Synthesis of fluoro-functionalized diaryl-λ3-iodonium salts and their cytotoxicity against human lymphoma U937 cells.
Prajwalita DasEtsuko TokunagaHidehiko AkiyamaHiroki DoiNorimichi SaitoNorio ShibataPublished in: Beilstein journal of organic chemistry (2018)
Conscious of the potential bioactivity of fluorine, an investigation was conducted using various fluorine-containing diaryliodonium salts in order to study and compare their biological activity against human lymphoma U937 cells. Most of the compounds tested are well-known reagents for fluoro-functionalized arylation reactions in synthetic organic chemistry, but their biological properties are not fully understood. Herein, after initially investigating 18 fluoro-functionalized reagents, we discovered that the ortho-fluoro-functionalized diaryliodonium salt reagents showed remarkable cytotoxicity in vitro. These results led us to synthesize more compounds, previously unknown sterically demanding diaryliodonium salts having a pentafluorosulfanyl (SF5) functional group at the ortho-position, that is, unsymmetrical ortho-SF5 phenylaryl-λ3-iodonium salts. Newly synthesized mesityl(2-(pentafluoro-λ6-sulfanyl)phenyl)iodonium exhibited the greatest potency in vitro against U937 cells. Evaluation of the cytotoxicity of selected phenylaryl-λ3-iodonium salts against AGLCL (a normal human B cell line) was also examined.
Keyphrases
- positron emission tomography
- induced apoptosis
- endothelial cells
- ionic liquid
- cell cycle arrest
- quantum dots
- computed tomography
- induced pluripotent stem cells
- diffuse large b cell lymphoma
- pluripotent stem cells
- oxidative stress
- endoplasmic reticulum stress
- signaling pathway
- pet imaging
- high resolution
- pet ct
- human health
- drug discovery