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T3580

Sigma-Aldrich

Toyocamycin

≥98% (HPLC), from Streptomyces rimosus

Synonyme(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

Formule empirique (notation de Hill):
C12H13N5O4
Numéro CAS:
606-58-6
Poids moléculaire :
291.26
Numéro MDL:
MFCD00866513
Code UNSPSC :
12352200
ID de substance PubChem :
329826772
Nomenclature NACRES :
NA.77

Source biologique

Streptomyces rimosus

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

solid

Solubilité

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

Spectre d'activité de l'antibiotique

fungi

Mode d’action

DNA synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

XOKJUSAYZUAMGJ-WOUKDFQISA-N

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Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Notes préparatoires

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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