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 IC50 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.
BARRAJA, P., DIANA, P., MONTALBANO, A., CARBONE, A., CIRRINCIONE, G., VIOLA, G., et al. (2008). THIOPYRANO[2,3-E]INDOL-2-ONES: ANGELICIN HETEROANALOGUES WITH POTENT PHOTOANTIPROLIFERATIVE ACTIVITY. BIOORGANIC & MEDICINAL CHEMISTRY, 16(22), 9668-9683 [10.1016/j.bmc.2008.10.002].
THIOPYRANO[2,3-E]INDOL-2-ONES: ANGELICIN HETEROANALOGUES WITH POTENT PHOTOANTIPROLIFERATIVE ACTIVITY
BARRAJA, Paola;DIANA, Patrizia;MONTALBANO, Alessandra;CARBONE, Anna;CIRRINCIONE, Girolamo;
2008-01-01
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 IC50 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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