title: Selective arylthiolane deprotection by singlet oxygen: a promising tool for sensors and prodrugs.
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.
authors.affiliation: The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA. bmlamb@scripps.edu.
authors.forename: Brian M
authors.initials: BM
authors.lastname: Lamb
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D004317:Doxorubicin / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008027:Light; D008751:Methylene Blue / Q000737:chemistry; D017319:Photosensitizing Agents / Q000737:chemistry; D011355:Prodrugs; D017382:Reactive Oxygen Species / Q000737:chemistry*; D012395:Rose Bengal / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D007659:Ketones; D017319:Photosensitizing Agents; D011355:Prodrugs; D017382:Reactive Oxygen Species; D013876:Thiophenes; D012395:Rose Bengal; C013177:1,3-oxathiolane; C012948:1,3-dithiolane; D004317:Doxorubicin; D008751:Methylene Blue