A novel photosensitizer based on hypocrellin B activated by cysteine over-expressed in cancer cells

Org Biomol Chem. 2024 Sep 11;22(35):7187-7193. doi: 10.1039/d4ob01288g.

Abstract

L-Cysteine (Cys)-activatable photosensitizer 3 was designed and synthesized based on hypocrellin B (1). Cys is a novel tumor-associated biomarker. 3 exhibited negligible photosensitizing ability without Cys. However, when 1 was released from 3 by reaction with Cys, the photosensitizing activity was restored. Furthermore, 3 showed selective and effective photo-cytotoxicity against only cancer cells such as HeLa and A549 cells that highly express Cys when irradiated with 660 nm light, which is inside the phototherapeutic window.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • A549 Cells
  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Cell Survival / drug effects
  • Cysteine* / chemistry
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Perylene* / analogs & derivatives
  • Perylene* / chemical synthesis
  • Perylene* / chemistry
  • Perylene* / pharmacology
  • Photochemotherapy
  • Photosensitizing Agents* / chemical synthesis
  • Photosensitizing Agents* / chemistry
  • Photosensitizing Agents* / pharmacology
  • Quinones* / chemical synthesis
  • Quinones* / chemistry
  • Quinones* / pharmacology

Substances

  • Quinones
  • Photosensitizing Agents
  • Perylene
  • hypocrellin B
  • Cysteine
  • Antineoplastic Agents