Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210097, China.
J Photochem Photobiol B. 2013 Jun 5;123:32-40. doi: 10.1016/j.jphotobiol.2013.03.009. Epub 2013 Apr 4.
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.
多环芳烃衍生物（PAHs）已被证实具有致癌、致畸和致突变作用，并有可能导致人类恶性疾病。在这项工作中，使用光谱和聚丙烯酰胺凝胶电泳（PAGE）方法评估了两种选定的氨基-PAHs（氨基芘衍生物）与人肿瘤相关 DNA 的相互作用。光谱结果表明，PAHs 与靶向 DNA 之间存在显著的相互作用，结合能力的顺序为 1-AP>1-PBA。1-AP 与靶向 DNA 的结合常数约为 10(6)L/mol，而 1-PBA 仅约为 10(3)L/mol。具有短侧链的 1-AP 主要作为嵌入剂，其与 DNA 的相互作用通过静电力得到加强。而对于具有柔性长侧链的 1-PBA，嵌入模式主要以范德华力和氢键的辅助作用为主。此外，氨基-PAHs 与 p53 DNA 的结合能力似乎比与 C-myc DNA 的结合能力更强。PAGE 结果表明，氨基-PAHs 的结合可以进一步将 DNA 序列的构象从双链体改变为反平行 G-四链体。
