Transport Characteristics of Endomorphin-2 Analogues in Brain Capillary Endothelial Cells

Chemical Biology and Drug Design

Volumn 79, Issue 4, 2012, Pages 507-513

  Mallareddy, Jayapal Reddy ^a   Tóth, Géza ^a   Fazakas, Csilla ^a   Molnár, Judit ^a   Nagyoszi, Péter ^a   Lipkowski, Andrzej W ^b   Krizbai, István A ^a   Wilhelm, Imola ^a  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^b MOSSAKOWSKI MEDICAL RESEARCH CENTRE   (Poland)

Author keywords

Analogues; Blood brain barrier; Cerebral endothelial cell; Endomorphin; Influx; Opioid peptides; Transport

Indexed keywords

ENDOMORPHIN 2;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BLOOD BRAIN BARRIER; BRAIN CAPILLARY; BRAIN MEMBRANE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYTOTOXICITY; ENDOTHELIUM CELL; HALF LIFE TIME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; LIPOPHILICITY; MEMBRANE PERMEABILITY; NEWBORN; NONHUMAN; PARTITION COEFFICIENT; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN FUNCTION; PROTEIN STRUCTURE; PROTEIN TRANSPORT; RAT;

ANALGESICS, OPIOID; ANIMALS; BLOOD-BRAIN BARRIER; BRAIN; CELLS, CULTURED; ENDOTHELIAL CELLS; OLIGOPEPTIDES; PERMEABILITY; RATS;

EID: 84858797643     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01306.x     Document Type: Article

References (29)

1. Janecka A., Fichna T., Janecki J. (2004) Opioid receptors and their ligands. Curr Top Med Chem;4:1-17.
2. Minnis J.G., Patierno S., Kohlmeier S.E., Brecha N.C., Tonini M., Sternini C. (2003) Ligand-induced mu opioid receptor endocytosis and recycling in enteric neurons. Neuroscience;119:33-42.
3. Wilhelm I., Fazakas C., Krizbai I.A. (2011) In vitro models of the blood-brain barrier. Acta Neurobiol Exp (Wars);71:113-128.
4. Abbott N.J., Rönnbäck L., Hansson E. (2006) Astrocyte-endothelial interactions at the blood-brain barrier. Nat Rev Neurosci;7:41-53.
5. Tömböly C., Péter A., Tóth G. (2002) In vitro quantitative study of the degradation of endomorphins. Peptides;23:1571-1578.
6. Liu H.M., Liu X.F., Yao J.L., Wang C.L., Yu Y., Wang R. (2006) Utilization of combined chemical modifications to enhance the blood-brain barrier permeability and pharmacological activity of endomorphin-1. J Pharmacol Exp Ther;319:308-316.
7. Wang C.L., Guo C., Wang Y.Q., Zhou Y., Li Q., Ni J.M., Wang R. (2011) Synthesis and antinociceptive effects of endomorphin-1 analogs with C-terminal linked by oligoarginine. Peptides;32:293-299.
8. Hau V.S., Huber J.D., Campos C.R., Lipkowski A.W., Misicka A., Davis T.P. (2002) Effect of guanidino modification and proline substitution on the in vitro stability and blood-brain barrier permeability of endomorphin II. J Pharm Sci;91:2140-2149.
9. Keresztes A., Tóth G., Fülöp F., Szucs M. (2006) Synthesis, radiolabeling and receptor binding of [3H][(1S, 2R)ACPC2]endomorphin-2. Peptides;27:3315-3321.
10. Keresztes A., Birkás E., Páhi A., Tóth G., Bakota L., Gulya K., Szücs M. (2011) Pharmacology of a new tritiated endomorphin-2 analog containing the proline mimetic cis-2-aminocyclohexanecarboxylic acid. Peptides;32:722-728.
11. Mallareddy J.R., Borics A., Keresztes A., Kövér K.E., Tourwé D., Tóth G. (2011) Design, synthesis, pharmacological evaluation, and structure-activity study of novel endomorphin analogues with multiple structural modifications. J Med Chem;54:1462-1472.
12. Kaiser E., Colescott R.L., Bossinger C.D., Cook P.I. (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal Biochem;34:595-598.
13. Tömböly C., Dixit R., Lengyel I., Borsodi A., Toth G. (2001) Preparation of specifically tritiated endomorphins. J Label Comp Radiopharm;44:355-363.
14. Tömböly Cs., Tóth G. (2001) Tritiated endomorphins: exclusive ligands for the research of μ opioid system. (7th International Symposium on The Synthesis and Applications of Isotopes and Isotopically Labelled Compounds, Dresden, Germany, 2000.) In: Pleiss U., Voges R., editors. Synthesis and Applications of Isotopically Labelled Compounds 7. Chichester; John Wiley & Sons Ltd., p. 126-129.
15. Szemenyei E., Tóth G. (2007) Tritium labelling and degradation studies of Dmt1-endomorphin 2. J Label Comp Radiopharm;50:1148-1152.
16. Tóth G., Szemenyei E., Keresztes A., Fülöp F. (2005) Tritium labeling of novel endomorphin analogues containing unnatural α-and β-amino acids. Proceedings of the 5th International Conference on Isotopes, Brussels (Belgium), 295-299.
17. Wilhelm I., Farkas A.E., Nagyoszi P., Váró G., Bálint Z., Végh G.A., Couraud P.O., Romero I.A., Weksler B., Krizbai I.A. (2007) Regulation of cerebral endothelial cell morphology by extracellular calcium. Phys Med Biol;52:6261-6274.
18. Hutamekalin P., Farkas A.E., Orbók A., Wilhelm I., Nagyoszi P., Veszelka S., Deli M.A., Buzás K., Hunyadi-Gulyás E., Medzihradszky K.F., Meksuriyen D., Krizbai I.A. (2008) Effect of nicotine and polyaromatic hydrocarbons on cerebral endothelial cells. Cell Biol Int;32:198-209.
19. Fazakas C., Wilhelm I., Nagyoszi P., Farkas A.E., Haskó J., Molnár J., Bauer H., Bauer H.C., Ayaydin F., Dung N.T., Siklós L., Krizbai I.A. (2011) Transmigration of melanoma cells through the blood-brain barrier: role of endothelial tight junctions and melanoma-released serine proteases. PLoS One;6:e20758.
20. Sziráki I., Erdo F., Beéry E., Molnár P.M., Fazakas C., Wilhelm I., Makai I., Kis E., Herédi-Szabó K., Abonyi T., Krizbai I., Tóth G.K., Krajcsi P. (2011) Quinidine as an ABCB1 probe for testing drug interactions at the blood-brain barrier: an in vitro in vivo correlation study. J Biomol Screen;16:886-894.
21. Keresztes A., Borics A., Tóth G. (2010) Recent advances in endomorphin engineering. ChemMedChem;5:1176-1196.
22. Tóth G., Keresztes A., Tömböly C., Péter A., Fülöp F., Tourwé D., Navratilova E., Varga É., Roeske W.R., Yamamura H.I., Szücs M., Borsodi A. (2004) New endomorphin analogs with μ-agonist and δ-antagonist properties. Pure Appl Chem;76:951-957.
23. Keresztes A., Szucs M., Borics A., Kövér K.E., Forró E., Fülöp F., Tömböly C., Péter A., Páhi A., Fábián G., Murányi M., Tóth G. (2008) New endomorphin analogues containing alicyclic beta-amino acids: influence on bioactive conformation and pharmacological profile. J Med Chem;51:4270-4279.
24. Kastin A.J., Fasold M.B., Smith R.R., Horner K.A., Zadina J.E. (2011) Saturable brain-to-blood transport of endomorphins. Exp Brain Res;139:70-75.
25. Somogyvari-Vigh A., Kastin A.J., Liao J., Zadina J.E., Pan W. (2004) Endomorphins exit the brain by a saturable efflux system at the basolateral surface of cerebral endothelial cells. Exp Brain Res;156:224-230.
26. Liu W.X., Wang R. (2011) Endomorphins: potential roles and therapeutic indications in the development of opioid peptide analgesic drugs. Med Res Rev; in press.
27. Van Dorpe S., Adriaens A., Polis I., Peremans K., Van Bocxlaer J., De Spiegeleer B. (2010) Analytical characterization and comparison of the blood-brain barrier permeability of eight opioid peptides. Peptides;31:1390-1399.
28. Banks W.A., Kastin A.J. (1985) Peptides and the blood-brain barrier: lipophilicity as a predictor of permeability. Brain Res Bull;15:287-292.
29. Ecker G.F., Noe C.R. (2004) In silico prediction models for blood-brain barrier permeation. Curr Med Chem;11:1617-1628.