Comparison of the dark and light-induced toxicity of thio and seleno analogues of the thiopyrylium dye AA1

  • Detty M
  • Gibson S
  • Hilf R
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Abstract

2,6-Bis(4-anilino)-4-(4-N,N-dimethylanilino)thiopyrylium chloride (AA1) and -selenopyrylium chloride (AA1-Se) and 2,6-bis(4-anilino)-4-(4-N- morpholinophenyl)thiopyrylium chloride (1) and -selenopyrylium chloride (2) were prepared via the addition of 4-N,N-dimethylanilino magnesium bromide and 4-N-morpholinophenyl magnesium bromide to chalcogenopyranones 3 followed by treatment with HCl gas then water. Cellular uptake of these dyes varied from 12±3fmol/cell for AA1 to 150±40fmol/cell for AA1-Se. upon exposure to 5×10-5M solutions of the dyes for 3h. Exposure of cell cultures to 1.8J/cm2of 360-750-nm light following incubation with 1×10-6M of either AA1, 1, or 2 for 24h resulted in no significant additional phototoxicity while AA1-Se showed a significant (P

Author-supplied keywords

  • Anticancer
  • Chalcogenopyrylium
  • Cytochrome c oxidase activity
  • JC-1 efflux
  • Photodynamic therapy
  • Photosensitizers
  • Selenopyrylium
  • Thiopyrylium

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