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S8559

Sigma-Aldrich

Sinefungin

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

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C15H23N7O5
Número CAS:
58944-73-3
Peso molecular:
381.39
Código UNSPSC:
12352200
ID de substância PubChem:
24899800
NACRES:
NA.77

Nome do produto

Sinefungin, 95% (HPLC), powder

Nível de qualidade

200

Ensaio

95% (HPLC)

Formulário

powder

cor

white to yellow

solubilidade

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

espectro de atividade do antibiótico

neoplastics

Modo de ação

DNA synthesis | interferes
enzyme | inhibits

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

LMXOHSDXUQEUSF-YECHIGJVSA-N

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Descrição geral

Chemical structure: nucleoside

Aplicação

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

Ações bioquímicas/fisiológicas

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.
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.

Características e benefícios

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
039M4046V
14180415
036M4106V
14150304
045M4096V

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Visite a Biblioteca de Documentos

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).
Razvan F Albu et al.
Nucleic acids research, 40(4), 1708-1716 (2011-09-20)
The specificity and processivity of DNA methyltransferases have important implications regarding their biological functions. We have investigated the sequence specificity of CcrM and show here that the enzyme has a high specificity for GANTC sites, with only minor preferences at
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
Ben Youngblood et al.
The Journal of biological chemistry, 281(37), 26821-26831 (2006-07-18)
Changes in DNA bending and base flipping in a previously characterized specificity-enhanced M.EcoRI DNA adenine methyltransferase mutant suggest a close relationship between precatalytic conformational transitions and specificity (Allan, B. W., Garcia, R., Maegley, K., Mort, J., Wong, D., Lindstrom, W.
Kevin Bonham et al.
The FEBS journal, 277(9), 2096-2108 (2010-03-30)
The protein arginine methyltransferase (PRMT) family of enzymes catalyzes the transfer of methyl groups from S-adenosylmethionine to the guanidino nitrogen atom of peptidylarginine to form monomethylarginine or dimethylarginine. We created several less polar analogs of the specific PRMT inhibitor arginine
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