4-oxo-4-HPR|4-oxo-4-fenretinide|cas 865536-65-8|DC Chemicals

Cas No.:	865536-65-8
Chemical Name:	3-Keto fenretinide
Synonyms:	3-Keto fenretinide;4-Oxofenretinide;4-Oxo-N-(4-hydroxyphenyl)retinamide;(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)nona-2,4,6,8-tetraenamide;N-(4-hydroxyphenyl)-4-oxoRetinamide;4-Keto-4-HPR;4-oxo-4-HPR;N-(4-Hydroxyphenyl)-4-oxoretinamide (ACI)
SMILES:	C(/C1=C(C)C(=O)CCC1(C)C)=C\C(\C)=C\C=C\C(\C)=C\C(=O)NC1C=CC(O)=CC=1
Formula:	C₂₆H₃₁NO₃
M.Wt:	405.529247522354
Purity:	>98%
Sotrage:	4°C for 1 year, -20°C for more than 2 years

Description:

4-oxo-4-HPR was two to four times more effective than 4-HPR in most cell lines, was effective in both 4-HPR-sensitive and 4-HPR-resistant cells, and, in combination with 4-HPR, caused a synergistic effect. The tumor growth-inhibitory effects of 4-oxo-4-HPR seem to be independent of nuclear retinoid receptors (RAR), as indicated by the failure of RAR antagonists to inhibit its effects and by its poor ability to bind and transactivate RARs. Unlike 4-HPR, which only slightly affected the G(1) phase of the cell cycle, 4-oxo-4-HPR caused a marked accumulation of cells in G(2)-M. This effect was associated with a reduction in the expression of regulatory proteins of G(2)-M (cyclin-dependent kinase 1 and cdc25c) and S (cyclin A) phases, and with an increase in the expression of apoptosis-related proteins, such as p53 and p21. Apoptosis was induced by 4-oxo-4-HPR in both 4-HPR-sensitive and 4-HPR-resistant cells and involved activation of caspase-3 and caspase-9 but not caspase-8. We also showed that 4-oxo-4-HPR, similarly to 4-HPR, increased reactive oxygen species generation and ceramide levels by de novo synthesis. In conclusion, 4-oxo-4-HPR is an effective 4-HPR metabolite that might act as therapeutic agent per se and, when combined with 4-HPR, might improve 4-HPR activity or overcome 4-HPR resistance.

MSDS

COA

LOT NO.	DOWNLOAD

2018-0101
2018-0101

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