Abstract
A routine thioketal protecting group reacts rapidly and selectively with singlet oxygen to reveal ketone products in good (aryl 1,3-dithiolane) to excellent (aryl 1,3-oxathiolane) yields. Arylthiolanes are stable to biologically relevant reactive oxygen species and can be used as a light-activated gating mechanism for activating fluorescent sensors or small molecule prodrugs.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Doxorubicin / chemistry
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Heterocyclic Compounds / chemistry*
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Ketones / chemistry*
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Light
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Methylene Blue / chemistry
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Photosensitizing Agents / chemistry
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Prodrugs
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Reactive Oxygen Species / chemistry*
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Rose Bengal / chemistry
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Thiophenes / chemistry*
Substances
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Heterocyclic Compounds
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Ketones
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Photosensitizing Agents
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Prodrugs
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Reactive Oxygen Species
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Thiophenes
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Rose Bengal
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1,3-oxathiolane
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1,3-dithiolane
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Doxorubicin
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Methylene Blue