Orehovec, Iva published the artcileBis-pyrene photo-switch open- and closed-form differently bind to ds-DNA, ds-RNA and serum albumin and reveal light-induced bioactivity, Application In Synthesis of 219537-97-0, the publication is International Journal of Molecular Sciences (2021), 22(9), 4916, database is CAplus and MEDLINE.
Newly designed and synthesized diarylethene (DAE) derivatives with aliphatic amine sidearms I and one with two pyrenes II, revealed excellent photo-switching property of central DAE core in MeOH and water. The only exception was bis-pyrene analog, its DAE core very readily photochem. closed, but reversible opening completely hampered by aromatic stacking interaction of pyrene(s) with cyclic DAE. In this process, pyrene fluorescence showed to be a reliable monitoring method, an open form characterized by strong emission at 480 nm (typical for pyrene-aggregate), while closed form emitted weakly at 400 nm (typical for pyrene-DAE quenching). Only open DAE-bis-pyrene form interacted measurably with ds-DNA/RNA by flexible insertion in polynucleotide grooves, while self-stacked closed form did not bind to DNA/RNA. For the same steric reasons, flexible open DAE-bis-pyrene form was bound to at least three different binding sites at bovine serum albumin (BSA), while rigid, self-stacked closed form interacted dominantly with only one BSA site. Preliminary screening of antiproliferative activity against human lung carcinoma cell line A549 revealed that all DAE-derivatives were non-toxic. However, bis-pyrene analog efficiently entered cells and located in the cytoplasm, whereby irradiation by light (315-400 nm) resulted in a strong, photo-induced cytotoxic effect, typical for pyrene-related singlet oxygen species production
International Journal of Molecular Sciences published new progress about 219537-97-0. 219537-97-0 belongs to chlorides-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Cyclopentenes, name is 5-Chloro-3-[2-(5-chloro-2-methylthien-3-yl)cyclopent-1-en-1-yl]-2-methylthiophene, and the molecular formula is C15H14Cl2S2, Application In Synthesis of 219537-97-0.
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