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New proline-based single-chain lipids, including a bolalipid, form stable vesicles. These amphiphiles show tunable properties influenced by headgroup structure, offering insights for designing functional systems.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Biophysical Chemistry

Background:

  • Single-chain bolalipids (bolaamphiphiles) are poorly understood regarding their self-assembly into vesicular structures.
  • Understanding their behavior is crucial for developing novel functional amphiphilic systems.

Purpose of the Study:

  • To synthesize and characterize new proline-based single-chain lipids, including a symmetric bolalipid (2Pro-C18:1) and a unipolar analogue (1Pro-C18:1).
  • To investigate their self-assembly into vesicles and their interfacial properties.

Main Methods:

  • Synthesis of proline-based lipids.
  • Confocal fluorescence microscopy.
  • Encapsulation assays.
  • Fluorescence spectroscopy.
  • Zeta potential measurements.
  • Vibrational sum frequency generation (vSFG) spectroscopy.

Main Results:

  • Both the bolalipid and unipolar analogue form stable vesicles capable of entrapping small molecules.
  • Vesicle formation is pH-dependent, with the bolalipid favoring higher pH.
  • The bolalipid exhibits lower surface activity and a bent interfacial conformation compared to the unipolar analogue.
  • Both lipids show dynamic exchange between interfacial and bulk aggregates, with complex concentration-dependent behavior for the bolalipid.

Conclusions:

  • Single-chain bolalipids can form stable, dynamic aggregates with properties governed by hydrophobic chain effects and headgroup architecture.
  • These findings provide valuable molecular design principles for creating functional amphiphilic systems.