Biotin-decorated NIR-absorbing nanosheets for targeted photodynamic cancer therapy

Org Biomol Chem. 2021 Mar 28;19(12):2804-2810. doi: 10.1039/d1ob00002k. Epub 2021 Mar 15.

Abstract

Targeted photodynamic therapy (PDT) is one of the promising approaches for the selective killing of cancerous cells without affecting the normal cells, and hence designing new strategies for targeted PDT is extremely important. Herein we report the design and synthesis of a new class of nanosheets derived from the self-assembly of the iodo-BODIPY-biotin conjugate as a photosensitizer for targeted PDT applications. The nanosheet exhibits a high extinction coefficient in the NIR region, high singlet oxygen efficiency, no toxicity in the dark and cell targeting ligands (biotin) on the surface, which are necessary features required for an ideal photosensitizer. Overexpression of sodium-dependent multivitamin transporters (SMVTs) in HeLa and A549 (biotin receptor positive cell lines) is explored for the selective uptake of the nanophotosensitizer through receptor mediated endocytosis (interaction between biotin and SMVT). Control experiments using a biotin receptor negative cell line (WI-38) are also carried out to confirm that the specific interaction between the SMVTs and biotin is mainly responsible for the selective uptake of the photosensitizer. Efficient killing of cancerous cells is demonstrated upon light irradiation through the generation of singlet oxygen and other reactive oxygen species around the cellular environment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Biotin / chemistry
  • Biotin / pharmacology*
  • Boron Compounds / chemistry
  • Boron Compounds / pharmacology*
  • Cell Adhesion / drug effects
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Cells, Cultured
  • Drug Screening Assays, Antitumor
  • Humans
  • Infrared Rays
  • Ligands
  • Molecular Structure
  • Nanoparticles / chemistry*
  • Photochemotherapy*
  • Photosensitizing Agents / chemical synthesis
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacology*

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Antineoplastic Agents
  • Boron Compounds
  • Ligands
  • Photosensitizing Agents
  • Biotin