Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H23N7O5 |
Molecular Weight | 381.387 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=CN=C3N
InChI
InChIKey=LMXOHSDXUQEUSF-YECHIGJVSA-N
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
Sinefungin, a natural nucleoside isolated from cultures of Streptomyces incarnatus and S. griseolus, is structurally related to S-adenosylhomocysteine and S-adenosylmethionine. Sinefungin is a DNA methyltransferase (DNMT) inhibitor (IC₅₀ = 0.1 - 20 uM). Sinefungin has been shown to inhibit the development of various fungi and viruses, but its major attraction to date resides in its potent antiparasitic activity. This compound has been reported to display antiparasitic activity against malarial, trypanosomal, and leishmanial species. Sinefungin inhibits pneumococcal biofilm growth in vitro and colonization in vivo, decreases AI-2 production, and downregulates luxS, pfs, and speE gene expressions. Sinefungin was significantly suppressive against both L. donovani and L. braziliensis panamensis infections in hamsters when compared with meglumine antimonate. An immunosuppressed rat model was used to investigate the anti-Cryptosporidium parvum activity of sinefungin. In infected animals, oral sinefungin therapy resulted in a dose-related suppression of oocyst shedding, which correlated with oocyst disappearance from ileal sections. When administered prior to or on the day of oocyst challenge, sinefungin successfully prevented infection. These data suggest that sinefungin could be considered as a candidate molecule in the treatment of human cryptosporidiosis, considered to be the most significant enteric opportunistic infection in AIDS.
Approval Year
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19441289
Investigations in rats showed that only 1.23 mg of sinefungin loaded in PLGA nanoparticles led to a decrease of sinefungin in the urine (0.23 mg vs. 4.27 mg for IV administration of free sinefungin) and to an increase of sinefungin concentration in the bile (6.63 microg/ml vs. 3.89 microg/ml for IV administration of free sinefungin). But the biliary concentration of encapsulated sinefungin (6.63 microg/ml) is still nearly 2 times lower than the MIC50
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19721445 https://www.ncbi.nlm.nih.gov/pubmed/1396713
Curator's Comment: Sinefungin was potent against dengue N-7 and 2'-O MTase activity, exhibiting IC(50) values of 30 and 41nM, respectively. https://www.ncbi.nlm.nih.gov/pubmed/20350738
Sinefungin is a DNA methyltransferase (DNMT) inhibitor (IC₅₀ = 0.1 - 20 uM). Sinefungin was shown to be a very strong inhibitor (Ki = 3.5 nM) of the DNA methyltransferase reaction.
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NCI_THESAURUS |
C514
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NCI_THESAURUS |
C471
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45453
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C73041
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CHEMBL1214186
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100000083537
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C006235
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W2U467CIIL
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SUB10532MIG
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58944-73-3
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m9952
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4450
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DB01910
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DTXSID10207689
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65482
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ACTIVE MOIETY