L-Ala(10)-Cetrorelix introduces an alanine substitution at position ten within the cetrorelix framework. The change influences steric profile, local hydrophobicity, and conformational stability. Researchers compare its structural and chromatographic characteristics with native analogs. Applications include SAR analysis, impurity profiling, and analog development.
CAT No: Z10-101-175
Synonyms/Alias:Ac-D-2Nal-D-Phe(4-Cl)-D-3Pal-Ser-Tyr-D-Cit-Leu-Arg-Pro-Ala-NH2; (S)-N-((S)-1-amino-1-oxopropan-2-yl)-1-((2S,5S,8R,11S,14S,17R,20R,23R)-20-(4-chlorobenzyl)-2-(3-((diaminomethylene)amino)propyl)-11-(4-hydroxybenzyl)-14-(hydroxymethyl)-5-isobutyl-23-(naphthalen-2-ylmethyl)-4,7,10,13,16,19,22,25-octaoxo-17-(pyridin-3-ylmethyl)-8-(3-ureidopropyl)-3,6,9,12,15,18,21,24-octaazahexacosanoyl)pyrrolidine-2-carboxamide; N-acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-L-tyrosyl-D-citrullyl-L-leucyl-L-arginyl-L-prolyl-L-alaninamide
L-Ala(10)-Cetrorelix is a synthetic decapeptide analog belonging to the class of gonadotropin-releasing hormone (GnRH) antagonists, specifically engineered for research involving peptide hormone regulation. As a modified version of cetrorelix, it features an L-alanine substitution at the tenth position, which can influence its receptor binding characteristics, metabolic stability, and biological activity. The compound's structural modifications make it a valuable tool for investigating the molecular mechanisms of GnRH receptor antagonism, peptide-receptor interactions, and structure-activity relationships within the context of reproductive endocrinology and peptide drug discovery. Its defined sequence and functional specificity have positioned it as a relevant probe in diverse biochemical and pharmacological studies.
Peptide hormone signaling research: Utilization of L-Ala(10)-Cetrorelix in studies of GnRH receptor antagonism enables researchers to dissect the regulatory pathways governing gonadotropin release. By introducing this modified peptide into in vitro or ex vivo systems, investigators can evaluate its competitive inhibition of endogenous GnRH, thereby elucidating the downstream effects on luteinizing hormone (LH) and follicle-stimulating hormone (FSH) secretion. Such studies are essential for understanding the fine-tuned control of reproductive hormone cascades and the impact of specific amino acid substitutions on antagonist potency and selectivity.
Structure-activity relationship analysis: The L-alanine substitution at position 10 offers a unique opportunity to explore how side chain variations influence peptide-receptor affinity and functional outcomes. Researchers can employ this analog in systematic SAR studies, comparing its binding kinetics and antagonistic efficacy to those of unmodified cetrorelix and other GnRH antagonists. Insights gained from these comparative analyses support rational peptide design and the optimization of bioactive analogs for future research use.
Peptide stability and metabolism studies: L-Ala(10)-Cetrorelix provides a model substrate for investigating the effects of targeted amino acid modifications on peptide degradation pathways. By tracking its metabolic fate in biological matrices, scientists can assess resistance to proteolytic enzymes and gain a deeper understanding of how structural changes modulate peptide half-life and bioavailability. Such data are instrumental in guiding the development of more stable peptide-based probes for experimental applications.
Receptor binding assays: The compound serves as a reference ligand in assays designed to quantify GnRH receptor occupancy and antagonist binding affinity. Radioligand displacement experiments or fluorescence-based binding studies employing this analog allow for precise measurement of receptor-ligand interactions, supporting both basic research and high-throughput screening efforts. These assays contribute to the identification of novel modulators of the GnRH signaling axis and the validation of new assay platforms.
Peptide synthesis and analytical method development: L-Ala(10)-Cetrorelix is also relevant for evaluating synthetic methodologies and analytical techniques in peptide chemistry. Its defined sequence and physicochemical properties make it a suitable standard for optimizing solid-phase peptide synthesis protocols, chromatographic separation methods, and mass spectrometric detection strategies. By serving as a benchmark compound, it aids in the refinement of procedures critical to the production and characterization of complex peptide analogs in research settings.
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