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Design, Synthesis, and Molecular Modeling of a Novel Amide-Linked Cyclic GnRH Analogue Cyclo(4-9)[Lys4,d-Trp6,Glu9]GnRH:  Stimulation of Gonadotropin Gene Expression

Keramida, Maria K., Tselios, Theodore, Mantzourani, Efthymia D., Papazisis, Kostas, Mavromoustakos, Thomas, Klaussen, Christian, Agelis, George, Deraos, Spyros, Friligou, Irene, Habibi, Hamid and Matsoukas, John 2006. Design, Synthesis, and Molecular Modeling of a Novel Amide-Linked Cyclic GnRH Analogue Cyclo(4-9)[Lys4,d-Trp6,Glu9]GnRH:  Stimulation of Gonadotropin Gene Expression. Journal of Medicinal Chemistry 49 (1) , pp. 105-110. 10.1021/jm050683z

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Abstract

This report describes the rational design, synthesis, and pharmacological properties of an amide-linked cyclic analogue of gonadotropin-releasing hormone (GnRH) namely Cyclo(4−9)[Lys4,d-Trp6,Glu9]GnRH. The conformationally restricted analogue is characterized by reduced flexibility of the peptide strand due to the introduction of a β-turn mimetic through 4,9 residue amide cyclization. The cyclic analogue was found to stimulate gonadotropin gene expression in the goldfish pituitary with similar potency compared to two native forms of GnRH. Simulation studies based on ROE connectivities in linear GnRH and potency of cyclic analogue supports the His2, Trp3, Tyr5 clustering considered important for triggering receptor activation.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Subjects: Q Science > QD Chemistry
R Medicine > RS Pharmacy and materia medica
Publisher: American Chemical Society
ISSN: 0022-2623
Last Modified: 04 Jun 2017 03:12
URI: http://orca-mwe.cf.ac.uk/id/eprint/18097

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