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T3580

Sigma-Aldrich

Toyocamycin

≥98% (HPLC), from Streptomyces rimosus

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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:
Molecular Weight:
291.26
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

Streptomyces rimosus

Quality Level

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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This Item
SMB00287T8552SML2409
Toyocamycin ≥98% (HPLC), from Streptomyces rimosus

T3580

Toyocamycin

Formycin A from Streptomyces kaniharaensis, ≥98% (HPLC)

SMB00287

Formycin A

Trichostatin A ≥98% (HPLC), from Streptomyces sp.

T8552

Trichostatin A

NITD008 ≥98% (HPLC)

SML2409

NITD008

form

solid

form

powder

form

powder

form

powder

Quality Level

200

Quality Level

200

Quality Level

300

Quality Level

-

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

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

solubility

DMSO: soluble 1 mg/mL, H2O: soluble 3 mg/mL

solubility

methanol: soluble 1.90-2.10 mg/mL, clear, colorless to faint yellow or tan, DMF: soluble, DMSO: soluble, H2O: insoluble, acetone: slightly soluble, acetonitrile: soluble, benzene: slightly soluble, chloroform: slightly soluble, ethyl acetate: slightly soluble, lower alcohols: soluble

solubility

DMSO: 2 mg/mL, clear (warmed)

biological source

Streptomyces rimosus

biological source

Streptomyces kaniharaensis

biological source

Streptomyces sp.

biological source

-

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
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
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
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
Janelle M Wright et al.
The Journal of eukaryotic microbiology, 57(2), 171-176 (2009-12-18)
Trichomonas vaginalis is the most common sexually transmitted protozoan in the world and its resistance to metronidazole is increasing. The purpose of this study was to demonstrate that clinical metronidazole resistance in T. vaginalis does not occur via the same

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