ChemicalBook > CAS DataBase List > 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE

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
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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.
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Safety

WGK Germany 
3
Toxicity
LD100 s.c. in mice: 10-20 mg/kg (Nishimura)
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T3580
Product name
Toyocamycin
Purity
≥98% (HPLC), from Streptomyces rimosus
Packaging
10mg
Price
$82.8
Updated
2024/03/01
Cayman Chemical
Product number
17371
Product name
Toyocamycin
Purity
≥98%
Packaging
1mg
Price
$25
Updated
2021/12/16
Cayman Chemical
Product number
17371
Product name
Toyocamycin
Purity
≥98%
Packaging
5mg
Price
$56
Updated
2021/12/16
Cayman Chemical
Product number
17371
Product name
Toyocamycin
Purity
≥98%
Packaging
10mg
Price
$63
Updated
2021/12/16
Cayman Chemical
Product number
17371
Product name
Toyocamycin
Purity
≥98%
Packaging
25mg
Price
$125
Updated
2021/12/16
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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

Raw materials

Preparation Products

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4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE Suppliers

China 56 India 1 United Kingdom 4 United States 13 Global 74
TargetMol Chemicals Inc.
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Alfa Chemistry
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606-58-6, 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINERelated Search:

TCPOBOP CYCLOPAMINE (+)-Camptothecin Sunitinib Malate Ligumycin Gamithromycin 4-Amino-7H-pyrrolo[2,3-d]pyrimidine TUBERCIDIN DEAZAPURINE 7-DEAZA-2'-DEOXYADENOSINE 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE

  • NSC 63701
  • NSC 99843
  • TOYOCAMYCIN
  • 3-d)pyrimidine-5-carbonitrile,4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(
  • 4-amino-5-cyano-7-(d-ribofuranosyl)-7h-pyrrolo(2,3-d)pyrimidine
  • 4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine-5-carbonitrile
  • a-399-y4
  • ahygroscopin-b
  • antibiotic1037
  • antibiotica-399-y4
  • antibiotice212
  • cyanotubericidin
  • e-212
  • e-212-1
  • naritheracin
  • siromycin
  • toyocamycinnucleoside
  • unamycin-b
  • uramycinb
  • vengicide
  • 7-CYANO-7-DEZXAADENOSINE
  • 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE
  • 4-AMINO-7-SS-D-RIBOFURANOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE
  • Cyanotubercidin, UnaMycin B, Vengicide, E 212, 1037, E 212, Anhygroscopin B, Naritheracin
  • 4-Aminopyrrolo[2,3-d]pyrimidine-5-carbonitrile 7-(β-D-ribofuranoside)
  • 7-Deaza-7-cyanoadenosine
  • Neuro 000027
  • 4-Amino-5-cyano-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2.3-d]pyrimidine
  • 4-Amino-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
  • TOYOCAMYCIN (VENGICIDE)
  • 7H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile, 4-amino-7-β-D-ribofuranosyl-
  • 4-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
  • Toyacamycin
  • RNA synthesis,CDK,mRNA cleavage,epigenetics,Toyocamycin,IRE1,CDK9 inhibitor,Cyclin dependent kinase,molecular docking,reactive oxygen species,CDKs,RNA Pol II phosphorylation,Inositol requiring enzyme 1,Fungal,Inhibitor,adenosine analog,Antibiotic,drug screening,ribosome function,inhibit,Apoptosis,extracellular signal-regulated kinases,cancer
  • 7H-Pyrrolo[2,3-D]pyrimidine-5-carbonitrile,4-amino-7-b-d-ribofuranosyl-
  • fungamycin
  • 7-Cyano-7-deoxyadenosine
  • 606-58-6
  • C12H13N5O4
  • C12H13N5O4H2O