Selenorhodamine photosensitizers with the Texas-red core for photodynamic therapy of cancer cells

Bioorg Med Chem. 2015 Aug 1;23(15):4501-4507. doi: 10.1016/j.bmc.2015.06.006. Epub 2015 Jun 12.

Abstract

We examined two selenorhodamines with amide and thioamide functionality at the 5-position of a 9-(2-thienyl) substituent on the selenoxanthylium analogue of the Texas-red core for their potential as photosensitizers for photodynamic therapy (PDT) in P-glycoprotein (P-gp)-expressing Colo-26 cells. These compounds were examined for their photophysical properties (absorption, fluorescence, and ability to generate singlet oxygen), for their uptake into Colo-26 cells in the absence or presence of verapamil, for their dark and phototoxicity toward Colo-26 cells, and for their co-localization with mitochondrial-specific agents in Colo-26 cells. Both compounds were extremely effective photosensitizers with values of EC50 ⩽ 4 × 10(-8)M toward Colo-26 cells with 1.0 J cm(-2) laser light delivered at 630 ± 2 nm.

Keywords: P-glycoprotein; Photodynamic therapy; Photosensitizers; Selenorhodamine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Humans
  • Mitochondria / metabolism
  • Organoselenium Compounds / chemistry
  • Organoselenium Compounds / pharmacokinetics
  • Organoselenium Compounds / therapeutic use*
  • Organoselenium Compounds / toxicity
  • Photochemotherapy*
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacokinetics
  • Photosensitizing Agents / therapeutic use*
  • Photosensitizing Agents / toxicity
  • Rhodamines / chemistry
  • Rhodamines / pharmacokinetics
  • Rhodamines / therapeutic use*
  • Rhodamines / toxicity
  • Singlet Oxygen / metabolism
  • Spectrometry, Fluorescence
  • Xanthenes / chemistry*

Substances

  • Organoselenium Compounds
  • Photosensitizing Agents
  • Rhodamines
  • Xanthenes
  • Singlet Oxygen
  • Texas red