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

Beijing LAL Pharmaceutical Co., Ltd.

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ChemStrong Scientific Co.,Ltd

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Sigma-Aldrich

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ShangHai Biochempartner Co.,Ltd

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Beijing Jin Ming Biotechnology Co., Ltd.

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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