Yunden Jinsmaa

Summary

Affiliation: National Institutes of Health
Country: USA

Publications

  1. ncbi request reprint Differentiation of opioid receptor preference by [Dmt1]endomorphin-2-mediated antinociception in the mouse
    Yunden Jinsmaa
    Medicinal Chemistry Group, Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709, USA
    Eur J Pharmacol 509:37-42. 2005
  2. ncbi request reprint Potent in vivo antinociception and opioid receptor preference of the novel analogue [Dmt1]endomorphin-1
    Yunden Jinsmaa
    Medicinal Chemistry Group, Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709, USA
    Pharmacol Biochem Behav 84:252-8. 2006
  3. ncbi request reprint Novel 2',6'-dimethyl-L-tyrosine-containing pyrazinone opioid mimetic mu-agonists with potent antinociceptive activity in mice
    Yunden Jinsmaa
    Medicinal Chemistry Group, Laboratory of Computational Biology and Risk Analysis, National Institute of Environmental Health Sciences, P O Box 12233, Research Triangle Park, NC 27709, USA
    J Pharmacol Exp Ther 309:432-8. 2004
  4. ncbi request reprint Oral bioavailability of a new class of micro-opioid receptor agonists containing 3,6-bis[Dmt-NH(CH(2))(n)]-2(1H)-pyrazinone with central-mediated analgesia
    Yunden Jinsmaa
    Medicinal Chemistry Group, LCBRA, National Institutes of Environmental Health Sciences, Research Triangle Park, North Carolina 27709, USA
    J Med Chem 47:2599-610. 2004
  5. pmc Inhibition of the development of morphine tolerance by a potent dual mu-delta-opioid antagonist, H-Dmt-Tic-Lys-NH-CH2-Ph
    Yunden Jinsmaa
    Medicinal Chemistry Group, Laboratory of Pharmacology, National Institute of Environmental Health Sciences, Research Triangle Park, North Carolina 27709, USA
    Pharmacol Biochem Behav 90:651-7. 2008
  6. ncbi request reprint [N-allyl-Dmt1]-endomorphins are micro-opioid receptor antagonists lacking inverse agonist properties
    Ewa D Marczak
    Medicinal Chemistry Group, Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, P O Box 12233, MD C304, Research Triangle Park, NC 27709, USA
    J Pharmacol Exp Ther 323:374-80. 2007
  7. pmc Orally administered H-Dmt-Tic-Lys-NH-CH2-Ph (MZ-2), a potent mu/delta-opioid receptor antagonist, regulates obese-related factors in mice
    Ewa D Marczak
    Medicinal Chemistry Group, Laboratory of Pharmacology, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709, USA
    Eur J Pharmacol 616:115-21. 2009
  8. ncbi request reprint Unique high-affinity synthetic mu-opioid receptor agonists with central- and systemic-mediated analgesia
    Yoshio Okada
    Faculty of Pharmaceutical Sciences, Department of Medicinal Chemistry and High Technology Research Center, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    J Med Chem 46:3201-9. 2003
  9. ncbi request reprint Dmt and opioid peptides: a potent alliance
    Sharon D Bryant
    Peptide Neurochemistry, LCBRA, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709, USA
    Biopolymers 71:86-102. 2003
  10. pmc 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
    Tingyou Li
    The Graduate School of Food and Medicinal Sciences and Faculty of Pharmaceutical Sciences, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    J Med Chem 50:2753-66. 2007

Collaborators

Detail Information

Publications31

  1. ncbi request reprint Differentiation of opioid receptor preference by [Dmt1]endomorphin-2-mediated antinociception in the mouse
    Yunden Jinsmaa
    Medicinal Chemistry Group, Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709, USA
    Eur J Pharmacol 509:37-42. 2005
    ..The data indicated that [Dmt1]endomorphin-2-induced spinal antinociception was primarily mediated by both mu2- and delta-opioid receptors, while a supraspinal mechanism involved only mu1/mu2-subtypes...
  2. ncbi request reprint Potent in vivo antinociception and opioid receptor preference of the novel analogue [Dmt1]endomorphin-1
    Yunden Jinsmaa
    Medicinal Chemistry Group, Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709, USA
    Pharmacol Biochem Behav 84:252-8. 2006
    ..In terms of the CNS action, [Dmt1]endomorphin-1 appears to act through mu2-opioid receptor subtypes...
  3. ncbi request reprint Novel 2',6'-dimethyl-L-tyrosine-containing pyrazinone opioid mimetic mu-agonists with potent antinociceptive activity in mice
    Yunden Jinsmaa
    Medicinal Chemistry Group, Laboratory of Computational Biology and Risk Analysis, National Institute of Environmental Health Sciences, P O Box 12233, Research Triangle Park, NC 27709, USA
    J Pharmacol Exp Ther 309:432-8. 2004
    ..c. dosing of mice with 1 for 1 week developed tolerance in a similar manner to that of morphine in TF and HP tests, implicating that 1 also acts through a similar mechanism analogous to morphine at mu-opioid receptors...
  4. ncbi request reprint Oral bioavailability of a new class of micro-opioid receptor agonists containing 3,6-bis[Dmt-NH(CH(2))(n)]-2(1H)-pyrazinone with central-mediated analgesia
    Yunden Jinsmaa
    Medicinal Chemistry Group, LCBRA, National Institutes of Environmental Health Sciences, Research Triangle Park, North Carolina 27709, USA
    J Med Chem 47:2599-610. 2004
    ..The data open new possibilities for the rational design of potential opioid-mimetic drugs that pass through the epithelium of the gastrointestinal tract and the blood-brain barrier to target brain receptors...
  5. pmc Inhibition of the development of morphine tolerance by a potent dual mu-delta-opioid antagonist, H-Dmt-Tic-Lys-NH-CH2-Ph
    Yunden Jinsmaa
    Medicinal Chemistry Group, Laboratory of Pharmacology, National Institute of Environmental Health Sciences, Research Triangle Park, North Carolina 27709, USA
    Pharmacol Biochem Behav 90:651-7. 2008
    ..Mice pretreated with 3 before morphine did not develop morphine tolerance indicative of a potential clinical role to inhibit development of drug tolerance...
  6. ncbi request reprint [N-allyl-Dmt1]-endomorphins are micro-opioid receptor antagonists lacking inverse agonist properties
    Ewa D Marczak
    Medicinal Chemistry Group, Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, P O Box 12233, MD C304, Research Triangle Park, NC 27709, USA
    J Pharmacol Exp Ther 323:374-80. 2007
    ..This suggests their potential therapeutic application in the treatment of drug addiction and alcohol abuse without the adverse effects observed with inverse agonist alkaloid-derived compounds that produce severe withdrawal symptoms...
  7. pmc Orally administered H-Dmt-Tic-Lys-NH-CH2-Ph (MZ-2), a potent mu/delta-opioid receptor antagonist, regulates obese-related factors in mice
    Ewa D Marczak
    Medicinal Chemistry Group, Laboratory of Pharmacology, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709, USA
    Eur J Pharmacol 616:115-21. 2009
    ..Thus, MZ-2 has potential application in the clinical management of obesity, insulin and glucose levels, and the amelioration of osteoporosis...
  8. ncbi request reprint Unique high-affinity synthetic mu-opioid receptor agonists with central- and systemic-mediated analgesia
    Yoshio Okada
    Faculty of Pharmaceutical Sciences, Department of Medicinal Chemistry and High Technology Research Center, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    J Med Chem 46:3201-9. 2003
    ..5- to 2.5-fold greater than and 10-12% relative to morphine, respectively); these activities were reversed by naloxone to the same degree. It appears that the bis-Dmt compounds indiscriminately act as both message and address domains...
  9. ncbi request reprint Dmt and opioid peptides: a potent alliance
    Sharon D Bryant
    Peptide Neurochemistry, LCBRA, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709, USA
    Biopolymers 71:86-102. 2003
    ..The future of these compounds as therapeutic applications for various medical syndromes including the control of cancer-associated pain is only a matter of time and perseverance...
  10. pmc 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
    Tingyou Li
    The Graduate School of Food and Medicinal Sciences and Faculty of Pharmaceutical Sciences, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    J Med Chem 50:2753-66. 2007
    ..12 and pA2 = 8.15; for 6', IC50mu = 0.21 nM and pA2 = 9.05) and 7' was a dual mu-agonist/delta-agonist (IC50mu = 0.17 nM; IC50delta = 0.51 nM)...
  11. pmc 6-N,N-dimethylamino-2,3-naphthalimide: a new environment-sensitive fluorescent probe in delta- and mu-selective opioid peptides
    M Eugenio Vazquez
    Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
    J Med Chem 49:3653-8. 2006
    ....
  12. pmc New 2',6'-dimethyl-L-tyrosine (Dmt) opioid peptidomimetics based on the Aba-Gly scaffold. Development of unique mu-opioid receptor ligands
    Steven Ballet
    Department of Organic Chemistry, Vrije Universiteit Brussels, Pleinlaan 2, B 1050 Brussels, Belgium
    J Med Chem 49:3990-3. 2006
    ..48, and 19.9 nM, respectively), selectivity, and bioactivity to micro-opioid receptors. These compounds represent templates for a new class of lead opioid agonists that are easily synthesized and suitable for therapeutic pain relief...
  13. pmc Effect of lysine at C-terminus of the Dmt-Tic opioid pharmacophore
    Gianfranco Balboni
    Department of Toxicology, University of Cagliari, I 09124, Cagliari, Italy
    J Med Chem 49:5610-7. 2006
    ..0)]. The presence of a Lys linker provides new lead compounds in the formation of opioid peptidomimetics containing the Dmt-Tic pharmacophore with distinct agonist and/or antagonist properties...
  14. ncbi request reprint Transformation of mu-opioid receptor agonists into biologically potent mu-opioid receptor antagonists
    Tingyou Li
    The Graduate School of Food and Medicinal Sciences, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    Bioorg Med Chem 15:1237-51. 2007
    ..Thus, N-allylation of Dmt containing opioid peptides or opioidmimetics continues to provide a facile means to convert selective mu-opioid agonists into potent mu-opioid antagonists...
  15. pmc Further studies on the effect of lysine at the C-terminus of the Dmt-Tic opioid pharmacophore
    Gianfranco Balboni
    Department of Toxicology, University of Cagliari, I 09124 Cagliari, Italy
    Bioorg Med Chem 15:3143-51. 2007
    ....
  16. ncbi request reprint Synthesis of opioidmimetics, 3-[H-Dmt-NH(CH(2))(m)]-6-[H-Dmt-NH(CH(2))(n)]-2(1H)-pyrazinones, and studies on structure-activity relationships
    Kimitaka Shiotani
    Graduate School of Food and Medicinal Sciences, Kobe Gakuin University, Kobe 651 2180, Japan
    Med Chem 3:583-98. 2007
    ..47 and 6.56, respectively). The data verify that a specific length of aliphatic linker is required between the Dmt pharmacophore and the pyrazinone ring to produce unique mu-opioid receptor ligands...
  17. pmc Conversion of the potent delta-opioid agonist H-Dmt-Tic-NH-CH(2)-bid into delta-opioid antagonists by N(1)-benzimidazole alkylation(1)
    Gianfranco Balboni
    Department of Toxicology, University of Cagliari, I 09124, Cagliari, Italy
    J Med Chem 48:8112-4. 2005
    ..44-1.42 nM). Only delta antagonism (pA(2)=8.52-10.14) was observed; micro agonism (IC(50)=30-450 nM) was not correlated with changes in alkylating agent or delta antagonism, and some compounds yielded mixed delta antagonism/micro agonism...
  18. ncbi request reprint Potent Dmt-Tic pharmacophoric delta- and mu-opioid receptor antagonists
    Tingyou Li
    The Graduate School of Food and Medicinal Sciences and Faculty of Pharmaceutical Sciences, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    J Med Chem 48:8035-44. 2005
    ..These data are the first evidence that a single dimeric opioid ligand containing the Dmt-Tic pharmacophore exhibits highly potent delta- and mu-opioid antagonist activities...
  19. ncbi request reprint New series of potent delta-opioid antagonists containing the H-Dmt-Tic-NH-hexyl-NH-R motif
    Tingyou Li
    The Graduate School of Food and Medicinal Sciences, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    Bioorg Med Chem Lett 15:5517-20. 2005
    ..Tsuda, Y.; Fujita, Y.; Yokoi, T.; Sasaki, Y.; Ambo, A.; Konishi, R.; Nagata, M.; Salvadori, S.; Jinsmaa, Y.; Bryant, S. D.; Lazarus, L. H. J. Med. Chem.2003, 46, 3201), which exhibited both high mu affinity and bioactivity...
  20. ncbi request reprint Synthesis and opioid activity of N,N-dimethyl-Dmt-Tic-NH-CH(R)-R' analogues: acquisition of potent delta antagonism
    Gianfranco Balboni
    Department of Toxicology, University of Cagliary, I 09126, Cagliary, Italy
    Bioorg Med Chem 11:5435-41. 2003
    ..With the exception of compound 1', the change in the hydrophobic environment at the N-terminus and formation of a tertiary amine by N,N-dimethylation in analogues of the Dmt-Tic pharmacophore produced potent delta-selective antagonists...
  21. ncbi request reprint Neurite outgrowth-stimulating activities of beta-casomorphins in Neuro-2a mouse neuroblastoma cells
    Minoru Sakaguchi
    Laboratory of Cell Biology, Osaka University of Pharmaceutical Sciences, Takatsuki, Japan
    Biosci Biotechnol Biochem 67:2541-7. 2003
    ..These results suggest that the stimulatory effects of beta-CMs on neurite outgrowth were mediated through G protein-coupled micro-opioid receptors...
  22. ncbi request reprint Development of potent bifunctional endomorphin-2 analogues with mixed mu-/delta-opioid agonist and delta-opioid antagonist properties
    Yoshio Fujita
    Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    J Med Chem 47:3591-9. 2004
    ..Thus, [Dmt(1)]EM-2 analogues with hydrophobic C-terminal extensions provide model compounds with potent mu-opioid receptor bioactivity and dual functional agonism...
  23. ncbi request reprint Direct influence of C-terminally substituted amino acids in the Dmt-Tic pharmacophore on delta-opioid receptor selectivity and antagonism
    Gianfranco Balboni
    Department of Toxicology, University of Cagliary, I 09126 Cagliary, Italy
    J Med Chem 47:4066-71. 2004
    ....
  24. ncbi request reprint Highly selective fluorescent analogue of the potent delta-opioid receptor antagonist Dmt-Tic
    Gianfranco Balboni
    Department of Toxicology, University of Cagliary, I 09126, Cagliary, Italy
    J Med Chem 47:6541-6. 2004
    ..This probe should prove useful in the study of the distribution of delta-opioid receptors in tissues and the internalization of opioid peptides during signal transduction...
  25. ncbi request reprint Development of potent mu-opioid receptor ligands using unique tyrosine analogues of endomorphin-2
    Tingyou Li
    The Graduate School of Food and Medicinal Sciences, Faculty of Pharmaceutical Sciences, and High Technology Research Center, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    J Med Chem 48:586-92. 2005
    ..Bioorg. Med. Chem. 2003, 11, 1983-1984) except [Mmt(1)]EM-2 (7). The active profile of the [Xaa(1)]EM-2 analogues indicated that significant modifications on the tyramine ring are possible while high biological activity is maintained...
  26. ncbi request reprint Studies on the structure-activity relationship of 2',6'-dimethyl-l-tyrosine (Dmt) derivatives: bioactivity profile of H-Dmt-NH-CH(3)
    Yoshio Fujita
    The Graduate School of Food and Medicinal Sciences, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    Bioorg Med Chem Lett 15:599-602. 2005
    ..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...
  27. ncbi request reprint From the potent and selective mu opioid receptor agonist H-Dmt-d-Arg-Phe-Lys-NH(2) to the potent delta antagonist H-Dmt-Tic-Phe-Lys(Z)-OH
    Gianfranco Balboni
    Department of Toxicology, University of Cagliari, I 09124, Cagliari, Italy
    J Med Chem 48:5608-11. 2005
    ..Such a delta antagonist could be used as a pharmacological tool...
  28. ncbi request reprint Potent delta-opioid receptor agonists containing the Dmt-Tic pharmacophore
    Gianfranco Balboni
    Department of Toxicology, University of Cagliari, I 09126 Cagliari, Italy
    J Med Chem 45:5556-63. 2002
    ....
  29. pmc A new opioid designed multiple ligand derived from the micro opioid agonist endomorphin-2 and the delta opioid antagonist pharmacophore Dmt-Tic
    Severo Salvadori
    Department of Pharmaceutical Science and Biotechnology Center, University of Ferrara, I 44100 Ferrara, Italy
    Bioorg Med Chem 15:6876-81. 2007
    ..As predicted, the resulting bivalent ligand showed a micro agonist/delta antagonist profile deriving from the corresponding activities of each pharmacophore...
  30. ncbi request reprint Antinociception induced by beta-lactotensin, a neurotensin agonist peptide derived from beta-lactoglobulin, is mediated by NT2 and D1 receptors
    Rena Yamauchi
    Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto, 611 0011, Japan
    Life Sci 73:1917-23. 2003
    ..c.v.), while a D2 receptor antagonist, raclopride (0.5 microg/mouse, i.c.v.), did not block the activity. These results indicate that the antinociceptive activity of beta-lactotensin is mediated by NT2 and D1 receptors...
  31. ncbi request reprint Structural studies of [2',6'-dimethyl-L-tyrosine1]endomorphin-2 analogues: enhanced activity and cis orientation of the Dmt-Pro amide bond
    Yoshio Okada
    Faculty of Pharmaceutical Sciences, Department of Medicinal Chemistry, Kobe Gakuin University, Nishi ku, Kobe 651 2180, Japan
    Bioorg Med Chem 11:1983-94. 2003
    ..05). 1H NMR spectroscopy revealed a trans configuration (1:2 to 1:3, cis/trans) in the Tyr-Pro amide bond, but a cis configuration (5:3 to 13:7, cis/trans) with Dmt-Pro analogues...