Toxoflavin

Modify Date: 2024-01-06 15:35:11

Toxoflavin Structure
Toxoflavin structure
Common Name Toxoflavin
CAS Number 84-82-2 Molecular Weight 193.16300
Density 1.65g/cm3 Boiling Point 276.7ºC at 760 mmHg
Molecular Formula C7H7N5O2 Melting Point N/A
MSDS Chinese USA Flash Point 121.1ºC
Symbol GHS06
GHS06
Signal Word Danger

 Use of Toxoflavin


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].

 Names

Name 1,6-dimethylpyrimido[5,4-e][1,2,4]triazine-5,7-dione
Synonym More Synonyms

 Toxoflavin 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
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

 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
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%

 Articles24

More 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...

 Synonyms

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
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