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AdipoGen Life Sciences
Opaganib
110
CHF
CHF 110.00
In stock
AG-CR1-3749-M0055 mgCHF 110.00
AG-CR1-3749-M02525 mgCHF 440.00
AG-CR1-3749-M100100 mgCHF 970.00
| Product Details | |
|---|---|
| Synonyms | 3-(4-Chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amide; ABC294640; Yeliva |
| Product Type | Chemical |
| Properties | |
| Formula |
C23H25ClN2O |
| MW | 380.9 |
| CAS | 915385-81-8 |
| Purity Chemicals | ≥98% (HPLC) |
| Appearance | White to off-white solid. |
| Solubility | Soluble in DMSO (10mg/ml) or DMF (20mg/ml). Insoluble in water. |
| Identity | Determined by 1H-NMR. |
| InChi Key | CAOTVXGYTWCKQE-BRNYJPRKSA-N |
| Smiles | O=C(NCC1=CC=NC=C1)[C@]23C[C@](C[C@H](C4)C3)(C5=CC=C(Cl)C=C5)C[C@@H]4C2 |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice | Keep cool and dry. |
| Use/Stability | Stable for at least 2 years after receipt when stored at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Opaganib is a selective inhibitor of sphingosine kinase 2 (SPHK2; Ki = 9.8 μM), a lipid kinase that catalyzes formation of the lipid signaling molecule sphingosine 1-phosphate (S1P). S1P promotes cancer growth, and proliferation and pathological inflammation, including TNF-α signaling and other inflammatory cytokine production. By inhibiting the SK2 enzyme, opaganib blocks the synthesis of S1P which regulates fundamental biological processes such as cell proliferation, migration, immune cell trafficking and angiogenesis, and is also involved in immune-modulation and suppression of innate immune responses from T cells.
- Opaganip has similar potency toward sphingosine kinase (SK2) and dihydroceramide desaturase (DES1). Inhibition of SK2 activity causes downregulation of the expression of myeloid cell leukemia 1 (Mcl-1) and c-Myc and suppresses the activation of nuclear factor-kappa B (NF-kB), thereby promoting apoptosis and inhibiting proliferation and inflammation. In parallel, inhibition of DES1 promotes autophagy and promotes Rb phosphorylation resulting in suppression of proliferation.
- Opaganib inhibits proliferation of a variety of cancer cells, including HepG2 liver, A-498 kidney, PANC-1 pancreas and HT-29 colon cells (IC50s = 6, 12.2, 32.8, and 48.1 µM, respectively). It also has been used in vivo to reduce tumor growth in a mouse syngeneic model of mammary adenocarcinoma and to reduce colonic inflammation in mouse and rat models of Crohn’s disease.
- Opaganib shows anticancer, anti-inflammatory and antiviral activities. Opaganib is an investigational drug targeting several potential oncology, inflammatory and gastrointestinal indications and it is also under development as a potential therapy for COVID-19.
Product References
- Pharmacology and antitumor activity of ABC294640, a selective inhibitor of sphingosine kinase-2: K.J. French, et al.; J. Pharmacol. Exp. Ther. 333, 129 (2010)
- Efficacy of a novel sphingosine kinase inhibitor in experimental Crohn’s disease: L.W. Maines, et al.; Inflammopharmacol. 18, 73 (2010)
- Combined anticancer effects of sphingosine kinase inhibitors and sorafenib: V. Beljanski, et al.; Invest. New Drugs 29, 1132 (2011)
- Inhibition of sphingosine kinase-2 suppresses inflammation and attenuates graft injury after liver transplantation in rats: Q. Liu, et al.; PLoS One 7, e41834 (2012)
- Proteasomal degradation of sphingosine kinase 1 and inhibition of dihydroceramide desaturase by the sphingosine kinase inhibitors, SKi or ABC294640, induces growth arrest in androgen-independent LNCaP-AI prostate cancer cells: M. McNaughton, et al.; Oncotarget 7, 16663 (2016)
- ABC294640, A Novel Sphingosine Kinase 2 Inhibitor, Induces Oncogenic Virus-Infected Cell Autophagic Death and Represses Tumor Growth: L Dai, et al.; Mol. Cancer Ther. 16, 2724 (2017)
- The sphingosine kinase 2 inhibitor ABC294640 displays anti-non-small cell lung cancer activities in vitro and in vivo: L. Dai, et al.; Int. J. Cancer 142, 2153 (2018)
- Targeting Sphingosine Kinases for the Treatment of Cancer: C.S. Lewis, et al.; Adv. Cancer Res. 140, 295 (2018) (Review)
- Transient inhibition of sphingosine kinases confers protection to influenza A virus infected mice: C. Xia, et al.; Antiviral Res. 158, 171 (2018)
- In vitro and in vivo roles of sphingosine kinase 2 during dengue virus infection: W.H. Al-Shujairi, et al.; J. Gen. Virol. 100, 629 (2019)
- Sphingosine kinase 2 inhibitor ABC294640 displays anti-epithelial ovarian cancer activities in vitro and in vivo: K. Song, et al.; Onco. Targets Ther. 12, 4437 (2019)
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