Cycloepoxydon
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01109 |
| CAS | |
| Molecular Weight | 240.25 |
| Molecular Formula | C12H16O5 |
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Description
It is produced by the strain of Duteromycete 45-93. It can inhibit TPA induced expression of k gene binding nuclear factor (NF-KB) and activator protein-1 (APT-1) mediated secreted alkaline phosphatase (SEAP), with IC50 of 4.2-9.4 mol/L and 4.2-9.4 mol/L, respectively.
Specification
| IUPAC Name | (1aR,5R,6S,7S,7aR)-6,7-dihydroxy-5-propyl-1a,3,5,6,7,7a-hexahydrooxireno[2,3-g]isochromen-2-one |
| Canonical SMILES | CCCC1C(C2=C(CO1)C(=O)C3C(C2O)O3)O |
| InChI | InChI=1S/C12H16O5/c1-2-3-6-9(14)7-5(4-16-6)8(13)11-12(17-11)10(7)15/h6,9-12,14-15H,2-4H2,1H3/t6-,9-,10+,11+,12-/m1/s1 |
| InChI Key | FQEOCFATKIDBGB-OVBJLEGISA-N |
Reference Reading
1. Naturally occurring and synthetic inhibitors of NF-kappaB functions
K Umezawa, A Ariga, N Matsumoto Anticancer Drug Des. 2000 Aug;15(4):239-44.
Nuclear factor (NF)-kappaB is a transcription factor that induces the immunoglobulin kappa chain, cytokines such as interleukin (IL)-1, IL-2, IL-6, IL-8, tumor necrosis factor (TNF)-alpha and interferon gamma, and cell adhesion proteins. It also induces anti-apoptotic proteins, and inhibits TNF-alpha and anticancer drug-induced apoptosis. Therefore, NF-kappaB function inhibitors may be useful as anti-inflammatory and anticancer agents. Microbial products such as panepoxydone, cycloepoxydon and gliotoxin are known to inhibit activation of NF-kappaB. We have designed and synthesized new NF-kappaB inhibitors from the structure of an antibiotic, epoxyquinomicin C. The designed compound, DHM2EQ, inhibited TNF-alpha-induced activation of NF-kappaB and showed a therapeutic effect in mouse rheumatoid arthritis model.
2. Total synthesis of the novel NF-kappaB inhibitor (-)-cycloepoxydon
Goverdhan Mehta, Kabirul Islam Org Lett. 2004 Mar 4;6(5):807-10. doi: 10.1021/ol036521j.
An enantioselective total synthesis of the novel, biologically active epoxyquinone natural product (-)-cycloepoxydon has been accomplished from the readily available Diels-Alder adduct of cyclopentadiene and p-benzoquinone. A new cycloepoxydon related heptacyclic dimer has been prepared and characterized. [reaction: see text]
3. Cycloepoxydon, 1-hydroxy-2-hydroxymethyl-3-pent-1-enylbenzene and 1-hydroxy-2-hydroxymethyl-3-pent-1,3-dienylbenzene, new inhibitors of eukaryotic signal transduction
A Gehrt, G Erkel, T Anke, O Sterner J Antibiot (Tokyo). 1998 May;51(5):455-63. doi: 10.7164/antibiotics.51.455.
In a screening for new inhibitors of NF-KB and AP-1 mediated signal transduction pathways in COS-7 cells using secreted alkaline phosphatase (SEAP) as a reporter gene three novel compounds, cycloepoxydon (1), 1-hydroxy-2-hydroxymethyl-3-pent-1-enylbenzene (2) and 1-hydroxymethyl-3-pent-1,3-dienylbenzene (3) were isolated from fermentations of the deuteromycete strain 45-93. Cycloepoxydon inhibits the TPA-induced NF-KB and AP-1 mediated SEAP expression with an IC50 of 1-2 micrograms/ml (4.2-8.4 microns) and 3-5 micrograms/ml (12.6-21 microns) respectively. 1-Hydroxy-2-hydroxymethyl-3-pent-1-enylbenzene (2) inhibits the TPA-induced NF-KB and AP-1 mediated SEAP expression with an IC50 of 7 micrograms/ml (36.4 microns) and 5 micrograms/ml (26 microns). 3 showed only a weak inhibition of the AP-1 and no influence on NF-KB dependent reporter gene expression. In COS-7 and HeLa S3 cells electrophoretic mobility shift assays showed that cycloepoxydon strongly reduced the TPA and TNF- alpha mediated binding of NF-KB to a high affinity consensus sequence which was due to the inhibition of phosphorylation of the protein IKB.
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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 ╳
