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.

Chemical Structure

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Panepoxydone
CAS# 31298-54-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 531391
Name: Panepoxydone
CAS#: 31298-54-1
Chemical Formula: C11H14O4
Exact Mass: 210.09
Molecular Weight: 210.229
Elemental Analysis: C, 62.85; H, 6.71; O, 30.44

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5mg USD 800
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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

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

More Info:

Product Data:
Product Data
Instruction:
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Biological target: 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.
In vitro activity: Panepoxydone (PP), a natural NF-kB inhibitor, significantly reduces the oxygen consumption and lactate production of MCF-7 and triple negative (MDA-MB-231, MDA-MB-468 and MDA-MB-453) breast cancer cells. This study further observed that PP inhibited mitochondrial membrane potential and the ATP synthesis using flow cytometry. PP also up-regulated LDH-B and down-regulated LDH-A expression levels in all breast cancer cells to similar levels observed in HMEC cells. Reference: Oncotarget. 2015 Jan 20;6(2):662-78. https://pubmed.ncbi.nlm.nih.gov/25575825/
In vivo activity: TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 210.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. 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. doi: 10.18632/oncotarget.2689. PMID: 25575825; PMCID: PMC4359247. 2. 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. doi: 10.1006/bbrc.1996.1335. PMID: 8806616.
In vitro protocol: 1. 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. doi: 10.18632/oncotarget.2689. PMID: 25575825; PMCID: PMC4359247. 2. 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. doi: 10.1006/bbrc.1996.1335. PMID: 8806616.
In vivo protocol: TBD

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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.