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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:
254109-22-3
Molecular Weight:
496.42
MDL number:
MFCD16872050
UNSPSC Code:
12352200
PubChem Substance ID:
329798717
NACRES:
NA.77

Quality Level

100

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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Longmei Zhai et al.
Plant physiology and biochemistry : PPB, 109, 515-524 (2016-11-12)
To cope with iron (Fe) deficiency, plants have evolved a wide range of adaptive responses from changes in morphology to altered physiological responses. Recent studies have demonstrated that nitric oxide (NO) is involved in the Fe-deficiency response through hormonal signaling
Bing Fang Luo et al.
Journal of experimental botany, 63(8), 3127-3136 (2012-03-02)
Nitrogen (N) management is a promising agronomic strategy to minimize cadmium (Cd) contamination in crops. However, it is unclear how N affects Cd uptake by plants. Wild-type and iron uptake-inefficient tomato (Solanum lycopersicum) mutant (T3238fer) plants were grown in pH-buffered
Jarod T Horobin et al.
Clinical hemorheology and microcirculation, 71(2), 203-214 (2018-12-26)
Red blood cells (RBC) are exposed to varying shear stress while traversing the circulatory system; this shear initiates RBC-derived nitric oxide (NO) production. The current study investigated the effect of varying shear stress dose on RBC-derived NO production. Separated RBC
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)
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
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