Lanreotide (Deamidized) features one or more deamidated Asn or Gln residues, converting side chains to acidic forms. The modification shifts local charge, hydrogen-bonding capacity, and conformational preferences. Researchers use it to analyze degradation mechanisms and activity changes. Applications include stability testing, impurity characterization, and structure-function comparisons with native lanreotide.
CAT No: R2588
CAS No:150155-56-9
Synonyms/Alias:((4R,7S,10S,13R,16S,19R)-13-((1H-Indol-3-yl)methyl)-19-((R)-2-amino-3-(naphthalen-2-yl)propanamido)-10-(4-aminobutyl)-16-(4-hydroxybenzyl)-7-isopropyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)-L-threonine; Lanreotide (Deamidized);150155-56-9;CHEMBL3350155;
Lanreotide (Deamidized) is a synthetic peptide analog of somatostatin, distinguished by a specific deamidation modification that alters its biochemical profile. As a member of the cyclic octapeptide family, it exhibits high affinity for certain somatostatin receptor subtypes, making it a valuable tool for probing peptide-receptor interactions and signal transduction pathways. The deamidized form presents unique structural and functional characteristics, providing researchers with opportunities to dissect the influence of post-synthetic modifications on peptide stability, receptor binding, and downstream biological effects. Due to its well-characterized sequence and modifiable nature, this compound holds significant relevance in peptide chemistry, receptor pharmacology, and structure-activity relationship studies.
Peptide Structure-Activity Relationship Studies: Lanreotide (Deamidized) serves as a key reference in structure-activity relationship (SAR) investigations, particularly for understanding the impact of deamidation on peptide conformation and function. By comparing the biological activity and receptor affinity of the deamidized variant to its native counterpart, researchers can elucidate how specific post-translational modifications influence peptide-receptor interactions. Such comparative studies are critical in optimizing peptide analogs for enhanced selectivity, stability, or altered pharmacodynamic properties in non-clinical research settings.
Receptor Binding Assays: In the context of receptor pharmacology, the deamidized form of lanreotide is frequently utilized to characterize somatostatin receptor subtype specificity and binding kinetics. Its defined structural features enable precise mapping of ligand-receptor interactions through radioligand binding assays, surface plasmon resonance, or fluorescence-based detection systems. These applications facilitate the identification of critical amino acid residues involved in receptor engagement and support the development of novel ligands with tailored receptor profiles for research use.
Peptide Stability and Degradation Analysis: The presence of a deamidation modification in lanreotide provides a robust model for studying peptide stability and degradation pathways under various physiological and experimental conditions. Analytical chemists and peptide scientists employ this compound to monitor the effects of pH, temperature, enzymatic activity, and storage parameters on peptide integrity. Insights gained from such studies inform strategies for improving peptide formulation, storage, and handling, which are essential for maintaining experimental reproducibility and reliability in the laboratory.
Analytical Method Development: As a well-characterized peptide standard, lanreotide (deamidized) is instrumental in the development and validation of analytical methods for peptide identification and quantification. Its unique mass spectral signature and chromatographic behavior make it suitable for calibrating liquid chromatography-mass spectrometry (LC-MS) and high-performance liquid chromatography (HPLC) systems. Method developers utilize it to assess the sensitivity, specificity, and robustness of analytical protocols, ensuring accurate detection and quantification of peptide analytes in complex biological or synthetic matrices.
Peptide Synthesis Optimization: The synthesis of deamidized lanreotide offers valuable insights into the challenges and solutions associated with post-synthetic peptide modifications. Peptide chemists employ this compound as a model to optimize solid-phase peptide synthesis (SPPS) protocols, purification strategies, and deamidation control measures. By systematically analyzing the occurrence and consequences of deamidation during synthesis and downstream processing, researchers can refine manufacturing processes to minimize unwanted modifications and enhance overall peptide yield and quality for research applications.
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