Novel side-chain glucosylated and adamantylated [Asp2/Glu 2]enkephalin analogs: Synthesis and in vitro growth inhibition of human tumor cells

Chemical Biology and Drug Design

Volumn 73, Issue 2, 2009, Pages 253-257

  Horvat, Štefica ^a   Kralj, Marijeta ^a   Perc, Milica ^a   Jerić, Ivanka ^a   Varga Defterdarović, Lidija ^a   Jakas, Andreja ^a   Roščić, Maja ^a   Šuman, Lidija ^a   Gredičak, Matija ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Analogs; In vitro antiproliferative activity; Leu enkephalin; Met enkephalin; Opioid peptides; Peptide synthesis

Indexed keywords

ADAMANTANE DERIVATIVE; ENKEPHALIN DERIVATIVE; ENKEPHALIN[2 ASPARTATE 2 GLUTAMINE] DERIVATIVE; METENKEPHALIN; TYROSYL DEXTRO GLUTAMYL (1 ADAMANTYLAMINE)GLYCYLPHENYLALANYLMETHIONINE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; DRUG EFFECT; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

AMINO ACID SEQUENCE; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; ENKEPHALINS; HELA CELLS; HUMANS; INHIBITORY CONCENTRATION 50;

EID: 58849135839     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2008.00763.x     Document Type: Article

References (21)

1. Bodnar R.J. (2007) Endogenous opiates and behavior: 2006. Peptides 28 : 2435 2513.
2. Hughes J., Smith T.W., Kosterlitz H.W., Fothergill L.A., Morgan B.A., Morris H.R. (1975) Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature 258 : 577 579.
3. Cheng F., McLaughlin P.J., Verderame M.F., Zagon I.S. (2008) The OGF-OGFr axis utilizes the p21 pathway to restrict progression of human pancreatic cancer. Mol Cancer 7 : 5 16.
4. Zagon I.S., Verderame M.F., McLaughlin P.J. (2002) The biology of the opioid growth factor receptor (OGFr). Brain Res Rev 38 : 351 376.
5. Cudic P., Stawikowski M. (2007) Pseudopeptide synthesis via Fmoc solid-phase synthetic methodology. Mini Rev Org Chem 4 : 268 280.
6. Aina O.H., Liu R.W., Sutcliffe J.L., Marik J., Pan C.X., Lam K.S. (2007) From combinatorial chemistry to cancer-targeting peptides. Mol Pharm 4 : 631 651.
7. Horvat Š., Mlinarić-Majerski K., Glavaš-Obrovac Lj., Jakas A., Veljković J., Marczi S., Kragol G., Rošč ić M., Matković M., Milostić-Srb A. (2006) Tumor-cell-targeted methionine-enkephalin analogues containing unnatural amino acids: Design, synthesis, and in vitro antitumor activity. J Med Chem 49 : 3136 3142.
8. Koda Y., Del Borgo M., Wessling S.T., Lazarus L.H., Okada Y., Toth I., Blanchfield J.T. (2008) Synthesis and in vitro evaluation of a library of modified endomorphin 1 peptides. Bioorg Med Chem 16 : 6286 6296.
9. 7)-dermorphin analogues: synthesis, biological activity and conformational investigations. J Pept Sci 13 : 179 189.
10. Lowery J.J., Yeomans L., Keyari C.M., Davis P., Porreca F., Knapp B.I., Bidlack J.M., Bilsky E.J., Polt R. (2007) Glycosylation improves the central effects of DAMGO. Chem Biol Drug Des 69 : 41 47.
11. Cohen-Anisfeld S.T., Lansbury P.T. (1993) A practical, convergent method for glycopeptide synthesis. J Am Chem Soc 115 : 10531 10537.
12. Taylor C.M. (1998) Glycopeptide and glycoproteins: Focus on the glycosidic linkage. Tetrahedron 54 : 11317 11362.
13. Davis B.G. (2002) Synthesis of glycoproteins. Chem Rev 102 : 579 602.
14. Lauer J.L., Fields C.G., Fields G.B. (1994) Sequence dependence of aspartimide formation during 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis. Lett Pept Sci 1 : 197 205.
15. Kaiser T., Nicholson G., Kohlbau H., Voelter W. (1996) Racemization studies of Fmoc-Cys(Trt)-OH during stepwise Fmoc-solid phase peptide synthesis. Tetrahedron Lett 37 : 1187 1190.
16. Marfey P. (1984) Determination of D-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res Commun 49 : 591 596.
17. Hranjec M., Kralj M., Piantanida I., Sedić M., Šuman L., Pavelić K., Karminski-Zamola G. (2007) Novel cyano- and amidino-substituted derivatives of styryl-2-benzimidazoles and benzimidazo[1,2-a]quinolines. Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation, part 3. J Med Chem 50 : 5696 5711.
18. Zagon I.S., Verderame M.F., McLaughlin P.J. (2003) The expression and function of the OGF-OGFr axis - a tonically active negative regulator of growth - in COS cells. Neuropeptides 37 : 290 297.
19. McLaughlin P.J., Zagon I.S., Skitzki J. (1999) Human neuroblastoma cell growth in tissue culture is regulated by opioid growth factor. Int J Oncol 14 : 373 380.
20. Maneckjee R., Biswas R., Vonderhaar B.K. (1990) Binding of opioids to human MCF-7 breast cancer cells and their effects on growth. Cancer Res 50 : 2234 2238.
21. Chatikhine W.A., Chevrier A., Chauzy C., Duval C., d'Anjou J., Girard N., Delpech B. (1994) Expression of opioid peptides in cells and stroma of human breast cancer and adenofibromas. Cancer Lett 77 : 51 56.