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

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.

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] 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

SINEFUNGIN(58944-73-3)Related Product Information

• Micafungin
• Micafungin sodium
• AFC
• Chaetocin
• FARNESYLTHIOACETIC ACID
• 10-AMINO-1-DECANOL
• 1,9-DIAMINONONANE
• 2-AMINOHEPTANOIC ACID
• SINEFUNGIN
• DL-2-AMINOOCTANOIC ACID
• 2-(TETRAHYDROFURAN-2-YL)ETHANAMINE
• 6,7-DIHYDROXY-4-OXAHEPTYLAMINE
• 2-AMINONONANOIC ACID
• 5-AMINO CAPROIC ACID
• 10-AMINODECANOIC ACID
• 1-OCTYLIMIDAZOLE
• 1-(10-HYDROXYDECYL)IMIDAZOLE
• 2-AMINOCAPRIC ACID