UBS109

CHF 90.00
In stock
AG-CR1-3704-M0011 mgCHF 90.00
AG-CR1-3704-50015 x 1 mgCHF 190.00
AG-CR1-3704-M01010 mgCHF 320.00
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Product Details
Synonyms (3E,5E)-1-Methyl-3,5-bis(2-pyridinylmethylene)-4-piperidinone; Monocarbonyl Analog of Curcumin
Product Type Chemical
Properties
Formula

C18H17N3O

MW 291.4
CAS 1258513-40-4
Purity Chemicals ≥95% (HPLC)
Appearance Yellow solid.
Solubility Soluble in DMSO (10mg/ml). Insoluble in water.
Identity Determined by 1H-NMR.
Other Product Data

Note: Always prepare and use fresh solution. We recommend to immediately use the fresh solution. In methanol and ethanol the compound decomposes rapidly. 

InChi Key VCLPNFMJSSBBKX-WFYKWJGLSA-N
Smiles O=C(/C(CN(C)C/1)=C/C2=NC=CC=C2)C1=C\C3=CC=CC=N3
Shipping and Handling
Shipping BLUE ICE
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light.
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
  • Most water soluble synthetic monocarbonyl analog of curcumin (MAC) for in vitro and in vivo application.
  • Potently inhibits NF-κB and its nuclear translocation by suppressing IKK-α and IKK-β, consequently leading to apoptosis.
  • Potent DNA hypomethylating agent. Inhibits HSP90 and NF-κB leading to downregulation of DNA methyltransferase-1 (DNMT-1) expression.
  • Cytotoxic against several cancers in vitro and in vivo. Shows excellent activity against xenografts of head and neck squamous cell carcinoma, pancreatic cancer, colon cancer and breast cancer.
  • Antiangiogenic agent. Induces the downregulation of HIF-1α, HSP90, COX-2 and VEGF in tumor samples from xenograft models compared to untreated xenografts.
  • Shows preventive effects on bone loss induced by breast cancer cell bone metastasis. Found to have a potential stimulating effect on osteoblastogenesis and a suppressive effect on osteoclastogenesis in vitro through Smad activation and NF-κB inhibition. May have promise in the development into an antiosteoporotic agent capable of promoting new bone formation while simultaneously reducing bone resorption.
Product References
  1. Novel curcumin analogue UBS109 potently stimulates osteoblastogenesis and suppresses osteoclastogenesis: involvement in Smad activation and NF-kB inhibition: M. Yamaguchi, et al.; Integr. Biol. 4, 905 (2012)
  2. Novel synthetic curcumin analogues EF31 and UBS109 are potent DNA hypomethylating agents in pancreatic cancer: G. Nagaraju, et al.; Cancer Lett. 341, 195 (2013)
  3. Curcumin analogue UBS109 prevents bone loss in breast cancer bone metastasis mouse model: involvement in osteoblastogenesis and osteoclastogenesis: M. Yamaguchi, et al.; Cell Tissue Res. 357, 245 (2014)
  4. Liver S9 Fraction-Derived Metabolites of Curcumin Analogue UBS109: T.W. Moore, et al.; Med. Chem. Lett. 5, 288 (2014)
  5. Curcumin analog UBS109 prevents bone marrow osteoblastogenesis and osteoclastogenesis disordered by coculture with breast cancer MDA-MB-231 bone metastatic cells in vitro: M. Yamaguchi, et al.; Mol. Cell Biochem. 401, 1 (2015)
  6. Eliminating the Heart from the Curcumin Molecule: Monocarbonyl Curcumin Mimics (MACs): D. Shetty, et al.; Molecules 20, 249 (2015) (Review)
  7. Inhibition of breast cancer metastasis to the lungs with UBS109: M. Shoji, et al.; Oncotarget 9, 36102 (2018)
  8. Curcumin and derivatives function through protein phosphatase 2A and presenilin orthologues in Dictyostelium discoideum: M. Cocorocchio, et al.; Dis. Mod. Mechan. 11, dmm032375 (2018)
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