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T3580

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C12H13N5O4
CAS Number:
606-58-6
Molecular Weight:
291.26
MDL number:
MFCD00866513
UNSPSC Code:
12352200
PubChem Substance ID:
329826772
NACRES:
NA.77

biological source

Streptomyces rimosus

Quality Level

200

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

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

InChI key

XOKJUSAYZUAMGJ-WOUKDFQISA-N

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Biochem/physiol Actions

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
Frank Seela et al.
Acta crystallographica. Section C, Crystal structure communications, 65(Pt 9), o431-o434 (2009-09-04)
The title compound [systematic name: 4-amino-5-cyano-1-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine hemihydrate], C(12)H(13)N(5)O(4).0.5H(2)O, is a regioisomer of toyocamycin with the ribofuranosyl residue attached to the pyrimidine moiety of the heterocycle. This analogue exhibits a syn glycosylic bond conformation with a chi torsion angle of 57.51
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