A novel method for conjugating the terminal amine of peptide ligands to cholesterol: Synthesis iRGD-cholesterol
Document Type
Article
Publication Date
1-1-2019
Abstract
Aim: Conventional conjugation reactions often involve the use of activated PEG as a linker, but concerns about PEG-mediated reduction in intracellular delivery and enhanced immunogenicity have generated interest in developing methods that eliminate the need for a PEG linker. Materials & methods: Reaction conditions were identified that specifically couples the terminal amine of a cyclic iRGD peptide (CRGDRGPDC) to the hydroxyl moiety of cholesterol through a short carbamate linker. Results & conclusion: Using this method for synthesizing iRGD-cholesterol, peptide ligands can be incorporated into lipid-based delivery systems, thereby eliminating concerns about adverse reactions to PEG. Toxicity and stability data indicate low toxicity and adequate serum stability at low ligand levels.
Recommended Citation
Fete, Matthew G.; Betker, Jamie L.; Shoemaker, Richard K.; and Anchordoquy, Thomas J., "A novel method for conjugating the terminal amine of peptide ligands to cholesterol: Synthesis iRGD-cholesterol" (2019). Regis University Faculty Publications (comprehensive list). 280.
https://epublications.regis.edu/facultypubs/280