble DAF-FM by cytosolic esterases.

Features and Benefits

This compound is featured on the Nitric Oxide Synthases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Hygroscopic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Shaoting Du et al.
Journal of experimental botany, 67(3), 893-904 (2015-11-27)
CO2 elevation often alters the plant's nitrate reductase (NR) activity, the first enzyme acting in the nitrate assimilation pathway. However, the mechanism underlying this process remains unknown. The association between elevated CO2-induced alterations of NR activity and nitric oxide (NO)
Good hydration and cell-biological performances of superparamagnetic calcium phosphate cement with concentration-dependent osteogenesis and angiogenesis induced by ferric iron
Zhang J, et al
Journal of Material Chemistry B: Materials for Biology and Medicine, 3(45), 8782-8795 (2015)
Verena K Capellini et al.
PloS one, 8(5), e62887-e62887 (2013-05-22)
It has been known for more than a century that pH changes can alter vascular tone. However, there is no consensus about the effects of pH changes on vascular response. In this study, we investigated the effects of extracellular pH
Christopher Groth et al.
Cancers, 13(4) (2021-02-14)
Despite recent improvement in the treatment of malignant melanoma by immune-checkpoint inhibitors, the disease can progress due to an immunosuppressive tumor microenvironment (TME) mainly represented by myeloid-derived suppressor cells (MDSC). However, the relative contribution of the polymorphonuclear (PMN) and monocytic
Concentration-dependent osteogenic and angiogenic biological performances of calcium phosphate cement modified with copper ions
Zhang J, et al.
Materials Science and Engineering, C, 99, 1199-1212 (2019)

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