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Literature DB >> 21925887

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

Ruben Vardanyan¹, Vlad K Kumirov, Gary S Nichol, Peg Davis, Erika Liktor-Busa, David Rankin, Eva Varga, Todd Vanderah, Frank Porreca, Josephine Lai, Victor J Hruby.

Abstract

Newly designed bivalent ligands-opioid agonist/NK1-antagonists have been synthesized. The synthesis of new starting materials-<class="Chemical">span class="Chemical">carboxy-derivatives of Fentanyl (1a-1c) was developed. These products have been transformed to 'isoimidium perchlorates' (2a-c). The new isoimidium perchlorates have been successfully implemented in nucleophilic addition reactions, with l-tryptophan 3,5-bis(trifluoromethyl)benzyl ester to give the target compounds-amides (3a-c). Perchlorates (2a-c) successfully undergo reactions with other nucleophiles such as alcohols, amines or hydrazines. The obtained compound 3b exhibited μ-opioid agonist activity and NK1-antagonist activity and may serve as a useful lead compound for the further design of a new series of opioid agonist/NK1-antagonist compounds. Published by Elsevier Ltd.

Entities: Chemical Disease Gene Species

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Year: 2011 PMID： 21925887 PMCID： PMC4137774 DOI： 10.1016/j.bmc.2011.08.027

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

16 in total

1. Spinal antinociceptive effects of AA501, a novel chimeric peptide with opioid receptor agonist and tachykinin receptor antagonist moieties.

Authors: Iwona Maszczynska Bonney; Stacy E Foran; James E Marchand; Andrzej W Lipkowski; Daniel B Carr
Journal: Eur J Pharmacol Date: 2004-03-19 Impact factor: 4.432

Review 2. Multiple ligands in opioid research.

Authors: Steven Ballet; Markus Pietsch; Andrew D Abell
Journal: Protein Pept Lett Date: 2008 Impact factor: 1.890

Review 3. New paradigms and tools in drug design for pain and addiction.

Authors: Victor J Hruby; Frank Porreca; Henry I Yamamura; Gordon Tollin; Richard S Agnes; Yeon Sun Lee; Minying Cai; Isabel Alves; Scott Cowell; Eva Varga; Peg Davis; Zdzislaw Salamon; William Roeske; Todd Vanderah; Josephine Lai
Journal: AAPS J Date: 2006-07-14 Impact factor: 4.009

Review 4. Kappa receptor bivalent ligands.

Authors: Xuemei Peng; John L Neumeyer
Journal: Curr Top Med Chem Date: 2007 Impact factor: 3.295

5. 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

6. Opioid and melanocortin receptors: do they have overlapping pharmacophores?

Authors: Yeon Sun Lee; Richard S Agnes; James P Cain; Vinod Kulkarni; Minying Cai; Christine Salibay; Kathy Ciano; Ravil Petrov; Alexander Mayorov; Josef Vagner; Dev Trivedi; Peg Davis; Shou-wu Ma; Josephine Lai; Frank Porreca; Ruben Vardanyan; Victor J Hruby
Journal: Biopolymers Date: 2008 Impact factor: 2.505

7. 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

8. Induced association of mu opioid (MOP) and type 2 cholecystokinin (CCK2) receptors by novel bivalent ligands.

Authors: Yaguo Zheng; Eyup Akgün; Kaleeckal G Harikumar; Jessika Hopson; Michael D Powers; Mary M Lunzer; Laurence J Miller; Philip S Portoghese
Journal: J Med Chem Date: 2009-01-22 Impact factor: 7.446

9. Synthesis and investigations of double-pharmacophore ligands for treatment of chronic and neuropathic pain.

Authors: Ruben Vardanyan; Gokhale Vijay; Gary S Nichol; Lu Liu; Isuru Kumarasinghe; Peg Davis; Todd Vanderah; Frank Porreca; Josephine Lai; Victor J Hruby
Journal: Bioorg Med Chem Date: 2009-06-02 Impact factor: 3.641

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

12 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

Review 2. Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications.

Authors: Ruben S Vardanyan; Victor J Hruby
Journal: Future Med Chem Date: 2014-03 Impact factor: 3.808

Review 3. G Protein-Coupled Receptor Heteromers.

Authors: Ivone Gomes; Mohammed Akli Ayoub; Wakako Fujita; Werner C Jaeger; Kevin D G Pfleger; Lakshmi A Devi
Journal: Annu Rev Pharmacol Toxicol Date: 2015-10-22 Impact factor: 13.820

Review 4. Revolution in GPCR signalling: opioid receptor heteromers as novel therapeutic targets: IUPHAR review 10.

Authors: Wakako Fujita; Ivone Gomes; Lakshmi A Devi
Journal: Br J Pharmacol Date: 2014-09 Impact factor: 8.739

5. Development and characterisation of novel fentanyl-delta opioid receptor antagonist based bivalent ligands.

Authors: M F Bird; R S Vardanyan; V J Hruby; G Calò; R Guerrini; S Salvadori; C Trapella; J McDonald; D J Rowbotham; D G Lambert
Journal: Br J Anaesth Date: 2015-02-13 Impact factor: 9.166

6. Dual Alleviation of Acute and Neuropathic Pain by Fused Opioid Agonist-Neurokinin 1 Antagonist Peptidomimetics.

Authors: Cecilia Betti; Joanna Starnowska; Joanna Mika; Jolanta Dyniewicz; Lukasz Frankiewicz; Alexandre Novoa; Marta Bochynska; Attila Keresztes; Piotr Kosson; Wioletta Makuch; Joost Van Duppen; Nga N Chung; Jozef Vanden Broeck; Andrzej W Lipkowski; Peter W Schiller; Frans Janssens; Marc Ceusters; François Sommen; Theo Meert; Barbara Przewlocka; Dirk Tourwé; Steven Ballet
Journal: ACS Med Chem Lett Date: 2015-10-31 Impact factor: 4.345

7. Synthesis and Investigation of Mixed μ-Opioid and δ-Opioid Agonists as Possible Bivalent Ligands for Treatment of Pain.

Authors: Ruben S Vardanyan; James P Cain; Saghar Mowlazadeh Haghighi; Vlad K Kumirov; Mary I McIntosh; Alexander J Sandweiss; Frank Porreca; Victor J Hruby
Journal: J Heterocycl Chem Date: 2016-06-01 Impact factor: 2.193