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Synthesis of Hydroxy and Methoxy Perylene Quinones, Their Spectroscopic and Computational Characterization, and Their Antiviral Activity

Authors

  • G. Krishnamoorthy,

    1. Department of Chemistry, Iowa State University, Ames, IA
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  • S. P. Webb,

    Corresponding author
    1. Advanced Biomedical Computing Center, SAIC-Frederick, National Cancer Institute at Frederick, P.O. Box B, Frederick, MD
      *To whom correspondence should be addressed: Department of Chemistry, Iowa State University, Ames, IA 50011, USA (JWP and MSG) emails: jwp@iastate.edu, mark@si.fi.ameslab.gov and Advanced Biomedical Computing Center, NCI, Frederick, MD 21702-1201 email: simonw@ncifcrf.gov.
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  • T. Nguyen,

    1. Department of Chemistry, Iowa State University, Ames, IA
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  • P. K. Chowdhury,

    1. Department of Chemistry, Iowa State University, Ames, IA
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  • M. Halder,

    1. Department of Chemistry, Iowa State University, Ames, IA
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  • N. J. Wills,

    1. Department of Veterinary Microbiology and Preventive Medicine, Iowa State University, Ames, IA
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  • S. Carpenter,

    1. Department of Veterinary Microbiology and Preventive Medicine, Iowa State University, Ames, IA
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  • G. A. Kraus,

    1. Department of Chemistry, Iowa State University, Ames, IA
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  • M. S. Gordon,

    Corresponding author
    1. Department of Chemistry, Iowa State University, Ames, IA
      *To whom correspondence should be addressed: Department of Chemistry, Iowa State University, Ames, IA 50011, USA (JWP and MSG) emails: jwp@iastate.edu, mark@si.fi.ameslab.gov and Advanced Biomedical Computing Center, NCI, Frederick, MD 21702-1201 email: simonw@ncifcrf.gov.
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  • J. W. Petrich

    Corresponding author
    1. Department of Chemistry, Iowa State University, Ames, IA
      *To whom correspondence should be addressed: Department of Chemistry, Iowa State University, Ames, IA 50011, USA (JWP and MSG) emails: jwp@iastate.edu, mark@si.fi.ameslab.gov and Advanced Biomedical Computing Center, NCI, Frederick, MD 21702-1201 email: simonw@ncifcrf.gov.
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  • Posted on the website on 10 May 2005.

*To whom correspondence should be addressed: Department of Chemistry, Iowa State University, Ames, IA 50011, USA (JWP and MSG) emails: jwp@iastate.edu, mark@si.fi.ameslab.gov and Advanced Biomedical Computing Center, NCI, Frederick, MD 21702-1201 email: simonw@ncifcrf.gov.

ABSTRACT

Hydroxy and methoxy perylene quinones are synthesized in an attempt to isolate the essential spectroscopic and biological features of light-induced antiviral agents such as hypericin and hypocrellin. Unlike their naturally occurring counterparts, these synthetic quinones bear the carbonyl, hydroxyl, and methoxy groups in the “bay region.” The hydroxy and methoxy compounds have rich absorption spectra with broad features in the visible (∼450–800 nm) and relatively more intense and narrow features at wavelengths ≤350 nm. High-level ab initio quantum mechanical calculations assign the features in the absorption spectra to electronic transitions from So to S2 and to higher-lying electronic states. The calculations indicate that in the ground state the trans dihydroxy isomer is 12.5 kcal/mol lower in energy than the cis dihydroxy isomer and is thus the only species present. The lowest-energy trans methoxy ground state isomer and the lowest-energy cis methoxy ground state isomer are found to be degenerate. An additional cis methoxy isomer 6.3 kcal/mol higher in energy than the global minimum is assumed to contribute to the spectrum and is also considered. Finally, the synthetic compounds exhibit similar light-induced antiviral activity to each other, but significantly less than that of hypericin.

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