Antinociceptive potency of a fluorinated cyclopeptide Dmt-c[D-Lys-Phe-p-CF₃-Phe-Asp]NH₂

References

• Breivik H, Collett B, Ventafridda V, et al. Survey of chronic pain in Europe: prevalence, impact on daily life, and treatment. Eur. J Pain 2006;10:287–333.
   Web of Science ®Google Scholar
• Chu GH, Gu M, Cassel JA, et al. Novel malonamide derivatives as potent kappa opioid receptor agonists. Bioorg Med Chem Lett 2007;17:1951–5.
   PubMed Web of Science ®Google Scholar
• Brock C, Olesen SS, Olesen AE, et al. Opioid-induced bowel dysfunction: pathophysiology and management. Drugs 2012;72:1847–65.
   PubMed Web of Science ®Google Scholar
• Corbett AD, Henderson G, McKnight AT, Paterson SJ. 75 years of opioid research: the exciting but vain quest for the Holy Grail. Br J Pharmacol 2006;147:S153–S62.
   PubMed Web of Science ®Google Scholar
• Labuz D, Berger S, Mousa SA, et al. Peripheral antinociceptive effects of exogenous and immune cell-derived endomorphins in prolonged inflammatory pain. J Neurosci 2006;26:4350–8.
   PubMed Web of Science ®Google Scholar
• Labuz D, Mousa SA, Schäfer M, et al. Relative contribution of peripheral versus central opioid receptors to antinociception. Brain Res 2007;1160:30–8.
   PubMed Web of Science ®Google Scholar
• Luster AD, Alon R, von Andrian UH. Immune cell migration in inflammation: present and future therapeutic targets. Nat Immunol 2005;6:1182–90.
   PubMed Web of Science ®Google Scholar
• Hua S, Cabot PJ. Mechanisms of peripheral immune-cell-mediated analgesia in inflammation: clinical and therapeutic implications. Trends Pharmacol Sci 2010;31:427–33.
   PubMed Web of Science ®Google Scholar
• Iwaszkiewicz KS, Schneider JJ, Hua S. Targeting peripheral opioid receptors to promote analgesic and anti-inflammatory actions. Front Pharmacol 2013;4:132.
   PubMed Web of Science ®Google Scholar
• O'Connor TM, O'Connell J, O'Brien DI, et al. The role of substance P in inflammatory disease. J Cell Physiol 2004;201:167–80.
   PubMed Web of Science ®Google Scholar
• Rittner HL, Labuz D, Schaefer M, et al. Pain control by CXCR2 ligands through Ca2+-regulated release of opioid peptides from polymorphonuclear cells. Faseb J 2006;20:2627–9.
   PubMed Web of Science ®Google Scholar
• Walker JS. Anti-inflammatory effects of opioids. Adv Exp Med Biol 2003;521:148–60.
   PubMed Web of Science ®Google Scholar
• Czapla MA, Gozal D, Alea OA, et al. Differential cardiorespiratory effects of endomorphin 1, endomorphin 2, DAMGO, and morphine. Am J Respir Crit Care Med 2000;162:994–9.
   PubMed Web of Science ®Google Scholar
• Wilson AM, Soignier RD, Zadina JE, et al. Dissociation of analgesic and rewarding effects of endomorphin-1 in rats. Peptides 2000;21:1871–4.
   PubMed Web of Science ®Google Scholar
• Babst R, Bongiorno L, Marini M, et al. Trauma decreases leucine enkephalin hydrolysis in human plasma. J Pharmacol Exp Ther 1999;288:766–73.
   PubMed Web of Science ®Google Scholar
• Roques BP. Novel approaches to targeting neuropeptide systems. Trends Pharmacol Sci 2000;21:475–83.
   PubMed Web of Science ®Google Scholar
• Schäfer M, Carter L, Stein C. Interleukin 1 beta and corticotropin-releasing factor inhibit pain by releasing opioids from immune cells in inflamed tissue. Proc Natl Acad Sci USA 1994;91:4219–23.
   PubMed Web of Science ®Google Scholar
• Eisenach JC, Carpenter R, Curry R. Analgesia from a peripherally active kappa-opioid receptor agonist in patients with chronic pancreatitis. Pain 2003;101:89–95.
   PubMed Web of Science ®Google Scholar
• Stein C, Comisel K, Haimerl E, et al. Analgesic effect of intraarticular morphine after arthroscopic knee surgery. N Engl J Med 1991;325:1123–6.
   PubMed Web of Science ®Google Scholar
• Stein C, Küchler S. Targeting inflammation and wound healing by opioids. Trends Pharmacol Sci 2013;34:303–12.
   PubMed Web of Science ®Google Scholar
• Tegeder I, Meier S, Burian M, et al. Peripheral opioid analgesia in experimental human pain models. Brain 2003;126:1092–102.
   PubMed Web of Science ®Google Scholar
• Guan Y, Johanek LM, Hartke TV, et al. Peripherally acting mu-opioid receptor agonist attenuates neuropathic pain in rats after L5 spinal nerve injury. Pain 2008;138:318–29.
   PubMed Web of Science ®Google Scholar
• Mambretti EM, Kistner K, Mayer S, et al. Functional and structural characterization of axonal opioid receptors as targets for analgesia. Mol Pain 2016;12. DOI:10.1177/1744806916628734
   PubMed Web of Science ®Google Scholar
• Moon SW, Park EH, Suh HR, et al. The contribution of activated peripheral kappa opioid receptors (KORs) in the inflamed knee joint to anti-nociception. Brain Res 2016;1648:11–8.
   PubMed Web of Science ®Google Scholar
• Vanderah TW, Largent-Milnes T, Lai J, et al. amino acid tetrapeptides produce potent antinociception by selectively acting at peripheral kappa-opioid receptors. Eur J Pharmacol 2008;583:62–72.
   PubMed Web of Science ®Google Scholar
• Jeanjean AP, Moussaoui SM, Maloteaux JM, Laduron PM. Interleukin-1 beta induces long-term increase of axonally transported opiate receptors and substance P. Neuroscience 1995;68:151–7.
   PubMed Web of Science ®Google Scholar
• Schiller PW. Bi- or multifunctional opioid peptide drugs. Life Sci 2010;86:598–603.
   PubMed Web of Science ®Google Scholar
• Davis MP. Opioid receptor targeting ligands for pain management: a review and update. Expert Opin Drug Discov 2010;5:1007–22.
   PubMed Web of Science ®Google Scholar
• Varamini P, Toth I. Lipid- and sugar-modified endomorphins: novel targets for the treatment of neuropathic pain. Front Pharmacol 2013;4:155–62.
   PubMed Web of Science ®Google Scholar
• Zadina JE, Nilges MR, Morgenweck J, et al. Endomorphin analog analgesics with reduced abuse liability, respiratory depression, motor impairment, tolerance, and glial activation relative to morphine. Neuropharmacology 2016;105:215–27.
   PubMed Web of Science ®Google Scholar
• Perlikowska R, Malfacini D, Cerlesi MC, et al. Pharmacological characterization of endomorphin-2-based cyclic pentapeptides with methylated phenylalanine residues. Peptides 2014;55:145–50.
   PubMed Web of Science ®Google Scholar
• Piekielna J, Perlikowska R, do-Rego JC, et al. Synthesis of mixed opioid affinity cyclic endomorphin-2 analogues with fluorinated phenylalanines. ACS Med Chem Lett 2015;6:579–83.
   PubMed Web of Science ®Google Scholar
• Di L, Kerns EH, Fan K, et al. High throughput artificial membrane permeability assay for blood-brain barrier. Eur J Med Chem 2003;38:223–32.
   PubMed Web of Science ®Google Scholar
• Kilkenny C, Browne W, Cuthill IC, et al. Animal research: reporting in vivo experiments: the ARRIVE guidelines. Br J Pharmacol 2010;160:1577–9.
   PubMed Web of Science ®Google Scholar
• Perlikowska R, do-Rego JC, Cravezic A, et al. Synthesis and biological evaluation of cyclic endomorphin-2 analogs. Peptides 2010;31:339–45.
   PubMed Web of Science ®Google Scholar
• Litchfield JT Jr, Wilcox F. A simplified method of evaluating dose-effect experiments. J Pharmacol Exp Ther 1949;96:99–113.
   PubMed Web of Science ®Google Scholar
• Zielińska M, Lewandowska U, Podsędek A, et al. Orally available extract from Brassica oleracea var. capitata rubra attenuates experimental colitis in mouse models of inflammatory bowel diseases. J Funct Foods 2015;17:587–99.
   Web of Science ®Google Scholar
• Perlikowska R, Piekielna J, Mazur M, et al. Antinociceptive and antidepressant-like action of endomorphin-2 analogs with proline surrogates in position 2. Bioorg Med Chem 2014;22:4803–9.
   PubMed Web of Science ®Google Scholar
• Lesniak A, Lipkowski AW. Opioid peptides in peripheral pain control. Acta Neurobiol Exp 2011;71:129–38.
   PubMed Web of Science ®Google Scholar
• Sehgal N, Smith HS, Manchikanti L. Peripherally acting opioids and clinical implications for pain control. Pain Physician 2011;14:249–58.
   PubMed Web of Science ®Google Scholar
• Janecka A, Staniszewska R, Gach K, Fichna J. Enzymatic degradation of endomorphins. Peptides 2008;29:2066–73.
   PubMed Web of Science ®Google Scholar
• Di L, Kerns EH, Bezar IF, et al. Comparison of blood-brain barrier permeability assays: in situ brain perfusion, MDR1-MDCKII and it was stated there that PAMPA PAMPA-BBB. J Pharm Sci 2009;98:1980–91.
   PubMed Web of Science ®Google Scholar
• Weltrowska G, Nguyen TM, Chung NN, et al. A cyclic tetrapeptide (“cyclodal”) and its mirror-image isomer are both high-affinity μ opioid receptor antagonists. J Med Chem 2016;59:9243–54.
   PubMed Web of Science ®Google Scholar