One‐Photon and Two‐Photon Mitochondrial Fluorescent Probes Based on a Rhodol Chromophore. Issue 2 (13th December 2017)

• Record Type: Journal Article
• Authors: Poronik, Yevgen M.; Bernaś, Tytus; Wrzosek, Antoni; Banasiewicz, Marzena; Szewczyk, Adam; Gryko, Daniel T.
• Is Part Of: Asian journal of organic chemistry. Volume 7:Issue 2(2018)
• Page Start: 411
• Page End: 415
• Publication Date: 2017-12-13
• Subjects: dyes/pigments -- fluorescent probes -- heterocycles -- mitochondria -- two-photon absorption; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700600
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A synthesized water‐soluble rhodol derivative bearing a triphenylphosphonium moiety possesses an intense fluorescent light emission spectrum in the yellow range upon using one‐ or two‐photon excitation techniques. The presence of the positively charged triphenylphosphonium functional group gives rise to selective accumulation and labeling active and coupled mitochondria according to mitochondrial membrane potential Δ ψ . These chemical and spectroscopic properties of the rhodol derivative allow efficient labeling and imaging eukaryotic cell mitochondria with one‐photon excitation at 488 nm and two‐photon excitation at 800 nm. Selective staining of the coupled mitochondria has been confirmed by a decrease of emission intensity after treatment with protonophore, which acts as an inner mitochondrial membrane‐depolarizing agent. A rhodol‐based fluorescent probe possessing an uncharged structure also accumulates in the eukaryotic cells but with much lower selectivity in relation to the mitochondria. The uncharged rhodol molecule is spread more evenly in the cell without specific organelle labeling. In our experimental conditions, rhodol probes exhibit very low phototoxicity as evaluated based on the morphology of endothelial EA.hy 926 cells. Abstract : The island of Rhodols : Equipping rhodols with a quaternary phosphonium moiety increases their sensitivity towards the mitochondrial membrane potential that allows selective penetration and well‐resolved fluorescent imaging at nanomolar concentrations.