Sinefungin

SIGMA/S8559 - 95% (HPLC), powder

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

CAS Number: 58944-73-3
Empirical Formula (Hill Notation): C₁₅H₂₃N₇O₅
Molecular Weight: 381.39
Linear Formula: C₁₅H₂₃N₇O₅
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-S8559-10MG	10 mg	$658.00 1/EA	Add To Favorites

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Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	neoplastics
assay	95% (HPLC)
color	white to yellow
form	powder
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
mode of action	DNA synthesis \| interferes
	enzyme \| inhibits
Quality Level	200
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
solubility	H₂O: complete 20 mg/ml, clear, colorless to light yellow
	H₂O: soluble
storage temp.	2-8°C

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.
Biochem/physiol Actions:	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.
Biochem/physiol Actions:	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 .
General description:	Chemical structure: nucleoside
Packaging:	10 mg in glass bottle

Hazard Codes	Xn
Risk Statements	22
Safety Statements	36
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3

Purity	95% (HPLC)
Storage Temp.	2-8°C
UNSPSC	12352200

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