Studies on the interaction mechanism of aminopyrene derivatives with human tumor-related DNA

• The interaction of PAHs and DNA was investigated using spectroscopic and PAGE methods.
• Amino-PAHs bind with DNA mainly via intercalative modes.
• The binding ability of PAHs to p53 DNA was stronger than that for C-myc DNA.
• The binding of 1-PBA induced the transformation from the duplex DNA into the G-quadruplex DNA.

Polycyclic aromatic hydrocarbons derivatives (PAHs) have been confirmed to be carcinogenic, teratogenic and mutagenic, and have the potential to cause human malignant diseases. In this work, interactions of two selected amino-PAHs (aminopyrene derivatives) and human tumor-related DNA were evaluated using spectroscopic and polyacrylamide gel electrophoresis (PAGE) methods. Spectroscopic results demonstrated that there were remarkable interactions between PAHs and the targeted DNA with the order of the binding ability as 1-AP > 1-PBA. The binding constants of 1-AP with the targeted DNA were at the level of about 106 L/mol, while that of 1-PBA only to about 103 L/mol. 1-AP with a short side-chain acted mainly as an intercalator, and its interactions with DNA were strengthened with electrostatic forces. As for 1-PBA with a flexible long side-chain, the intercalation mode was dominated with an auxiliary role of Van der Wals forces and hydrogen bonds. Besides, the binding abilities of amino-PAHs to p53 DNA seemed stronger than that for C-myc DNA. PAGE results showed that the binding of amino-PAHs could further change the conformation of DNA sequences from the duplex to the antiparallel G-quadruplex.

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