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BASHY Dyes Are Highly Efficient Lipid Droplet-Targeting Photosensitizers that Induce Ferroptosis through Lipid Peroxidation

Ferroptosis is an iron-dependent lipid-peroxidation-driven mechanism of cell death and a promising therapeutic target to eradicate cancer cells. In this study, we discovered that boronic acid-derived salicylidenehydrazone (BASHY) dyes are highly efficient singlet-oxygen photosensitizers (PSs; ΦΔ up...

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Published in:	Bioconjugate chemistry 2023-12, Vol.34 (12), p.2337-2344
Main Authors:	Silva, Maria J. S. A., Zhang, Yiyi, Vinck, Robin, Santos, Fábio M. F., António, João P. M., Gourdon-Grünewaldt, Lisa, Zaouter, Charlotte, Castonguay, Annie, Patten, Shunmoogum A., Cariou, Kevin, Boscá, Francisco, Nájera, Francisco, Arteaga, Jesús F., Gasser, Gilles, Pischel, Uwe, Gois, Pedro M. P.
Format:	Article
Language:	English
Subjects:	Animals Cell death Chemical Sciences Coloring Agents Danio rerio Droplets Dyes Ferroptosis Glioblastoma Humans Lipid Droplets Lipid Peroxidation Lipids Medicinal Chemistry Peroxidation Photodynamic therapy Photosensitizing Agents - pharmacology Phototoxicity Therapeutic targets Zebrafish
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creator	Silva, Maria J. S. A. Zhang, Yiyi Vinck, Robin Santos, Fábio M. F. António, João P. M. Gourdon-Grünewaldt, Lisa Zaouter, Charlotte Castonguay, Annie Patten, Shunmoogum A. Cariou, Kevin Boscá, Francisco Nájera, Francisco Arteaga, Jesús F. Gasser, Gilles Pischel, Uwe Gois, Pedro M. P.
description	Ferroptosis is an iron-dependent lipid-peroxidation-driven mechanism of cell death and a promising therapeutic target to eradicate cancer cells. In this study, we discovered that boronic acid-derived salicylidenehydrazone (BASHY) dyes are highly efficient singlet-oxygen photosensitizers (PSs; ΦΔ up to 0.8) that induce ferroptosis triggered by photodynamic therapy. The best-performing BASHY dye displayed a high phototoxicity against the human glioblastoma multiform U87 cell line, with an IC50 value in the low nanomolar range (4.40 nM) and a remarkable phototoxicity index (PI > 22,700). Importantly, BASHY dyes were shown to accumulate in lipid droplets (LDs) and this intracellular partition was found to be essential for the enhanced phototoxicity and the induction of ferroptosis through lipid peroxidation. The safety and phototoxicity of this platform were validated using an in vivo zebrafish model (Danio rerio)
doi_str_mv	10.1021/acs.bioconjchem.3c00449
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S. A. ; Zhang, Yiyi ; Vinck, Robin ; Santos, Fábio M. F. ; António, João P. M. ; Gourdon-Grünewaldt, Lisa ; Zaouter, Charlotte ; Castonguay, Annie ; Patten, Shunmoogum A. ; Cariou, Kevin ; Boscá, Francisco ; Nájera, Francisco ; Arteaga, Jesús F. ; Gasser, Gilles ; Pischel, Uwe ; Gois, Pedro M. P.</creator><creatorcontrib>Silva, Maria J. S. A. ; Zhang, Yiyi ; Vinck, Robin ; Santos, Fábio M. F. ; António, João P. M. ; Gourdon-Grünewaldt, Lisa ; Zaouter, Charlotte ; Castonguay, Annie ; Patten, Shunmoogum A. ; Cariou, Kevin ; Boscá, Francisco ; Nájera, Francisco ; Arteaga, Jesús F. ; Gasser, Gilles ; Pischel, Uwe ; Gois, Pedro M. P.</creatorcontrib><description>Ferroptosis is an iron-dependent lipid-peroxidation-driven mechanism of cell death and a promising therapeutic target to eradicate cancer cells. In this study, we discovered that boronic acid-derived salicylidenehydrazone (BASHY) dyes are highly efficient singlet-oxygen photosensitizers (PSs; ΦΔ up to 0.8) that induce ferroptosis triggered by photodynamic therapy. The best-performing BASHY dye displayed a high phototoxicity against the human glioblastoma multiform U87 cell line, with an IC50 value in the low nanomolar range (4.40 nM) and a remarkable phototoxicity index (PI > 22,700). Importantly, BASHY dyes were shown to accumulate in lipid droplets (LDs) and this intracellular partition was found to be essential for the enhanced phototoxicity and the induction of ferroptosis through lipid peroxidation. 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S. A.</creatorcontrib><creatorcontrib>Zhang, Yiyi</creatorcontrib><creatorcontrib>Vinck, Robin</creatorcontrib><creatorcontrib>Santos, Fábio M. F.</creatorcontrib><creatorcontrib>António, João P. M.</creatorcontrib><creatorcontrib>Gourdon-Grünewaldt, Lisa</creatorcontrib><creatorcontrib>Zaouter, Charlotte</creatorcontrib><creatorcontrib>Castonguay, Annie</creatorcontrib><creatorcontrib>Patten, Shunmoogum A.</creatorcontrib><creatorcontrib>Cariou, Kevin</creatorcontrib><creatorcontrib>Boscá, Francisco</creatorcontrib><creatorcontrib>Nájera, Francisco</creatorcontrib><creatorcontrib>Arteaga, Jesús F.</creatorcontrib><creatorcontrib>Gasser, Gilles</creatorcontrib><creatorcontrib>Pischel, Uwe</creatorcontrib><creatorcontrib>Gois, Pedro M. P.</creatorcontrib><title>BASHY Dyes Are Highly Efficient Lipid Droplet-Targeting Photosensitizers that Induce Ferroptosis through Lipid Peroxidation</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>Ferroptosis is an iron-dependent lipid-peroxidation-driven mechanism of cell death and a promising therapeutic target to eradicate cancer cells. In this study, we discovered that boronic acid-derived salicylidenehydrazone (BASHY) dyes are highly efficient singlet-oxygen photosensitizers (PSs; ΦΔ up to 0.8) that induce ferroptosis triggered by photodynamic therapy. The best-performing BASHY dye displayed a high phototoxicity against the human glioblastoma multiform U87 cell line, with an IC50 value in the low nanomolar range (4.40 nM) and a remarkable phototoxicity index (PI > 22,700). Importantly, BASHY dyes were shown to accumulate in lipid droplets (LDs) and this intracellular partition was found to be essential for the enhanced phototoxicity and the induction of ferroptosis through lipid peroxidation. 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source	American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects	Animals Cell death Chemical Sciences Coloring Agents Danio rerio Droplets Dyes Ferroptosis Glioblastoma Humans Lipid Droplets Lipid Peroxidation Lipids Medicinal Chemistry Peroxidation Photodynamic therapy Photosensitizing Agents - pharmacology Phototoxicity Therapeutic targets Zebrafish
title	BASHY Dyes Are Highly Efficient Lipid Droplet-Targeting Photosensitizers that Induce Ferroptosis through Lipid Peroxidation
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