S8559

Sinefungin

95% (HPLC), powder

• Synonym(s): 5′-Deoxy-5′-(1,4-diamino-4-carboxybutyl)adenosine, A-9145, Adenosylornithine, Antibiotic 32232RP
• Empirical Formula (Hill Notation): C₁₅H₂₃N₇O₅
• CAS Number: 58944-73-3
• Molecular Weight: 381.39
• UNSPSC Code: 12352200
• PubChem Substance ID: 24899800

Properties

• Quality Level: 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

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.

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves