Water-Soluble Self-Assembled Butadiyne-Bridged Bisporphyrin: A Potential Two-Photon-Absorbing Photosensitizer for Photodynamic Therapy

Authors

  • Joanne T. Dy,

    1. Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0101, Japan, Fax: (+81) 743-72-6119
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  • Kazuya Ogawa Prof.,

    1. Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0101, Japan, Fax: (+81) 743-72-6119
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  • Akiharu Satake Prof.,

    1. Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0101, Japan, Fax: (+81) 743-72-6119
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  • Atsushi Ishizumi Prof.,

    1. Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0101, Japan, Fax: (+81) 743-72-6119
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  • Yoshiaki Kobuke Prof.

    1. Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0101, Japan, Fax: (+81) 743-72-6119
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Abstract

We have synthesized a novel, two-photon-absorbing photosensitizer for two-photon-absorption photodynamic therapy (2PA-PDT). The molecule is a butadiyne-bridged porphyrin dimer terminated with two water-soluble porphyrin monomers connected through Zn-imidazolyl self-assembly and covalently linked through olefin metathesis. It has an effective two-photon-absorption (2PA) cross-section value, σ(2), of 33 000±4600 GM with 5-ns pulses at 890 nm measured by using the open-aperture Z-scan technique. The compound was found to generate singlet oxygen, cytotoxic for tumor cells in photodynamic therapy (PDT), under 2PA conditions by conducting photobleaching experiments with anthracene-9,10-dipropionic acid sodium salt (ADPA).

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