Toxoflavin

Names

[ CAS No. ]:
84-82-2

[ Name ]:
Toxoflavin

[Synonym ]:
Toxoflavin
1,6-Dimethyl-1H-pyrimido[5,4-e][1,2,4]triazin-5,7-dion
1,6-dimethylpyrimido[5,4-e]-1,2,4-triazine-5,7(1H,6H)-dione
Xanthotricin
Xanthothricin (VAN)
Compound 7215
Toxoflavine
Xanthothricin
1,6-dimethyl-1H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione
GNF-Pf-67

Biological Activity

[Description]:

Toxoflavin (Xanthothricin) is an antagonist of transcription factor 4 (TCF4)/β-catenin complex, also acts as an inhibitor of KDM4A, with antitumor activity[1][2].

[Related Catalog]:

Research Areas >> Cancer

[Target]

TCF4/β-catenin[1], KDM4A[2]

[In Vitro]

Toxoflavin (Xanthothricin) exhibits dose-dependent cytotoxicity against the 3 hepatoma cell lines, and with IC50s of 0.66 μM, 0.36 μM and 0.98 μM for Hep40 cells, HepG2 cells and Huh7 cells respectively[1].

[References]

[1]. Wei W, et al. Small molecule antagonists of Tcf4/beta-catenin complex inhibit the growth of HCC cells in vitro and in vivo. Int J Cancer. 2010 May 15;126(10):2426-36.

[2]. Franci G, et al. Identification and characterization of PKF118-310 as a KDM4A inhibitor. Epigenetics. 2017 Mar 4;12(3):198-205.

Chemical & Physical Properties

[ Density]:
1.65g/cm3

[ Boiling Point ]:
276.7ºC at 760 mmHg

[ Molecular Formula ]:
C₇H₇N₅O₂

[ Molecular Weight ]:
193.16300

[ Flash Point ]:
121.1ºC

[ Exact Mass ]:
193.06000

[ PSA ]:
82.67000

[ Index of Refraction ]:
1.76

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UW7875000

CHEMICAL NAME :: Pyrimido(5,4-e)-as-triazine-5,7-(1H,6H)-dione, 1,6-dimethyl-

CAS REGISTRY NUMBER :: 84-82-2

BEILSTEIN REFERENCE NO. :: 0021014

LAST UPDATED :: 199709

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C7-H7-N5-O2

MOLECULAR WEIGHT :: 193.19

WISWESSER LINE NOTATION :: T66 BVNVN GNN JNJ C1 G1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8400 ug/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - hematuria Gastrointestinal - hypermotility, diarrhea Sense Organs and Special Senses (Eye) - lacrimation

REFERENCE :: ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 4,259,1954

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JOCEAH Journal of Organic Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1936- Volume(issue)/page/year: 31,900,1966

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1700 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Gastrointestinal - hypermotility, diarrhea Kidney, Ureter, Bladder - hematuria

REFERENCE :: ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 4,259,1954

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ RIDADR ]:
UN 2811 6.1 / PGIII

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Investigations into the Biosynthesis, Regulation, and Self-Resistance of Toxoflavin in Pseudomonas protegens Pf-5.

ChemBioChem. 16 , 1782-90, (2015)

Pseudomonas spp. are prolific producers of natural products from many structural classes. Here we show that the soil bacterium Pseudomonas protegens Pf-5 is capable of producing trace levels of the tr...

The quorum sensing-dependent gene katG of Burkholderia glumae is important for protection from visible light.

J. Bacteriol. 191(13) , 4152-7, (2009)

Quorum sensing (QS) plays important roles in the pathogenicity of Burkholderia glumae, the causative agent of bacterial rice grain rot. We determined how QS is involved in catalase expression in B. gl...

Identification of the product of toxoflavin lyase: degradation via a Baeyer-Villiger oxidation.

J. Am. Chem. Soc. 134(11) , 5326-30, (2012)

Toxoflavin (an azapteridine) is degraded to a single product by toxoflavin lyase (TflA) in a reaction dependent on reductant, Mn(II), and oxygen. The isolated product was fully characterized by NMR an...