Efficient visible/NIR light-driven uncaging of hydroxylated thiazole orange-based caged compounds in aqueous media. Issue 25 (13th June 2022)

• Record Type: Journal Article
• Authors: Hashimoto, Ryu; Minoshima, Masafumi; Sakata, Souhei; Ono, Fumihito; Ishii, Hirokazu; Watakabe, Yuki; Nemoto, Tomomi; Yanaka, Saeko; Kato, Koichi; Kikuchi, Kazuya
• Is Part Of: Chemical science. Volume 13:Issue 25(2022)
• Page Start: 7462
• Page End: 7467
• Publication Date: 2022-06-13
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc02364d
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A hydroxylated thiazole orange (HTO)-caged glutamate efficiently releases a glutamate for temporal activation of ion channels under visible-to-NIR light in aqueous media. Abstract : In photoactivation strategies with bioactive molecules, one-photon visible or two-photon near-infrared light-sensitive caged compounds are desirable tools for biological applications because they offer reduced phototoxicity and deep tissue penetration. However, visible-light-sensitive photoremovable protecting groups (PPGs) reported so far have displayed high hydrophobicity and low uncaging cross sections ( εΦ < 50) in aqueous media, which can obstruct the control of bioactivity with high spatial and temporal precision. In this study, we developed hydroxylated thiazole orange (HTO) derivatives as visible-light-sensitive PPGs with high uncaging cross sections ( εΦ ≈ 370) in aqueous solution. In addition, 2PE photolysis reactions of HTO-caged glutamate were achieved using a NIR laser (940 nm). Moreover, HTO-caged glutamate can activate N -methyl-d -aspartic acid receptors in Xenopus oocytes and mammalian cells with green-light illumination, thus allowing optical control of biological functions.