ω,ω'-Appended nucleo-base derivativeis of hypericin

摘要

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 de-rivative 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'-deoxyade-nylic acid) could be detected, it proved to be signifi-cantly better accumulating in the nucleus of prostatic cancer LNCaP cells than hypericin making it a promising candidate for a second-generation photodynamic hypericin agent.