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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


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

D1946-BULK:
D1946-1MG:
D1946-BULK-PW:
D1946-1MG-PW:
D1946-VAR:


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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Verena K Capellini et al.
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Zhang J, et al
Journal of Material Chemistry B: Materials for Biology and Medicine, 3(45), 8782-8795 (2015)
You Jin Lim et al.
Food chemistry, 303, 125376-125376 (2019-08-24)
This study investigated the effects of persistent ultraviolet B (UV-B) irradiation on isoflavone accumulation in soybean sprouts. Three malonyl isoflavones were increased by UV-B. Malonylgenistin specifically accumulated upon UV-B exposure, whereas the other isoflavones were significantly increased under both dark
Bin Li et al.
Journal of aging research, 2011, 673185-673185 (2011-05-18)
Calorie restriction (CR) induces a metabolic shift towards mitochondrial respiration; however, molecular mechanisms underlying CR remain unclear. Recent studies suggest that CR-induced mitochondrial activity is associated with nitric oxide (NO) production. To understand the role of mitochondria in CR, we
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)

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