Reporter affinity labels: An o-phthalaldehyde derivative of β- naltrexamine as a fluorogenic ligand for opioid receptors

Journal of Medicinal Chemistry

Volumn 43, Issue 13, 2000, Pages 2489-2492

  Le Bourdonnec, Bertrand ^a   El Kouhen, Rachid ^b   Lunzer, Mary M ^a   Law, Ping Y ^b   Loh, Horace H ^b   Portoghese, Philip S ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NALTREXAMINE DERIVATIVE; OPIATE RECEPTOR; PHTHALALDEHYDE;

AFFINITY LABELING; ANTINOCICEPTION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; LETTER;

AFFINITY LABELS; ANIMALS; CHO CELLS; CRICETINAE; LIGANDS; MICE; NALTREXONE; NARCOTIC ANTAGONISTS; O-PHTHALALDEHYDE; PAIN MEASUREMENT; RECEPTORS, OPIOID; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU;

EID: 0034729789     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000138s     Document Type: Letter

References (29)

1. Takemori, A. E.; Portoghese, P. S. Affinity Labels for Opioid Receptors. Annu. Rev. Pharmacol. Toxicol. 1985, 25, 193-223.
2. 3H]Funaltrexamine-Labeled μ-Opioid Receptors: Species Variations in Molecular Mass and Glycosylation by Complex-Type, N-Linked Oligosaccharides. Mol. Pharmacol. 1993, 44, 749-756.
3. Chen, C.; Xue, J.-C.; Zhu, J.; Chen, Y.-W.; Kunapuli, S.; de Riel, J. K.; Yu, L.; Liu-Chen, L.-Y. Characterization of Irreversible Binding of β-Funaltrexamine to the Cloned Rat μ Opioid Receptor. J. Biol. Chem. 1995, 270, 17866-17870.
4. (a) Portoghese, P. S.; Larson, D. L.; Sayre, L. M.; Fries, D. S.; Takemori, A. E. A Novel Opioid Receptor Site Directed Alkylating Agent with Irreversible Narcotic Antagonistic and Reversible Agonistic Activities. J. Med. Chem. 1980, 23, 233-234.
5. (b) Takemori, A. E.; Larson, D. L.; Portoghese, P. S. The Irreversible Narcotic Antagonist and Reversible Agonistic Properties of the Fumarate Methyl Ester Derivative of Naltrexone. Eur. J. Pharmacol. 1981, 70, 445-451.
6. 50 values of 2.2, 14, and 78 nM, respectively (Tam, S. W.; Liu-Chen, L.-Y. Reversible and Irreversible Binding of β-Funaltrexamine to Mu, Delta and Kappa Opioid Receptors in Guinea Pig Brain Membranes. J. Pharmacol. Exp. Ther. 1986, 239, 351-357).
7. 3H]β-Funaltrexamine Covalent Binding in the Cloned Rat μ Opioid Receptor. J. Biol. Chem. 1996, 35, 21422-21429.
8. Wong, O. S.; Sternson, L. A.; Schowen, R. L. Reaction of o-Phthalaldehyde with Alanine and Thiols: kinetics and mechanism. J. Am. Chem. Soc. 1985, 107, 6421-6422.
9. (a) Simmons, S. S., Jr.; Johnson, D. F. The Structure of the Fluorescent Adduct Formed in the Reaction of o-Phthalaldehyde and Thiols with Amines. J. Am. Chem. Soc. 1976, 98, 7098-7099.
10. (b) Simmons, S. S., Jr.; Johnson, D. F. Reaction of o-Phthalaldehyde and Thiols with Primary Amines: Fluorescence Properties of 1-Alkyl (and Aryl)thio-2-Alkylisoindoles. Anal. Biochem. 1978, 90, 705-725.
11. Garcia Alvarez-Coque, M. C.; Medina Hernandez, M. J.; Villanueva Camanas, R. M.; Mongay Fernandez, C. Formation and Instability of o-Phthalaldehyde Derivatives of Amino Acids. Anal. Biochem. 1989, 178, 1-7.
12. (a) Fekkes, D. State-of-The-Art of High-Performance Liquid Chromatographic Analysis of Amino Acids in Physiological Sample. J. Chromatogr., B: Biomed. Sci. Appl. 1996, 682, 3-22.
13. (b) Lee, K. S.; Drescher, D. G. Fluorometric Amino-Acid Analysis with o-Phthalaldehyde (OPA). Int. J. Biochem. 1978, 9, 457-467.
14. (a) Pandey, A.; Sheikh, S.; Katiyar, S. S. Identification of Cysteine and Lysine Residues Present at the Active Site of Beef Liver Glutamate Dehydrogenase by o-Phthalaldehyde. Biochim. Biophys. Acta 1996, 1293, 122-128.
15. (b) Blaner, W. S.; Churchich, J. Succinic Semialdehyde Dehydrogenase. J. Biol. Chem. 1979, 254, 1794-1798.
16. (c) Puri, R. N.; Bhatnagar, D.; Roskoski, R., Jr. Inactivation of Yeast Hexokinase by o-Phthalaldehyde: Evidence for the Presence of a Cysteine and a Lysine at or near the Active Site. Biochim. Biophys. Acta 1988, 957, 34-46.
17. (d) Giovannini, P. P.; Rippa, M.; Dallocchio, F.; Tetaud, M.; Barrett, M. P.; Hanau, S. The Cross-Linking by o-Phthalaldehyde of Two Amino Acid Residues at the Active Site of 6-Phosphogluconate Dehydrogenase. Biochem. Mol. Biol. Int. 1997, 43, 153-160.
18. (e) Matteucci, G.; Lanzara, V.; Ferrari, C.; Hanau, S.; Bergamini, C. M. Active Site of Erythrocyte Transglutaminase by o-Phthalaldehyde. Biol. Chem. 1998, 379, 921-924.
19. Sayre, L. M.; Portoghese, P. S. Stereospecific Synthesis of the 6α- and 6β-Amino Derivatives of Naltrexone and Oxymorphone. J. Org. Chem. 1980, 16, 3366-3368.
20. Amano, T.; Sakano, T. Studies on the Determination Methods with Polyaldehydes. VIII. Fluorescence of 2-phenyl-5,6-substituted Phthalimidine Derivatives. Yakugaku Zasshi 1968, 88, 247-253.
21. The hydration of OPTA has been previously documented. Thus, at room temperature, water reacts reversibly with OPTA to produce a hydrate (1,3-dihydroxyphthalan). See: McDonald, R. S.; Martin, E. The Kinetics of the Hydration of Phthalaldehyde. Can. J. Chem. 1979, 57, 506-512.
22. i reflects both the reversible and irreversible binding components.
23. Rang, H. P. Stimulant Actions of Volatile Anaesthetics on Smooth Muscle. Br. J. Pharmacol. 1964, 22, 356-365.
24. 50 in the same preparation.
25. Ward, S. J.; Portoghese, P. S.; Takemori, A. E. Pharmacological Characterization in Vivo of the Novel Opiate, β-Funaltrexamine. J. Pharmacol. Exp. Ther. 1982, 220, 494-498.
26. 7b,10
27. Prather, P. L.; Mcginn, T. M.; Claude, P. A.; Liu-Chen, L.-Y.; Loh, H. H.; Law, P. Y. Properties of a Kappa-Opioid Receptor Expressed in CHO Cells-Interaction with Multiple G-Proteins is not Specific for any Individual G-Alpha Subunit and is Similar to that of other Opioid Receptors. Mol. Brain Res. 1995, 29, 336-346.
28. Haley, T. J.; McCormack, W. G. Pharmacological Effects Produced by Intracerebral Injection of Drugs in the Conscious Mouse. Br. J. Pharmacol. 1957, 12, 12-15.
29. Hayashi, G.; Takemori, A. E. The Type of Analgesic-Receptor Interaction involved in Certain Analgesic Assays. Eur. J. Pharmacol. 1971, 16, 63-66.