Opioid peptide-derived analgesics

AAPS Journal

Volumn 7, Issue 3, 2005, Pages

  Schiller, Peter W ^a  

^a CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANALGESIC AGENT; LONG ACTING DRUG; MORPHINE; OPIATE PEPTIDE; TYROSYL DEXTRO ARGINYLPHENYLALANYLLYSINAMIDE; NARCOTIC ANALGESIC AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; BINDING AFFINITY; BLOOD BRAIN BARRIER; CONTROLLED STUDY; DRUG INDICATION; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG TOLERANCE; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; REVIEW; SPINAL ANESTHESIA; TAIL FLICK TEST; ANIMAL; DRUG EFFECT; HUMAN; METABOLISM; PAIN ASSESSMENT; PHYSIOLOGY; PROTEIN BINDING;

ANALGESICS, OPIOID; ANIMALS; HUMANS; OPIOID PEPTIDES; PAIN MEASUREMENT; PROTEIN BINDING;

EID: 33644805964     PISSN: 15221059     EISSN: 15221059     Source Type: Journal    
DOI: 10.1208/aapsj070356     Document Type: Review

References (43)

1. Pfeiffer A, Brantl V, Herz A, Emrich HM. Psychotomimesis mediated by kappa opiate receptors. Science. 1986;233:774-776.
2. Walsh SL, Strain EC, Abreu ME, Bigelow GE. Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans. Psychopharmacology (Bert). 2001;157:151-162.
3. Yaksh TL. In vivo studies on spinal opiate receptor systems mediating antinociception, I: mu and delta receptor profiles in the primate. J Pharmacol Exp Ther. 1983;226:303-316.
4. Porreca F, Mosberg HI, Hurst R, Hruby VJ, Burks TF. Roles of mu, delta and kappa opioid receptors in spinal and supraspinal mediation of gastrointestinal transit effects and hot-plate analgesia in the mouse. J Pharmacol Exp Ther. 1984;230:341-348.
5. Cowan A, Zhu XZ, Mosberg HI, Omnaas JR, Porreca F. Direct dependence studies in rats with agents selective for different types of opioid receptor. J Pharmacol Exp Ther. 1988;246:950-955.
6. 2]deltorphin, I. Eur J Pharmacol. 1993;230:85-88.
7. Galligan JJ, Mosberg HI, Hurst R, Hruby VJ, Burks TF. Cerebral delta opioid receptors mediate analgesia but not the intestinal motility effects of intracerebroventricularly administered opioids. J Pharmacol Exp Ther. 1984;229:641-648.
8. 5]enkephalin and two halogenated analogs after intravenous administration. J Pharmacol Exp Ther. 1991;259:1109-1117.
9. Svensson CI, Rew Y, Malkmus S, et al. Systemic and spinal analgesic activity of a δ-opioid-selective lanthionine enkephalin analog. J Pharmacol Exp Ther. 2003;304:827-832.
10. Kamei J, Saitoh A, Ohsawa M, et al. Antinociceptive effects of the selective non-peptidic δ-opioid receptor antagonist TAN-67 in diabetic mice. Eur J Pharmacol. 1995;276:131-135.
11. Chang K-J, Rigdon GC, Howard JL, McNutt RW. A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86. J Pharmacol Exp Ther. 1993;267:852-857.
12. Calderon SN, Rothman RB, Porreca F, et al. Probes for narcotic receptor mediated phenomena, 19: synthesis of (+)-4-(αR)-α-((2S,5R)- 4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide (SNC80): a highly selective, nonpeptide delta opioid receptor agonist. J Med Chem. 1994;37:2125-2128.
13. Plobeck N, Delorme D, Wei Z-Y, et al. New diarylmethylpiperazines as potent and selective nonpeptidic δ opioid receptor agonists with increased in vitro metabolic stability. J Med Chem. 2000;43:3878-3894.
14. DeHaven-Hudkins DL, Dolle RE. Peripherally restricted opioid agonists as novel analgesic agents. Curr Pharm Des. 2004;10:743-757.
15. Schiller PW, Nguyen TM-D, Chung NN, Lemieux C. Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high μ-opioid receptor selectivity. J Med Chem. 1989;32:698-703.
16. Schiller PW, Nguyen TM-D, Berezowska I, et al. Synthesis and in vitro opioid activity profiles of DALDA analogues. Eur J Med Chem. 2000;35:895-901.
17. 1]DALDA, a highly potent and selective μ-opioid peptide. Eur J Pharmacol. 2001; 419:15-23.
18. 2, a highly potent opioid peptide. J Pharmacol Exp Ther. 2003;306:430-436.
19. Szeto HH, Lovelace JL, Fridland G, et al. In vivo pharmacokinetics of selective μ-opioid peptide agonists. J Pharmacol Exp Ther. 2001;298:57-61.
20. 1]DALDA. J Pharmacol Exp Ther. 2001;297:364-371.
21. Reimann W, Schlutz H, Selve N. The antinociceptive effects of morphine, desipramine, and serotonin and their combinations after intrathecal injection in the rat. Anesth Analg. 1999;88:141-145.
22. 1]DALDA. J Pharmacol Exp Ther. 2003;305:696-702.
23. Zhao GM, Wu D, Soong Y, et al. Profound spinal tolerance after repeated exposure to a highly selective μ-opioid peptide agonist: role of μ-opioid receptors. J Pharmacol Exp Ther. 2002;302:188-196.
24. 1]DALDA treatment. Br J Pharmacol. 2004;143:987-993.
25. 1] DALDA analgesia. Brain Res. 2003;974:254-257.
26. 1]DALDA is highly selective and potent at μ opioid receptors, but is not cross-tolerant with systemic morphine. Curr Med Chem. 2002;9:31-39.
27. Zhao K, Luo G, Zhao G-M, Schiller PW, Szeto HH. Transcellular transport of a highly polar 3+ net charge opioid tetrapeptide. J Pharmacol Exp Ther. 2003;304:425-432.
28. 1]DALDA. Peptides. 2003;24:1195-1200.
29. Abdelhamid EE, Sultana M, Portoghese PS, Takemori AE. Selective blockage of delta opioid receptors prevents the development of morphine tolerance and dependence in mice. J Pharmacol Exp Ther. 1991;258:299-303.
30. 2-NH]Phe-Phe-OH (TIPP[ψ]) attenuates morphine tolerance and dependence. Eur J Pharmacol. 1995;286:105-108.
31. Rothman RB, Danks JA, Jacobson AE, Burke TR, Jr, Rice KE, Holaday JW. Morphine tolerance increases mu-noncompetitive delta binding sites. Eur J Pharmacol. 1986;124:113-119.
32. Yukhananov RY, Klodt PM, Riva AD, Zeitsev SV, Masky AI. Opiate withdrawal correlates with the presence of DSLET high-affinity binding. Pharmacol Biochem Behav. 1994;49:1109-1112.
33. Kest B, Lee CY, McLemore GL, Inturrisi CE. An antisense oligodeoxynucleotide to the delta opioid receptor (DOR-1) inhibits morphine tolerance and acute dependence in mice. Brain Res Bull. 1996;39:185-188.
34. Zhu Y, King MA, Schuller AG, et al. Retention of supraspinal delta-like analgesia and loss of morphine tolerance in delta opioid receptor knock-out mice. Neuron. 1999;24:243-252.
35. Gomes I, Gupta A, Filipovska J, Szeto HH, Pintar JE, Devi LA. A role for heterodimerization of μ and δ opiate receptors in enhancing morphine analgesia. Proc Natl Acad Sci USA. 2004;101:5135-5139.
36. Freye E, Latasch L, Portoghese PS. The delta receptor is involved in sufentanil-induced respiratory depression - opioid subreceptors mediate different effects. Eur J Anaesthesiol. 1992;9:457-462.
37. Foxx-Orenstein AE, Jin JG, Grider JR. 5HT4 receptor agonists and delta opioid receptor antagonists act synergistically to stimulate colonic propulsion. Am J Physiol. 1998;275-G979-G983.
38. Schiller PW. Nguyen TM-D. Weltrowska G. et al. Differential stereochemical requirements of μ vs δ opioid receptors for iigana binding and signal transauction: development of a class of potent ana nigniy o-selective peptide antagonists. Proc Natl Acad Sci USA. 1992;89:11871-11875.
39. 2-[ψ] produces a potent analgesic effect, no physical dependence, and less tolerance than morphine in rats. J Med Chem. 1999;42:3520-3526.
40. Schiller PW, Weltrowska G, Berezowska I, et al. The TIPP opioid peptide family: development of δ antagonists, δ agonists and mixed μ agonist/ δ antagonists. Biopolymers (Peptide Science). 1999; 51:411-425.
41. Weltrowska G, Lemieux C, Chung NN, Schiller PW. A chimeric opioid peptide with mixed μ agonist/δ antagonist properties. J Pept Res. 2004;63:63-68.
42. Ananthan S, Kezar HS, III, Carter RL, et al. Synthesis, opioid receptor binding, and biological activities of naltrexone-derived pyrido- and pyrimidomorphinans. J Med Chem. 1999;42:3527-3538.
43. Ananthan S, Khare NK, Saini SK, et al. Identification of opioid ligands possessing mixed δ agonist/δ antagonist activity among pyridomorphinans derived from naloxone, oxymorphone, and hydromorphone. J Med Chem. 2004;47:1400-1412.