Structure-activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH2 at the human melanocortin-1 and -4 receptors: Histidine substitution

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 1, 2003, Pages 133-137

  Cheung, Adrian Wai Hing ^a   Danho, Waleed ^a   Swistok, Joseph ^a   Qi, Lida ^a   Kurylko, Grazyna ^a   Rowan, Karen ^a   Yeon, Mitch ^a   Franco, Lucia ^a   Chu, Xin Jie ^a   Chen, Li ^a   Yagaloff, Keith ^a  

^a HOFFMANN LA ROCHE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYLHISTIDYL DEXTRO PHENYLALANYLARGINYLTRYPTOPHYLGLYCINAMIDE; HISTIDINE; MELANOCORTIN 1 RECEPTOR; MELANOCORTIN 4 RECEPTOR; PENTAPEPTIDE; UNCLASSIFIED DRUG; BU HIS(6) PHE(7) ARG(8) TRP(9) GLY(10) NH(2); BU-HIS(6)-PHE(7)-ARG(8)-TRP(9)-GLY(10)-NH(2); CORTICOTROPIN RECEPTOR; CYCLIC AMP; MELANOCORTIN RECEPTOR; OLIGOPEPTIDE;

AMINO ACID SUBSTITUTION; ARTICLE; BINDING ASSAY; DRUG MECHANISM; DRUG SELECTIVITY; PROTEIN ANALYSIS; AMINO ACID SEQUENCE; BIOSYNTHESIS; DRUG POTENTIATION; HUMAN; METABOLISM; PROTEIN BINDING; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; CYCLIC AMP; HISTIDINE; HUMANS; OLIGOPEPTIDES; PROTEIN BINDING; RECEPTOR, MELANOCORTIN, TYPE 4; RECEPTORS, CORTICOTROPIN; RECEPTORS, MELANOCORTIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 17444451027     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00830-2     Document Type: Article

References (24)

1. Cone, R. D., Ed. The Melanocortin Receptors; Humana: Totowa, 2000.
2. MacNeil D.J., Howard A.D., Guan X., Fong T.M., Nargund R.P., Bednarek M.A., Goulet M.T., Weinberg D.H., Strack A.M., Marsh D.J., Chen H.Y., Shen C.-P., Chen A.S., Rosenblum C.I., MacNeil T., Tota M., MacIntyre E.D., Van der Ploeg L.H.T. Eur. J. Pharmacol. 440:2002;141.
3. Cheung A.W.-H., Danho W., Swistok J., Qi L., Kurylko G., Franco L., Yagaloff K., Chen L. Bioorg. Med. Chem. Lett. 12:2002;2407.
4. (a) Chen, L.; Cheung, A. W.-H.; Chu, X.-J.; Danho, W.; Swistok, J.; Yagaloff, K. A. WO 0174844, 2001; CAN 135:304143.
5. (b) Chen, L.; Cheung, A. W.-H.; Chu, X.-J.; Danho, W.; Swistok, J.; Wang, Y.; Yagaloff, K. A. WO 0218437, 2002; CAN 136:217052.
6. Obrecht D., Spiegler C., Schonholzer P., Muller K., Heimgartner H., Stierli F. Helv. Chim. Acta. 75:1992;1666.
7. (a) Burckhalter J.H., Campbell J.R. J. Org. Chem. 26:1961;4232.
8. (b) Tschaen D.M., Abramson L., Cai D., Desmond R., Dolling U.-H., Frey L., Karady S., Shi Y.-J., Verhoeven T.R. J. Org. Chem. 60:1995;4324.
9. (a) Stjernlof P., Elebring T., Andersson B., Svensson A., Svensson K., Ekman A., Carlsson A., Wikstrom H. Eur. J. Med. Chem. 28:1993;693.
10. (b) Rosowsky A., Battaglia J., Chen K.K.N., Modest E.J. J. Org. Chem. 33:1968;4288.
11. (a) McKervey M.A., Tuladhar S.M., Twohig M.F. J. Chem. Soc., Chem. Commun. 1984;129.
12. (b) Kennedy M., McKervey M.A., Maguire A.R., Tuladhar S.M., Twohig M.F. J. Chem. Soc., Perkin Trans. 1. 1990;1047.
13. (c) Cordi A.A., Lacoste J.-M., Hennig P. J. Chem. Soc., Perkin Trans. 1. 1993;3.
14. 3OH, 10-15°C; Step 3: KOH, ethanol, water, reflux; overall yield for three steps: 50% for 2-Et and 64% for 2-iPr].
15. (a) Cornforth J.W., Cornforth R.H., Robinson R. J. Chem. Soc. 1942;689.
16. (b) Manitto P., Speranza G., Monti D., Fontana G., Panosetti E. Tetrahedron. 51:1995;11531.
17. Benoit S.C., Schwartz M.W., Lachey J.L., Hagan M.M., Rushing P.A., Blake K.A., Yagaloff K.A., Kurylko G., Franco L., Danho W., Seeley R.J. J. Neurosci. 20:2000;3442.
18. Sawyer T.K., Sanfillippo P.J., Hruby V.J., Engel M.H., Heward C.B., Burnett J.B., Hadley M.E. Proc. Natl. Acad. Sci. U.S.A. 77:1980;5754.
19. Yang Y., Fong T.M., Dickinson C.J., Mao C., Li J., Tota M.R., Mosley R., Van der Ploeg L.H.T., Gantz I. Biochemistry. 39:2000;14900.
20. Atc related non-coding amino acids used in our study include the following:
21. 3CN (buffer B) with UV detection at 280 nm.
22. After our discovery that histidine surrogates such as 5-BrAtc could give rise to excellent hMC4R selectivity, Hruby et al. independently proposed that "the position 6 of the synthetic melanocortin ligands is important for enhancing potency and selectivity at MC3 and MC4 melanocortin receptors". Hruby, V. J.; Grieco, P.; Balse, P.; Han, G.; Weinberg, D.; McNeil, T. Abstract of Papers, 217th National Meeting of the American Chemical Society, Anaheim, CA; American Chemical Society: Washington, DC, 1999; Abstract MEDI-231.
23. A portion of this work was previously presented. Danho, W.; Swistok, J.; Cheung, A.; Chu, X-J.; Wang, Y.; Chen, L.; Bartkovitz, D.; Gore, V.; Qi, L.; Fry, D.; Greeley, D.; Sun, H.; Guenot, J.; Franco, L.; Kurylko, G.; Rumennik, L.; Yagaloff, K. Abstracts of Papers, 2nd International/17th American Peptide Symposium; Kluwer Academic: The Netherlands, 2001; p 701.
24. 2 tetrapeptide template and the resulting peptides were characterized in mouse melanocortin receptors. Holder J.R., Bauzo R.M., Xiang Z., Haskell-Luevano C. J. Med. Chem. 45:2002;2801.