Toyocamycin

Names

[ CAS No. ]:
606-58-6

[ Name ]:
Toyocamycin

[Synonym ]:
TOYOCAMYCIN
vengicide
siromycin
a-399-y4
unamycin-b
e-212
uramycinb
7-Cyano-7-deazaadenosine
e-212-1

Biological Activity

[Description]:

Toyocamycin (Vengicide) is an adenosine analog produced by Actinomycete, acts as an XBP1 inhibitor, inhibits IRE1α-induced ATP-dependent XBP1 mRNA cleavage, with an IC50 of 80 nM. Toyocamycin (Vengicide) induces apoptosis. Toyocamycin (Vengicide) shows no effect on IRE1α auto-phosphorylation[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> IRE1

[Target]

IC50: 80 nM (XBP1 activation)[1]

[References]

[1]. Toyocamycin, et al. Identification of Toyocamycin, an agent cytotoxic for multiple myeloma cells, as a potent inhibitor of ER stress-induced XBP1 mRNA splicing. Blood Cancer J. 2012 Jul;2(7):e79.

Chemical & Physical Properties

[ Density]:
1.91g/cm3

[ Boiling Point ]:
721.1ºC at 760 mmHg

[ Molecular Formula ]:
C₁₂H₁₃N₅O₄

[ Molecular Weight ]:
291.26300

[ Flash Point ]:
389.9ºC

[ Exact Mass ]:
291.09700

[ PSA ]:
150.44000

[ Index of Refraction ]:
1.849

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY9100000

CHEMICAL NAME :: 7H-Pyrrolo(2,3-d)pyrimidine-5-carbonitrile, 4-amino-7-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 606-58-6

BEILSTEIN REFERENCE NO. :: 0048454

LAST UPDATED :: 199612

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C12-H13-N5-O4

MOLECULAR WEIGHT :: 291.30

WISWESSER LINE NOTATION :: T56 BN GN INJ DCN FZ B- BT5OTJ CQ DQ E1Q

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 :: 8 mg/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10 mg/kg

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

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 ug/kg

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

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 71 ug/L

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 30,481,1987

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin.

Carbohydr. Res. 331(1) , 77-82, (2001)

Syntheses of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides are reported. Treatment of pyranulose glycoside with aminoguanidine in acetic acid gave the corresponding semicarbazone in 96% yield. The ring ...

Synthesis of 2'-beta-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors.

Bioorg. Med. Chem. Lett. 15(3) , 725-7, (2005)

Coupling reaction of 2-beta-C-methyl-1,2,3,4-tetra-O-benzoyl-d-ribofuranose with 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine, followed by debromination and debenzoylation, gave the 2'-beta-C-methy...

Cell cycle arrest and cytochrome c-mediated apoptotic induction in human lung cancer A549 cells by MCS-C2, an analogue of sangivamycin.

J. Microbiol. Biotechnol. 20(2) , 433-7, (2010)

In the course of our screening for novel modulators on cell cycle progression and apoptosis as anticancer drug candidates, we generated an analogue of sangivamycin, MCS-C2, designated as 4-amino-6-bro...