Anionic amphiphilic calixarenes for peptide assembly and delivery

Area of Science:

• Supramolecular Chemistry
• Nanotechnology
• Biomaterials Science

Background:

• Shape-persistent macrocycles offer precise control over molecular self-assembly.
• Developing functional nanostructures for applications like intracellular delivery is a key research area.

Purpose of the Study:

• To investigate the self-assembly of anionic amphiphilic calixarenes in aqueous media.
• To evaluate their potential for intracellular delivery of peptides.

Main Methods:

• Synthesis of novel anionic amphiphilic calixarenes with phosphonate groups and long alkyl chains.
• Characterization of micelle formation and nanoparticle assembly with cationic peptides using techniques like dynamic light scattering.
• Cellular uptake studies using fluorescently labeled peptides and cytotoxicity assays.

Main Results:

• Newly synthesized calixarenes with long alkyl chains formed stable micelles (∼10 nm).
• These calixarenes effectively complexed both model and biologically relevant cationic peptides into nanoparticles (20-40 nm).
• Cellular studies demonstrated low cytotoxicity and successful internalization of peptide-loaded nanoparticles into live cells.

Conclusions:

• Anionic amphiphilic calixarenes are effective building blocks for peptide complexation and nanoparticle formation.
• The self-assembly into micelles is crucial for successful peptide complexation and delivery.
• These macrocycles show promise as safe and effective vehicles for intracellular peptide delivery.