Panepoxydone
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MedKoo CAT#: 531391

CAS#: 31298-54-1

Description: Panepoxydone is a fungal metabolite that inhibits NF-κB transcription factor by preventing IκB phosphorylation, thus inhibiting the release of NF-κB from the IκB : NF-κB complex and its translocation into the nucleus. Panepoxydone also has antimalarial, cytotoxic activities and anti-parasitic activity against Trypanosoma cruzi.


Price and Availability

Size Price Shipping out time Quantity
5mg USD 800 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-07-10. Prices are subject to change without notice.

Panepoxydone purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 531391
Name: Panepoxydone
CAS#: 31298-54-1
Chemical Formula: C11H14O4
Exact Mass: 210.0892
Molecular Weight: 210.229
Elemental Analysis: C, 62.85; H, 6.71; O, 30.44


Synonym: Panepoxydone

IUPAC/Chemical Name: (1S,5R,6S)-5-Hydroxy-3-[(1S)-1-hydroxy-3-methyl-2-buten-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

InChi Key: MBXKEYXHJAZKBP-GISOBZBCSA-N

InChi Code: InChI=1S/C11H14O4/c1-5(2)3-7(12)6-4-8(13)10-11(15-10)9(6)14/h3-4,7-8,10-13H,1-2H3/t7-,8+,10-,11+/m0/s1

SMILES Code: O=C1[C@@]2([H])O[C@@]2([H])[C@H](O)C=C1[C@@H](O)/C=C(C)\C


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Vásquez R, Rios N, Solano G, Cubilla-Rios L. Lentinoids A-D, New Natural Products Isolated from Lentinus strigellus. Molecules. 2018 Mar 28;23(4). pii: E773. doi: 10.3390/molecules23040773. PubMed PMID: 29597242; PubMed Central PMCID: PMC6017980.

2: Nordén R, Samuelsson E, Nyström K. NFκB-mediated activation of the cellular FUT3, 5 and 6 gene cluster by herpes simplex virus type 1. Glycobiology. 2017 Nov 1;27(11):999-1005. doi: 10.1093/glycob/cwx079. PubMed PMID: 28973293.

3: Isaka M, Palasarn S, Sappana M, Srichomthong K, Karunarathna SC, Hyde KD. Prenylhydroquinone-Derived Secondary Metabolites from Cultures of the Basidiomycete Lentinus similis BCC 52578. Nat Prod Commun. 2015 Aug;10(8):1391-3. PubMed PMID: 26434125.

4: Arora R, Schmitt D, Karanam B, Tan M, Yates C, Dean-Colomb W. Inhibition of the Warburg effect with a natural compound reveals a novel measurement for determining the metastatic potential of breast cancers. Oncotarget. 2015 Jan 20;6(2):662-78. PubMed PMID: 25575825; PubMed Central PMCID: PMC4359247.

5: Arora R, Yates C, Gary BD, McClellan S, Tan M, Xi Y, Reed E, Piazza GA, Owen LB, Dean-Colomb W. Panepoxydone targets NF-kB and FOXM1 to inhibit proliferation, induce apoptosis and reverse epithelial to mesenchymal transition in breast cancer. PLoS One. 2014 Jun 4;9(6):e98370. doi: 10.1371/journal.pone.0098370. eCollection 2014. PubMed PMID: 24896091; PubMed Central PMCID: PMC4045585.

6: Barros-Filho BA, de Oliveira MC, Mafezoli J, Barbosa FG, Rodrigues-Filho E. Secondary metabolite production by the basidiomycete, Lentinus strigellus, under different culture conditions. Nat Prod Commun. 2012 Jun;7(6):771-3. PubMed PMID: 22816304.

7: Jiang ZY, Guo YY, Ren HB, Zou YF, Fan MS, Lv Y, Han P, De W, Sun LZ. Tumor necrosis factor (TNF)-α upregulates progesterone receptor-A by activating the NF-κB signaling pathway in human decidua after labor onset. Placenta. 2012 Jan;33(1):1-7. doi: 10.1016/j.placenta.2011.09.004. Epub 2011 Nov 1. PubMed PMID: 22047608.

8: Padró M, Mejías-Luque R, Cobler L, Garrido M, Pérez-Garay M, Puig S, Peracaula R, de Bolós C. Regulation of glycosyltransferases and Lewis antigens expression by IL-1β and IL-6 in human gastric cancer cells. Glycoconj J. 2011 Feb;28(2):99-110. doi: 10.1007/s10719-011-9327-4. Epub 2011 Mar 2. PubMed PMID: 21365246.

9: Souza-Fagundes EM, Cota BB, Rosa LH, Romanha AJ, Corrêa-Oliveira R, Rosa CA, Zani CL, Teixeira-Carvalho A, Martins-Filho OA. In vitro activity of hypnophilin from Lentinus strigosus: a potential prototype for Chagas disease and leishmaniasis chemotherapy. Braz J Med Biol Res. 2010 Nov;43(11):1054-61. Epub 2010 Oct 14. PubMed PMID: 21088803.

10: Itani H, Liu X, Sarsour EH, Goswami PC, Born E, Keen HL, Sigmund CD. Regulation of renin gene expression by oxidative stress. Hypertension. 2009 Jun;53(6):1070-6. doi: 10.1161/HYPERTENSIONAHA.109.130633. Epub 2009 May 11. PubMed PMID: 19433777; PubMed Central PMCID: PMC2740736.

11: Cota BB, Rosa LH, Fagundes EM, Martins-Filho OA, Correa-Oliveira R, Romanha AJ, Rosa CA, Zani CL. A potent trypanocidal component from the fungus Lentinus strigosus inhibits trypanothione reductase and modulates PBMC proliferation. Mem Inst Oswaldo Cruz. 2008 May;103(3):263-70. PubMed PMID: 18592099.

12: Erkel G, Wisser G, Anke T. Influence of the fungal NF-kappaB inhibitor panepoxydone on inflammatory gene expression in MonoMac6 cells. Int Immunopharmacol. 2007 May;7(5):612-24. Epub 2007 Jan 29. PubMed PMID: 17386409.

13: Horie R, Watanabe T, Umezawa K. Blocking NF-kappaB as a potential strategy to treat adult T-cell leukemia/lymphoma. Drug News Perspect. 2006 May;19(4):201-9. Review. PubMed PMID: 16823495.

14: Rukachaisirikul V, Tansakul C, Saithong S, Pakawatchai C, Isaka M, Suvannakad R. Hirsutane sesquiterpenes from the fungus Lentinus connatus BCC 8996. J Nat Prod. 2005 Nov;68(11):1674-6. PubMed PMID: 16309322.

15: Grumbach IM, Chen W, Mertens SA, Harrison DG. A negative feedback mechanism involving nitric oxide and nuclear factor kappa-B modulates endothelial nitric oxide synthase transcription. J Mol Cell Cardiol. 2005 Oct;39(4):595-603. PubMed PMID: 16099468.

16: Shotwell JB, Koh B, Choi HW, Wood JL, Crews CM. Inhibitors of NF-kappaB signaling: design and synthesis of a biotinylated isopanepoxydone affinity reagent. Bioorg Med Chem Lett. 2002 Dec 2;12(23):3463-6. PubMed PMID: 12419384.

17: Umezawa K, Ariga A, Matsumoto N. Naturally occurring and synthetic inhibitors of NF-kappaB functions. Anticancer Drug Des. 2000 Aug;15(4):239-44. Review. PubMed PMID: 11200499.

18: Kleinert H, Wallerath T, Fritz G, Ihrig-Biedert I, Rodriguez-Pascual F, Geller DA, Förstermann U. Cytokine induction of NO synthase II in human DLD-1 cells: roles of the JAK-STAT, AP-1 and NF-kappaB-signaling pathways. Br J Pharmacol. 1998 Sep;125(1):193-201. PubMed PMID: 9776360; PubMed Central PMCID: PMC1565595.

19: Erkel G, Anke T, Sterner O. Inhibition of NF-kappa B activation by panepoxydone. Biochem Biophys Res Commun. 1996 Sep 4;226(1):214-21. PubMed PMID: 8806616.