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| | SINEFUNGIN Basic information |
| Product Name: | SINEFUNGIN | | Synonyms: | 6,7,8,9-hexadeoxy-yl)-5;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;compound57926;rp32232;SINEFUNGIN;5'-DEOXY-5'-(1,4-DIAMINO-4-CARBOXYBUTYL)ADENOSINE;ADENOSYLORNITHINE | | CAS: | 58944-73-3 | | MF: | C15H23N7O5 | | MW: | 381.39 | | EINECS: | 637-385-5 | | Product Categories: | | | Mol File: | 58944-73-3.mol |  |
| | 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. |
| 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.) |
| | 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 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) 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 |
| | SINEFUNGIN Preparation Products And Raw materials |
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