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Area of Science:

  • Physical Chemistry
  • Computational Chemistry
  • Drug Delivery

Background:

  • Levofloxacin is a widely used fluoroquinolone antibiotic.
  • Micelles, such as sodium dodecyl sulfate (SDS) and cetyltrimethylammonium bromide (CTAB), are crucial in drug formulation.
  • Understanding drug-micelle interactions is key to optimizing drug delivery systems.

Purpose of the Study:

  • To investigate the interaction dynamics and orientation of levofloxacin with anionic (SDS) and cationic (CTAB) micelles.
  • To determine the encapsulation efficiency and binding affinity of levofloxacin for both micelle types.
  • To elucidate the molecular mechanisms governing levofloxacin-micelle interactions.

Main Methods:

  • Extensive all-atom molecular dynamics simulations were employed.
  • Drug/micelle ratios, including loading capacity and entrapment efficiency, were estimated.
  • Relative binding energies and molecular orientations were calculated.

Main Results:

  • Levofloxacin exhibited significantly higher encapsulation efficiency in SDS micelles (∼80%) compared to CTAB micelles (∼8%).
  • Simulations showed tilted orientations for levofloxacin in both micelle types, with specific interactions of charged groups (piperazine and carboxylic acid) with micelle headgroups.
  • Levofloxacin demonstrated stronger binding to SDS micelles than CTAB micelles, supported by binding energy calculations.
  • Concerted columnar stacks of levofloxacin were observed in both micelle types, driven by π-π interactions and hydrogen bonding.

Conclusions:

  • Levofloxacin preferentially interacts with and is more efficiently encapsulated by anionic SDS micelles.
  • The charged nature of levofloxacin's functional groups and their interactions with micelle headgroups dictate binding affinity and orientation.
  • Molecular dynamics simulations provide valuable insights into the behavior of fluoroquinolone antibiotics within micellar systems, relevant for drug formulation.