Novel peptidomimetics related to gonadotropin-releasing hormone (GnRH)

Arianna Gelain, Luca Rizzi, Laura Legnani, Aurora Pacini, Katerina Spyridaki, Vlasios Karageorgos, George Liapakis, Stefania Villa

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Novel GnRH I and II analogues were designed and synthesized by Solid Phase Peptide Synthesis (SPPS), since GnRH has antiproliferative properties, but poor metabolic stability. To rationalize synthetic difficulties, molecular dynamics simulations were performed, showing the conformational behavior of three derivatives. Among the two series of peptidomimetics (Ie, f and IIe, f were GnRH I and GnRH II analogues, respectively), several compounds (Id-f and IIc-e) showed significant binding affinity. In particular, derivative Ie has an increased metabolic stability with respect to the physiological ligand (Ie t1/2 = 3.96 h versus GnRH I t1/2 = 2.63 h).

Original languageEnglish
Pages (from-to)1656-1665
Number of pages10
JournalMedChemComm
Volume6
Issue number9
DOIs
Publication statusPublished - Jul 27 2015

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Peptidomimetics
Gonadotropin-Releasing Hormone
Derivatives
Solid-Phase Synthesis Techniques
Molecular Dynamics Simulation
Molecular dynamics
Ligands
Peptides
Computer simulation

ASJC Scopus subject areas

  • Biochemistry
  • Pharmaceutical Science

Cite this

Gelain, A., Rizzi, L., Legnani, L., Pacini, A., Spyridaki, K., Karageorgos, V., ... Villa, S. (2015). Novel peptidomimetics related to gonadotropin-releasing hormone (GnRH). MedChemComm, 6(9), 1656-1665. https://doi.org/10.1039/c5md00259a

Novel peptidomimetics related to gonadotropin-releasing hormone (GnRH). / Gelain, Arianna; Rizzi, Luca; Legnani, Laura; Pacini, Aurora; Spyridaki, Katerina; Karageorgos, Vlasios; Liapakis, George; Villa, Stefania.

In: MedChemComm, Vol. 6, No. 9, 27.07.2015, p. 1656-1665.

Research output: Contribution to journalArticle

Gelain, A, Rizzi, L, Legnani, L, Pacini, A, Spyridaki, K, Karageorgos, V, Liapakis, G & Villa, S 2015, 'Novel peptidomimetics related to gonadotropin-releasing hormone (GnRH)', MedChemComm, vol. 6, no. 9, pp. 1656-1665. https://doi.org/10.1039/c5md00259a
Gelain A, Rizzi L, Legnani L, Pacini A, Spyridaki K, Karageorgos V et al. Novel peptidomimetics related to gonadotropin-releasing hormone (GnRH). MedChemComm. 2015 Jul 27;6(9):1656-1665. https://doi.org/10.1039/c5md00259a
Gelain, Arianna ; Rizzi, Luca ; Legnani, Laura ; Pacini, Aurora ; Spyridaki, Katerina ; Karageorgos, Vlasios ; Liapakis, George ; Villa, Stefania. / Novel peptidomimetics related to gonadotropin-releasing hormone (GnRH). In: MedChemComm. 2015 ; Vol. 6, No. 9. pp. 1656-1665.
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