Small-molecule optical probes for cell imaging of protein sulfenylation and their application to monitor cisplatin induced protein oxidation

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Title: Small-molecule optical probes for cell imaging of protein sulfenylation and their application to monitor cisplatin induced protein oxidation
Author(s): Cilibrizzi, A
Terenghi, M
Fedorova, M
Woscholski, R
Klug, D
Vilar, R
Item Type: Journal Article
Abstract: Reactive oxygen species (ROS) are considered versatile second messengers mediating fundamental biological functions. A molecular pathway by which ROS determine functional diversity is the selective oxidation of cysteine residues to form sulfenic acid (SOH) products, known as sulfenylation or S-hydroxylation. This crucial post-translational modification is responsible for the alteration of protein stability, function and signalling. Despite considerable advances on the identification of sulfenic residues on individual proteins, improved methods are needed for direct visualization and accurate quantification of the extent of total protein sulfenylation. Herein we present the synthesis of two new cell-permeable fluorescent probes containing dimedone (a cyclic β-diketone with high specificity for sulfenic acids), and apply them to study oxidation processes in individual cells via microscopy. The low cytotoxicity, cell permeability and optical features of the probes allowed us to visualize and quantify the oxidation of cysteine residues in live cells during H2O2-mediated oxidative burst (i.e. exogenously administered H2O2). We present preliminary cellular imaging studies with these probes to analyse the oxidation process in cells treated with the anticancer drug cisplatin.
Publication Date: 2-Apr-2017
Date of Acceptance: 31-Mar-2017
URI: http://hdl.handle.net/10044/1/50955
DOI: https://dx.doi.org/10.1016/j.snb.2017.03.171
ISSN: 0925-4005
Publisher: Elsevier
Start Page: 437
End Page: 446
Journal / Book Title: Sensors and Actuators B: Chemical
Volume: 248
Sponsor/Funder: Engineering & Physical Science Research Council (E
Funder's Grant Number: EP/I017887/1
Copyright Statement: © 2017 Elsevier Ltd. All rights reserved. This manuscript is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/
Keywords: Science & Technology
Physical Sciences
Technology
Chemistry, Analytical
Electrochemistry
Instruments & Instrumentation
Chemistry
Optical probe
Dimedone
Sulfenic acid
Cellular microscopy
Fluorescence co-localization
Cisplatin
SULFENIC ACID FORMATION
CYSTEINE OXIDATION
REDOX REGULATION
ENDOPLASMIC-RETICULUM
HYDROGEN-PEROXIDE
CHEMICAL PROBES
LIVING CELLS
CANCER-CELLS
STRESS
MECHANISMS
Science & Technology
Physical Sciences
Technology
Chemistry, Analytical
Electrochemistry
Instruments & Instrumentation
Chemistry
Optical probe
Dimedone
Sulfenic acid
Cellular microscopy
Fluorescence co-localization
Cisplatin
SULFENIC ACID FORMATION
CYSTEINE OXIDATION
REDOX REGULATION
ENDOPLASMIC-RETICULUM
HYDROGEN-PEROXIDE
CHEMICAL PROBES
LIVING CELLS
CANCER-CELLS
STRESS
MECHANISMS
0301 Analytical Chemistry
0912 Materials Engineering
Analytical Chemistry
Publication Status: Published
Appears in Collections:Chemistry
Biological and Biophysical Chemistry
Faculty of Natural Sciences



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