Excited-State Processes in Polycyclic Quinones:  The Light-Induced Antiviral Agent, Hypocrellin, and a Comparison with Hypericin

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1996-11-14
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Das, K.
English, D.
Fehr, Michael
Smirnov, Alexandre
Petrich, Jacob
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Chemistry

The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).

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Abstract

Hypocrellin is a naturally occurring perylene quinone that possesses light-induced antiviral activity, most notably against the human immunodeficiency virus (HIV), as does the related molecule, hypericin. White-light continuum is employed to examine the excited-state processes in hypocrellin from the picosecond to the nanosecond time scales. These processes are assigned to intramolecular proton transfer, intersystem crossing, and interconversion between different conformations of hypocrellin, which is constrained to be nonplanar in its ground-state owing to its bulky side chains. The ground state of hypocrellin is suggested to be heterogeneous and to be comprised of an equilibrium between at least two tautomeric forms. The results are discussed in terms of the properties of hypericin, which bears marked similarities and differences with respect to hypocrellin, both in terms of its excited-state properties as well as its mode of induced antiviral activity.

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Reprinted (adapted) with permission from Journal of Physical Chemistry 100 (1996): 18275, doi: 10.1021/jp961156h. Copyright 1996 American Chemical Society.

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Mon Jan 01 00:00:00 UTC 1996
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