Davidson M W, Griggs B G, Lopp I G, Wilson W D
Biochim Biophys Acta. 1977 Dec 14;479(4):378-90. doi: 10.1016/0005-2787(77)90031-4.
The interactions of a quinacrine derivative, methylated at both the aromatic and aliphatic nitrogens, and propidium diiodide with the dinucleoside monophosphates CpG, GpC, UpA and ApU have been investigated using 13C-NMR (for the quinacrine derivative prepared with [13C]methyl substituents and 1H-NMR and ultraviolet-visible spectroscopy. The quinacrine derivative displayed negligible interaction with the dinucleosides at concentrations up to 5 - 10(-4) M. Propidium did form complexes with dinucleosides even at concentrations as low as 10(-4) M. Propidium displayed a pyrimidine-purine binding preference and gave especially large changes in ultraviolet-visible and 1H-NMR spectra in the presence of CpG. This suggests that propidium forms an intercalated complex with a Watson-Crick hydrogen-bonded CpG dimer. At higher concentrations UpA and GpC gave similar spectral changes indicating that they could also form significant amounts of an intercalated complex with propidium under appropriate conditions. The changes caused by ApU were small under all conditions and were more similar to the effects caused by mononucleotides. These results indicate that, at least for phenanthridines, cationic side chains do not greatly inhibit complex formation with dinucleoside monophosphates, and suggest that the weak interaction of the quinacrine derivative with dinucleosides is due to weaker interactions of the acridine ring system with nucleoside bases relative to the phenanthridine ring system.
对一种在芳香族和脂肪族氮原子上均被甲基化的喹吖因衍生物以及碘化丙啶与二核苷单磷酸CpG、GpC、UpA和ApU的相互作用进行了研究，采用了13C-NMR（用于用[13C]甲基取代基制备的喹吖因衍生物）、1H-NMR和紫外可见光谱法。在浓度高达5×10(-4) M时，喹吖因衍生物与二核苷的相互作用可忽略不计。即使在低至10(-4) M的浓度下，碘化丙啶也确实与二核苷形成了复合物。碘化丙啶表现出嘧啶-嘌呤结合偏好，并且在存在CpG的情况下，紫外可见光谱和1H-NMR光谱发生了特别大的变化。这表明碘化丙啶与沃森-克里克氢键结合的CpG二聚体形成了插入复合物。在较高浓度下，UpA和GpC产生了类似的光谱变化，表明在适当条件下它们也能与碘化丙啶形成大量的插入复合物。在所有条件下，ApU引起的变化都很小，并且与单核苷酸引起的效应更相似。这些结果表明，至少对于菲啶类化合物来说，阳离子侧链不会极大地抑制与二核苷单磷酸的复合物形成，并且表明喹吖因衍生物与二核苷的弱相互作用是由于相对于菲啶环系统，吖啶环系统与核苷碱基的相互作用较弱。
