Synthesis and evaluation of cationic bacteriochlorin amphiphiles with effective in vitro photodynamic activity against cancer cells at low nanomolar concentration

Sulbha K. Sharma, Michael Krayer, Felipe F. Sperandio, Liyi Huang, Ying Ying Huang, Dewey Holten, Jonathan S. Lindsey, Michael R. Hamblin

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

Bacteriochlorins are attractive candidates as photosensitizers for photodynamic therapy (PDT) due to their intense absorption in the near-infrared (NIR) region of the spectrum where light transmission through tissue is maximal. Many naturally occurring bacteriochlorins are inherently unstable due to adventitious atmospheric oxidation. A de novo synthesis affords bacteriochlorins that contain a geminal dimethyl group in each reduced pyrrole ring to increase stability against oxidation. Here, three new synthetic bacteriochlorins, each bearing a single side-chain containing one or two positive charges, were investigated for their in vitro PDT activity against HeLa human cancer cells. All bacteriochlorins were active at low nanomolar concentration when activated with NIR light; those bearing a single positive charge exhibited faster uptake and higher activity. The bacteriochlorins were localized in mitochondria, lysosomes and endoplasmic reticulum as shown by organelle specific fluorescent probes. Cell death was via apoptosis as shown by cell morphology and nuclear condensation. Taken together, the results show the importance of appropriate peripheral groups about a photosensitizer for effective PDT applications.

Original languageEnglish
Pages (from-to)73-85
Number of pages13
JournalJournal of Porphyrins and Phthalocyanines
Volume17
Issue number1-2
DOIs
Publication statusPublished - 2013
Externally publishedYes

Keywords

  • HeLa cancer cells
  • apoptosis
  • bacteriochlorins
  • confocal microscopy
  • photodynamic therapy
  • subcellular localization

ASJC Scopus subject areas

  • General Chemistry

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