T3580

Toyocamycin

Name: Toyocamycin
Brand: SIGMA
Price: 147 EUR

≥98% (HPLC), from Streptomyces rimosus

Synonym(e):

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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10 MG

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Über diesen Artikel

Empirische Formel (Hill-System):

C₁₂H₁₃N₅O₄

CAS-Nummer:

606-58-6

Molekulargewicht:

291.26

NACRES:

NA.77

PubChem Substance ID:

329826772

UNSPSC Code:

12352200

MDL number:

MFCD00866513

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

200

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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

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Dieser Artikel	SMB00287	T8552	SML2409
Sigma-Aldrich T3580 Toyocamycin	Sigma-Aldrich SMB00287 Formycin A	Sigma-Aldrich T8552 Trichostatin A	Sigma-Aldrich SML2409 NITD008
form solid	form powder	form powder	form powder
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
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

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.

Lagerklasse

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Interaction of Rio1 kinase with toyocamycin reveals a conformational switch that controls oligomeric state and catalytic activity.

Irene N Kiburu et al.

PloS one, 7(5), e37371-e37371 (2012-05-26)

Rio1 kinase is an essential ribosome-processing factor required for proper maturation of 40 S ribosomal subunit. Although its structure is known, several questions regarding its functional remain to be addressed. We report that both Archaeoglobus fulgidus and human Rio1 bind

Revealing the quaternary structure of a heterogeneous noncovalent protein complex through surface-induced dissociation.

Anne E Blackwell et al.

Analytical chemistry, 83(8), 2862-2865 (2011-03-23)

As scientists begin to appreciate the extent to which quaternary structure facilitates protein function, determination of the subunit arrangement within noncovalent protein complexes is increasingly important. While native mass spectrometry shows promise for the study of noncovalent complexes, few developments

A toyocamycin analogue with the sugar moiety in a syn conformation.

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

Hydrogenosomes of laboratory-induced metronidazole-resistant Trichomonas vaginalis lines are downsized while those from clinically metronidazole-resistant isolates are not.

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

Induction of apoptosis in human leukemia cells by MCS-C2 via caspase-dependent Bid cleavage and cytochrome c release.

Min Kyoung Kim et al.

Cancer letters, 223(2), 239-247 (2005-05-18)

The purpose of the present study was to investigate the anti-proliferative and apoptotic effects of MCS-C2, a novel synthetic analogue of the pyrrolo[2,3-d]pyrimidine nucleoside toyocamycin and sangivamycin, in human promyelocytic leukemia (HL-60) cells. When treated with 5 microM MCS-C2, inhibited

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