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  • Title: Thiopyrano[2,3-e]indol-2-ones: angelicin heteroanalogues with potent photoantiproliferative activity.
    Author: Barraja P, Diana P, Montalbano A, Carbone A, Cirrincione G, Viola G, Salvador A, Vedaldi D, Dall'acqua F.
    Journal: Bioorg Med Chem; 2008 Nov 15; 16(22):9668-83. PubMed ID: 18951030.
    Abstract:
    A new class of compounds, the thiopyrano[2,3-e]indol-2-ones, bioisosters of the angular furocoumarin angelicin, was synthesized with the aim of obtaining new photochemotherapeutic agents. In particular 7,8-dimethyl-thiopyranoindolone 6c s showed a remarkable phototoxicity and a great dose UVA dependence reaching IC(50) values at submicromolar level. This latter photoinduced a massive apoptosis and a remarkable photodamage to lipids and proteins. Although it did not intercalate DNA, it was able to cause photooxidation of DNA bases.
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