Spectroscopic, cyto-, and photo-toxicity studies of substituted piperidones: potential sensitizers for two-photon photodynamic therapy

Kurt W. Short; Tiffany L. Kinnibrugh; David M. Sammeth; Tatiana V. Timofeeva

doi:10.1117/12.809904

18 February 2009 Spectroscopic, cyto-, and photo-toxicity studies of substituted piperidones: potential sensitizers for two-photon photodynamic therapy

Kurt W. Short, Tiffany L. Kinnibrugh, David M. Sammeth, Tatiana V. Timofeeva

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Proceedings Volume 7164, Optical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy XVIII; 716411 (2009) https://doi.org/10.1117/12.809904
Event: SPIE BiOS, 2009, San Jose, California, United States

Abstract

Two-photon photodynamic therapy has the advantages of being highly localized in its effects and allows for deeper tissue penetration, when compared to one-photon photodynamic therapy. N-alkylated 3,5-bis(arylidene)-4-piperidones, with a donor-pi-acceptor-pi-donor structure, have the potential to be useful two-photon sensitizers. We have measured two-photon cross sections (using femtosecond excitation), fluorescence quantum yields, fluorescence lifetimes, and xray crystal structures for a number of these compounds. Most two-photon cross sections are comparable to or larger than that of Rhodamine B. However, the fluorescence quantum yields are low (all less than 10%) and the fluorescence lifetimes are less than 1 ns (with one exception), suggesting that there may be a significant energy transfer to the triplet state. This would encourage singlet oxygen formation and increase cellular toxicity. Results of dark cyto-toxicity studies with several human cancer cell lines are presented. White light photo-toxicity results are also presented, and suggest that increasing the number of double bonds, from one to two, in the piperidone wings increases the photo-toxicity with little corresponding change in the dark cyto-toxicity.

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Kurt W. Short, Tiffany L. Kinnibrugh, David M. Sammeth, and Tatiana V. Timofeeva "Spectroscopic, cyto-, and photo-toxicity studies of substituted piperidones: potential sensitizers for two-photon photodynamic therapy", Proc. SPIE 7164, Optical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy XVIII, 716411 (18 February 2009); https://doi.org/10.1117/12.809904

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