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Merck
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Key Documents

S8559

Sigma-Aldrich

西奈芬净

95% (HPLC), powder

同義詞:

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

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About This Item

經驗公式(希爾表示法):
C15H23N7O5
CAS號碼:
分子量::
381.39
分類程式碼代碼:
12352200
PubChem物質ID:

品質等級

化驗

95% (HPLC)

形狀

powder

顏色

white to yellow

溶解度

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

抗生素活性譜

neoplastics

作用方式

DNA synthesis | interferes
enzyme | inhibits

儲存溫度

2-8°C

SMILES 字串

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 密鑰

LMXOHSDXUQEUSF-YECHIGJVSA-N

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一般說明

Chemical structure: nucleoside

應用

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

生化/生理作用

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.

特點和優勢

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.

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves


分析證明 (COA)

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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).
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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