Amphiphilic p-sulfonatocalix[6]arene based self-assembled nanostructures for enhanced clarithromycin activity against resistant Streptococcus Pneumoniae

Colloids Surf B Biointerfaces. 2020 Feb:186:110676. doi: 10.1016/j.colsurfb.2019.110676. Epub 2019 Nov 27.

Abstract

Amphiphilic calixarenes are preferred to generate nano-cargos for drugs due to their stability, possibilities for modification and intrinsic host cavities. Here we are reporting the synthesis of amphiphilic calixarene and its evaluation as drug delivery system. Water soluble amphiphilic p-sulfonatocalix[6]arene was synthesized through sulfonation and lipophilic conjugation on its upper and lower rims respectively. The synthesized amphiphile self-assembled into nanostructures in the presence of Clarithromycin and FITC as model hydrophobic drugs followed by a wide range of characterization. Clarithromycin loaded self-assembled nanostructures was screened for its bactericidal potential in resistant S. pneumonia through various in-vitro assays. The amphiphilic calixarene self-assembled into polydispersed nanostructures with 136.45 ± 2.41 nm mean diameter and -49.93 ± 0.35 mV surface charges. The amphiphile was capable to load Clarithromycin (57.54 ± 1.88 %) and fluorescent dye and was highly stable. Clarithromycin loaded nanostructures revealed significant biofilm and bacterial growth inhibition and cell destruction properties. Results authenticate calixarene amphiphile as an efficient nano-carrier for improving Clarithromycin efficacy.

Keywords: Amphiphile; Bactericidal; Calixarene; Clarithromycin; Self-assembled nanostructures.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Calixarenes / chemical synthesis
  • Calixarenes / chemistry*
  • Clarithromycin / chemistry
  • Clarithromycin / pharmacology*
  • Drug Resistance, Bacterial / drug effects
  • Microbial Sensitivity Tests
  • Nanostructures / chemistry*
  • Particle Size
  • Phenols / chemical synthesis
  • Phenols / chemistry*
  • Streptococcus pneumoniae / drug effects*
  • Surface Properties
  • Surface-Active Agents / chemical synthesis
  • Surface-Active Agents / chemistry*

Substances

  • Anti-Bacterial Agents
  • Phenols
  • Surface-Active Agents
  • calix(6)arene
  • Calixarenes
  • Clarithromycin