Octreotide-phenylalanine-d8 di-Trifluoroacetic Acid Salt

Octreotide acetate is a longer acting synthetic octapeptide analog of naturally occurring somatostatin. It inhibits the secretion of gastro-entero-pancreatic peptide hormones and the release of growth hormone.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: 10-101-198

Synonyms/Alias:D-(Phenylalanyl-d8)-L-cysteinyl-L-phenylalanyl-D-tryptophyl
-L-lysyl-L-threonyl-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]-L-cysteinamide Cyclic (2-7)-Disulfide di-Trifluoroacetic Acid Salt; SMS 201-995-d8 di-Trifluoroacetic Acid Salt; Sandostatin-d8 di-Trifluoroacetic Acid Salt; Sandostatin LAR-d8 di-Trifluoroacetic Acid Salt;

Custom Peptide Synthesis
cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C49H58N10O10S2D8, 2xC2HF3O2
M.W/Mr.
1027.31, 2x114.02
Application
Used in treatment of acromegaly.
Appearance
White Solid

Octreotide-phenylalanine-d8 di-Trifluoroacetic Acid Salt is a specialized synthetic peptide analog featuring a deuterated phenylalanine residue, formulated as a di-trifluoroacetic acid salt. This compound is distinguished by its stable isotope labeling, which incorporates eight deuterium atoms in the phenylalanine side chain, making it particularly valuable for advanced research applications that require precise molecular tracking and quantification. The unique structure of Octreotide-phenylalanine-d8 not only preserves the pharmacological and receptor-binding characteristics of the parent octreotide peptide but also enables enhanced analytical capabilities in mass spectrometry-based investigations. Its chemical stability and compatibility with various analytical platforms position it as a preferred internal standard and tracer in a range of scientific studies, from peptide metabolism to receptor-ligand interactions. Researchers benefit from its reliable performance in complex biological matrices, allowing for accurate peptide quantification and kinetic profiling in sophisticated experimental setups.

Stable Isotope-Labeled Internal Standard: In quantitative bioanalytical assays, Octreotide-phenylalanine-d8 di-Trifluoroacetic Acid Salt serves as a robust internal standard due to its isotopic enrichment. Its incorporation into liquid chromatography-mass spectrometry (LC-MS) workflows enables precise differentiation from endogenous or unlabeled octreotide, thereby improving the accuracy and reproducibility of peptide quantitation. The deuterium labeling ensures that the compound co-elutes with the analyte of interest while providing a distinct mass shift, facilitating reliable normalization of sample preparation variability and instrumental fluctuations. This application is particularly crucial in pharmacokinetic, metabolic, and biomarker studies where trace-level detection and quantification of peptide analogs are required.

Peptide Metabolism and Degradation Studies: The deuterated octreotide analog is instrumental in elucidating peptide stability and metabolic pathways. By incorporating Octreotide-phenylalanine-d8 into in vitro or ex vivo systems, researchers can monitor its degradation kinetics and metabolic fate using high-resolution mass spectrometry. The unique isotopic signature allows for unambiguous tracking of the labeled peptide and its metabolites even in complex biological samples. This facilitates in-depth investigation of proteolytic cleavage, post-translational modifications, and peptide transport mechanisms, thereby advancing the understanding of peptide pharmacology and stability under physiological and experimental conditions.

Receptor Binding and Ligand Interaction Analysis: Octreotide-phenylalanine-d8 di-Trifluoroacetic Acid Salt is widely utilized in receptor-ligand binding studies, especially those involving somatostatin receptor subtypes. Its structural similarity to native octreotide ensures comparable binding affinities, while the deuterium label permits simultaneous analysis of labeled and unlabeled ligand populations. This dual analysis capability is invaluable for competitive binding assays, receptor occupancy measurements, and kinetic binding studies, providing insights into the molecular determinants of receptor selectivity and affinity. Such applications are fundamental to the rational design and optimization of peptide therapeutics targeting G protein-coupled receptors.

Mass Spectrometry Method Development: The isotopically labeled octreotide analog plays a critical role in the development and validation of mass spectrometric methods for peptide analysis. Its defined mass increment and chemical behavior closely mimic those of the native peptide, enabling method optimization with respect to ionization efficiency, chromatographic separation, and fragmentation patterns. By spiking Octreotide-phenylalanine-d8 into calibration standards or biological samples, analytical scientists can assess method sensitivity, linearity, and matrix effects, thereby ensuring the robustness and reliability of quantitative assays for peptide-based analytes in diverse research contexts.

Quality Control and Analytical Validation: In peptide manufacturing and analytical laboratories, Octreotide-phenylalanine-d8 di-Trifluoroacetic Acid Salt is employed as a reference material for quality control and assay validation purposes. Its stable isotopic composition and well-characterized properties make it ideal for verifying system suitability, calibrating analytical instruments, and establishing assay performance parameters. By providing a consistent benchmark for retention time, mass accuracy, and signal intensity, it supports the rigorous quality assurance processes that underpin reproducible peptide research and development. Through these multifaceted applications, Octreotide-phenylalanine-d8 di-Trifluoroacetic Acid Salt demonstrates its indispensable value in peptide science, analytical chemistry, and molecular pharmacology, driving advancements in both fundamental research and applied biotechnology.

Long-term Storage Conditions
DMSO, Methanol
InChI
InChI=1S/C49H66N10O10S2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64)/i3D,5D,6D,13D,14D,21D2,34D
InChI Key
DEQANNDTNATYII-HZFLURHHSA-N
Isomeric SMILES
[2H]C1=C(C(=C(C(=C1[2H])[2H])C([2H])([2H])C([2H])(C(=O)NC2CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC2=O)CC3=CC=CC=C3)CC4=CNC5=CC=CC=C54)CCCCN)C(C)O)C(=O)NC(CO)C(C)O)N)[2H])[2H]
Melting Point
>168°C (dec.)

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