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S8559

Sigma-Aldrich

Sinefungin

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

product name

Sinefungin, 95% (HPLC), powder

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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Delphine Benarroch et al.
RNA (New York, N.Y.), 15(4), 666-674 (2009-02-17)
A 2,2,7-trimethylguanosine (TMG) cap is a signature feature of eukaryal snRNAs, telomerase RNAs, and trans-spliced nematode mRNAs. TMG and 2,7-dimethylguanosine (DMG) caps are also present on mRNAs of two species of alphaviruses (positive strand RNA viruses of the Togaviridae family).
Gustavo A Bezerra et al.
Biochimie, 183, 100-107 (2021-01-22)
The folate and methionine cycles, constituting one-carbon metabolism, are critical pathways for cell survival. Intersecting these two cycles, 5,10-methylenetetrahydrofolate reductase (MTHFR) directs one-carbon units from the folate to methionine cycle, to be exclusively used for methionine and S-adenosylmethionine (AdoMet) synthesis.
Alex Matsuda et al.
Nucleic acids research, 52(11), 6441-6458 (2024-03-19)
Coronaviruses modify their single-stranded RNA genome with a methylated cap during replication to mimic the eukaryotic mRNAs. The capping process is initiated by several nonstructural proteins (nsp) encoded in the viral genome. The methylation is performed by two methyltransferases, nsp14
Alessandra Galati et al.
FEBS letters, 596(1), 42-52 (2021-11-25)
Mutations in many genes that control the expression, the function, or the stability of telomerase cause telomere biology disorders (TBDs), such as dyskeratosis congenita, pulmonary fibrosis, and aplastic anemia. Mutations in a subset of the genes associated with TBDs cause
Tina Branscombe Miranda et al.
Molecular cancer therapeutics, 8(6), 1579-1588 (2009-06-11)
DNA methylation, histone modifications, and nucleosomal occupancy collaborate to cause silencing of tumor-related genes in cancer. The development of drugs that target these processes is therefore important for cancer therapy. Inhibitors of DNA methylation and histone deacetylation have been approved
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