Glycodermorphins: Opioid peptides with potent and prolonged analgesic activity and enhanced blood-brain barrier penetration

British Journal of Pharmacology

Volumn 124, Issue 7, 1998, Pages 1516-1522

  Negri, Lucia ^a   Lattanzi, Roberta ^a   Tabacco, Fabio ^a   Scolaro, Barbara ^b   Rocchi, Raniero ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

CNS permeability; Enzyme degradation; Peptide glycosylation; Specialized transport systems

Indexed keywords

DERMORPHIN; GLUCOSE; GLUCOSE TRANSPORTER; HYDROXYL GROUP; MU OPIATE RECEPTOR; OPIATE PEPTIDE;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLOOD BRAIN BARRIER; CONSTIPATION; CONTROLLED STUDY; DRUG ACETYLATION; DRUG PENETRATION; DRUG POTENCY; DRUG STABILITY; DRUG SYNTHESIS; INTRACEREBROVENTRICULAR DRUG ADMINISTRATION; MALE; NOCICEPTION; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR AFFINITY; SUBCUTANEOUS DRUG ADMINISTRATION;

AMINO ACID SEQUENCE; ANALGESICS, OPIOID; ANIMALS; BLOOD-BRAIN BARRIER; COLON; GASTROINTESTINAL MOTILITY; GUINEA PIGS; HALF-LIFE; ILEUM; MALE; MICE; NALOXONE; OPIOID PEPTIDES; RECEPTORS, OPIOID;

EID: 0031876658     PISSN: 00071188     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.bjp.0701971     Document Type: Article

References (26)

1. AUDUS, K.L., CHIKHALE, P.J., MILLER, D.W., THOMPSON, S.E. & BORCHARDT, R.T. (1992). Brain uptake of drugs: The influence of chemical and biological factors. Adv. Drug Res., 23, 3-64.
2. BANKS, W.A. & KASTIN, A.J. (1990). Peptide transport systems for opiates across the blood-brain barrier. Am. J. Physiol., 259, E1-E10.
3. BANKS, W.A. & KASTIN, A.J. (1994). Opposite direction of transport across the blood-brain barrier for Tyr-MIF-1 and MIF-1: comparison with morphine. Peptides, 15, 23-29.
4. BROCCARDO, M., IMPROTA, G., NARGI, M. & MELCHIORRI, P. (1982). Effects of dermorphin on gastrointestinal transit in rats. Reg. Pept., 4, 91-96.
5. D'AMOUR, F.E. & SMITH, D.L. (1941). Method for determining loss of pain sensation. J. Pharmacol. Exp. Ther., 72, 74-79.
6. DE LUCA. A. & COUPAR, I.M. (1996). Insights into opioid action in the intestinal tract. Pharmacol. Ther., 69, 103-115.
7. FILIRA, F., BIONDI, L., CAVAGGION, F., SCOLARO, B. & ROCCHI, R. (1990). Synthesis of O-glycosylated tuftsin by utilizing threonine derivatives containing an unprotected monosaccharide moiety. Int. J. Pept. Protein Res., 36, 86-96.
8. FIORI, A., CARDELLI, P., NEGRI, L., SAVI, M.R. & STROM, R. (1997). Deltorphin transport across the blood brain barrier. Proc. Natl. Acad. Sci. U.S.A., 94, 9469-9474.
9. KESSLER, H., WITTMANN, V., KOCK, M. & KOTTENHAHN, M. (1992). Synthesis of C-Glycopeptides via Free Radical Addition of Glycosyl Bromides to Dehydroalanine Derivatives. Angew. Chem. Int. Ed. Engl., 31, 902-904.
10. MANARA, L. & BIANCHETTI, A. (1985). The central and peripheral influences of opioids on gastrointestinal propulsion. Annu. Rev. Pharmacol. Toxicol., 25, 249-273.
11. MELCHIORRI, P., NEGRI, L., FALCONIERI ERSPAMER, G., SEVERINI, C., CORSI, R., SOAJE, M., ERSPAMER, V. & BARRA, D. (1991). Structure-activity relationships of the δ-opioid selective agonists, deltorphins. Eur. J. Pharmac., 195, 201-207.
12. MUNSON, P.J. & RODBARD, D. (1980). Ligand: a versatile computerized approach for the characterization of ligand binding systems. Anal. Biochem., 107, 220-224.
13. NFGRI, L. & IMPROTA, G. (1984). Distribution and metabolism of dermorphin in rats. Pharm. Res. Comm., 16, 1183-1191.
14. 7]dermorphin, a naturally occurring peptide with high affinity for μ-opioid receptors, produces antinociception by peripheral administration. Br. J. Pharmacol., 114, 57-66.
15. PARDRIDGE, W.M. (1991). Peptide drug delivery to the brain. New York: Raven Press.
16. PARDRIDGE, W.M. & MIETUS, L.J. (1981). Enkephalin and blood-brain barrier: Studies of binding and degradation in isolated brain microvassels. Endocrinology, 109, 1138-1143.
17. PARDRIDGE, W.M., TRIGUERO, D., YANG, J. & CANCILLA, P.A. (1990). Comparison of "in vitro" and "in vivo" models of drug transcytosis through the blood-brain barrier. J. Pharmacol. Exp. Ther., 253, 884-951.
18. PAXINOS, G. & WATSON, C. (1982). The rat brain in stereotaxis coordinates. New York: Academic Press.
19. PEDROSE, E., GRANDAS, A., DE LA HERAS, X., ERITJA, R. & GIRALT, E. (1986). Diketopiperazine Formation in Solid Phase Peptide Synthesis Using p-Alkoxybenzyl Ester Resins and F-moc Amino Acids. Tetrahedron Letters, 27, 743-746.
20. POLT, R., PORRECA, F., SZABÒ, L.Z, BILSKY, E.J., DAVIS, P., ABBRUSCATO, T.J., DAVI, T.P., HORVATH, R., YAMAMURA, H.I. & HRUBY, V.J. (1994). Glycopeptide enkephalin analogues produce analgesia in mice: evidence for penetration of the blood-brain barrier. Proc. Natl. Acad. Sci. U.S.A., 91, 7114-7118.
21. RAFFA, R.B. & JACOBY, H.I. (1990). Effect of the Phe-D-Met-Arg-Phe-NH2-related peptides on mouse colonic propulsive motility: a structure-activity relationship study. J. Pharm. Exp. Ther., 254, 809-814.
22. TALLARIDA, R.J. & MURRAY, R.B. (1986). Manual of Pharmacological Calculation. 2nd ed. New York: Springer-Verlag.
23. TERASAKI, T., ICHIHIRAI, K., SATO, H., KANG, Y.S. & TSUJI, A. (1989). Absorptive-mediated endocitosis of a dynorphin like analgesic peptide, E-2078, into the blood-brain barrier. J. Pharmacol. Exp. Ther., 251, 351-357.
24. THOMAS, S.A., ABBRUSCATO, T.J., HAU, V.S., GILLESPIE, T.J., ZSIGO, J., HRUBY, V.J. & DAVIS, T.P. (1997). Structure-activity relationships of a series of [D-Ala2]deltorphin I and II analogues; in vitro blood-brain barrier permeability and stability. J. Pharmacol. Exp. Ther., 281, 817-825.
25. TRIGUERO, D., BUCIAK, J.B., YANG, J. & PARDRIDGE, W.M. (1989). Blood-brain barrier transport of cationized immunoglobulin G: enhanced delivery compared to native protein. Proc. Natl. Acad. Sci. U.S.A., 86, 4761-4765.
26. WILLIAMS, S.A., ABBRUSCATO, T.J., HRUBY, V.J. & DAVIS, T.P. (1996). Passage of a delta-opioid receptor selective enkephalin, [D-Penicillamine2,5]enkephalin, across the blood-brain and the blood-cerebrospinal fluid barriers. J. Neurochem., 66, 1289-1299.