(Q37159251)

English

Bifunctional [2',6'-dimethyl-L-tyrosine1]endomorphin-2 analogues substituted at position 3 with alkylated phenylalanine derivatives yield potent mixed mu-agonist/delta-antagonist and dual mu-agonist/delta-agonist opioid ligands

scientific article published on 12 May 2007

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scholarly article

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Bifunctional [2',6'-dimethyl-L-tyrosine1]endomorphin-2 analogues substituted at position 3 with alkylated phenylalanine derivatives yield potent mixed mu-agonist/delta-antagonist and dual mu-agonist/delta-agonist opioid ligands (English)

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

0 references

author name string

Tingyou Li

1

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Kimitaka Shiotani

2

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Anna Miyazaki

3

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Yuko Tsuda

4

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Akihiro Ambo

5

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Yusuke Sasaki

6

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Yunden Jinsmaa

7

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Ewa Marczak

8

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Sharon D Bryant

9

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Lawrence H Lazarus

10

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Yoshio Okada

11

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

language of work or name

0 references

publication date

12 May 2007

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Journal of Medicinal Chemistry

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

50

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

12

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

2753-2766

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

Effect of lysine at C-terminus of the Dmt-Tic opioid pharmacophore.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Enantioselective synthesis of a phenylalanine library containing alkyl groups on the aromatic moiety: confirmation of stereostructure by X-ray analysis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Conversion of the potent delta-opioid agonist H-Dmt-Tic-NH-CH(2)-bid into delta-opioid antagonists by N(1)-benzimidazole alkylation(1).

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Opioid-induced tolerance and dependence in mice is modulated by the distance between pharmacophores in a bivalent ligand series

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Endomorphin-1 and endomorphin-2 differentially interact with specific binding sites for substance P (SP) aminoterminal SP1-7 in the rat spinal cord

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Synthesis and evaluation of the affinity toward mu-opioid receptors of atypical, lipophilic ligands based on the sequence c[-Tyr-Pro-Trp-Phe-Gly-].

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

A role for heterodimerization of mu and delta opiate receptors in enhancing morphine analgesia

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Some quantitative uses of drug antagonists

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Dmt and opioid peptides: a potent alliance

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Side chain modifications change the binding and agonist properties of endomorphin 2

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Enkephalin analogues with 2',6'-dimethylphenylalanine replacing phenylalanine in position 4.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Preferred conformation of endomorphin-1 in aqueous and membrane-mimetic environments

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Conformational analysis of the endogenous mu-opioid agonist endomorphin-1 using NMR spectroscopy and molecular modeling

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

A potent and selective endogenous agonist for the mu-opiate receptor

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Delta opioidmimetic antagonists: prototypes for designing a new generation of ultraselective opioid peptides.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Recent developments in the design of receptor specific opioid peptides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Permeability of the blood-brain barrier to peptides: an approach to the development of therapeutically useful analogs.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

6 September 2017

Mu-delta opioid receptor functional interaction: Insight using receptor-G protein fusions

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

14 September 2017

[D-1-Nal4]endomorphin-2 is a potent micro-opioid receptor antagonist in the aequorin luminescence-based calcium assay

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

14 September 2017

ORL1 and opioid receptor preferences of nociceptin and dynorphin A analogues with Dmp substituted for N-terminal aromatic residues

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

14 September 2017

Heterodimerization of mu- and delta-opioid receptors occurs at the cell surface only and requires receptor-G protein interactions.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

14 September 2017

Inverse agonism and neutral antagonism at wild-type and constitutively active mutant delta opioid receptors.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

14 September 2017

A bivalent ligand (KDN-21) reveals spinal delta and kappa opioid receptors are organized as heterodimers that give rise to delta(1) and kappa(2) phenotypes. Selective targeting of delta-kappa heterodimers

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

14 September 2017

Inverse agonism by Dmt-Tic analogues and HS 378, a naltrindole analogue.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

29 September 2017

Opioid infidelity: novel opioid peptides with dual high affinity for delta- and mu-receptors

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

29 September 2017

Dermorphin tetrapeptide analogues with 2',6'-dimethylphenylalanine (Dmp) substituted for aromatic amino acids have high mu opioid receptor binding and biological activities

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

27 June 2018

Differential effects of endomorphin-1, endomorphin-2, and Tyr-W-MIF-1 on activation of G-proteins in SH-SY5Y human neuroblastoma membranes

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

27 June 2018

Evolution of the Dmt-Tic pharmacophore: N-terminal methylated derivatives with extraordinary delta opioid antagonist activity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

27 June 2018

[3H]U-69593 a highly selective ligand for the opioid kappa receptor

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

27 June 2018

Transformation of mu-opioid receptor agonists into biologically potent mu-opioid receptor antagonists

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Potent in vivo antinociception and opioid receptor preference of the novel analogue [Dmt1]endomorphin-1.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Opioid receptor binding and antinociceptive activity of the analogues of endomorphin-2 and morphiceptin with phenylalanine mimics in the position 3 or 4.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Synthesis and antinociceptive activity of cyclic endomorphin-2 and morphiceptin analogs

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Endomorphins interact with tachykinin receptors

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Structure-activity relationships of novel endomorphin-2 analogues with N-O turns induced by alpha-aminoxy acids.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Structure-activity relationship of the novel bivalent and C-terminal modified analogues of endomorphin-2.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Differentiation of opioid receptor preference by [Dmt1]endomorphin-2-mediated antinociception in the mouse

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Development of potent mu-opioid receptor ligands using unique tyrosine analogues of endomorphin-2.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Development of potent bifunctional endomorphin-2 analogues with mixed mu-/delta-opioid agonist and delta-opioid antagonist properties

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

2',6'-dimethylphenylalanine (Dmp) can mimic the N-terminal Tyr in opioid peptides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Structure-activity study on the Phe side chain arrangement of endomorphins using conformationally constrained analogues

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Synthesis and opioid activity of N,N-dimethyl-Dmt-Tic-NH-CH(R)-R' analogues: acquisition of potent delta antagonism

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Endomorphin-1 and -2 induce naloxone-precipitated withdrawal syndromes in rats

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Structural studies of [2',6'-dimethyl-L-tyrosine1]endomorphin-2 analogues: enhanced activity and cis orientation of the Dmt-Pro amide bond

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Endomorphin 2 analogues containing Dmp residue as an aromatic amino acid surrogate with high mu-opioid receptor affinity and selectivity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Synthesis and evaluation of potential affinity labels derived from endomorphin-2.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Endomorphin-1 analogues containing beta-proline are mu-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Dermorphin and deltorphin heptapeptide analogues: replacement of Phe residue by Dmp greatly improves opioid receptor affinity and selectivity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Conformational comparison of mu-selective endomorphin-2 with its C-terminal free acid in DMSO solution, by 1H NMR spectroscopy and molecular modeling calculation

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Pseudoproline-containing analogues of morphiceptin and endomorphin-2: evidence for a cis Tyr-Pro amide bond in the bioactive conformation

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Dissociation of analgesic and rewarding effects of endomorphin-1 in rats.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Endomorphin-1 induces antinociception without immunomodulatory effects in the rat.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Analgesic effects of endomorphin-1 and endomorphin-2 in the formalin test in mice.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Retention of supraspinal delta-like analgesia and loss of morphine tolerance in delta opioid receptor knockout mice

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Transport of opioid peptides into the central nervous system.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Parallel stimulations of in vitro and in situ [35S]GTPgammaS binding by endomorphin 1 and DAMGO in mouse brains

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

New delta-opioid antagonists as pharmacological probes.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Blood-brain barrier permeability and bioavailability of a highly potent and mu-selective opioid receptor antagonist, CTAP: comparison with morphine

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Attenuation of morphine tolerance and dependence with the highly selective delta-opioid receptor antagonist TIPP[psi].

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Synthesis and Opioid Activities of (D-Leu8)Dynorphin(1-8) Analogs Containing a Reduced Peptide Bond, .PSI.(CH2NH)

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Selective blockage of delta opioid receptors prevents the development of morphine tolerance and dependence in mice

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2669435

3 September 2018

Endomorphin 1[psi] and endomorphin 2[psi], endomorphins analogues containing a reduced (CH2NH) amide bond between Tyr1 and Pro2, display partial agonist potency but significant antinociception

1 reference

https://pubmed.ncbi.nlm.nih.gov/17497839

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Conformational analysis of endomorphin-1 by molecular dynamics methods

1 reference

https://pubmed.ncbi.nlm.nih.gov/17497839

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Synthesis and biological activity of N-methylated analogs of endomorphin-2

1 reference

https://pubmed.ncbi.nlm.nih.gov/17497839

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identifiers

10.1021/JM061238M

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

PMC publication ID

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

PubMed publication ID

1 reference

Europe PubMed Central

PMC publication ID

18 August 2017

ResearchGate publication ID

0 references

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