Galiellalactone
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561877

CAS#: 133613-71-5

Description: Galiellalactone is a natural STAT3 inhibitor. It has been shown to inhibit IL-6-dependent JAK/STAT signaling and induce cell-cycle arrest in G2/M phase and apoptosis in androgen-insensitive prostate cancer cells via activation of ATM/ATR pathway.


Price and Availability

Size
Price

1mg
USD 550
Size
Price

5mg
USD 1650
Size
Price

Galiellalactone, 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#: 561877
Name: Galiellalactone
CAS#: 133613-71-5
Chemical Formula: C11H14O3
Exact Mass: 194.0943
Molecular Weight: 194.23
Elemental Analysis: C, 68.02; H, 7.27; O, 24.71


Synonym: Galiellalactone;

IUPAC/Chemical Name: (4S,5aR,7aR,7bS)-5,5a,6,7,7a,7b-Hexahydro-7b-hydroxy-4-methylindeno[1,7-bc]furan-2(4H)-one

InChi Key: SOIISBQQYAGDKM-QJSROADHSA-N

InChi Code: InChI=1S/C11H14O3/c1-6-4-7-2-3-9-11(7,13)8(5-6)10(12)14-9/h5-7,9,13H,2-4H2,1H3/t6-,7+,9+,11-/m0/s1

SMILES Code: O=C1C2=C[C@@H](C)C[C@@]3([H])CC[C@@]([C@@]23O)([H])O1


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:
>2 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).

Harmonized System Code:
2934990300


References

1: Schreiber D, Marx L, Felix S, Clasohm J, Weyland M, Schäfer M, Klotz M, Lilischkis R, Erkel G, Schäfer KH. Anti-inflammatory Effects of Fungal Metabolites in Mouse Intestine as Revealed by In vitro Models. Front Physiol. 2017 Aug 7;8:566. doi: 10.3389/fphys.2017.00566. eCollection 2017. PubMed PMID: 28824460; PubMed Central PMCID: PMC5545603.

2: Kim HS, Kim T, Ko H, Lee J, Kim YS, Suh YG. Identification of galiellalactone-based novel STAT3-selective inhibitors with cytotoxic activities against triple-negative breast cancer cell lines. Bioorg Med Chem. 2017 Oct 1;25(19):5032-5040. doi: 10.1016/j.bmc.2017.06.036. Epub 2017 Jun 23. PubMed PMID: 28705432.

3: Escobar Z, Bjartell A, Canesin G, Evans-Axelsson S, Sterner O, Hellsten R, Johansson MH. Preclinical Characterization of 3β-(N-Acetyl l-cysteine methyl ester)-2aβ,3-dihydrogaliellalactone (GPA512), a Prodrug of a Direct STAT3 Inhibitor for the Treatment of Prostate Cancer. J Med Chem. 2016 May 26;59(10):4551-62. doi: 10.1021/acs.jmedchem.5b01814. Epub 2016 May 3. PubMed PMID: 27111731.

4: García V, Lara-Chica M, Cantarero I, Sterner O, Calzado MA, Muñoz E. Galiellalactone induces cell cycle arrest and apoptosis through the ATM/ATR pathway in prostate cancer cells. Oncotarget. 2016 Jan 26;7(4):4490-506. doi: 10.18632/oncotarget.6606. PubMed PMID: 26683224; PubMed Central PMCID: PMC4826221.

5: Kim T, Han YT, An H, Kim K, Lee J, Suh YG. Diastereoselective Total Synthesis of (-)-Galiellalactone. J Org Chem. 2015 Dec 18;80(24):12193-200. doi: 10.1021/acs.joc.5b02121. Epub 2015 Nov 13. PubMed PMID: 26544529.

6: Canesin G, Evans-Axelsson S, Hellsten R, Sterner O, Krzyzanowska A, Andersson T, Bjartell A. The STAT3 Inhibitor Galiellalactone Effectively Reduces Tumor Growth and Metastatic Spread in an Orthotopic Xenograft Mouse Model of Prostate Cancer. Eur Urol. 2016 Mar;69(3):400-4. doi: 10.1016/j.eururo.2015.06.016. Epub 2015 Jul 2. PubMed PMID: 26144873.

7: Bollmann F, Jäckel S, Schmidtke L, Schrick K, Reinhardt C, Jurk K, Wu Z, Xia N, Li H, Erkel G, Walter U, Kleinert H, Pautz A. Anti-Inflammatory and Anti-Thrombotic Effects of the Fungal Metabolite Galiellalactone in Apolipoprotein E-Deficient Mice. PLoS One. 2015 Jun 15;10(6):e0130401. doi: 10.1371/journal.pone.0130401. eCollection 2015. PubMed PMID: 26076475; PubMed Central PMCID: PMC4468253.

8: Tian JF, Yu RJ, Li XX, Gao H, Guo LD, Li Y, Li J, Tang JS, Yao XS. Galiellalactone analogs and their possible precursors from Sarcosomataceae. Fitoterapia. 2015 Mar;101:92-8. doi: 10.1016/j.fitote.2015.01.002. Epub 2015 Jan 12. PubMed PMID: 25592721.

9: Don-Doncow N, Escobar Z, Johansson M, Kjellström S, Garcia V, Munoz E, Sterner O, Bjartell A, Hellsten R. Galiellalactone is a direct inhibitor of the transcription factor STAT3 in prostate cancer cells. J Biol Chem. 2014 Jun 6;289(23):15969-78. doi: 10.1074/jbc.M114.564252. Epub 2014 Apr 22. PubMed PMID: 24755219; PubMed Central PMCID: PMC4047371.

10: Pérez M, Soler-Torronteras R, Collado JA, Limones CG, Hellsten R, Johansson M, Sterner O, Bjartell A, Calzado MA, Muñoz E. The fungal metabolite galiellalactone interferes with the nuclear import of NF-κB and inhibits HIV-1 replication. Chem Biol Interact. 2014 May 5;214:69-76. doi: 10.1016/j.cbi.2014.02.012. Epub 2014 Mar 11. PubMed PMID: 24631022.

11: Rudolph K, Serwe A, Erkel G. Inhibition of TGF-β signaling by the fungal lactones (S)-curvularin, dehydrocurvularin, oxacyclododecindione and galiellalactone. Cytokine. 2013 Jan;61(1):285-96. doi: 10.1016/j.cyto.2012.10.011. Epub 2012 Nov 5. PubMed PMID: 23134667.

12: Hellsten R, Johansson M, Dahlman A, Sterner O, Bjartell A. Galiellalactone inhibits stem cell-like ALDH-positive prostate cancer cells. PLoS One. 2011;6(7):e22118. doi: 10.1371/journal.pone.0022118. Epub 2011 Jul 11. PubMed PMID: 21779382; PubMed Central PMCID: PMC3133629.

13: Hausding M, Tepe M, Ubel C, Lehr HA, Röhrig B, Höhn Y, Pautz A, Eigenbrod T, Anke T, Kleinert H, Erkel G, Finotto S. Induction of tolerogenic lung CD4+ T cells by local treatment with a pSTAT-3 and pSTAT-5 inhibitor ameliorated experimental allergic asthma. Int Immunol. 2011 Jan;23(1):1-15. doi: 10.1093/intimm/dxq451. Epub 2010 Dec 6. PubMed PMID: 21135031.

14: Gidlöf R, Johansson M, Sterner O. Tandem Pd-catalyzed carbonylation and intramolecular vinyl allene Diels-Alder reaction toward galiellalactone analogues. Org Lett. 2010 Nov 19;12(22):5100-3. doi: 10.1021/ol101989m. Epub 2010 Oct 27. PubMed PMID: 20979411.

15: Hellsten R, Johansson M, Dahlman A, Dizeyi N, Sterner O, Bjartell A. Galiellalactone is a novel therapeutic candidate against hormone-refractory prostate cancer expressing activated Stat3. Prostate. 2008 Feb 15;68(3):269-80. doi: 10.1002/pros.20699. PubMed PMID: 18163422.

16: Lebel H, Parmentier M. Copper-catalyzed methylenation reaction: total synthesis of (+)-desoxygaliellalactone. Org Lett. 2007 Aug 30;9(18):3563-6. Epub 2007 Aug 1. PubMed PMID: 17665920.

17: Johansson M, Sterner O. Synthesis of (-)-galiellalactone. J Antibiot (Tokyo). 2002 Jul;55(7):663-5. PubMed PMID: 12243458.

18: Köpcke B, Weber RW, Anke H. Galiellalactone and its biogenetic precursors as chemotaxonomic markers of the Sarcosomataceae (Ascomycota). Phytochemistry. 2002 Aug;60(7):709-14. PubMed PMID: 12127588.

19: Johansson M, Köpcke B, Anke H, Sterner O. Cyclization of (-)-pregaliellalactone in the fungus Galiella rufa. Angew Chem Int Ed Engl. 2002 Jun 17;41(12):2158-60. PubMed PMID: 19746629.

20: Köpcke B, Johansson M, Sterner O, Anke H. Biologically active secondary metabolites from the ascomycete A111-95. 1. Production, isolation and biological activities. J Antibiot (Tokyo). 2002 Jan;55(1):36-40. PubMed PMID: 11918063.