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Toyocamycin

SIGMA/T3580 - ≥98% (HPLC), from Streptomyces rimosus

Synonym: 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

CAS Number: 606-58-6
Empirical Formula (Hill Notation): C12H13N5O4
Molecular Weight: 291.26
MDL Number: MFCD00866513
Linear Formula: C12H13N5O4
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-T3580-10MG 10 mg
 $138.00
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antibiotic activity spectrum fungi
assay ≥98% (HPLC)
biological source Streptomyces rimosus
form solid
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
InChI key XOKJUSAYZUAMGJ-WOUKDFQISA-N
mode of action DNA synthesis | interferes
Quality Level 200 
SMILES string Nc1ncnc2n(cc(C#N)c12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
solubility aqueous acid: moderately soluble
  DMSO: soluble 0.90-1.10 mg/mL, clear, colorless
  ethanol: moderately soluble
  H2O: moderately soluble
  methanol: moderately soluble
storage temp. 2-8°C
Biochem/physiol Actions: Studies have implicated that toyocamycin blocks the replication of fowl plague virus.
Biochem/physiol Actions: 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.
Features and Benefits: 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 .
Preparation Note: 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.
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
Storage Temp. 2-8°C
UNSPSC 12352200

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