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- W2034140246 abstract "When administered in vivo, amylin (1–8) stimulates osteoblast proliferation increasing bone volume and bone strength. The native cyclic octapeptide amylin (1–8) is unstable, however, it provides an attractive framework for the creation of more stable, orally active synthetic analogues using various peptidomimetic techniques. On-resin ring closing metathesis (RCM) on the olefinic side chains of allylglycine residues and lysine moieties functionalized with an allyloxycarbonyl (Alloc) group, was used to prepare novel carba-bridged surrogates of the disulfide bridge between Cys/2 and Cys/7 in amylin-(1–8). Commercially available Nα-Fmoc Nε-Alloc protected lysine was used as a convenient substrate for Grubbs’ ring closing metathesis. Analogues of amylin-(1–8) prepared by cyclization of allylglycine residues that also contained proline residues at either position 4 or 6, or both, were also prepared to investigate the effect of proline as a ‘kink-inducing’ residue on the efficiency of the RCM reaction. Of the nine novel alkene-bridged analogues prepared, five showed promising biological activity in a proliferation study in primary foetal rat osteoblasts at physiological concentrations. Two of these analogues were chosen for further in vivo evaluation." @default.
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- W2034140246 date "2012-10-01" @default.
- W2034140246 modified "2023-10-07" @default.
- W2034140246 title "How to blast osteoblasts? Novel dicarba analogues of amylin-(1–8) to treat osteoporosis" @default.
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- W2034140246 doi "https://doi.org/10.1016/j.bmc.2012.08.053" @default.
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