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

Abstract

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.

Ultrafast Dynamics of C30 in Solution and within CDs and HSA Protein

“…Intimate information about the nature of the interactions between chromophores and chemical or biological cavities, as well as on the time scales of the involved processes, is crucial for the understanding of the overall activity of ligands and drugs in the human body, and for the development of effective fluorescent labels. − One can use advanced laser-based techniques to investigate the excited-state behavior and the structural transitions of dyes and drugs in solutions and in chemical and biological caging media, such as cyclodextrins and the human serum albumin (HSA) protein for example. ,− …”

X-ray-induced radiophotodynamic therapy (RPDT) using lanthanide micelles: Beyond depth limitations

“…A fundamentally different approach is to circumvent external ultraviolet-visible (UV-VIS) excitation by using a locally generated light source in the tissue for PDT. Carpenter et al [20] have demonstrated that chemiluminescence produced from the reaction of luciferin with luciferase and molecular oxygen could yield sufficiently intense and long-lived emission for exciting Hyp [21,22]. Despite the promising in vitro results, in vivo applications were hampered by the delivery of the chemiluminescence components and/or the viral vectors required to transfect the target cells with the luciferase gene.…”

The light-sensitive cytotoxicity of Hypericum perforatum extracts, fractions and individual and combined constituents in cell culture models

“…The dependence of hypericin on light activation for the most efficient antiviral activity poses problems for in vivo treatment where light exposure is difficult to obtain ( 34,49,58). Models have been developed to assess the possibility of introducing an internal energy source, such as the luciferin/luciferase reaction that occurs in the North American firefly ( 15,95 ). Carpenter, et al, have reported that this type of model provides enough internal light energy to adequately excite hypericin ( 15,95 ).…”

“…Models have been developed to assess the possibility of introducing an internal energy source, such as the luciferin/luciferase reaction that occurs in the North American firefly ( 15,95 ). Carpenter, et al, have reported that this type of model provides enough internal light energy to adequately excite hypericin ( 15,95 ). However, the mode of hypericin activation in this type of energy transfer reaction is different than hypericin activation by a continual light source, which may challenge the effectiveness of this photodynamic therapy agent (15,95).…”

“…Carpenter, et al, have reported that this type of model provides enough internal light energy to adequately excite hypericin ( 15,95 ). However, the mode of hypericin activation in this type of energy transfer reaction is different than hypericin activation by a continual light source, which may challenge the effectiveness of this photodynamic therapy agent (15,95).…”