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T3580

Toyocamycin

≥98% (HPLC), from Streptomyces rimosus

别名:

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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关于此项目

经验公式（希尔记法）:
C12H13N5O4
化学文摘社编号:
606-58-6
分子量:
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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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

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.
Toyocamycin is a nucleoside-type antibiotic analogue of adenosine, isolated from Streptomyces species. Toyocamycin is an anti-tumor antibiotic with various target inhibitory activities.

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.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number
0000173614
0000159442
0000159442
0000173614
14180312

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相关内容

Data Sheet - T3580

Instructions

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
Becker Y
Replication of Viral and Cellular Genomes: Molecular events at the origins of replication and biosynthesis of viral and cellular genomes (2012)
Chamakura V N S Varaprasad et al.
Bioorganic chemistry, 35(1), 25-34 (2006-09-02)
Several Toyocamycin (4) analogues were examined for their ability to inhibit HCV RNA in a replicon assay. Among the compounds examined 4-methylthio (18) and 5-carboxamide oxime derivatives (23 and 27) of Toyocamycin were found to have good activity and selectivity.
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全球贸易项目编号

货号GTIN
T3580-10MG04061832649443