New opioid designed multiple ligand from Dmt-Tic and morphinan pharmacophores

Journal of Medicinal Chemistry

Volumn 49, Issue 18, 2006, Pages 5640-5643

  Neumeyer, John L ^a   Peng, Xuemei ^a   Knapp, Brian I ^b   Bidlack, Jean M ^b   Lazarus, Lawrence H ^c   Salvadori, Severo ^d   Trapella, Claudio ^d   Balboni, Gianfranco ^d,e  

^a MCLEAN HOSPITAL   (United States)

^b UNIVERSITY OF ROCHESTER SCHOOL OF MEDICINE AND DENTISTRY   (United States)

^c NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^d UNIVERSITY OF FERRARA   (Italy)

^e UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BUTORPHANOL; MORPHINAN DERIVATIVE; OPIATE;

ARTICLE; DRUG ABUSE; DRUG DEPENDENCE; DRUG EFFICACY; DRUG POTENCY; DRUG SAFETY; DRUG TARGETING; LIGAND BINDING; OLIGOMERIZATION; PATIENT COMPLIANCE; PHARMACOPHORE; RECEPTOR BINDING; SYNTHESIS;

ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; DIPEPTIDES; LIGANDS; MORPHINANS; RADIOLIGAND ASSAY; RECEPTORS, OPIOID; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROISOQUINOLINES;

EID: 33748573311     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0605785     Document Type: Article

References (20)

1. Hopkins, A. L.; Mason, J. S.; Overington, J. P. Can we rationally design promiscuous drugs? Curr. Opin. Struct. Biol. 2006, 16, 127-136.
2. Morphy, R.; Rankovic, Z. Designed multiple ligands. An emerging drug discovery paradigm. J. Med. Chem. 2005, 48, 6523-65433.
3. Morphy, R.; Kay, C.; Rankovic, Z. From magic bullets to designed multiple ligands. Drug Discovery Today 2004, 9, 641-651.
4. Weltrowska, G.; Lemieux, C.; Chung, N. N.; Schiller, P. W. A chimeric opioid peptide with mixed μ agonist/δ antagonist properties. J. Pept. Res. 2004, 63, 63-68.
5. Peng, X.; Knapp, B. I.; Bidlack, J. M.; Neumeyer, J. L. Synthesis and preliminary in vitro investigation of bivalent ligands containing homo- and heterodimeric pharmacophores at μ, δ, and κ opioid receptors. J. Med. Chem. 2006, 49, 256-262.
6. Jordan, B. A.; Cvejic, S.; Devi, L. A. Opioid and their complicated receptor complexes. Neuropsycopharmacology 2000, 23, S5-S18.
7. George, S. R.; Fan, T.; Xie, Z.; Tse, R.; Tam, V.; Vargase, G.; O'Dowd, F. Oligomerization of μ- and δ-opioid receptors. Generation of novel functional properties. J. Biol. Chem. 2000, 275, 26128-26135.
8. Portoghese, P. S.; Nagase, H.; Takemori, A. E. Only one pharmacophore is required for the κ opioid antagonist selectivity of norbinaltorphimine. J. Med. Chem. 1988, 31, 1344-1347.
9. Portoghese, P. S. From models to molecules: Opioid receptor dimers, bivalent ligands, and selective opioid receptor probes. J. Med. Chem. 2001, 44, 2259-2269.
10. 1 opioid receptor phenotypes. J. Med. Chem. 2005, 48, 1713-1716.
11. Neumeyer, J. L.; Bidlack, J. M.; Zong, R.; Bakthavachalam, V.; Gao, P.; Cohen, D. J.; Negus, S. S.; Mello, N. K. Synthesis and opioid receptor affinity of morphinan and benzomorphan derivatives: mixed κ agonists and μ agonists/antagonists as potential pharmatherapeutic for cocaine dependence. J. Med. Chem. 2000, 43, 114-122.
12. Ogawa, T.; Araki, M.; Miyamae, T.; Okayama, T.; Hagiwara, M.; Sakurada, S.; Morikawa, T. Synthesis and antinociceptive activity of orally active opioid peptides: improvement of oral bioavailability by esterification. Chem. Pharm. Bull 2003, 51, 759-771.
13. Baxter, A. J. G.; Robinson, D. H.; Brown, R. C. Pharmaceutically active compounds. EP0384636, 1990.
14. Salvadori, S.; Guerrini, R.; Balboni, G.; Bianchi, C.; Bryant, S. D.; Cooper, P. S.; Lazarus, L. H. Further studies on the Dmt-Tic pharmacophore: hydrophobic substituents at the C-terminus endow δ antagonists to manifest μ agonism or μ antagonism. J. Med. Chem. 1999, 42, 5010-5019.
15. Balboni, G.; Salvadori, S.; Guerrini, R.; Negri, L.; Giannini, E.; Bryant, S. D.; Jinsmaa, Y.; Lazarus, L. H. Direct influence of C-terminally substituted amino acids in the Dmt-Tic pharmacophore on δ-opioid receptor selectivity and antagonism. J. Med. Chem. 2004, 47, 4066-4071.
16. Salvadori, S.; Attila, M.; Balboni, G.; Bianchi, C.; Bryant, S. D.; Crescenzi, O.; Guerrini, R.; Picone, D.; Tancredi, T.; Temussi, P. A.; Lazarus, L. H. δ Opioidmimetic antagonists: prototypes for designing a new generation of ultraselective opioid peptides. Mol. Med. 1995, 1, 678-689.
17. Salvadori, S.; Balboni, G.; Guerrini, R.; Tomatis, R.; Bianchi, C.; Bryant, S. D.; Cooper, P. S.; Lazarus, L. H. Evolution of the Dmt-Tic pharmacophore: N-terminal methylated derivatives with extra-ordinary δ opioid antagonist activity. J. Med. Chem. 1997, 40, 3100-3108.
18. 1-benzimidazole alkylation. J. Med. Chem. 2005, 48, 8112-8114.
19. Balboni, G.; Salvadori, S.; Dal Piaz, A.; Bortolotti, F.; Argazzi, R.; Negri, L.; Lattanzi, R.; Bryant, S. D.; Jinsmaa, Y.; Lazarus, L. H. Highly selective fluorescent analogue of the potent δ-opioid receptor antagonist Dmt-Tic. J. Med. Chem. 2004, 47, 6541-6546.
20. Vázquez, M. E.; Blanco, J. B.; Salvadori, S.; Trapella, C.; Argazzi, R.; Bryant, S. D.; Jinsmaa, Y.; Lazarus, L. H.; Negri, L.; Giannini, E.; Lattanzi, R.; Colucci, M.; Balboni, G. 6-N,N-Dimethylamino-2,3-naphthalimide a new environment-sensitive fluorescent probe in δ-selective and μ-selective opioid peptides. J. Med. Chem. 2006, 49, 3653-3658.