Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Hae Young Park et al.
Cancer science, 97(5), 430-436 (2006-04-25)
The purpose of the present study was to investigate the mechanisms involved in the antiproliferative and apoptotic effects of MCS-C2, a novel analog of the pyrrolo[2,3-d]pyrimidine nucleoside toyocamycin and sangivamycin, in human prostate cancer LNCaP cells. MCS-C2, a selective inhibitor
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
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
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
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
View All Related Papers

Articles

Adenosine Receptors

We offers many products related to adenosine receptors for your research needs.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service