Galiellalactone
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| Category | Bioactive by-products |
| Catalog number | BBF-01864 |
| CAS | 133613-71-5 |
| Molecular Weight | 194.23 |
| Molecular Formula | C11H14O3 |
| Purity | >95% by HPLC |
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Description
Originally is isolated from galiella rufa as a plant growth regulator; also inhibits IL-6 induced SEAP expression with IC50 values of 250-500 nm, blocking the binding of the activated stat3 dimers to their DNA binding sites without inhibiting the tyrosine and serine phosphorylation of the stat3 transcription factor.
Specification
| Synonyms | (7bS)-5,5aR,6,7,7aR,7b-hexahydro-7b-hydroxy-4S-methyl-indeno[1,7-bc]furan-2(4H)-one |
| Storage | -20°C |
| IUPAC Name | 11-hydroxy-9-methyl-3-oxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one |
| Canonical SMILES | CC1CC2CCC3C2(C(=C1)C(=O)O3)O |
| InChI | 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 |
| InChI Key | SOIISBQQYAGDKM-UHFFFAOYSA-N |
| Source | Unidentified fungus |
Properties
| Appearance | White Crystalline |
| Boiling Point | 400.7±38.0 °C at 760 mmHg |
| Melting Point | 53-56°C |
| Density | 1.29±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Diastereoselective Total Synthesis of (-)-Galiellalactone
Kyeojin Kim, Young-Ger Suh, Young Taek Han, Taewoo Kim, Hongchan An, Jeeyeon Lee J Org Chem . 2015 Dec 18;80(24):12193-200. doi: 10.1021/acs.joc.5b02121.
An enantioselective total synthesis of (-)-galiellalactone has been accomplished. The key features of the synthesis involve the highly stereoselective construction of the cis-trisubstituted cyclopentane intermediate by a Pd(0)-catalyzed cyclization, the stereospecific introduction of an angular hydroxyl group by Riley oxidation, and the efficient construction of the tricyclic system of (-)-galiellalactone via a combination of diastereoselective Hosomi-Sakurai crotylation and ring-closing metathesis (RCM).
2. STAT3 inhibition with galiellalactone effectively targets the prostate cancer stem-like cell population
Giacomo Canesin, Enrique A Castellón, Macarena Palominos, Rosanna Paciucci, Anders Bjartell, Juan Morote, Valentina Maggio, Rebecka Hellsten, Norman J Maitland, Hector R Contreras, Anna Stiehm Sci Rep . 2020 Aug 18;10(1):13958. doi: 10.1038/s41598-020-70948-5.
Cancer stem cells (CSCs) are a small subpopulation of quiescent cells with the potential to differentiate into tumor cells. CSCs are involved in tumor initiation and progression and contribute to treatment failure through their intrinsic resistance to chemo- or radiotherapy, thus representing a substantial concern for cancer treatment. Prostate CSCs' activity has been shown to be regulated by the transcription factor Signal Transducer and Activator of Transcription 3 (STAT3). Here we investigated the effect of galiellalactone (GL), a direct STAT3 inhibitor, on CSCs derived from prostate cancer patients, on docetaxel-resistant spheres with stem cell characteristics, on CSCs obtained from the DU145 cell line in vitro and on DU145 tumors in vivo. We found that GL significantly reduced the viability of docetaxel-resistant and patient-derived spheres. Moreover, CSCs isolated from DU145 cells were sensitive to low concentrations of GL, and the treatment with GL suppressed their viability and their ability to form colonies and spheres. STAT3 inhibition down regulated transcriptional targets of STAT3 in these cells, indicating STAT3 activity in CSCs. Our results indicate that GL can target the prostate stem cell niche in patient-derived cells, in docetaxel-resistant spheres and in an in vitro model. We conclude that GL represents a promising therapeutic approach for prostate cancer patients, as it reduces the viability of prostate cancer-therapy-resistant cells in both CSCs and non-CSC populations.
3. Novel Galiellalactone Analogues Can Target STAT3 Phosphorylation and Cause Apoptosis in Triple-Negative Breast Cancer
Young-Ger Suh, Kwang Seok Ahn, Young Taek Han, Taewoo Kim, Jong Hyun Lee, Hyejin Ko, Yeong Shik Kim, Hyun Su Kim, Jaemoo Chun Biomolecules . 2019 May 3;9(5):170. doi: 10.3390/biom9050170.
Aberrant activation of signal transducer and activator of transcription 3 (STAT3) has been documented in various malignancies including triple-negative breast cancers (TNBCs). The STAT3 transcription factor can regulate the different important hallmarks of tumor cells, and thus, targeting it can be a potential strategy for treating TNBC, for which only limited therapeutic options are available. In this study, we analyzed the possible effect of (-)-galiellalactone and its novel analogues, SG-1709 and SG-1721, and determined whether these agents exerted their antineoplastic effects by suppressing the STAT3 signaling pathway in TNBC cells. The two analogues, SG-1709 and SG-1721, inhibited both constitutive as well as inducible STAT3 phosphorylation at tyrosine 705 more effectively than (-)-galiellalactone, which indicates that the analogues are more potent STAT3 blockers. Moreover, SG-1721 not only inhibited nuclear translocation and DNA binding of STAT3 but also induced apoptosis, and decreased expression of diverse oncogenic proteins. Interestingly, SG-1721 also exhibited an enhanced apoptotic effect when combined with radiotherapy. Furthermore, in vivo administration of SG-1721 significantly attenuated breast xenograft tumor growth via decreasing levels of p-STAT3. Therefore, SG-1721 may be a promising candidate for further application as a pharmacological agent that can target STAT3 protein in treating TNBC.
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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 ╳
