| Identification | Back Directory | [Name]
SINEFUNGIN | [CAS]
58944-73-3 | [Synonyms]
SF
A-9145
rp32232
32232RP
SINEFUNGIN
SCF from rat
Steel Factor
compound57926
A 9145, RP 32232
ANTIBIOTIC A-9145
ADENOSYLORNITHINE
Antibiotic 32232RP
Kit ligand Precursor
InSolution? Sinefungin
6,7,8,9-hexadeoxy-yl)-5
Mast Cell Growth Factor (MGF)
(2S,5S)-5-(5'-Adenosyl)-2,5-diaminopentanoic acid
5'-DEOXY-5'-(1,4-DIAMINO-4-CARBOXYBUTYL)ADENOSINE
Anti-Foxp3 (C-terminal) antibody produced in rabbit
InSolution Sinefungin - CAS 58944-73-3 - Calbiochem
6,9-diamino-1-(6-amino-9h-purin-9-d-glycero-alpha-l-talo-decofuranuronicaci
6,9-diamino-1-(6-amino-9h-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronica
(2S,5S)-2,5-Diamino-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-D-glycero-α-L-talo-decofuranuronic acid
D-glycero-a-L-talo-Decofuranuronic acid,6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-
D-glycero-α-L-talo-Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-
Sinefungin,5′-Deoxy-5′-(1,4-diamino-4-carboxybutyl)adenosine, A-9145, Adenosylornithine, Antibiotic 32232RP | [EINECS(EC#)]
637-385-5 | [Molecular Formula]
C15H23N7O5 | [MDL Number]
MFCD00057013 | [MOL File]
58944-73-3.mol | [Molecular Weight]
381.39 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [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.) |
| Hazard Information | Back Directory | [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. | [Definition]
ChEBI: An adenosine that is the the delta-(5'-adenosyl) derivative of ornithine. | [General Description]
Chemical structure: nucleoside | [Biological Activity]
Strong competitive inhibitor of methyltransferases which uses S-adenosyl-1-methionine as the methyl group donor to yield methylated products such as 5-methylcytosine or N6-methyl adenosine on DNA and RNA. In addition, sinefungin is involved in a number of physiological processes. | [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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Sigma-Aldrich
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