Literature DB >> 23899615

Truncation of the peptide sequence in bifunctional ligands with mu and delta opioid receptor agonist and neurokinin 1 receptor antagonist activities.

Padma Nair1, Takashi Yamamoto, Tally M Largent-Milnes, Scott Cowell, Vinod Kulkarni, Sharif Moye, Edita Navratilova, Peg Davis, Shou-Wu Ma, Todd W Vanderah, Josephine Lai, Frank Porreca, Victor J Hruby.   

Abstract

The optimization and truncation of our lead peptide-derived ligand TY005 possessing eight amino-acid residues was performed. Among the synthesized derivatives, NP30 (Tyr(1)-DAla(2)-Gly(3)-Phe(4)-Gly(5)-Trp(6)-O-[3',5'-Bzl(CF3)2]) showed balanced and potent opioid agonist as well as substance P antagonist activities in isolated tissue-based assays, together with significant antinociceptive and antiallodynic activities in vivo. Published by Elsevier Ltd.

Entities:  

Keywords:  Bifunctional compounds; NMR structure; Neutokinin-1 receptor antagonists; Opioid receptor agonists; Truncation of peptide sequence

Mesh：

Substances：

Year:  2013        PMID： 23899615      PMCID： PMC3810412          DOI： 10.1016/j.bmcl.2013.06.065

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


  19 in total

1.  Design of novel neurokinin 1 receptor antagonists based on conformationally constrained aromatic amino acids and discovery of a potent chimeric opioid agonist-neurokinin 1 receptor antagonist.

Authors:  Steven Ballet; Debby Feytens; Koen Buysse; Nga N Chung; Carole Lemieux; Suneeta Tumati; Attila Keresztes; Joost Van Duppen; Josephine Lai; Eva Varga; Frank Porreca; Peter W Schiller; Jozef Vanden Broeck; Dirk Tourwé
Journal:  J Med Chem       Date:  2011-03-17       Impact factor: 7.446

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

Authors:  A W Lipkowski; A Misicka; P Davis; D Stropova; J Janders; M Lachwa; F Porreca; H I Yamamura; V J Hruby
Journal:  Bioorg Med Chem Lett       Date:  1999-09-20       Impact factor: 2.823

Review 3.  Is paradoxical pain induced by sustained opioid exposure an underlying mechanism of opioid antinociceptive tolerance?

Authors:  Tamara King; Michael H Ossipov; Todd W Vanderah; Frank Porreca; Josephine Lai
Journal:  Neurosignals       Date:  2005

4.  Conformation of the tripeptide Cbz-Pro-Leu-Trp-OBzl(CF3)2 deduced from two-dimensional 1H-NMR and conformational energy calculations is related to its affinity for NK1-receptor.

Authors:  R Millet; L Goossens; J F Goossens; P Chavatte; K Bertrand-Caumont; R Houssin; J P Hénichart
Journal:  J Pept Sci       Date:  2001-06       Impact factor: 1.905

5.  N-acyl-L-tryptophan benzyl esters: potent substance P receptor antagonists.

Authors:  A M MacLeod; K J Merchant; M A Cascieri; S Sadowski; E Ber; C J Swain; R Baker
Journal:  J Med Chem       Date:  1993-07-09       Impact factor: 7.446

Review 6.  Improving opioid effectiveness: from ideas to evidence.

Authors:  Eija Kalso
Journal:  Eur J Pain       Date:  2005-04       Impact factor: 3.931

7.  Characterization of the interaction of N-acyl-L-tryptophan benzyl ester neurokinin antagonists with the human neurokinin-1 receptor.

Authors:  M A Cascieri; A M Macleod; D Underwood; L L Shiao; E Ber; S Sadowski; H Yu; K J Merchant; C J Swain; C D Strader
Journal:  J Biol Chem       Date:  1994-03-04       Impact factor: 5.157

8.  Design, synthesis, and biological evaluation of novel bifunctional C-terminal-modified peptides for delta/mu opioid receptor agonists and neurokinin-1 receptor antagonists.

Authors:  Takashi Yamamoto; Padma Nair; Peg Davis; Shou-wu Ma; Edita Navratilova; Sharif Moye; Suneeta Tumati; Josephine Lai; Todd W Vanderah; Henry I Yamamura; Frank Porreca; Victor J Hruby
Journal:  J Med Chem       Date:  2007-05-22       Impact factor: 7.446

9.  Rapid endocytosis of a G protein-coupled receptor: substance P evoked internalization of its receptor in the rat striatum in vivo.

Authors:  P W Mantyh; C J Allen; J R Ghilardi; S D Rogers; C R Mantyh; H Liu; A I Basbaum; S R Vigna; J E Maggio
Journal:  Proc Natl Acad Sci U S A       Date:  1995-03-28       Impact factor: 11.205

10.  A structure-activity relationship study and combinatorial synthetic approach of C-terminal modified bifunctional peptides that are delta/mu opioid receptor agonists and neurokinin 1 receptor antagonists.

Authors:  Takashi Yamamoto; Padma Nair; Josef Vagner; Tally Largent-Milnes; Peg Davis; Shou-Wu Ma; Edita Navratilova; Sharif Moye; Suneeta Tumati; Josephine Lai; Henry I Yamamura; Todd W Vanderah; Frank Porreca; Victor J Hruby
Journal:  J Med Chem       Date:  2008-02-12       Impact factor: 7.446
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  4 in total

1.  Neurokinin 1 and opioid receptors: relationships and interactions in nervous system.

Authors:  Jie Xiao; Si Zeng; Xiangrui Wang; Hasan Babazada; Zhanchun Li; Renyu Liu; Weifeng Yu
Journal:  Transl Perioper Pain Med       Date:  2016

2.  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

Review 3.  Novel Molecular Strategies and Targets for Opioid Drug Discovery for the Treatment of Chronic Pain.

Authors:  Keith M Olson; Wei Lei; Attila Keresztes; Justin LaVigne; John M Streicher
Journal:  Yale J Biol Med       Date:  2017-03-29

Review 4.  Biphalin-A Potent Opioid Agonist-As a Panacea for Opioid System-Dependent Pathophysiological Diseases?

Authors:  Patrycja Redkiewicz; Jolanta Dyniewicz; Aleksandra Misicka
Journal:  Int J Mol Sci       Date:  2021-10-21       Impact factor: 5.923
  4 in total

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