Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells
Abstract
Novel caged nitroxides (nitroxide donors) with near-infrared two-photon (TP) responsive character, 2,2,6,6-tetramethyl-1-(1-(2-(4-nitrophenyl)benzofuran-6-yl)ethoxy)piperidine (2a) and its regioisomer 2b, were designed and synthesized. The one-photon (OP)(365 ± 10 nm) and TP (710–760 nm) triggered release (i.e., uncaging) of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radicalunder air atmosphere were discovered. The quantum yields for the release of the TEMPO radical were 2.5% (2a) and 0.8% (2b) inbenzene at ≈1% conversion of 2, and 13.1% (2a) and 12.8% (2b) in DMSO at ≈1% conversion of 2. The TP uncaging efficiencieswere determined to be 1.1 GM at 740 nm for 2a and 0.22 GM at 730 nm for 2b in benzene. The cytocidal effect of compound 2a onlung cancer cells under photolysis conditions was also assessed to test the efficacy as anticancer agents. In a medium containing100 μg mL−1 of 2a exposed to light, the number of living cells decreased significantly compared to the unexposed counterparts(65.8% vs 85.5%).
Journal
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- Beilstein Journal of Organic Chemistry
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Beilstein Journal of Organic Chemistry 15 863-873, 2019-04
Beilstein-Institut
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Keywords
Details 詳細情報について
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- CRID
- 1050001339197984000
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- NII Article ID
- 120007127956
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- ISSN
- 18605397
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- HANDLE
- 2241/00157106
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- Text Lang
- en
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- Article Type
- journal article
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- Data Source
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- IRDB
- Crossref
- CiNii Articles
- KAKEN