T3580

Toyocamycin

≥98% (HPLC), from Streptomyces rimosus

• Synonym(s): 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
• Empirical Formula (Hill Notation): C₁₂H₁₃N₅O₄
• CAS Number: 606-58-6
• Molecular Weight: 291.26
• NACRES: NA.77
• PubChem Substance ID: 329826772
• UNSPSC Code: 12352200
• MDL number: MFCD00866513
• Assay: ≥98% (HPLC)
• Form: solid
• Quality level: 200

Properties

• InChI key: XOKJUSAYZUAMGJ-WOUKDFQISA-N
• SMILES string: 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
• biological source: Streptomyces rimosus
• assay: ≥98% (HPLC)
• form: solid
• solubility: DMSO: soluble 0.90-1.10 mg/mL, clear, colorless, H₂O: moderately soluble, aqueous acid: moderately soluble, ethanol: moderately soluble, methanol: moderately soluble
• antibiotic activity spectrum: fungi
• mode of action: DNA synthesis | interferes
• storage temp.: 2-8°C
• Quality Level: 200

Description

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.

Toyocamycin is a nucleoside-type antibiotic analogue of adenosine, isolated from Streptomyces species. Toyocamycin is an anti-tumor antibiotic with various target inhibitory activities.

Studies have implicated that toyocamycin blocks the replication of fowl plague virus.

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable