Translator Disclaimer
1 July 2005 Synthesis of Hydroxy and Methoxy Perylene Quinones, Their Spectroscopic and Computational Characterization, and Their Antiviral Activity
Author Affiliations +
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 S0 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.

G. Krishnamoorthy, S. P. Webb, T. Nguyen, P. K. Chowdhury, M. Halder, N. J. Wills, S. Carpenter, G. A. Kraus, M. S. Gordon, and J. W. Petrich "Synthesis of Hydroxy and Methoxy Perylene Quinones, Their Spectroscopic and Computational Characterization, and Their Antiviral Activity," Photochemistry and Photobiology 81(4), 924-933, (1 July 2005). https://doi.org/10.1562/2004-11-23-RA-378R1.1
Received: 19 November 2004; Accepted: 1 May 2005; Published: 1 July 2005
JOURNAL ARTICLE
10 PAGES

This article is only available to subscribers.
It is not available for individual sale.
+ SAVE TO MY LIBRARY

SHARE
ARTICLE IMPACT
RIGHTS & PERMISSIONS
Get copyright permission
Back to Top