A purine nucleoside with diverse biological activities
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Sinefungin (trifluoroacetate salt)

Item No. 41004

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S,5S-diamino-6-((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)hexanoic acid, trifluoroacetate salt
Synonyms
  • A 9145
  • Adenosyl-ornithine
  • Antibiotic A 9145
Molecular Formula
C15H23N7O5 • XCF3COOH
Formula Weight
381.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly soluble: 0.1-1mg/mlWater: Sparingly soluble: 1-10 mg/ml
SMILES
O[C@H]1[C@@H](O)[C@H](N2C(N=CN=C3N)=C3N=C2)O[C@@H]1C[C@H](CC[C@H](N)C(O)=O)N.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C15H23N7O5.C2HF3O2/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;3-2(4,5)1(6)7/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20);(H,6,7)/t6-,7-,8+,10+,11+,14+;/m0./s1
InChi Key
YKVMVLBLFFQJHJ-CBZNOUFBSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $109

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    5 mg

    $409

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    10 mg

    $654

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    Product Description

    Sinefungin is a purine nucleoside and derivative of S-adenosylhomocysteine (Item No. 13603) that has been found in Streptomyces and has diverse biological activities.1,2 It inhibits G9a methyltransferase and SET domain-containing protein 7 (SET7) with IC50 values of 10.4 and 2.38 µM, respectively, using histone H3 (1-21) peptide as a substrate and 150 and 9.1 µM, respectively, using full-length histone H3 as a substrate.3 It also inhibits protein arginine methyltransferase 5 (PRMT5) with IC50 values of 0.31 and 0.69 µM using histone H4 (1-21) peptide and full-length histone H4, respectively, as substrates. Sinefungin (10 mg/kg) reduces renal levels of the mesenchymal marker α-smooth muscle actin (α-SMA), fibrosis markers ferroptosis suppressor protein 1 (Fsp1), collagen 1, collagen 3, and fibronectin, and monomethylation of histone H3 lysine 4 (H3K4me1) in a mouse model of unilateral ureteral obstruction.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nolan, L.L. Molecular target of the antileishmanial action of sinefungin. Antimicrob. Agents Chemother. 31(10), 1542-1548 (1987).

    2. Maguire, M.P., Feldman, P.L., and Rapoport, H. Stereoselective synthesis and absolute stereochemistry of sinefungin. The Journal of Organic Chemistry 55(3), 948-955 (1990).

    3. Horiuchi, K.Y., Eason, M.M., Ferry, J.J., et al. Assay development for histone methyltransferases. Assay Drug Dev. Technol. 11(4), 227-236 (2013).

    4. Sasaki, K., Doi, S., Nakashima, A., et al. Inhibition of SET domain-containing lysine methyltransferase 7/9 ameliorates renal fibrosis. J. AM. Soc. Nephrol. 27(1), 203-215 (2016).