A photochemical approach for evaluating the reactivity of substituted lappaconitines,Photochemical & Photobiological Sciences

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A photochemical approach for evaluating the reactivity of substituted lappaconitines
Photochemical & Photobiological Sciences ( IF 2.7 ) Pub Date : 2017-12-04 00:00:00 , DOI: 10.1039/c7pp00366h
Aleksandra A. Ageeva _{1,

2,

3} , Ekaterina A. Khramtsova _{1,

2,

2,

3,

4} , Viktor F. Plyusnin _{1,

2,

2,

3,

4} , Aleksandr A. Stepanov _{1,

2,

3} , Tatyana V. Leshina _{1,

2,

3}

Affiliation

Lappaconitine (LC) is a natural diterpenoid alkaloid (DTA), acting as a human heart sodium channel blocker and possessing a wide range of biological activities, the cellular and molecular mechanisms of which are widely studied. This interest is due to the fact that various representatives of this DTA class show opposite biological activities. The possible reasons for this difference seem to be related to the peculiarities of the substituent effect on the drug–receptor binding process. In this work, the influence of substituents on the reactivity of LC and its derivatives has been studied by using elementary processes of photodecomposition. The given approach includes the joint analysis of the photophysical properties of the studied systems and their photodecomposition quantum yields. It allows us to trace the influence of substituents, located in the diterpenoid skeleton and anthranilic fragment, on processes in both moieties of LC. Summarizing the data obtained, an inverse dependence of fluorescence and photodegradation quantum yields has been observed. This correlation established for LCs, in particular, allows one to propose a way to evaluate the photostability of potential drugs based on fluorescence analysis. This would be appropriate for compounds in which the reactivity depends on intersystem crossing, i.e. in the cases where the initial and reacting excited states differ in multiplicity.

中文翻译：

一种评估取代拉帕尼汀反应性的光化学方法

拉帕尼汀（LC）是一种天然的二萜类生物碱（DTA），可作为人的心脏钠通道阻滞剂，具有广泛的生物学活性，其细胞和分子机制已得到广泛研究。这种兴趣是由于DTA类的各种代表显示相反的生物活性这一事实。这种差异的可能原因似乎与取代基对药物-受体结合过程的影响有关。在这项工作中，已经通过使用光分解的基本过程研究了取代基对LC及其衍生物的反应性的影响。给定的方法包括对所研究系统的光物理性质及其光分解量子产率的联合分析。它使我们能够追踪取代基的影响，在LC的两个部分中的过程中，位于二萜骨架和邻氨基苯甲酸片段中。总结所获得的数据，已经观察到荧光和光降解量子产率的反比关系。特别为LC建立的这种相关性使人们可以提出一种基于荧光分析评估潜在药物的光稳定性的方法。对于反应性取决于系统间交叉的化合物，这将是适当的，即在初始和反应激发态的多重性不同的情况下。

更新日期：2017-12-04

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