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Proceedings Paper

Synthesis and cellular localization of porphyrinic pigments
Author(s): Sarah Sareh; Sarah Kong; Lenin Parrales; Anna Jung; Kara Cross; Beate Röder; Meden Isaac; Ursula Simonis
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Paper Abstract

To determine factors that govern the uptake preference of photosensitizers in cellular organelles of human adenocarcinoma cells, diarginyl-dialkoxy- and diarginyl-dimethoxyphenylporphyrins (TPPs) and two of their corresponding indium(III) complexes were synthesized, characterized and incubated in androgen-sensitive human prostate adenocarcinoma cells LNCaP. The porphyrins revealed properties that are of importance for phototherapy. They are water-soluble, have their fourth Q-band absorbing at ≈ 650 nm, are taken up in relatively high concentrations in LNCaP cells, and are phototoxic. Colocalization and phototoxicity studies revealed that all porphyrins localized preferentially to the lysosomes and invoked cell death when excited with 650 nm light. Compared to the corresponding methoxy-substituted TPPs, the diargininyl-dialkoxy-substituted porphyrins localized to a small extent in the mitochondria. The corresponding In(III) chloride complexes that are slightly less water-soluble were also taken up in the lysosomes of LnCaP cells. When the TPPs were compared to a pheophorbide derivative recently synthesized in our laboratory, it was determined that the TPPs have a preference for lysosomal localization, whereas the pheophorbide derivative co-localized to the mitochondria. Phototoxicity studies revealed that the longer chain dialkoxyTPPs were more effective in cell killing and induced greater morphological changes typical of apoptotic cell death than the shorter chain methoxy substituted porphyrins. The In(III) complexes seemed to be the most phototoxic. These results highlight that the type, nature, and substitution pattern of the chromophore modulate the extent of apoptotic cell death and influence cellular targeting.

Paper Details

Date Published: 14 July 2009
PDF: 13 pages
Proc. SPIE 7380, Photodynamic Therapy: Back to the Future, 73804R (14 July 2009); doi: 10.1117/12.823023
Show Author Affiliations
Sarah Sareh, San Francisco State Univ. (United States)
Sarah Kong, San Francisco State Univ. (United States)
Lenin Parrales, San Francisco State Univ. (United States)
Anna Jung, San Francisco State Univ. (United States)
Kara Cross, San Francisco State Univ. (United States)
Beate Röder, Humboldt-Univ. zu Berlin (Germany)
Meden Isaac, San Francisco State Univ. (United States)
Ursula Simonis, San Francisco State Univ. (United States)


Published in SPIE Proceedings Vol. 7380:
Photodynamic Therapy: Back to the Future
David H. Kessel, Editor(s)

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