Thermal Half-Lives of Azobenzene Derivatives: Virtual Screening Based on Intersystem Crossing Using a Machine Learning Potential.
ACS Cent Sci
; 9(2): 166-176, 2023 Feb 22.
Article
en En
| MEDLINE
| ID: mdl-36844486
ABSTRACT
Molecular photoswitches are the foundation of light-activated drugs. A key photoswitch is azobenzene, which exhibits trans-cis isomerism in response to light. The thermal half-life of the cis isomer is of crucial importance, since it controls the duration of the light-induced biological effect. Here we introduce a computational tool for predicting the thermal half-lives of azobenzene derivatives. Our automated approach uses a fast and accurate machine learning potential trained on quantum chemistry data. Building on well-established earlier evidence, we argue that thermal isomerization proceeds through rotation mediated by intersystem crossing, and incorporate this mechanism into our automated workflow. We use our approach to predict the thermal half-lives of 19,000 azobenzene derivatives. We explore trends and trade-offs between barriers and absorption wavelengths, and open-source our data and software to accelerate research in photopharmacology.
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MEDLINE
Tipo de estudio:
Diagnostic_studies
/
Screening_studies
Idioma:
En
Revista:
ACS Cent Sci
Año:
2023
Tipo del documento:
Article