Structural investigation of Cetrorelix, a new potent and long‐acting LH‐RH antagonist

A. MÜLLER, E. BUSKER, J. ENGEL, B. KUTSCHER, M. BERND, A. V. SCHALLY

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

The new decapeptide SB-75 (INN: Cetrorelix) has been characterized as a potent antagonist of luteinizing-hormone releasing hormone (LH-RH). Such derivatives are of great medicinal interest owing to their potential application in areas such as hormone-dependent tumors, uterine fibroids, and in diseases and conditions which result from inappropriate hormone levels or which can be treated by suppression of estrogens. SB-75 is the subject of intensive ongoing clinical evaluation and is an accepted standard for the design of new LH-RH antagonists. We characterized SB-75 by means of modern MS and NMR techniques to demonstrate the significance of both sequencing methods on a complicated unnatural decapeptide. Our structural elucidations with nuclear Overhauser (NOE) experiments revealed clear evidence for a highly flexible molecule with no single predominant conformation even in sodium dodecyl sulfate (SDS) mimicking a cellular membrane.

Original languageEnglish (US)
Pages (from-to)264-270
Number of pages7
JournalInternational journal of peptide and protein research
Volume43
Issue number3
DOIs
StatePublished - Mar 1994
Externally publishedYes

Keywords

  • Cetrorelix
  • LH‐RH
  • NMR spectroscopy
  • NOE
  • antagonist
  • conformation
  • decapeptide
  • mass spectrometry

ASJC Scopus subject areas

  • Biochemistry

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