New potent biphalin analogues containing p-fluoro-L-phenylalanine at the 4,4' positions and non-hydrazine linkers.

Adriano Mollica, Francesco Pinnen, Federica Feliciani, Azzurra Stefanucci, Gino Lucente, Peg Davis, Frank Porreca, Shou Wu Ma, Josephine Lai, Victor J. Hruby

Research output: Contribution to journalArticle

29 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)1503-1511
Number of pages9
JournalAmino Acids
Volume40
Issue number5
DOIs
StatePublished - May 2011
Externally publishedYes

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hydrazine
Phenylalanine
Opioid Peptides
biphalin
piperazine
1,2-diaminobenzene

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

New potent biphalin analogues containing p-fluoro-L-phenylalanine at the 4,4' positions and non-hydrazine linkers. / Mollica, Adriano; Pinnen, Francesco; Feliciani, Federica; Stefanucci, Azzurra; Lucente, Gino; Davis, Peg; Porreca, Frank; Ma, Shou Wu; Lai, Josephine; Hruby, Victor J.

In: Amino Acids, Vol. 40, No. 5, 05.2011, p. 1503-1511.

Research output: Contribution to journalArticle

Mollica, A, Pinnen, F, Feliciani, F, Stefanucci, A, Lucente, G, Davis, P, Porreca, F, Ma, SW, Lai, J & Hruby, VJ 2011, 'New potent biphalin analogues containing p-fluoro-L-phenylalanine at the 4,4' positions and non-hydrazine linkers.', Amino Acids, vol. 40, no. 5, pp. 1503-1511. https://doi.org/10.1007/s00726-010-0760-7
Mollica, Adriano ; Pinnen, Francesco ; Feliciani, Federica ; Stefanucci, Azzurra ; Lucente, Gino ; Davis, Peg ; Porreca, Frank ; Ma, Shou Wu ; Lai, Josephine ; Hruby, Victor J. / New potent biphalin analogues containing p-fluoro-L-phenylalanine at the 4,4' positions and non-hydrazine linkers. In: Amino Acids. 2011 ; Vol. 40, No. 5. pp. 1503-1511.
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AU - Stefanucci, Azzurra

AU - Lucente, Gino

AU - Davis, Peg

AU - Porreca, Frank

AU - Ma, Shou Wu

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AU - Hruby, Victor J.

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