SINEFUNGIN

Product NameSINEFUNGIN
CAS58944-73-3
MFC15H23N7O5
MW381.39
EINECS637-385-5
MOL File58944-73-3.mol

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
biological source	rat
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.
InChIKey	LMXOHSDXUQEUSF-YECHIGJVSA-N
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

Safety Information

Hazard Codes	Xn
Risk Statements	22
Safety Statements	36
WGK Germany	3
RTECS	HE3140000
HS Code	29419090
Storage Class	11 - Combustible Solids
Toxicity	LD50 s.c. in mice: 185 mg/kg (Hamill, Hoehn, J. Antibiot.)

MSDS

Provider	Language
SigmaAldrich	English

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.1,2IC50< 1.0 and 2.5 μM for PRMT1 and SET7/9, respectively.3Sinefungin binds with greater affinity to the adenine-specific DNA methyltransferase M.TaqI than S-adenosyl-L-homocysteine.4Inhibits biofilm formation byStreptococcus pneumoniae.5

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.

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.

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] C BARBÉS. Effects of sinefungin and S-adenosylhomocysteine on DNA and protein methyltransferases from Streptomyces and other bacteria.[J]. Fems Microbiology Letters, 1990, 57 3: 239-243.
[2] M J YEBRA. The effect of sinefungin and synthetic analogues on RNA and DNA methyltransferases from Streptomyces.[J]. Journal of Antibiotics, 1991, 44 10: 1141-1147. DOI:10.7164/antibiotics.44.1141
[3] DONGHANG CHENG. Small molecule regulators of protein arginine methyltransferases.[J]. The Journal of Biological Chemistry, 2004, 279 23: 23892-23899. DOI:10.1074/jbc.m401853200
[4] GERD SCHLUCKEBIER . Differential binding of S-adenosylmethionine S-adenosylhomocysteine and Sinefungin to the adenine-specific DNA methyltransferase M.TaqI1[J]. Journal of Molecular Biology, 1997, 265 1: Pages 56-67. DOI:10.1006/jmbi.1996.0711
[5] MUKESH KUMAR YADAV. Sinefungin, a natural nucleoside analogue of S-adenosylmethionine, inhibits Streptococcus pneumoniae biofilm growth.[J]. BioMed Research International, 2014: 156987. DOI:10.1155/2014/156987

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