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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-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

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Certificates of Analysis (COA)

Lot/Batch Number
0000073468
0000086670
0000074015
0000044855
0000044237

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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
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)
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
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
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