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Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor
Campos-Sandoval, José Angel,Redondo, Clara,Kinsella, Gemma K.,Pal, Akos,Jones, Geraint,Eyre, Gwen S.,Hirst, Simon C.,Findlay, John B. C.
experimental part, p. 4378 - 4387 (2011/09/14)
Serum retinol binding protein (sRBP) is released from the liver as a complex with transthyretin (TTR), a process under the control of dietary retinol. Elevated levels of sRBP may be involved in inhibiting cellular responses to insulin and in generating first insulin resistance and then type 2 diabetes, offering a new target for therapeutic attack for these conditions. A series of retinoid analogues were synthesized and examined for their binding to sRBP and their ability to disrupt the sRBP-TTR and sRBP-sRBP receptor interactions. A number inhibit the sRBP-TTR and sRBP-sRBP receptor interactions as well as or better than Fenretinide (FEN), presenting a potential novel dual mechanism of action and perhaps offering a new therapeutic intervention against type 2 diabetes and its development. Shortening the chain length of the FEN derivative substantially abolished binding to sRBP, indicating that the strength of the interaction lies in the polyene chain region. Differences in potency against the sRBP-TTR and sRBP-sRBP receptor interactions suggest variant effects of the compounds on the two loops of sRBP guarding the entrance of the binding pocket that are responsible for these two protein-protein interactions.
Solid phase-assisted synthesis and screening of a small library of N-(4-hydroxyphenyl)retinamide (4-HPR) analogs
Mershon, Serena M.,Anding, Allyson L.,Chapman, Jason S.,Clagett-Dame, Margaret,Stonerock, Laura A.,Curley Jr., Robert W.
, p. 836 - 840 (2007/10/03)
Using solid phase-assisted synthesis and purification, a 49 member library of analogs of the mammary tumor chemopreventive retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) has been prepared. After prescreening for growth inhibitory activity in human mammary tumor cells (MCF-7) in culture, most of those analogs which showed activity (12 of them) were assayed for apoptosis-inducing activity in the MCF-7 cells. At least 3 of the analogs (13, 24, and 28) showed activity approaching that of 4-HPR.
A simple, general and efficient method for O and N-retinoylation. Application to the synthesis of 2-retinoyl-lecithin
Sangmam, Charles,Winum, Jean-Yves,Lucas, Marc,Montero, Jean-Louis,Chavis, Claude
, p. 2945 - 2958 (2007/10/03)
The synthesis of the new 1-stearoyl-2-retinoyl-glycero-3- phosphorylcholine by coupling of retinoic acid and lysolecithin with DCC- DMAP (1.2 eq.) is reported. This method is applied to O and N-retinoylation of uncharged organic substrates such as aliphatic alcohols, free hydroxyl anomeric sugars, aromatic amines and C-protected α-aminoacids.