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T3580

Sigma-Aldrich

Toyocamycin

≥98% (HPLC), from Streptomyces rimosus

Sinonimo/i:

4-Aminopyrrolo[2,3-d]pyrimidine-5-carbonitrile 7-(β-D-ribofuranoside), 7-Deaza-7-cyanoadenosine, NSC 63701, NSC 99843, Neuro 000027, Unamycin B, Vengicide

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10 MG
131,00 €

131,00 €

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131,00 €

About This Item

Formula empirica (notazione di Hill):
C12H13N5O4
Numero CAS:
606-58-6
Peso molecolare:
291.26
Numero MDL:
MFCD00866513
Codice UNSPSC:
12352200
ID PubChem:
329826772
NACRES:
NA.77

131,00 €

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Origine biologica

Streptomyces rimosus

Livello qualitativo

200

Saggio

≥98% (HPLC)

Stato

solid

Solubilità

DMSO: soluble 0.90-1.10 mg/mL, clear, colorless
H2O: moderately soluble
aqueous acid: moderately soluble
ethanol: moderately soluble
methanol: moderately soluble

Spettro attività antibiotica

fungi

Modalità d’azione

DNA synthesis | interferes

Temperatura di conservazione

2-8°C

Stringa SMILE

Nc1ncnc2n(cc(C#N)c12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

1S/C12H13N5O4/c13-1-5-2-17(11-7(5)10(14)15-4-16-11)12-9(20)8(19)6(3-18)21-12/h2,4,6,8-9,12,18-20H,3H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1
XOKJUSAYZUAMGJ-WOUKDFQISA-N

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Categorie correlate

Azioni biochim/fisiol

Studies have implicated that toyocamycin blocks the replication of fowl plague virus.[1]
Toyocamycin is a nucleoside- type antibiotic analogue of adenosine, isolated from Streptomyces species. Toyocamycin is an anti-tumor antibiotic with various target activities. Toyocamycin is a potent inhibitor of RNA self-cleavage in mammalian cells. It also inhibits phosphatidylinositol kinase, a cell proliferation regulator. Toyocamycin was also found to inhibit Auxin signaling. Auxins are plant hormones with a crucial role in plant development regulation, and Toyocamycin was found to specifically inhibit auxin-responsive gene expression.
Toyocamycin is a nucleoside-type antibiotic analogue of adenosine, isolated from Streptomyces species. Toyocamycin is an anti-tumor antibiotic with various target inhibitory activities.

Caratteristiche e vantaggi

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Nota sulla preparazione

Toyocamycin is soluble in DMSO at 0.90 - 1.10 mg/ml and yields a clear, colorless solution. It is also soluble in acidic solutions and is moderately soluble in water, methanol and ethanol. Solutions prepared in DMSO can be diluted 10-fold in water.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
0000173614
0000159442
0000159442
0000173614
14180312

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Sigma-Aldrich

SML2381

APY29

PERK Inhibitor I, GSK2606414 GSK2606414 is a cell-permeable, highly potent inhibitor of EIF2AK3/PERK (IC₅₀ = 0.4 nM; [ATP] = 5 µM). Targets PERK in its inactive DFG conformation at the ATP-binding region.

Sigma-Aldrich

516535

PERK Inhibitor I, GSK2606414

2-Fluoroadenosine 97%

Sigma-Aldrich

656402

2-Fluoroadenosine

ISRIB ≥98% (HPLC)

Sigma-Aldrich

SML0843

ISRIB

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C3350000

Cytarabine

Tunicamicina

Sigma-Aldrich

T7765

Tunicamicina

Tamoxifene ≥99%

Sigma-Aldrich

T5648

Tamoxifene

Yosuke Kurihara et al.
Biological & pharmaceutical bulletin, 25(10), 1272-1276 (2002-10-24)
We constructed an assay system of a luciferase reporter with p16/lNK4a gene transcriptional regulatory domain to identify p16-inducing substances, and found toyocamycin to induce gene expression from the screening of culture fluids of Streptomyces. Toyocamycin is a nucleoside analog, and
E Gunic et al.
Bioorganic & medicinal chemistry, 9(1), 163-170 (2001-02-24)
Toyocamycin and some analogues have shown potent antitumor activities; however, none of them could be used clinically primarily owing to their cytotoxicity to normal human cells. In order to overcome the weakness of these nucleoside analogues, substitution of a variety
Carolina Agop-Nersesian et al.
International journal for parasitology, 38(6), 673-681 (2007-12-08)
The ability to control expression of a specific gene is a prerequisite to understand the function of essential genes. Many gene regulation systems operate on the transcriptional level by employing heterologous cis- and trans-acting elements. Recently, novel approaches employing autocatalytic
Laising Yen et al.
Nature, 431(7007), 471-476 (2004-09-24)
Recent studies on the control of specific metabolic pathways in bacteria have documented the existence of entirely RNA-based mechanisms for controlling gene expression. These mechanisms involve the modulation of translation, transcription termination or RNA self-cleavage through the direct interaction of
Becker Y
Replication of Viral and Cellular Genomes: Molecular events at the origins of replication and biosynthesis of viral and cellular genomes (2012)
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