title: Development of a Photoactivatable Phosphine Probe for Induction of Intracellular Reductive Stress with Single-Cell Precision.
abstract: Photoactivatable phosphines that induce intracellular reductive stress are reported. The design of these probes takes advantage of the conjugate addition of trialkylphosphines to carbocyanine dyes, which can be reverted photochemically to produce the trialkylphosphine and a fluorescent reporter. The photochemical release depends on the efficiency of photoinduced electron transfer from the indolenine arm of the probe to the coumarin acceptor. These probes readily permeate the mammalian plasma membrane and can be photoactivated in live cells. Upon irradiation of the probe, the released trialkylphosphine induces intracellular reductive stress, which ultimately leads to formation of thioflavin-positive intracellular protein aggregates. These effects could be induced in individual cells within a monolayer, with minimal disturbance of neighboring cells.
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, HCI G329, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
authors.forename: Alina
authors.initials: A
authors.lastname: Tirla
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, HCI G329, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
authors.forename: Pablo
authors.identifier: 0000-0001-8558-2828
authors.initials: P
authors.lastname: Rivera-Fuentes
mesh_terms: D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010720:Phosphines / Q000138:chemical synthesis / Q000737:chemistry*; D055668:Photochemical Processes; D059010:Single-Cell Analysis
chemical_list: D005456:Fluorescent Dyes; D007211:Indoles; D010720:Phosphines; C044646:phosphine
keywords: fluorescent probes; imaging agents; photoactivation; reduction; uncaging