Facile Synthesis of a Phototoxic Monofunctionalized Tetraarylporphyrin as Scaffold for Porphyrin-Quinone Conjugates

Abstract

A new carboxy-monofunctionalized tertraarylporphyrin has been tested for cytotoxicity toward OV2008 human ovarian cancer cells. This compound acutely inhibits growth of ovarian cancer cells upon exposure to ambient light while suppresses long-term clonogenic survival of cells under both dark and light stimulated conditions. Because of the variable length of the linkage between the anthraquinone and porphyrin moieties, the synthesized monocarboxylated porphyrin presents a versatile scaffold for fine-tuning of the photoelectron transfer in the quinone-porphyrin conjugate. To demonstrate its synthetic value, we converted the carboxy derivative to its amino counterpart.

GRAPHICAL ABSTRACT

Keywords:

• Cytotoxicity
• ovarian cancer
• phototoxicity
• porphyrins
• quinones

ACKNOWLEDGMENTS

This work was supported by the State of South Dakota (2010 Research Initiative) and National Science Foundation (EPSCoR Grant Nos. 0554609 and 0903804), the University of South Dakota (USD) Department of Chemistry, the South Dakota Board of Regents competitive Research Grant Award No. SDBOR/USD 2011-10-06, and the USD Nelson Endowment Fund.