Photoresponsive transformation from spherical to nanotubular assemblies: anticancer drug delivery using macrocyclic cationic gemini amphiphiles

Chem Commun (Camb). 2021 May 11;57(38):4646-4649. doi: 10.1039/d1cc01468d.

Abstract

We developed NIR-light-responsive macrocyclic cationic gemini amphiphiles, one of which displayed various favorable properties of lipids. The NIR-light-mediated cleavage of the strained dioxacycloundecine ring led to the conversion of the spherical to a nanotubular self-assembly in the aqueous medium. This photo-mediated transformation from the spherical to nanotubular self-assembly resulted in the release of encapsulated hydrophobic anticancer drug molecule doxorubicin (Dox) in a controlled manner. The potent cationic gemini amphiphile also displayed lower cytotoxicity and efficient NIR-light-mediated Dox release efficacy to cancerous cells.

MeSH terms

  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / pharmacology*
  • Calcitriol / analogs & derivatives
  • Calcitriol / chemistry
  • Cations
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Doxorubicin / chemistry
  • Doxorubicin / pharmacology*
  • Drug Carriers / chemistry
  • Drug Screening Assays, Antitumor
  • Humans
  • Macrocyclic Compounds / chemistry
  • Molecular Structure
  • Photochemical Processes
  • Surface-Active Agents / chemistry

Substances

  • 1,25-dihydroxy-21-(3-hydroxy-3-methylbutyl)vitamin D(3)
  • Antibiotics, Antineoplastic
  • Cations
  • Drug Carriers
  • Macrocyclic Compounds
  • Surface-Active Agents
  • Doxorubicin
  • Calcitriol