Schulman S G, Naik D V, Capomacchia A C, Roy T
J Pharm Sci. 1975 Jun;64(6):982-6. doi: 10.1002/jps.2600640619.
The shifts in the absorption and fluorescence spectra of 3-aminoacridine, proflavine, acridine orange, and acridine yellow were employed to show that the singly charged cations, the predominant species at biological pH, exist in the ground state in the amino form. In the lowest excited singlet state, however, the monocations of the diaminoacridines have the imino structure, a conclusion supported by the relative ground- and excited-state pKa values of the reactions of the monocation with H-+. The ground-state amino structure has its positive charge concentrated at the heterocyclic nitrogen atom, a fact that is of primary importance in determining the geometry of binding to DNA.
利用3-氨基吖啶、硫酸普罗黄素、吖啶橙和吖啶黄的吸收光谱和荧光光谱的变化表明,在生理pH值下占主导地位的单电荷阳离子在基态时以氨基形式存在。然而,在最低激发单重态下,二氨基吖啶的单阳离子具有亚氨基结构,这一结论得到了单阳离子与H⁺反应的相对基态和激发态pKa值的支持。基态氨基结构的正电荷集中在杂环氮原子上,这一事实在确定与DNA结合的几何结构方面至关重要。