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S8559

Sinefungin

Name: Sinefungin
Brand: SIGMA

95% (HPLC), powder, methylation of bases in DNA & RNA inhibitor

Synonym(s):

5′-Deoxy-5′-(1,4-diamino-4-carboxybutyl)adenosine, A-9145, Adenosylornithine, Antibiotic 32232RP

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₂₃N₇O₅

CAS Number:

58944-73-3

Molecular Weight:

381.39

UNSPSC Code:

12352200

PubChem Substance ID:

24899800

NACRES:

NA.77

Assay:

95% (HPLC)

Form:

powder

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Properties

Product Name

Sinefungin, 95% (HPLC), powder

Quality Segment

200

assay

95% (HPLC)

form

powder

color

white to yellow

solubility

H₂O: complete 20 mg/ml, clear, colorless to light yellow, H₂O: soluble

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes, enzyme | inhibits

storage temp.

2-8°C

SMILES string

N[C@@H](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23

InChI

1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1

InChI key

LMXOHSDXUQEUSF-YECHIGJVSA-N

Description

General description

Chemical structure: nucleoside

Application

Sinefungin was used to inhibit global methyltransferases in breast cancer cell line, MCF7² and Jurkat cells.³ It was used as S-adenosylmethionine analogue in equilibrium FRET experiments.⁴

Biochem/physiol Actions

Blocks the methylation of bases in DNA and RNA; involved in physiological processes such as aging and carcinogenesis.

Sinefungin blocks the methylation of bases in DNA and RNA, such as 5-methylcytosine or N⁶-methyladenosine, suggesting a role in gene expression. In addition, sinefugin is involved in physiological processes such as aging and carcinogenesis.
Methylation inhibition by sinefugin is often accompanied by an altered rate of cytosine deamination that is coupled to transition mutation in the DNA. Sinefugin inhibits Epstein-Barr viral activity and this inhibition is related to the change in DNA methylation and gene expression. It can cause a rate change in several restriction DNA endonuclease activities, including Mme I, which is not connected to the inhibition of the methytransferase activity.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品

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Certificates of Analysis (COA)

Lot/Batch Number

0000488212

0000407546

0000258273

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Articles

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Global Trade Item Number

SKU	GTIN
S8559-10MG	04061836960889