CAS 606-58-6|Toyocamycin
| Common Name | Toyocamycin | ||
|---|---|---|---|
| CAS Number | 606-58-6 | Molecular Weight | 291.26300 |
| Density | 1.91g/cm3 | Boiling Point | 721.1ºC at 760 mmHg |
| Molecular Formula | C12H13N5O4 | Melting Point | / |
| MSDS | ChineseUSA | Flash Point | 389.9ºC |
Names
| Name | 4-AMINO-5-CYANO-7-(β-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE |
|---|---|
| Synonym | More Synonyms |
Toyocamycin BiologicalActivity
| 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 >>CancerSignaling 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 |
| InChIKey | XOKJUSAYZUAMGJ-WOUKDFQISA-N |
| SMILES | N#Cc1cn(C2OC(CO)C(O)C2O)c2ncnc(N)c12 |
| Storage condition | -20°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
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
- 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 |
Articles24
More 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... |
Synonyms
| TOYOCAMYCIN |
| vengicide |
| siromycin |
| a-399-y4 |
| unamycin-b |
| e-212 |
| uramycinb |
| 7-Cyano-7-deazaadenosine |
| e-212-1 |
