o-naphthalenedicarboxaldehyde derivative of 7′-aminonaltrindole as a selective δ-opioid receptor affinity label

Journal of Medicinal Chemistry

Volumn 50, Issue 14, 2007, Pages 3392-3396

  Haris, Sarika Prabhu ^a   Zhang, Yan ^a   Le Bourdonnec, Bertrand ^a   McCurdy, Christopher R ^a   Portoghese, Philip S ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

17 (CYCLOPROPYLMETHYL) 7' (3,4 DIFORMYLNAPHTHOYLAMINO) 6,7 DIDEHYDRO 4,5ALPHA EPOXY 14 HYDROXYINDOLO[2',3':6,7]MORPHINAN; 6' AMINONALTRINDOLE DERIVATIVE; 7' AMINONALTRINDOLE DERIVATIVE; ALDEHYDE DERIVATIVE; CYSTEINE; DELTA OPIATE RECEPTOR; DELTA OPIATE RECEPTOR AGONIST; LYSINE; NALTRINDOLE; NAPHTHALENE DERIVATIVE; NAPHTHALENEDICARBOXALDEHYDE DERIVATIVE; SCHIFF BASE; UNCLASSIFIED DRUG;

AFFINITY LABELING; ARTICLE; BIOLOGICAL ACTIVITY; CONFORMATIONAL TRANSITION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; FLOW CYTOMETRY; FLUORESCENCE; HUMAN; HUMAN CELL; RECEPTOR AFFINITY;

AFFINITY LABELS; MAGNETIC RESONANCE SPECTROSCOPY; NALTREXONE; NARCOTIC ANTAGONISTS; RECEPTORS, OPIOID, DELTA; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 34447540010     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061194h     Document Type: Article

References (27)

1. (a) Coleman, R. F.; Creighton, T. E. Protein Function; IRL Press: Oxford, U.K., 1997; p 155.
2. (b). Oppenheimer, C. L.; Czech, M. P. Affinity Labeling of Receptors. Growth Maturation Factors 1984, 2, 193-221.
3. (c) Sokolovsky, M. Affinity and Photoafinity Labeling of Receptors. Brain Recept. Methodol. 1984, A, 153-167.
4. Takemori, A. E.; Portoghese, P. S. Development of Non-Equilibrium Opioid Receptor Probes. New Methods Drug Res. 1985, 1, 113-128.
5. Le Bourdonnec, B.; Kouhen, R. E.; Lunzer, M. M.; Law, P. Y.; Loh, H. H.; Portoghese, P. S. Reporter Affinity Labels: An o-Phthalaldehyde Derivative of β-Naltrexamine as a Fluorogenic Ligand for Opioid Receptors. J. Med. Chem. 2000, 43 (13), 2489-2492.
6. McCurdy, C. R.; Le Bourdonnec, B.; Metzger, T. G.; Kouhen, R. E.; Zhang, Y.; Law, P. Y.; Portoghese, P. S. Naphthalene Carboxaldehyde As An Electrophilic Moiety for Affinity Labeling: Application to Opioid Receptor Affinity Labels With Greatly Improved Fluorogenic Properties. J. Med. Chem. 2002, 45 (14), 2887-2890.
7. (a) Chiu, D. T.; Lillard, S. J.; Scheller, R. H.; Zare. R. N.; Rodriguez-Crz, S. E.; Williams, E. R.; Orwar, O.; Sandberg, M.; Lundqvist, J. A. Probing Single Secretory Vesicles with Capillary Electrophoresis. Science 1998, 279, 1190-1193.
8. (b) Gilman, S. D.; Ewing, A. G. Post-Column Derivatization For Capillary Electrophoresis Using Naphthalene-2,3-dicarboxaldehyde and 2-Mercaptoethanol. Anal. Methods Instrum. 1995, 2, 133-141.
9. (c) Lai, F.; Sheehan, T. Matrix Effects in the Derivatization of Amino Acids with Naphthalene Dicarboxaldehyde, 9-Fluorenylmethyl Chloroformate and Phenylisothiocyanate. BioTechniques 1993, 14, 642-644.
10. (d) De Montigny, P.; Stobaugh, J. F.; Givens, R. S.; Carlson, R. G.; Srinivasachar, K.; Sternson, L. A.; Higuchi, T. Naphthalene-2,3- dicarboxaldehyde/Cyanide Ion: A Rationally Designed Fluorogenic Reagent for Primary Amines. Anal. Chem. 1987, 59, 1096-1101.
11. (e) Roach, M. C.; Harmony, M. D. Determination of Amino Acids at Subfemtomole Levels by High Performance Liquid Chromatography with Laser-Induced Fluorescence Detection. Anal. Chem. 1987, 59, 411-415.
12. (f) Miura, T.; Kashiwamura, M. A Sensitive Fluorometric determination of Erythrocyte and Serum Argininosuccinate Lyase Activities with 2,3- Naphthalenedicarboxaldehyde. Anal. Sci. 1986, 2, 473-476.
13. Zhang, Y.; McCurdy, C. R.; Metzger, T. G.; Portoghese, P. S. Specific Cross-Linking of Lys 233 and Cys 235 in the Mu Opioid Receptor By A Reporter Affinity Label. Biochemistry 2005, 22 (44), 2271-2275.
14. Orrwar, O.; Fishman, H. A.; Ziv, N. W.; Scheller, R. H.; Zare, R. N. Use of 2,3-Naphthalenedicarboxaldehyde Derivatization for Single-Cell Analysis of Glutathione by Capillary Electrophoresis and Histochemical Localization by Fluorescence Microscopy Anal. Chem. 1995, 67, 4261-4268.
15. Takemori, A. E.; Portoghese, P. S. Selective Naltrexone-Derived Opioid Receptor Antagonists. Annu. Rev. Pharmacol. Toxicol. 1992, 32, 239-269.
16. Portoghese, P. S.; Sultana, M.; Takemori, A. E.; Design of Peptidomimetic δ Opioid Receptor Antagonists Using the Message-Address Concept. J. Med. Chem. 1990, 33, 1714-1720.
17. Ananthan, A.; Johnson, C. A.; Carter, R. L.; Clayton, S. D.; Rice, K. C.; Xu, H.; Davis, P.; Porreca, F.; Rothman, R. B. Synthesis, Opioid Receptor Binding, and Bioassay of Naltrindole Analogs Substituted in the Benzene Indolic Moiety. J. Med. Chem. 1998, 41, 2872-2881.
18. Kshirsagar, T.; Nakano, A. H.; Law, P. Y.; Elde, R.; Portoghese, P. S. NTI4F: A Non-Peptide Fluorescent Probe Selective for Functional Delta Opioid Receptors. Neurosci. Lett. 1998, 249, 83-86.
19. Le Bourdonnec, B.; El Kouhen, R.; Poda, G.; Law, P. Y.; Loh, H. H.; Ferguson, D. M.; Portoghese, P. S. Covalently Induced Inactivation of the δ Opioid Receptor Using Fluorogenic Affinity Label, 7- (Phthalaldehydecarboxamido)naltrindole (PNTI). J. Med. Chem. 2001, 44, 1017-1020.
20. Portoghese, P. S.; Sultana, M.; Nelson, W. L.; Klein, P.; Takemori, A. E. δ Opioid Antagonistic Activity and Binding Studies of Regioisomeric Isothiocyanate Derivatives of Naltrindole: Evidence for u Receptor Subtypes. J. Med. Chem. 1992, 35, 4086-4091.
21. Henderson, G.; Hughes, J.; Kosterlitz, H. W. New Example of a Morphine-Sensitive Neuro-effector Junction: Adrenergic Transmission in the Mouse Vas Deferens. Br. J. Pharmacol. 1972, 46, 764-766.
22. Rang, H. P. Stimulant Actions of Volatile Anesthetics on Smooth Muscles. Br. J. Pharmacol. 1964, 22, 356-365.
23. Portoghese, P. S.; Takemori, A. E. Tena A Selective Kappa Opioid Receptor Antagonist. Life Sci. 1985, 36, 801-805.
24. Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Sheely, M.; Perry, J. K.; Shaw, D. E.; Francis, P.; Shenkin, P. S. Glide: A New Approach for Rapid, Accurate Docking and Scoring. 1. Method and Assessment of Docking Accuracy. J. Med. Chem. 2004, 47, 1739-1749.
25. Chen, C.; Okayama, H. High-Efficiency Transformation of Mammalian Cells by Plasmid DNA. Mol. Cell. Biol. 1987, 7, 2745-2752.
26. Bradford, M. M. A Rapid and Sensitive Method for Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding. Anal. Biochem. 1976, 72, 248-254.
27. 50) of An Enzymic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.