Activity of 3-carbethoxyangelicin photolysis products.
3-Carbethoxyangelicin (3-CA), carrying an electron-withdrawing group at the pyrone side, has been prepared to have a fully monofunctional angelicin derivative. 3-CA does not photoreact with DNA and induces a moderate antiproliferative activity. 3-CA proved to be extremely sensitive to ultraviolet A (UVA) light, undergoing rapid photolysis. Only one photolysis product has been isolated and identified. By means of alkaline elution, we observed that 3-CA and its photolysis products are able to induce a large amount of single-strand breaks in DNA in vivo. The results obtained from studying the capacity to produce singlet oxygen suggest that the photodynamic mechanism of action of 3-CA very likely results from its capacity--as well as that of its photolysis products--to produce singlet oxygen.
Marzano
C
C
Department of Pharmaceutical Sciences, University of Padova, CNR, Italy.
Caffieri
S
S
Fossa
P
P
Bordin
F
F
D000818:Animals; D016466:CHO Cells; D002999:Clone Cells / Q000378:metabolism; D006224:Cricetinae; D004249:DNA Damage; D011564:Furocoumarins / Q000378:metabolism* / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010100:Oxygen / Q000378:metabolism; D010782:Photolysis; D017319:Photosensitizing Agents / Q000378:metabolism* / Q000494:pharmacology; D026082:Singlet Oxygen; D013056:Spectrophotometry, Ultraviolet; D014466:Ultraviolet Rays
C107371:3-carbethoxyangelicin; D011564:Furocoumarins; D017319:Photosensitizing Agents; D026082:Singlet Oxygen; D010100:Oxygen