TY - JOUR

T1 - A photochemical approach for evaluating the reactivity of substituted lappaconitines

AU - Ageeva, Aleksandra A.

AU - Khramtsova, Ekaterina A.

AU - Plyusnin, Viktor F.

AU - Stepanov, Aleksandr A.

AU - Leshina, Tatyana V.

PY - 2018/2

Y1 - 2018/2

N2 - 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.

AB - 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.

KW - PHOTOPHYSICAL PROPERTIES

KW - ALKALOID LAPPACONITINE

KW - DITERPENOID ALKALOIDS

KW - N-DEACETYLLAPPACONITINE

KW - MENTHYL ANTHRANILATE

KW - DERIVATIVES

KW - ACONITUM

KW - PHOTOTRANSFORMATION

KW - AGENTS

KW - PLANTS

UR - http://www.scopus.com/inward/record.url?scp=85042156922&partnerID=8YFLogxK

U2 - 10.1039/c7pp00366h

DO - 10.1039/c7pp00366h

M3 - Article

C2 - 29255820

AN - SCOPUS:85042156922

VL - 17

SP - 192

EP - 199

JO - Photochemical and Photobiological Sciences

JF - Photochemical and Photobiological Sciences

SN - 1474-905X

IS - 2

ER -