Literature DB >> 19762245

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

Takashi Yamamoto1, Padma Nair, Shou-wu Ma, Peg Davis, Henry I Yamamura, Todd W Vanderah, Frank Porreca, Josephine Lai, Victor J Hruby.   

Abstract

In order to improve metabolic stability, a ring structure with a cystine moiety was introduced into TY027 (Tyr-D-Ala-Gly-Phe-Met-Pro-Leu-Trp-NH-[3',5'-(CF(3))(2)Bzl]), which is a lead compound of our developing bifunctional peptide possessing opioid agonist and NK1 antagonist activities. TY038 (Tyr-cyclo[D-Cys-Gly-Phe-Met-Pro-D-Cys]-Trp-NH-[3',5'-(CF(3))(2)Bzl]) was found as a highly selective delta opioid agonist over mu receptor in conventional tissue-based assays, together with an effective NK1 antagonist activity and good metabolic stability with more than 24h half life in rat plasma.

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Year:  2009        PMID： 19762245      PMCID： PMC2775479          DOI： 10.1016/j.bmc.2009.08.035

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  36 in total

1.  Morphine treatment induced calcitonin gene-related peptide and substance P increases in cultured dorsal root ganglion neurons.

Authors:  W Ma; W H Zheng; S Kar; R Quirion
Journal:  Neuroscience       Date:  2000       Impact factor: 3.590

2.  Direct dependence studies in rats with agents selective for different types of opioid receptor.

Authors:  A Cowan; X Z Zhu; H I Mosberg; J R Omnaas; F Porreca
Journal:  J Pharmacol Exp Ther       Date:  1988-09       Impact factor: 4.030

Review 3.  Recent developments in the design of receptor specific opioid peptides.

Authors:  V J Hruby; C A Gehrig
Journal:  Med Res Rev       Date:  1989 Jul-Sep       Impact factor: 12.944

4.  Design principles: enkephalins with predictable mu/delta receptor specificity.

Authors:  Y Shimohigashi
Journal:  NIDA Res Monogr       Date:  1986

Review 5.  Spinal opiate analgesia: characteristics and principles of action.

Authors:  T L Yaksh
Journal:  Pain       Date:  1981-12       Impact factor: 6.961

6.  Improving metabolic stability by glycosylation: bifunctional peptide derivatives that are opioid receptor agonists and neurokinin 1 receptor antagonists.

Authors:  Takashi Yamamoto; Padma Nair; Neil E Jacobsen; Josef Vagner; 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:  2009-08-27       Impact factor: 7.446

7.  Carboxyl-terminal tripeptidyl hydrolysis of substance P by purified rabbit lung angiotensin-converting enzyme and the potentiation of substance P activity in vivo by captopril and MK-422.

Authors:  M A Cascieri; H G Bull; R A Mumford; A A Patchett; N A Thornberry; T Liang
Journal:  Mol Pharmacol       Date:  1984-03       Impact factor: 4.436

8.  Opioid regulation of mucosal ion transport in the mouse isolated jejunum.

Authors:  R J Sheldon; P J Rivière; M E Malarchik; H I Moseberg; T F Burks; F Porreca
Journal:  J Pharmacol Exp Ther       Date:  1990-04       Impact factor: 4.030

9.  Bis-penicillamine enkephalins possess highly improved specificity toward delta opioid receptors.

Authors:  H I Mosberg; R Hurst; V J Hruby; K Gee; H I Yamamura; J J Galligan; T F Burks
Journal:  Proc Natl Acad Sci U S A       Date:  1983-10       Impact factor: 11.205

10.  Lack of self-administration and behavioural sensitisation to morphine, but not cocaine, in mice lacking NK1 receptors.

Authors:  Tamzin L Ripley; Christopher A Gadd; Carmen De Felipe; Stephen P Hunt; David N Stephens
Journal:  Neuropharmacology       Date:  2002-12       Impact factor: 5.250
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  17 in total

Review 1.  Targeting blood-brain barrier changes during inflammatory pain: an opportunity for optimizing CNS drug delivery.

Authors:  Patrick T Ronaldson; Thomas P Davis
Journal:  Ther Deliv       Date:  2011-08

2.  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

3.  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

4.  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

5.  Discovery of a potent and efficacious peptide derivative for δ/μ opioid agonist/neurokinin 1 antagonist activity with a 2',6'-dimethyl-L-tyrosine: in vitro, in vivo, and NMR-based structural studies.

Authors:  Takashi Yamamoto; Padma Nair; Tally M Largent-Milnes; Neil E Jacobsen; Peg Davis; Shou-Wu Ma; Henry I Yamamura; Todd W Vanderah; Frank Porreca; Josephine Lai; Victor J Hruby
Journal:  J Med Chem       Date:  2011-03-02       Impact factor: 7.446

6.  Discovery of Novel Multifunctional Ligands with μ/δ Opioid Agonist/Neurokinin-1 (NK1) Antagonist Activities for the Treatment of Pain.

Authors:  Aswini Kumar Giri; Christopher R Apostol; Yue Wang; Brittany L Forte; Tally M Largent-Milnes; Peg Davis; David Rankin; Gabriella Molnar; Keith M Olson; Frank Porreca; Todd W Vanderah; Victor J Hruby
Journal:  J Med Chem       Date:  2015-10-30       Impact factor: 7.446

7.  Synthesis and biological evaluation of new opioid agonist and neurokinin-1 antagonist bivalent ligands.

Authors:  Ruben Vardanyan; Vlad K Kumirov; Gary S Nichol; Peg Davis; Erika Liktor-Busa; David Rankin; Eva Varga; Todd Vanderah; Frank Porreca; Josephine Lai; Victor J Hruby
Journal:  Bioorg Med Chem       Date:  2011-08-24       Impact factor: 3.641

Review 8.  Investigational peptide and peptidomimetic μ and δ opioid receptor agonists in the relief of pain.

Authors:  Aswini Kumar Giri; Victor J Hruby
Journal:  Expert Opin Investig Drugs       Date:  2013-12-13       Impact factor: 6.206

9.  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

10.  Building a better analgesic: multifunctional compounds that address injury-induced pathology to enhance analgesic efficacy while eliminating unwanted side effects.

Authors:  T M Largent-Milnes; S W Brookshire; D P Skinner; K E Hanlon; D Giuvelis; T Yamamoto; P Davis; C R Campos; P Nair; S Deekonda; E J Bilsky; F Porreca; V J Hruby; T W Vanderah
Journal:  J Pharmacol Exp Ther       Date:  2013-07-16       Impact factor: 4.030
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