Literature DB >> 15664820

Studies on the structure-activity relationship of 2',6'-dimethyl-l-tyrosine (Dmt) derivatives: bioactivity profile of H-Dmt-NH-CH(3).

Yoshio Fujita1, Yuko Tsuda, Takashi Motoyama, Tingyou Li, Anna Miyazaki, Toshio Yokoi, Yusuke Sasaki, Akihiro Ambo, Hideko Niizuma, Yunden Jinsmaa, Sharon D Bryant, Lawrence H Lazarus, Yoshio Okada.   

Abstract

The 2',6'-dimethyl-l-tyrosine (Dmt) enhances receptor affinity, functional bioactivity and in vivo analgesia of opioid peptides. To further investigate its direct influence on these opioid parameters, we developed a series of compounds (H-Dmt-NH-X). Among them, H-Dmt-NH-CH(3) showed the highest affinity (K(i)mu=7.45 nM) equal to that of morphine, partial mu-opioid agonism (E(max)=66.6%) in vitro and a moderate antinociception in mice.

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Year:  2005        PMID： 15664820     DOI： 10.1016/j.bmcl.2004.11.040

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


  5 in total

1.  Synthesis of 3,6-bis[H-Tyr/H-Dmt-NH(CH2)m,n]-2(1H)pyrazinone derivatives: function of alkyl chain length on opioid activity.

Authors:  Kimitaka Shiotani; Tingyou Li; Anna Miyazaki; Yuko Tsuda; Sharon D Bryant; Akihiro Ambo; Yusuke Sasaki; Lawrence H Lazarus; Yoshio Okada
Journal:  Bioorg Med Chem Lett       Date:  2006-09-01       Impact factor: 2.823

2.  New 2',6'-dimethyl-L-tyrosine (Dmt) opioid peptidomimetics based on the Aba-Gly scaffold. Development of unique mu-opioid receptor ligands.

Authors:  Steven Ballet; Severo Salvadori; Claudio Trapella; Sharon D Bryant; Yunden Jinsmaa; Lawrence H Lazarus; Lucia Negri; Elisa Giannini; Roberta Lattanzi; Dirk Tourwé; Gianfranco Balboni
Journal:  J Med Chem       Date:  2006-06-29       Impact factor: 7.446

Review 3.  Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications.

Authors:  Jacek Zielonka; Joy Joseph; Adam Sikora; Micael Hardy; Olivier Ouari; Jeannette Vasquez-Vivar; Gang Cheng; Marcos Lopez; Balaraman Kalyanaraman
Journal:  Chem Rev       Date:  2017-06-27       Impact factor: 60.622

4.  Design and synthesis of opioidmimetics containing 2',6'-dimethyl-L-tyrosine and a pyrazinone-ring platform.

Authors:  Kimitaka Shiotani; Tingyou Li; Anna Miyazaki; Yuko Tsuda; Toshio Yokoi; Akihiro Ambo; Yusuke Sasaki; Sharon D Bryant; Lawrence H Lazarus; Yoshio Okada
Journal:  Bioorg Med Chem Lett       Date:  2007-08-28       Impact factor: 2.823

Review 5.  Developmental potential for endomorphin opioidmimetic drugs.

Authors:  Yoshio Okada; Yuko Tsuda; Severo Salvadori; Lawrence H Lazarus
Journal:  Int J Med Chem       Date:  2012-06-15
  5 in total

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