4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE
- Product Name
- 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE
- CAS No.
- 606-58-6
- Chemical Name
- 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE
- Synonyms
- e-212;e-212-1;a-399-y4;NSC 99843;NSC 63701;siromycin;uramycinb;vengicide;unamycin-b;fungamycin
- CBNumber
- CB0235800
- Molecular Formula
- C12H13N5O4
- Formula Weight
- 291.26
- MOL File
- 606-58-6.mol
4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE Property
- Melting point:
- 243°; mp 239-243°
- alpha
- D16 -45.7° (c = 1.05 in 0.1N HCl)
- Boiling point:
- 433.28°C (rough estimate)
- Density
- 1.3067 (rough estimate)
- refractive index
- 1.7000 (estimate)
- storage temp.
- 2-8°C
- solubility
- DMSO: soluble0.90 - 1.10mg/mL, clear, colorless
- form
- solid
- pka
- 12.31±0.70(Predicted)
- color
- White or off-white
- Stability:
- Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
Safety
- WGK Germany
- 3
- Toxicity
- LD100 s.c. in mice: 10-20 mg/kg (Nishimura)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- T3580
- Product name
- Toyocamycin
- Purity
- ≥98% (HPLC), from Streptomyces rimosus
- Packaging
- 10mg
- Price
- $82.8
- Updated
- 2024/03/01
- Product number
- 17371
- Product name
- Toyocamycin
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $25
- Updated
- 2021/12/16
- Product number
- 17371
- Product name
- Toyocamycin
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $56
- Updated
- 2021/12/16
- Product number
- 17371
- Product name
- Toyocamycin
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $63
- Updated
- 2021/12/16
- Product number
- 17371
- Product name
- Toyocamycin
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $125
- Updated
- 2021/12/16
4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE Chemical Properties,Usage,Production
Description
Toyocamycin (606-58-6) is an adenosine analog which inhibits ribozyme self cleavage in mammalian cells, EC50?= 0.4 μM (for expression of a luciferase reporter).1?A potent inhibitor of ER stress-induced XBP1 mRNA splicing.2?It suppresses thapsigargin-, tunicamycin- and 2-deoxyglucose-induced XBP1 mRNA splicing in HeLa cells without affecting ATF6 and PERK activation. Although unable to inhibit IRE1α phosphorylation, toyocamycin prevented IRE1α-induced XBP1 mRNA cleavage in vitro.?It inhibits not only ER stress-induced but also constitutive activation of XBP1 expression in multiple myeloma cell lines as well as in primary patient samples.2?Displays synergistic effects with bortezomib. Toyocamycin inhibits unfolded protein response and induces apoptosis in pancreatic cancer cells.3
Uses
Toyocamycin is a pyrrolopyrimidine nucleoside isolated from Streptomyces toyocaensis in 1956. Toyocamycin, like other members of pyrrolopyrimidine class, is an adenosine nucleotide antimetabolite, with a broad spectrum of action against bacteria, fungi, protozoans and mammalian cell lines.
Uses
Toyocamycin is a natural adenosine analog first isolated from Streptomyces and shown in early studies to be cytotoxic to bacteria, fungi, and cancer cells and to have antiviral activities. Toyocamycin prevents IRE1α-induced mRNA cleavage (IC50 = 80 nM) and inhibits constitutive activation of XBP1 in multiple myeloma cell lines. It is used to study IRE1α action in the endoplasmic reticulum stress response, particularly in the context of cancer. It also inhibits phosphatidylinositol kinase in vitro (IC50 = 3.3 μg/ml), but not in cells, and blocks the ribosomal RNA-processing kinase Rio1 (IC50 = ~30 nM).[Cayman Chemical]
Uses
Toyocamycin Improves antibiotic production and silent gene activation in streptomyces diastatochromogenes by ribosome engineering, Preparation of tricyclic chromenone-based inhibitors of IRE-1 RNase activity.
Definition
ChEBI: Toyocamycin is an N-glycosylpyrrolopyrimidine that is tubercidin in which the hydrogen at position 5 of the pyrrolopyrimidine moiety has been replaced by a cyano group. It has a role as an antimetabolite, an antineoplastic agent, a bacterial metabolite and an apoptosis inducer. It is a N-glycosylpyrrolopyrimidine, a nitrile, a ribonucleoside and an antibiotic antifungal agent.
Biochem/physiol Actions
Studies have implicated that toyocamycin blocks the replication of fowl plague virus.
storage
Store at +4°C
References
1) Yen?et al. (2006),?Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries; RNA,?12?797 2) Ri?et al.?(2012),?Identification of Toyocamycin, an agent cytotoxic for multiple myeloma cells, as a potent inhibitor of ER stress-induced XBP1 mRNA splicing; Blood Cancer J.,?2?e79 3) Chien?et al.?(2014),?Selective inhibition of unfolded protein response induces apoptosis in pancreatic cancer cells; Oncotarget,?5?4881
4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE Preparation Products And Raw materials
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