SINEFUNGIN

Synonym(s):sf;Foxp3;JM2;Mast Cell Growth Factor (MGF);scurfin

CAS NO.：58944-73-3
Empirical Formula: C15H23N7O5
Molecular Weight: 381.39
MDL number: MFCD00865623
EINECS: 637-385-5
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-08 20:21:46

What is SINEFUNGIN?

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

The Uses of SINEFUNGIN

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.

The Uses of SINEFUNGIN

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.

What are the applications of Application

Sinefungin is a SAM analog and Dnmt inhibitor

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

Properties of SINEFUNGIN

Boiling point:	783.2±70.0 °C(Predicted)
alpha	D25 -2.61° (c = 5 in water); D23 +12 ±2° (c = 0.227 in water)
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 for SINEFUNGIN

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.