Literature DB >> 10509931

Biological activity of fragments and analogues of the potent dimeric opioid peptide, biphalin.

A W Lipkowski1, A Misicka, P Davis, D Stropova, J Janders, M Lachwa, F Porreca, H I Yamamura, V J Hruby.   

Abstract

The synthesis and biological activity of two fragments of the very potent opioid peptide biphalin, showed that Tyr-D-Ala-Gly-Phe-NH-NH<-Phe is the minimal fragment necessary to express equal affinities and the same biological activity profile as the parent biphalin. The replacement of N'-Phe with other L- or D- lipophilic amino acids showed the possibility of modification of receptor efficacy of the analogues.

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Year:  1999        PMID： 10509931     DOI： 10.1016/s0960-894x(99)00464-3

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  16 in total

1.  Biological and conformational evaluation of bifunctional compounds for opioid receptor agonists and neurokinin 1 receptor antagonists possessing two penicillamines.

Authors:  Takashi Yamamoto; Padma Nair; Neil E Jacobsen; Vinod Kulkarni; Peg Davis; Shou-Wu Ma; Edita Navratilova; Henry I Yamamura; Todd W Vanderah; Frank Porreca; Josephine Lai; Victor J Hruby
Journal:  J Med Chem       Date:  2010-08-12       Impact factor: 7.446

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

Authors:  Adriano Mollica; Francesco Pinnen; Federica Feliciani; Azzurra Stefanucci; Gino Lucente; Peg Davis; Frank Porreca; Shou-Wu Ma; Josephine Lai; Victor J Hruby
Journal:  Amino Acids       Date:  2010-10-06       Impact factor: 3.520

3.  A molecular dynamics study on opioid activities of biphalin molecule.

Authors:  Jin-Yuan Hsieh; Tzen-Yuh Chiang; Jun-Liang Chen; Yun-Wen Chen; Hong-Chang Lin; Chi-Chuan Hwang
Journal:  J Mol Model       Date:  2010-12-23       Impact factor: 1.810

4.  Biological active analogues of the opioid peptide biphalin: mixed α/β(3)-peptides.

Authors:  Adriano Mollica; Francesco Pinnen; Roberto Costante; Marcello Locatelli; Azzurra Stefanucci; Stefano Pieretti; Peg Davis; Josephine Lai; David Rankin; Frank Porreca; Victor J Hruby
Journal:  J Med Chem       Date:  2013-04-12       Impact factor: 7.446

5.  Novel cyclic biphalin analogue with improved antinociceptive properties.

Authors:  Adriano Mollica; Alfonso Carotenuto; Ettore Novellino; Antonio Limatola; Roberto Costante; Francesco Pinnen; Azzurra Stefanucci; Stefano Pieretti; Anna Borsodi; Reza Samavati; Ferenc Zador; Sándor Benyhe; Peg Davis; Frank Porreca; Victor J Hruby
Journal:  ACS Med Chem Lett       Date:  2014-07-14       Impact factor: 4.345

6.  Synthesis and evaluation of 3-aminopropionyl substituted fentanyl analogues for opioid activity.

Authors:  Ravil R Petrov; Ruben S Vardanyan; Yeon S Lee; Shou-wu Ma; Peg Davis; Lucinda J Begay; Josephine Y Lai; Frank Porreca; Victor J Hruby
Journal:  Bioorg Med Chem Lett       Date:  2006-07-07       Impact factor: 2.823

7.  Hydrazone Linker as a Useful Tool for Preparing Chimeric Peptide/Nonpeptide Bifunctional Compounds.

Authors:  Jolanta Dyniewicz; Piotr F J Lipiński; Piotr Kosson; Anna Leśniak; Marta Bochyńska-Czyż; Adriana Muchowska; Dirk Tourwé; Steven Ballet; Aleksandra Misicka; Andrzej W Lipkowski
Journal:  ACS Med Chem Lett       Date:  2016-11-01       Impact factor: 4.345

8.  The importance of micelle-bound states for the bioactivities of bifunctional peptide derivatives for delta/mu opioid receptor agonists and neurokinin 1 receptor antagonists.

Authors:  Takashi Yamamoto; Padma Nair; Neil E Jacobsen; Peg Davis; Shou-wu Ma; Edita Navratilova; Sharif Moye; Josephine Lai; Henry I Yamamura; Todd W Vanderah; Frank Porreca; Victor J Hruby
Journal:  J Med Chem       Date:  2008-09-27       Impact factor: 7.446

9.  The biological activity and metabolic stability of peptidic bifunctional compounds that are opioid receptor agonists and neurokinin-1 receptor antagonists with a cystine moiety.

Authors:  Takashi Yamamoto; Padma Nair; Shou-wu Ma; Peg Davis; Henry I Yamamura; Todd W Vanderah; Frank Porreca; Josephine Lai; Victor J Hruby
Journal:  Bioorg Med Chem       Date:  2009-08-21       Impact factor: 3.641

10.  Discovery of tripeptide-derived multifunctional ligands possessing delta/mu opioid receptor agonist and neurokinin 1 receptor antagonist activities.

Authors:  Padma Nair; Takashi Yamamoto; Scott Cowell; Vinod Kulkarni; Sharif Moye; Edita Navratilova; Peg Davis; Shou-Wu Ma; Todd W Vanderah; Josephine Lai; Frank Porreca; Victor J Hruby
Journal:  Bioorg Med Chem Lett       Date:  2015-06-15       Impact factor: 2.823
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