1-pyrenebutylamine and 1-aminopyrene

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 10(6) L/mol, while that of 1-PBA only to about 10(3) 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.

Topics: Butylamines; Carcinogens; Circular Dichroism; DNA; Electrophoresis, Polyacrylamide Gel; Genes, myc; Humans; Intercalating Agents; Mutagens; Nucleic Acid Conformation; Osmolar Concentration; Polycyclic Aromatic Hydrocarbons; Potassium Iodide; Pyrenes; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet; Thermodynamics; Tumor Suppressor Protein p53