Arylacetamide-derived fluorescent probes: Synthesis, biological evaluation, and direct fluorescent labeling of k opioid receptors in mouse microglial cells

Journal of Medicinal Chemistry

Volumn 39, Issue 8, 1996, Pages 1729-1735

  Chang, An Chih ^a   Chao, Chun C ^b   Takemori, Akira E ^c   Gekker, Genya ^b   Hu, Shuxian ^b   Peterson, Phillip K ^b   Portoghese, Philip S ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b MINNEAPOLIS MEDICAL RESEARCH FOUNDATION   (United States)

^c UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3,4 DICHLOROPHENYL) N [1 [N (FLUORESCEINYL 5 THIOUREIDO) 3 AMINOPHENYL] 2 (1 PYRROLIDINYL)ETHYL] N METHYLACETAMIDE; 2 (3,4 DICHLOROPHENYL) N [1 [N (N FLUORESCEINYL 5 THIOUREIDOGLYCYLGLYCYLGLYCYLGLYCINAMIDO) 3 AMINOPHENYL] 2 (1 PYRROLIDINYL)ETHYL] N METHYLACETAMIDE; 3,4 DICHLORO N METHYL N [1 PHENYL 2 (1 PYRROLIDINYL)ETHYL]BENZENEACETAMIDE; FLUORESCEIN ISOTHIOCYANATE; FLUORESCENT DYE; KAPPA OPIATE RECEPTOR; N [1 (3 AMINOPHENYL) 2 (1 PYRROLIDINYL)ETHYL] 2 (3,4 DICHLOROPHENYL) N METHYLACETAMIDE; N [1 (4 AMINOPHENYL) 2 (1 PYRROLIDINYL)ETHYL] 2 (3,4 DICHLOROPHENYL) N METHYLACETAMIDE; NORBINALTORPHIMINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONJUGATION; DRUG INHIBITION; DRUG SYNTHESIS; FLOW CYTOMETRY; FLUORESCENCE; MICROGLIA; RECEPTOR AFFINITY; RECEPTOR BINDING; SMOOTH MUSCLE; STAINING; STRUCTURE ACTIVITY RELATION;

ACETAMIDES; AMINO ACID SEQUENCE; ANIMALS; FLUORESCENT DYES; GUINEA PIGS; MALE; MICE; MICROGLIA; MOLECULAR SEQUENCE DATA; MUSCLE CONTRACTION; RECEPTORS, OPIOID, KAPPA;

EID: 0029880450     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950813b     Document Type: Review

References (36)

1. Simon, E. J.; Gioannini, T. L. Opioid Receptor Multiplicity: Isolation, Purification, and Chemical Characterization of Binding Sites. In Opioids I; Herz, A., Ed.; Springer-Verlag: Berlin, 1993; pp 3-26.
2. Millan, M. J. κ-Opioid Receptors and Analgesia. Trends Pharmacol. Sci. 1990, 11, 70-76.
3. Olson, G. A.; Olson, R. D.; Kastin, A. J. Endogenous Opiates: 1992. Peptides 1993, 14, 1339-1378.
4. Yasuda, K.; Raynor, K.; Kong, H.; Breder, C. D.; Takeda, J.; Reisine, T.; Bell, G. I. Cloning and Functional Comparison of Kappa and Delta Opioid Receptors from Mouse Brain. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6736-6740.
5. Chen, Y.; Mestek, A.; Liu, J.; Yu, L. Molecular Cloning of a Rat Kappa Opioid Receptor Reveals Sequence Similarities to the Mu and Delta Opioid Receptors. Biochem. J. 1993, 295, 625-628.
6. Li, S.; Zhu, J.; Chen, C.; Chen, Y. W.; Deriel, J. K.; Ashby, B.; Liu-Chen, L. Y. Molecular Cloning and Expression of a Rat Kappa Opioid Receptor. Biochem. J. 1993, 295, 629-633.
7. Meng, F.; Xie, G. X.; Thompson, R. C.; Mansour, A.; Goldstein, A.; Watson, S. J.; Akil, H. Cloning and Pharmacological Characterization of a Rat Kappa Opioid Receptor. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 9954-9958.
8. Nishi, M.; Takeshima, H.; Fukuda, K.; Kato, S.; Mon, K. cDNA Cloning and Pharmacological Characterization of an Opioid Receptor with High Affinities for Kappa-Subtype-Selective Ligands. FEBS Lett. 1993, 330, 77-80.
9. Minami, M.; Toya, T.; Katao, Y.; Maekawa, K.; Nakamura, S.; Onogi, T.; Kaneko, S.; Satoh, M. Cloning and Expression of a cDNA for the Rat Kappa-Opioid Receptor. FEBS Lett. 1993, 329, 291-295.
10. Ariano, M. A.; Kang, H. C.; Haugland, R. P.; Sibley, D. R. Multiple Fluorescent Ligands for Dopamine Receptors. II. Visualization in Neural Tissues. Brain Res. 1991, 547, 208-222.
11. Muresan, Z.; Besharse, J. C. D2-Like Dopamine Receptors in Amphibian Retina: Localization with Fluorescent Ligands. J. Compar. Neurol. 1993, 331, 149-160.
12. Methods in Cell Biology: Cell Biological Applications of Confocal Microscopy; Matsumoto, B., Ed.; Academic Press: San Diego, 1993; Vol. 38.
13. Lawrence, D. M. P.; El-Hamouly, W.; Archer, S.; Leary, J. F.; Bidlack, J. M. Identification of κ Opioid Receptors in the Immune System by Indirect Immunofluorescence. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 1062-1066.
14. Dado, R. J.; Law, P. Y.; Loh, H. H.; Elde, R. Immunofluorescent Identification of a Delta (δ)-Opioid Receptor on Primary Afferent Nerve Terminals. Neuroreport 1993, 5, 341-344.
15. Archer, S.; Medzihradsky, F.; Seyed-Mozaffari, A.; Emmerson, P. J. Synthesis and Characterization of 7-Nitrobenzo-2-oxa-1,3-diazole (NBD)-Labeled Fluorescent Opioids. Biochem. Pharmacol. 1992, 43, 301-306.
16. Mihara, H.; Lee, S.; Shimohigashi, Y.; Aoyagi, H.; Kato, T.; Izumiya, N.; Costa, T. Synthesis, Receptor Binding Activity and Fluorescence Property of Fluorescent Enkephalin Analogs Containing L-1-Pyrenylalanine. Int. J. Pept. Protein Res. 1987, 30, 605-612.
17. I-Enkephalins Bind Strongly and Selectively to μ and δ Opiate Receptors. Biochem. Biophys. Res. Commun. 1986, 136, 1170-1176.
18. Kolb, V. M.; Koman, A.; Neil, A. Synthesis and Pharmacological Characterization of Fluorescent Opioid Receptor Probes. Pharm. Res. 1985, 266-271.
19. Kolb, V. M; Koman, A.; Terenius, L. Fluorescent Probes for Opioid Receptors. Life Sci. 1983, 33, 423-426.
20. Barlow, J. J.; Blackburn, T. P.; Costello, G. F.; James, J.; Le Count, D. J.; Main, B. G.; Pearce, R. J.; Russell, K.; Shaw, J. S. Structure/Activity Studies Related to 2-(3,4-Dichlorophenyl)-N-methyl-N-[2-(1-pyrrolidinyl)-1-substituted-ethyl]- acetamides: A Novel Series of Potent and Selective κ-Opioid Agonists. J. Med. Chem. 1991, 34, 3149-3158.
21. Chang, A.-C.; Takemori, A. E.; Ojala, W. H.; Gleason, W. B.; Portoghese, P. S. κ Opioid Receptor Selective Affinity Labels: Electrophilic Benzeneacetamides as κ-Selective Opioid Antagonists. J. Med. Chem. 1994, 37, 4490-4498.
22. Boyapati, V. L. Design and Synthesis of Nalrindole Analogues as Delta Opioid Receptor Probes. Ph.D. Thesis, University of Minnesota-Twin Cities, 1992.
23. Ionova, L. V.; Mozzhukhin, D. D.; Morozova, E. A. Synthesis of Tetrapeptides. J. Gen. Chem. USSR 1964, 34, 768-770.
24. Beecham, A. F. The Synthesis of Some Peptides of L-Leucine and Glycine. Aust. J. Chem. 1963, 16, 160-164.
25. Rang, H. P. Stimulant Actions of Volatile Anaesthetics on Smooth Muscle. Br. J Pharmacol. 1964, 22, 356-365.
26. Henderson, G.; Hughes, J.; Kosterlitz, H. W. A New Example of a Morphine-sensitive Neuro-effector Junction: Adrenergic Transmission in the Mouse Vas Deferens. Br. J. Pharmacol. 1972, 46, 764-766.
27. Portoghese, P. S.; Takemori, A. E. TENA, a Selective Kappa Opioid Receptor Antagonist. Life Sci. 1985, 36, 801-805.
28. Werling, L. L.; Zarr, G. D.; Brown, S. R.; Cox, B. M. Opioid Binding to Rat and Guinea Pig Neural Membranes in the Presence of Physiological Cations at 37 °C. J. Pharmacol. Exp. Ther. 1985, 233, 722-728.
29. 3H]U69,593 A Highly Selective Ligand for the Opioid κ Receptor. Eur. J. Pharmacol. 1985, 109, 281-284.
30. Handa, B. K.; Lane, A. C.; Lord, J. A. H.; Morgan, B. A.; Rance, M. J.; Smith, C. F. C. Analogs of β-LPH61-64 Possessing Selective Agonist Activity at Mu-Opiate Receptors. Eur. J. Pharmacol. 1981, 70, 531-540.
31. Mosberg, H. I.; Hurst, R.; Hruby, V. J.; Gee, K.; Yamamura, H. I.; Galligan, J. J.; Burks, T. S. Bis-penicillamine Enkephalins Possess Highly Improved Specificity Toward δ Opioid Receptor. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 5871-5874.
32. Gacel, G.; Fourine-Zaluski, M.-C.; Roques, B. P. Tyr-D-Ser-GlyPhe-Leu-Thr, a Highly Preferential Ligand for δ Opiate Receptors. FEBS Lett. 1980, 118, 245-247.
33. Chao, C. C.; Gekker, G.; Sheng, W. S.; Hu, S.; Bu, D.-F.; Archer, S.; Bidlack, J. M.; Peterson, P. K. Kappa Opioid Receptors in Human Microglia: Suppression of HIV-1 Replication. Problems of Drug Dependence, 1995: Proceedings of the 57th Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc., in press.
34. Chao, C. C.; Gekker, G.; Sheng, W. S.; Hu, S.; Tsang, M.; Peterson, P. K. Priming Effect of Morphine on the Production of Tumor Necrosis Factor-aα by Microglia: Implications in Respiratory Burst Activity and Human Immunodeficiency Virus-1 Expression, J. Pharmaco. Exp. Ther. 1994, 269, 198-203.
35. Portoghese, P. S.; Lipkowski, A. W.; Takemori, A. E. Binaltorphimine and Nor-Binaltorphimine, Potent and Selective κ-Opioid Receptor Antagonists. Life Sci. 1987, 40, 1287-1292.
36. Takemori, A. E.; Larson, D. L.; Portoghese, P. S. The Irreversible Narcotic Antagonistic and Reversible Agonistic Properties of the Fumaramide Methyl Ester Derivative of Naltrexone. Eur. J. Pharmacol. 1981, 70, 445-451.