| Title | Gonadotropin-releasing hormone (GnRH) analogues containing Tyr(OMe) at position 5 | |
| Authors | M. Keramida1, J.M Matsoukas1, G. Agelis1, D. Panagiotopoulos1, J. Cladas2, H.L.S. Maia3, R. Yamdagni4, Q. Wu4, D. Pati5, G.J. Moore6 and H.R. Habibi5
1. Department of Chemistry, University of Patras, Patras, Greece 2. Thalassa Fish Hatchery, Patras, Greece 3. Department of Chemistry, University of Minho, Gualtar, P-4700 Braga, Portugal 4. Department of Chemistry, University of Calgary, Calgary, Alberta, Canada 5. Department of Biological Sciences University of Calgary, Calgary, Alberta, Canada 6. Department of Pharmacology and Therapeutics, University of Calgary, Calgary, Alberta, Canada |
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| Citation | Keramida, M., Matsoukas, J.M., Agelis, G., Panagiotopoulos, D., Cladas, J., et al.: Gonadotropin-releasing hormone (GnRH) analogues containing Tyr(OMe) at position 5, Epitheorese Klin. Farmakol. Farmakokinet. 9(2-3): 67-69 (1995) | |
| Publication Date | 1995 | |
| Full Text Language | English | |
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| Keywords | Conformational analysis, NMR spectroscopy, GnRH analogues. | |
| Other Terms | review article | |
| Summary | Peptide analogues of the hypothalamic hormone GnRH (Gonadotropin Releasing Hormone), altered at positions 5 (Tyr-OMe), 6(D-Glu), 9(Aze) and 10 (NHEt, NHCH2CH2OH, Glyamide) were synthesized by Fmoc solid phase methodology using the acid sensitive 2-chlorotrityl resin as solid support. The synthesized analogues were purified by reverse phase HPLC and tested for biological activity in terms of pituitary gonadotropin releasing in vivo and in vitro. Relative potencies were estimated using cultured pituitary tissues in vitro, rat pituitary GnRH receptors assay and ovulation in vivo. [Tyr(OMe)5, Aze9– NHEt]GnRH and Tyr(OMe)5, D-GIu6, Aze9-NHEt]GnRH were found to be effective in terms of inducing ovulation at 50 μg/Kg in seabass. The conformational properties of GnRH in dimethylsulfoxide-d6 were investigated by Nuclear Overhauser Effect (NOE) enhancement studies. Assignment of all backbone and side-chain protons was possible by combining information from intraresidue NOE studies with two-dimensional correlated spectroscopy (COSY) studies. Saturation of distinct proton resonances of the three aromatic residues Tyr, His, Trp in dear areas of the NMR spectrum resulted in interresidue enhancements of aromatic resonances indicating proximity of the three aromatic rings. | |
| References | 1. Karten, M., Rivier, J.: Endocrine Reviews 7: 44-46 (1986)
2. Coy, D, Coy, Schally, E.: J. Med. Chem. 16: 827-829 (1973) 3. Conn, P.M., Crowley,Jr., W.F.: N. Engl. J. Med. 324: 93-103 (1990) 4. Matsoukas, J.M., Hondrelis, J., Keramida, M., Mavromoustakos, T., Makriyannis, A., Yamdagni, R., Wu, Q., Moore, G.J.: J. Biol. Chem. 269: 5303-5312 (1994) 5. Matsoukas, J.M., Agelis, G., Hondrelis, J., Yamdagni, R., Wu, Q., Ganter, R., Smith, J., Moore, D., Moore, G.J.: J. Med. Chem. 36: 904-911 (1993) 6. Barlos, Κ.; Gatos, D.; Hondrelis, J.; Matsoukas, J. M., Moore, G. J.; Schafer, W., Sotiriou, P.: Liebigs Ann. Chem.: 951-955 (1989) 7. Habibi, H.R., Peter, R.E, Nahorniak, C.S., Milton, R.C., Millar, R.P.: Reg. Peptides 37: 271-284 (1992) 8. Habibi, H.R., Marchant, T.A., Nahorniak, C.S., Van Der Loo, H., Peter, R.E., Rivier, J.E., Vale, W.W.: Biol. Reprod. 40: 1152-1161 (1989) 9. Habibi, H.R., Peter, R.E.: In: Reproductive Physiology of Fish (Eds A.P. Scott, J.P. Sumpter, D.E. Kime, M.S. Rolfe), pp. 109-113, University of East Anglia, U.K., 1991 |
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Online ISSN 1011-6575
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