Toward the Molecular Flashlight: Preparation, Properties, and Photophysics of a Hypericin–luciferin Tethered Molecule

• Published in: Photochemistry and photobiology 2002-08, Vol.76 (2), p.153-157
• Main Authors: Wen, Jin, Chowdhury, Pramit, Wills, Nick J., Wannemuehler, Yvonne, Park, Jaehun, Kesavan, Sarathy, Carpenter, S., Kraus, G. A., Petrich, J. W.
• Format: Article
• Language: English
• Subjects: Firefly Luciferin - chemical synthesis; Firefly Luciferin - chemistry; Firefly Luciferin - radiation effects; Perylene - analogs & derivatives; Perylene - chemical synthesis; Perylene - chemistry; Perylene - radiation effects; Photochemistry; PHOTOCHEMISTRY, PHOTOPHYSICS AND PHOTOTECHNOLOGY; Photochemotherapy; Photosensitizing Agents - chemical synthesis; Photosensitizing Agents - chemistry; Photosensitizing Agents - radiation effects
• ISSN: 0031-8655; 1751-1097
• DOI: 10.1562/0031-8655(2002)076<0153:TTMFPP>2.0.CO;2

The synthesis of a molecule containing hypericin and luciferin moieties joined by a tether is reported. The light-induced (in vitro) antiviral activity as well as the photophysical properties of this new compound are measured and compared with those of the parent compounds, hypericin and pseudohypericin. This tethered molecule exhibits excited-state behavior that is very similar to that of its parent compounds and antiviral activity that is identical, within experimental error, to that of its more closely related parent compound, pseudohypericin. The implications for a photodynamic therapy that is independent of external light sources are discussed.