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EnglishThe 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 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 salts was investigated as a pH function and compared to that of other quaternary ammonium salts capable of benzo-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.
BINOL Quinone Methides as Bis-Alkylating and DNA Cross-Linking Agents / RICHTER SARA, MAGGI STEFANO; COLLOREDO MELS, Stefano; Freccero, Mauro. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - STAMPA. - 126(2004), pp. 13973-13979.
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| Titolo: | BINOL Quinone Methides as Bis-Alkylating and DNA Cross-Linking Agents |
| Autori: | FRECCERO, MAURO (Corresponding) |
| Data di pubblicazione: | 2004 |
| Rivista: | |
| Citazione: | BINOL Quinone Methides as Bis-Alkylating and DNA Cross-Linking Agents / RICHTER SARA, MAGGI STEFANO; COLLOREDO MELS, Stefano; Freccero, Mauro. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - STAMPA. - 126(2004), pp. 13973-13979. |
| Abstract: | 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 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 salts was investigated as a pH function and compared to that of other quaternary ammonium salts capable of benzo-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. |
| Handle: | http://hdl.handle.net/11571/108116 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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