Abstract
ω,ω′-Disubstituted hypericin derivatives with the nucleo-bases thymine, cytosine, and adenine in these positions were prepared starting from tri-O-methyl-ω-bromoemodin. The most promising derivative proved to be that with a thymine moiety. It displayed the best solubility of the three products together with a potency to produce singlet oxygen and/or reactive oxygen species comparable to the parent compound hypericin. In addition, although no specific interaction with DNA or poly(2′-deoxyadenylic acid) could be detected, it proved to be significantly better accumulating in the nucleus of prostatic cancer LNCaP cells than hypericin making it a promising candidate for a second-generation photodynamic hypericin agent.
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Correspondence: Heinz Falk, Institute of Organic Chemistry, Johannes Kepler University, Altenbergerstraße 69, 4040 Linz, Austria, Europe.
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Geißlmeir, D., Falk, H. ω,ω′-Appended nucleo-base derivatives of hypericin. Monatsh Chem 139, 1127–1136 (2008). https://doi.org/10.1007/s00706-008-0898-0
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DOI: https://doi.org/10.1007/s00706-008-0898-0