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Application of 4-amino-N-adamantylphthalimide solvatochromic dye for fluorescence microscopy in selective visualization of lipid droplets and mitochondria

Benčić, Patricia; Mandić, Leo; Džeba, Iva; Tartaro Bujak, Ivana; Biczók, László; Mihaljević, Branka; Mlinarić-Majerski, Kata; Weber, Igor; Kralj, Marijeta; Basarić, Nikola (2019) Application of 4-amino-N-adamantylphthalimide solvatochromic dye for fluorescence microscopy in selective visualization of lipid droplets and mitochondria. SENSORS AND ACTUATORS B-CHEMICA, 286 . pp. 52-61. ISSN 0925-4005

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Abstract

4-Amino-N-adamantylphthalimide (1) is a dye with moderate absorptivity (in CH3CN ε363 = 4200 M-1 cm-1) and high quantum yield of fluorescence (ΦF = 0.15-0.80) that exhibits fluorosolvatochromic properties. The dye can be excited at 405 nm and the position of fluorescence maximum and the Stokes shift are well correlated with the ET(30) parameter. The excitation in the near-visible part of the spectrum and low cytotoxicity allow use of the dye in live cell microscopy. Due to its amphiphilic character, the dye stains artificial membranes in liposomes. Using confocal microscopy on two human cancer cell lines, we have shown that 1 stains primarily intracellular lipid droplets. Colocalization experiments with different organelle markers indicated that 1 additionally stains mitochondrial membranes. The fluorosolvatochromism of 1 allows the simultaneous visualization of mitochondria and intracellular lipid droplets in two separate emission channels, which has a potential use in cells and tissues exhibiting intense oxidative metabolism of lipids.

Item Type: Article
Uncontrolled Keywords: aminophthalimide; biological membranes; fluorescent dyes; confocal fluorescence microscopy; nonpolar lipids
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Materials Chemistry
Division of Molecular Biology
Division of Molecular Medicine
Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Supramolekulska kontrola fotokemijskih reakcija eliminacije-SupraPhotoENikola BasarićIP-2014-09-6312HRZZ
Mulitidisciplinarni pristup otkriću lijekova s ciljanim djelovanjem na matične stanice tumora – uloga transporta kalija-MultiCaSTMarijeta KraljIP-2013-11-5660HRZZ
Depositing User: Lidija Uzelac
Date Deposited: 03 Dec 2020 13:50
Last Modified: 01 May 2021 23:15
URI: http://fulir.irb.hr/id/eprint/6038
DOI: 10.1016/j.snb.2019.01.102

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