Sinefungin
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| Category | Antibiotics |
| Catalog number | BBF-03483 |
| CAS | 58944-73-3 |
| Molecular Weight | 381.39 |
| Molecular Formula | C15H23N7O5 |
| Purity | >95% by HPLC |
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Description
It is a nucleoside antibiotic produced by the strain of Streptomyces griseolus (NRRL 3739). It has the effect against plant pathogenic fungi, candida, Pasteur's yeast and trypanosome. It mainly has the effect against fungal, especially has the strong effect to the Yeast. LD50 is greater than 400 mg/kg.
Specification
| Synonyms | Antibiotic A 9145; A 9145; Antibiotic RP 32232; Sinefungina; Sinefungine; Sinefunginum; 6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-beta-D-ribo-decofuranuronic acid |
| Storage | Store at 2-8°C |
| IUPAC Name | (2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid |
| Canonical SMILES | C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CC(CCC(C(=O)O)N)N)O)O)N |
| InChI | InChI=1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1 |
| InChI Key | LMXOHSDXUQEUSF-YECHIGJVSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White solid |
| Application | Antimalarials |
| Antibiotic Activity Spectrum | Fungi; Parasites; Yeast |
| Boiling Point | 783.2±70.0°C (Predicted) |
| Density | 1.91±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Water; Slightly soluble in Methanol, Ethanol; Insoluble in other organic solvents |
Reference Reading
1. Sinefungin, a natural nucleoside analogue of S-adenosylmethionine, inhibits Streptococcus pneumoniae biofilm growth
Jae-Jun Song, Mukesh Kumar Yadav, Sung-Won Chae, Seok-Won Park Biomed Res Int . 2014;2014:156987. doi: 10.1155/2014/156987.
Pneumococcal colonization and disease is often associated with biofilm formation, in which the bacteria exhibit elevated resistance both to antibiotics and to host defense systems, often resulting in infections that are persistent and difficult to treat. We evaluated the effect of sinefungin, a nucleoside analogue of S-adenosylmethionine, on pneumococcal in vitro biofilm formation and in vivo colonization. Sinefungin is bacteriostatic to pneumococci and significantly decreased biofilm growth and inhibited proliferation and structure of actively growing biofilms but did not alter growth or the matrix structure of established biofilms. Sinefungin significantly reduced pneumococcal colonization in rat middle ear. The quorum sensing molecule (autoinducer-2) production was significantly reduced by 92% in sinefungin treated samples. The luxS, pfs, and speE genes were downregulated in biofilms grown in the presence of sinefungin. This study shows that sinefungin inhibits pneumococcal biofilm growth in vitro and colonization in vivo, decreases AI-2 production, and downregulates luxS, pfs, and speE gene expressions. Therefore, the S-adenosylmethionine (SAM) inhibitors could be used as lead compounds for the development of novel antibiofilm agents against pneumococci.
2. Cycloalkane analogues of sinefungin as EHMT1/2 inhibitors
Yi Chen, Ming-Wei Wang, Yafang Wang, Qing Liu, Dehua Yang, Liming Shao, Xiaoqing Cai Bioorg Med Chem . 2017 Sep 1;25(17):4579-4594. doi: 10.1016/j.bmc.2017.06.032.
A series of cycloalkyl substituted analogues of the natural product sinefungin lacking the amino-acid moiety was designed and synthesized. Two stereoisomers (6-R and 6-S) were separated and their bioactivities examined against EHMT1/2. Of which, compound 14d showed an inhibitory activity against EHMT1/2 (88.9%, IC50=21.8μM for EHMT1 and 77.6%, IC50=39.6μM for EHMT2, respectively) similar to that of sinefungin (100.0%, IC50=28.4μM for EHMT1 and 79.5%, IC50=30.1μM for EHMT2, respectively). Further studies against other methyltransferases such as PRMT1 showed no activity except that 12d displayed about 20% inhibition.
3. Asymmetric Total Synthesis of C9'- epi-Sinefungin
Rocco L Policarpo, Danny Huang, Ludovic Decultot, Brandon A Wright, Matthew D Shair Org Lett . 2020 Jul 17;22(14):5594-5599. doi: 10.1021/acs.orglett.0c01956.
The natural nucleoside (+)-sinefungin, structurally similar to cofactorS-adenosyl-l-methionine, inhibits various SAM-dependent methyltransferases (MTs). Access to sinefungin analogues could serve as the basis for the rational design of small molecule methyltransferase inhibitors. We developed a route to the unnatural C9' epimer of sinefungin that employed a diastereoselective Overman rearrangement to install the key C6' amino stereocenter. The ability for late-stage modification is highlighted, opening an avenue for the discovery of new MT inhibitors.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
