Opioids and efflux transporters. Part 2: P-glycoprotein substrate activity of 3- and 6-substituted morphine analogs

Journal of Medicinal Chemistry

Volumn 51, Issue 7, 2008, Pages 2316-2320

  Cunningham, Christopher W ^a   Mercer, Susan L ^a   Hassan, Hazem E ^a   Traynor, John R ^b   Eddington, Natalie D ^a   Coop, Andrew ^a  

^a UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 DESOXYMORPHINE; 7,8 DIHYDRO 3 DESOXYHETEROCODEINE; GLYCOPROTEIN P; MORPHINE DERIVATIVE; OPIATE; OPIATE RECEPTOR; UNCLASSIFIED DRUG;

ANALGESIA; ANIMAL EXPERIMENT; ANTINOCICEPTION; ARTICLE; BINDING AFFINITY; ENZYME ACTIVITY; MOUSE; NONHUMAN;

ANALGESICS, NON-NARCOTIC; ANALGESICS, OPIOID; ANIMALS; BINDING SITES; CELL LINE, TUMOR; CHO CELLS; CRICETINAE; CRICETULUS; MICE; MOLECULAR CONFORMATION; MORPHINE DERIVATIVES; P-GLYCOPROTEINS; PAIN MEASUREMENT; RATS; RECEPTORS, OPIOID; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 41849098861     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701457j     Document Type: Article

References (30)

1. Mercandante, S. Opioid Rotation for Cancer Pain: Rationale and Clinical Aspects. Cancer 1999, 86, 1856-1866.
2. DeLuca, A.; Coupar, I. M. Insights Into Opioid Action in the Intestinal Tract. Pharmacol. Ther. 1996, 69, 103-115.
3. Kieffer, B. L.; Evans, C. J. Opioid Tolerance In Search of the Holy Grail. Cell 2002, 108, 587-590.
4. He, L.; Fong, J.; von Zastrow, M.; Whistler, J. L. Regulation of Opioid Receptor Trafficking and Morphine Tolerance by Receptor Oligomerization. Cell 2002, 106, 271-282.
5. Williams, J. T.; MacDonald, J. C.; Manzoni, O. Cellular and Synaptic Adaptations Mediating Opioid Dependence. Physiol. Rev. 2001, 81, 299-343.
6. Zhang, J.; Ferguson, S. S.; Barak, L. S.; Bodduluri, S. R.; Laporte, S. A.; Law, P. Y.; Caron, M. G. Role for G Protein-Coupled Receptor Kinase in Agonist-Specific Regulation of Mu-Opioid Receptor Responsiveness. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 7157-7162.
7. Tamayo, A. C.; Diaz-Zuluaga, P. A. Management of Opioid-Induced Bowel Dysfunction in Cancer Patients. Supportive Care Cancer 2004, 12, 613-618.
8. King, M.; Su, W.; Chang, A.; Zuckerman, A.; Pasternak, G. W. Transport of Opioids From the Brain to the Periphery by P-Glycoprotein: Peripheral Actions of Central Drugs. Nat. Neurosci. 2001, 4, 268-274.
9. Drewe, J.; Ball, H. A.; Beglinger, C.; Peng, B.; Kemmler, A.; Schachinger, H.; Haefeli, W. E. Effect of P-Glycoprotein Modulation on the Clinical Pharmacokinetics and Adverse Effects of Morphine. Br. J. Clin. Pharmacol. 2000, 50, 237-246.
10. Xie, R.; Hammarlund-Udenaes, M.; de Boer, A. G.; de Lange, E. C. The Role of P-Glycoprotein in Blood-Brain Barrier Transport of Morphine: Transcortical Microdialysis Studies in mdr1a (-/-) and (+-+) mice. Br. J. Pharmacol. 1999, 128, 563-568.
11. Dagenais, C.; Graff, C. L.; Pollack, G. M. Variable Modulation of Opioid Brain Uptake by P-Glycoprotein in Mice. Biochem. Pharmacol. 2004, 67, 269-276.
12. Ambudkar, S. V.; Kimchi-Sarfarty, C.; Sauna, Z. E.; Gottesman, M. M. P-Glycoprotein: From Genomics to Mechanism. Oncogene 2003, 22, 7468-7485.
13. Hassan, H. E.; Myers, A. L.; Lee, I. J.; Coop, A.; Eddington, N. D. Oxycodone Induces Overexpression of P-Glycoprotein (ABCB1) and Affects Paclitaxel's Tissue Distribution in Sprague Dawley Rats. J. Pharm. Sci. 2007, 96, 2494-2506.
14. Hennessy, M.; Spiers, J. P. A Primer on the Mechanics of P-Glycoprotein the Multidrug Transporter. Pharmacol. Res. 2007, 55, 1-15.
15. Casy, A. F.; Parfitt, R. F. Opioid Analgesics; Plenum Press: New York, 1986.
16. Raub, T. J. P-Glycoprotein Recognition of Substrates and Circumvention Through Rational Drug Design. Mol. Pharm. 2006, 1, 3-25.
17. Xie, R.; Hammerlund-Udenaes, M. Blood-Brain Barrier Equilibration of Codeine in Rats Studied with Microdialysis. Pharm. Res. 1998, 15, 570-575.
18. Mercer, S. L.; Hassan, H. E.; Cunningham, C. W.; Eddington, N. D.; Coop, A. Opioids and Efflux Transporters. Part 1: P-Glycoprotein Substrate Activity of N-Substituted Analogs of Meperidine. Bioorg. Med. Chem. Lett. 2007, 17, 1160-1162.
19. Reden, J.; Reich, M. F.; Rice, K. C.; Jacobson, A. E.; Brossi, A.; Streaty, R. A.; Klee, W. A. Deoxymorphines: Role of the Phenolic Hydroxyl in Antinociception and Opiate Receptor Interactions. J. Med. Chem. 1979, 22, 256-259.
20. Maeda, D. Y.; Coop, A. Studies into the Direct Conversion of Indolomorphinans to Their 4-Phenolic Derivatives. Tetrahedron 2000, 56, 7399-7402.
21. Cunningham, C. W.; Thatcher, L. N.; Coop, A. Methylation of Non-Acidic Alcohols of Alkaloids with TMS-diazomethane: Conversion of Codeine to Codeine-6-methyl Ether. Heterocycles 2006, 68, 837-840.
22. 8- Desoxycodeine. J. Am. Chem. Soc. 1951, 73, 2872-2876.
23. Rice, K. C. A Rapid, High-Yield Conversion of Codeine to Morphine. J. Med. Chem. 1977, 20, 164-165.
24. Ambudkar, S. V.; Dey, S.; Hrycyna, C. A.; Ramachandra, M.; Pastan, I.; Gottesman, M. M. Biochemical, Cellular, and Pharmacological Aspects of the Multidrug Transporter. Annu. Rev. Pharmacol Toxicol. 1999, 39, 361-398.
25. Polli, J. W.; Wring, S. A.; Humphreys, J. E.; Huang, L.; Morgan, J. B.; Webster, L. O.; Serabjit-Singh, C. S. Rational Use of in Vitro P-Glycoprotein Assays in Drug Discovery. J. Pharmacol. Exp. Ther. 2001, 299, 620-628.
26. Peckham, E. M.; Traynor, J. R. Comparison of the Antinociceptive Response to Morphine and Morphine-Like Compounds in Male and Female Sprague-Dawley Rats. J. Pharmacol. Exp. Ther. 2005, 316, 1195-1201.
27. Traynor, J. R.; Woods, J. H. Drug Evaluation Committee Report On: Evaluation of New Compounds for Opioid Activity (2006). NIDA Res. Monogr. 2007, 187, 113-132.
28. Aceto, M. D.; Bowman, E. R.; Harris, L. S.; Hughes, L. D.; Kipps, B. R.; Lobe, S. L.; May, E. L. Evaluation of New Compounds in the Rhesus Monkey, Rat and Mouse. NIDA Res. Monogr. 2007, 187, 136-164.
29. Aceto, M. D.; Bowman, E. R.; Harris, L. S.; May, E. L. Dependence Studies of New Compounds in the Rhesus Monkey, Rat, and Mouse (1997). NIDA Res. Monogr. 1998, 178, 363-407.
30. Small, L. F.; Morris, D. E. Desoxymorphines. J. Am. Chem. Soc. 1933, 55, 2874-2885.