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Binol Quinone Methides as Bisalkylating and DNA Cross-Linking Agents

2004; American Chemical Society; Volume: 126; Issue: 43 Linguagem: Inglês

10.1021/ja047655a

1943-2984

Sara N. Richter, Stefano Maggi, Stefano Colloredo Mels, Manlio Palumbo, Mauro Freccero,

Bioactive Compounds and Antitumor Agents

The photogeneration and detection of new binol quinone methides undergoing mono- and bisalkylation of free nucleophiles was investigated by product distribution analysis and laser flash photolysis in water solution using binol quaternary ammonium derivatives 2 and 12 as photoactivated precursors. The alkylation processes of N and S nucleophiles are strongly competitive with the hydration reaction. DNA cross-linking potency of the water-soluble binol quaternary ammonium salt 2 was investigated as a pH function and compared to that of other quaternary ammonium salts capable of benzo-QM (QM = quinone methide) photogeneration by gel electrophoresis. DFT calculations in the gas phase and in water bulk on the binol and benzo quaternary ammonium salts 2 and 4 evidence structural and electrostatic features of the binol derivative which might offer a rationalization of its promising high photo-cross-linking efficiency.