Concise synthesis and voltammetric studies of dielsiquinone, a cytotoxic azaanthraquinone.
We have developed a concise synthesis of dielsiquinone 1, a potent cytotoxic agent related to anthraquinones. Electrochemical studies have shown that dielsiquinone is reduced to a semiquinone radical that does not react with O2 to generate toxic reactive oxygen species. These results strongly suggest that 1 should be less cardiotoxic than anthracyclines used in clinic and may therefore provide the basis for the development of safer anticancer drugs.
Brisach-Wittmeyer
Anne
A
UMR 7512, Institut le Bel, 4 rue Blaise Pascal, 67070 Strasbourg Cedex, France.
Souna Sido
Abdelkarim Sani
AS
Guilini
Pauline
P
Désaubry
Laurent
L
D000818:Animals; D018943:Anthracyclines / Q000494:pharmacology / Q000633:toxicity; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D016227:Benzoquinones / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D011199:Potentiometry / Q000379:methods; D017382:Reactive Oxygen Species / Q000737:chemistry / Q000633:toxicity; D013329:Structure-Activity Relationship
D018943:Anthracyclines; D000880:Anthraquinones; D000903:Antibiotics, Antineoplastic; D001372:Aza Compounds; D016227:Benzoquinones; D017382:Reactive Oxygen Species; C504381:dielsiquinone; C025232:semiquinone radicals; D010100:Oxygen