Extended rhodamine photosensitizers for photodynamic therapy of cancer cells

Kellie S Davies; Michelle K Linder; Mark W Kryman; Michael R Detty

doi:10.1016/j.bmc.2016.05.033

Extended rhodamine photosensitizers for photodynamic therapy of cancer cells

Bioorg Med Chem. 2016 Sep 1;24(17):3908-3917. doi: 10.1016/j.bmc.2016.05.033. Epub 2016 May 20.

Authors

Kellie S Davies¹, Michelle K Linder², Mark W Kryman³, Michael R Detty⁴

Affiliations

¹ Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, United States. Electronic address: kdavies@buffalo.edu.
² Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, United States. Electronic address: mklinder@buffalo.edu.
³ Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, United States. Electronic address: markkrym@buffalo.edu.
⁴ Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, United States; Institute for Lasers, Photonics and Biophotonics, Department of Chemistry, State University of New York, Buffalo, NY 14260, United States. Electronic address: mdetty@buffalo.edu.

PMID: 27246858
DOI: 10.1016/j.bmc.2016.05.033

Abstract

Extended thio- and selenorhodamines with a linear or angular fused benzo group were prepared. The absorption maxima for these compounds fell between 640 and 700nm. The extended rhodamines were evaluated for their potential as photosensitizers for photodynamic therapy in Colo-26 cells. These compounds were examined for their photophysical properties (absorption, fluorescence, and ability to generate singlet oxygen), for their dark and phototoxicity toward Colo-26 cells, and for their co-localization with mitochondrial-specific agents in Colo-26 and HUT-78 cells. The angular extended rhodamines were effective photosensitizers toward Colo-26 cells with 1.0Jcm(-2) laser light delivered at λmax±2nm with values of EC50 of (2.8±0.4)×10(-7)M for sulfur-containing analogue 6-S and (6.4±0.4)×10(-8)M for selenium-containing analogue 6-Se. The linear extended rhodamines were effective photosensitizers toward Colo-26 cells with 5 and 10Jcm(-2) of broad-band light (EC50's⩽2.4×10(-7)M).

Keywords: Extended rhodamines; Photodynamic therapy; Photosensitizers.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Animals
Cell Line, Tumor
Fluorescent Dyes / chemistry
Humans
Light
Lysosomes / metabolism
Mice
Mitochondria / metabolism
Organoselenium Compounds / chemical synthesis
Organoselenium Compounds / pharmacology*
Photochemotherapy
Photosensitizing Agents / chemical synthesis
Photosensitizing Agents / pharmacology*
Rhodamines / chemical synthesis
Rhodamines / pharmacology*

Substances

Fluorescent Dyes
Organoselenium Compounds
Photosensitizing Agents
Rhodamines