Conjugated porphyrin dimers with large two-photon absorption cross section for photodynamic therapy

MEDI 118

Milan Balaz, milan.balaz@chem.ox.ac.uk1, Hazel A. Collins1, Marina K. Kuimova2, Emma Dahlstedt1, Klaus Suhling3, David Phillips2, and Harry L. Anderson, harry.anderson@chem.ox.ac.uk1. (1) Department of Chemistry, University of Oxford, Mansfield Road, OX1 3TA Oxford, United Kingdom, (2) Department of Chemistry, Imperial College, London, United Kingdom, (3) Department of Physics, Kings’ College, London, United Kingdom
Two-photon excited photodynamic therapy (TPE-PDT) is the use of a chromophore with a high TPE cross section as a photosensitizer in PDT. The main advantage of two-photon excitation is that it allows the generation of singlet oxygen to be pin-pointed to a small volume reducing collateral damage. In addition, near-infrared light of twice the wavelength of the absorption band can be used to produce the excited state of the sensitizer increasing biological tissue penetration. Recently we have discovered that porphyrin dimer such as 1 has an exceptionally high two-photon absorption cross-section of ca 6,000 GM at 780 nm and high singlet oxygen yields. The main challenge is the functionalization of large porphyrin dimers in order to achieve good cellular uptake and low dark toxicity. The synthesis of hydrophilic positively and negatively charged porphyrin dimers, their singlet oxygen yields, and in vitro one–photon PDT results will be presented.

 

Poster Session
7:00 PM-9:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Medicinal Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007