SINEFUNGIN Chemical Properties

alpha 

D25 -2.61° (c = 5 in water); D23 +12 ±2° (c = 0.227 in water)

Boiling point:

783.2±70.0 °C(Predicted)

Density 

1.91±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

H₂O: soluble

form 

powder

pka

pKa (66% DMF): 2.9, 3.9, 8.9, 10.2(at 25℃)

color 

white to yellow

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 month.

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

WGK Germany 

3

RTECS 

HE3140000

HS Code 

29419090

Toxicity

LD50 s.c. in mice: 185 mg/kg (Hamill, Hoehn, J. Antibiot.)

MSDS

• Language:English Provider:SigmaAldrich

SINEFUNGIN Usage And Synthesis

Description

Sinefungin (58944-73-3) is a nucleoside S-adenosyl-1-methionine analog. Potent, competitive methyltransferase (protein, DNA, and RNA methyltransferases) inhibitor.1,2?IC50?< 1.0 and 2.5 μM for PRMT1 and SET7/9, respectively.3?Sinefungin binds with greater affinity to the adenine-specific DNA methyltransferase M.TaqI than S-adenosyl-L-homocysteine.4?Inhibits biofilm formation by?Streptococcus pneumoniae.5

Uses

Sinefungin, a polar nucleoside antifungal active with broad biological activity, was isolated from a number of species of Streptomyces in the early 1970s. Sinefungin acts by inhibiting a wide range of methyltransferases, including the methylation of bases in DNA and RNA which alters cytosine deamination and gene expression. Sinefungin is widely used as a bioprobe to block methyltransferase-dependent pathways.

Uses

Sinefungin is a natural nucleoside analog of S-adenosylmethionine and inhibits Streptococcus pneumoniae biofilm growth. Its derivatives can be used as inhibitors and structure probes for human protein lysine methyltransferase SETD2.

Definition

ChEBI: An adenosine that is the the delta-(5'-adenosyl) derivative of ornithine.

General Description

Chemical structure: nucleoside

Biochem/physiol Actions

Probable transcription factor. Plays a critical role in the control of immune response.

References

1) Barbes?et al. (1990),?Effects of sinefungin and S-adenosylhomocysteine on DNA and protein methyltransferases from Streptomyces and other bacteria;? FEMS Microbiol. Lett.,?57?239 2) Yebra?et al. (1991),?The effect of sinefungin and synthetic analogues on RNA and DNA methyltransferases from Streptomyces;? J. Antibiot. (Tokyo),?44?1141 3) Cheng?et al. (2004),?Small molecule regulators of protein arginine methyltransferases;? J. Biol. Chem.,?279?23892 4) Schluckebier?et al. (1997), Differential binding of S-adenosylmethionine S-adenosylhomocysteine and Sinefungin to adenine-specific DNA methyltransferase M. TaqI;? J. Mol. Biol., 265?56 5) Yadav?et al. (2014),?Sinefungin, a natural nucleoside analogue of S-adenosylmethionine, inhibits Streptococcus pneumonia biofilm growth;? Biomed. Res. Int.,?2014?156987

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