ArticleACS chemical neuroscience2010
Evolution of the Bifunctional Lead μ Agonist / δ Antagonist Containing the Dmt-Tic Opioid Pharmacophore.
Article in ACS chemical neuroscience, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 44 citations in OpenAlex.
- Differential Effects of a Novel Opioid Ligand UTA1003 on Antinociceptive Tolerance and Motor Behaviour.Pharmaceuticals (Basel, Switzerland) · 2022Article
- In Vivo, In Vitro and In Silico Studies of the Hybrid Compound AA3266, an Opioid Agonist/NK1R Antagonist with Selective Cytotoxicity.International journal of molecular sciences · 2020Article
- Structure-Activity Relationships of 7-Substituted Dimethyltyrosine-Tetrahydroisoquinoline Opioid Peptidomimetics.Molecules (Basel, Switzerland) · 2019Article
- Simultaneous Activation of Mu and Delta Opioid Receptors Reduces Allodynia and Astrocytic Connexin 43 in an Animal Model of Neuropathic Pain.Molecular neurobiology · 2019Article
- Novel Dimethyltyrosine-Tetrahydroisoquinoline Peptidomimetics with Aromatic Tetrahydroisoquinoline Substitutions ShowACS chemical neuroscience · 2019Article
- Targeting multiple opioid receptors - improved analgesics with reduced side effects?British journal of pharmacology · 2018Review
- In vitro and in vivo characterization of the bifunctional μ and δ opioid receptor ligand UFP-505.British journal of pharmacology · 2018Article
- Synthesis and Investigation of Mixed μ-Opioid and δ-Opioid Agonists as Possible Bivalent Ligands for Treatment of Pain.Journal of heterocyclic chemistry · 2017Article
- Rapid Synthesis of Boc-2',6'-dimethyl-l-tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics.ACS medicinal chemistry letters · 2015Article
- Synthesis of Carfentanil Amide Opioids Using the Ugi Multicomponent Reaction.ACS chemical neuroscience · 2015Article
- Asymmetric synthesis and in vitro and in vivo activity of tetrahydroquinolines featuring a diverse set of polar substitutions at the 6 position as mixed-efficacy μ opioid receptor/δ opioid receptor ligands.ACS chemical neuroscience · 2015Article
- Designing bifunctional NOP receptor-mu opioid receptor ligands from NOP-receptor selective scaffolds. Part II.Bioorganic & medicinal chemistry · 2014Article
- Development of a bioavailable μ opioid receptor (MOPr) agonist, δ opioid receptor (DOPr) antagonist peptide that evokes antinociception without development of acute tolerance.Journal of medicinal chemistry · 2014Article
- Heteromeric dopamine receptor signaling complexes: emerging neurobiology and disease relevance.Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology · 2014Review
- Chiral Effect of a Phe Residue in Position 3 of the DmtACS medicinal chemistry letters · 2013Article
- Opioid peptidomimetics: leads for the design of bioavailable mixed efficacy μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist ligands.Journal of medicinal chemistry · 2013Article
- A DFT and semiempirical model-based study of opioid receptor affinity and selectivity in a group of molecules with a morphine structural core.International journal of medicinal chemistry · 2012Article
- Development and in vitro characterization of a novel bifunctional μ-agonist/δ-antagonist opioid tetrapeptide.ACS chemical biology · 2011Article
- Opioid bifunctional ligands from morphine and the opioid pharmacophore Dmt-Tic.European journal of medicinal chemistry · 2011Article
- Role of 2',6'-dimethyl-l-tyrosine (Dmt) in some opioid lead compounds.Bioorganic & medicinal chemistry · 2010Article
Corrections and comments
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Authors and funding
8 authors at 5 institutions in 2 countries.
Funding
Abstract
Based on a renewed importance recently attributed to bi- or multifunctional opioids, we report the synthesis and pharmacological evaluation of some analogues derived from our lead μ agonist / δ antagonist, H-Dmt-Tic-Gly-NH-Bzl. Our previous studies focused on the importance of the C-teminal benzyl function in the induction of such bifunctional activity. The introduction of some substituents in the para position of the phenyl ring (-Cl, -CH(3), partially -NO(2), inactive -NH(2)) was found to give a more potent μ agonist / antagonist effect associated with a relatively unmodified δ antagonist activity (pA(2) = 8.28-9.02). Increasing the steric hindrance of the benzyl group (using diphenylmethyl and tetrahydroisoquinoline functionalities) substantially maintained the μ agonist and δ antagonist activities of the lead compound. Finally and quite unexpectedly D-Tic2, considered as a wrong opioid message now; inserted into the reference compound in lieu of L-Tic, provided a μ agonist / δ agonist better than our reference ligand (H-Dmt-Tic-Gly-NH-Ph) and was endowed with the same pharmacological profile.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.