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K4394

Sigma-Aldrich

PKF118-310

≥98% (HPLC)

Synonym(s):

1,6-Dimethyl-pyrimido[5,4-e]-1,2,4-triazine-5,7(1H,6H)-dione, Toxoflavin, Xanthothricin

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About This Item

Empirical Formula (Hill Notation):
C7H7N5O2
CAS Number:
84-82-2
Molecular Weight:
193.16
MDL number:
MFCD00459812
UNSPSC Code:
12352200
PubChem Substance ID:
329817147
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

H2O: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN1N=CN=C(C1=N2)C(N(C)C2=O)=O

InChI

1S/C7H7N5O2/c1-11-6(13)4-5(10-7(11)14)12(2)9-3-8-4/h3H,1-2H3

InChI key

SLGRAIAQIAUZAQ-UHFFFAOYSA-N

Biochem/physiol Actions

PKF118-310 is an antagonist of the Tcf4/b-catenin signaling. The compound disrupts the Tcf4/b-catenin complex and inhibits expression of Tcf4 responsive genes. PKF118-310 inhibits expression of survivin and induces apoptosis in HCC, colon tumor and lymphocytic leukemia cell lines.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

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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Radosveta Gencheva et al.
Biochimica et biophysica acta. General subjects (2018-05-29)
Toxoflavin (1,6-dimethylpyrimido[5,4-e][1,2,4]triazine-5,7-dione; xanthothricin) is a well-known natural toxin of the pyrimidinetriazinedione type that redox cycles with oxygen under reducing conditions. In mammalian systems, toxoflavin is an inhibitor of Wnt signaling as well as of SIRT1 and SIRT2 activities, but other
Hari S Karki et al.
PloS one, 7(9), e45376-e45376 (2012-10-03)
Burkholderia glumae is the primary causal agent of bacterial panicle blight of rice. In this study, 11 naturally avirulent and nine virulent strains of B. glumae native to the southern United States were characterized in terms of virulence in rice
Shusheng Wang et al.
Carbohydrate research, 342(9), 1254-1260 (2007-04-07)
Eight novel toxoflavin glycosides, which are potential prodrugs in antibody directed enzyme prodrug therapy (ADEPT), were synthesized. The structures of all toxoflavin glycosides were characterized by (13)C NMR spectroscopy, elemental analysis, and MS. Their enzymatic hydrolysis activities were tested against
Serry Koh et al.
Plant biotechnology journal, 9(3), 348-358 (2010-08-25)
Photosensitizers are common in nature and play diverse roles as defense compounds and pathogenicity determinants and as important molecules in many biological processes. Toxoflavin, a photosensitizer produced by Burkholderia glumae, has been implicated as an essential virulence factor causing bacterial
Giulia Devescovi et al.
Applied and environmental microbiology, 73(15), 4950-4958 (2007-06-15)
Burkholderia glumae is an emerging rice pathogen in several areas around the world. Closely related Burkholderia species are important opportunistic human pathogens for specific groups of patients, such as patients with cystic fibrosis and patients with chronic granulomatous disease. Here
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