Title |
New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers
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Published in |
Amino Acids, October 2010
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DOI | 10.1007/s00726-010-0760-7 |
Pubmed ID | |
Authors |
Adriano Mollica, Francesco Pinnen, Federica Feliciani, Azzurra Stefanucci, Gino Lucente, Peg Davis, Frank Porreca, Shou-Wu Ma, Josephine Lai, Victor J. Hruby |
Abstract |
We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4' positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-L-phenylalanine residues at 4 and 4' positions. Binding values are: Kμ(i)=0.51 nM and Kδ(i)=12.8 nM for compound 9, Kμ(i)=0.09 nM and Kδ(i)=0.11 nM for analogue 10. |
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