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

doi:10.1111/j.1399-3011.1994.tb00389.x

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 journal › Article › peer-review

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 language	English (US)
Pages (from-to)	264-270
Number of pages	7
Journal	International journal of peptide and protein research
Volume	43
Issue number	3
DOIs	https://doi.org/10.1111/j.1399-3011.1994.tb00389.x
State	Published - Mar 1994
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Biochemistry

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

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.",

keywords = "Cetrorelix, LH‐RH, NMR spectroscopy, NOE, antagonist, conformation, decapeptide, mass spectrometry",

author = "A. M{\"U}LLER and E. BUSKER and J. ENGEL and B. KUTSCHER and M. BERND and SCHALLY, {A. V.}",

year = "1994",

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AU - MÜLLER, A.

AU - BUSKER, E.

AU - ENGEL, J.

AU - KUTSCHER, B.

AU - BERND, M.

AU - SCHALLY, A. V.

PY - 1994/3

Y1 - 1994/3

N2 - 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.

AB - 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.

KW - Cetrorelix

KW - LH‐RH

KW - NMR spectroscopy

KW - NOE

KW - antagonist

KW - conformation

KW - decapeptide

KW - mass spectrometry

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