Lipid Peroxidation Assay Using BODIPY-Phenylbutadiene Probes: A Methodological Overview

Stockert, Juan C.

doi:10.1007/978-1-0716-0896-8_16

Cited by 6 publications

(4 citation statements)

References 72 publications

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“… Reaction between MDA and TBA to form the MDA-TBA adduct. Fluorescent probes: BODIPY dyes, such as BODIPY-581/591-C11 and BODIPY-665/676, are commonly used for the detection of lipid peroxidation [ 285 ]. BODIPY-581/591-C11 undergoes a fluorescence shift from red to green when its unsaturated diene bridge is oxidatively disrupted ( Figure 10A ).…”

Section: Methods For Monitoring Autophagy-dependent Ferroptosismentioning

confidence: 99%

International consensus guidelines for the definition, detection, and interpretation of autophagy-dependent ferroptosis

Chen,

Tsvetkov,

Shen

et al. 2024

Autophagy

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Macroautophagy/autophagy is a complex degradation process with a dual role in cell death that is influenced by the cell types that are involved and the stressors they are exposed to. Ferroptosis is an iron-dependent oxidative form of cell death characterized by unrestricted lipid peroxidation in the context of heterogeneous and plastic mechanisms. Recent studies have shed light on the involvement of specific types of autophagy (e.g. ferritinophagy, lipophagy, and clockophagy) in initiating or executing ferroptotic cell death through the selective degradation of anti-injury proteins or organelles. Conversely, other forms of selective autophagy (e.g. reticulophagy and lysophagy) enhance the cellular defense against ferroptotic damage. Dysregulated autophagy-dependent ferroptosis has implications for a diverse range of pathological conditions. This review aims to present an updated definition of autophagy-dependent ferroptosis, discuss influential substrates and receptors, outline experimental methods, and propose guidelines for interpreting the results. Abbreviation : 3-MA:3-methyladenine; 4HNE: 4-hydroxynonenal; ACD: accidentalcell death; ADF: autophagy-dependentferroptosis; ARE: antioxidant response element; BH2:dihydrobiopterin; BH4: tetrahydrobiopterin; BMDMs: bonemarrow-derived macrophages; CMA: chaperone-mediated autophagy; CQ:chloroquine; DAMPs: danger/damage-associated molecular patterns; EMT,epithelial-mesenchymal transition; EPR: electronparamagnetic resonance; ER, endoplasmic reticulum; FRET: Försterresonance energy transfer; GFP: green fluorescent protein;GSH: glutathione;IF: immunofluorescence; IHC: immunohistochemistry; IOP, intraocularpressure; IRI: ischemia-reperfusion injury; LAA: linoleamide alkyne;MDA: malondialdehyde; PGSK: Phen Green™ SK;RCD: regulatedcell death; PUFAs: polyunsaturated fatty acids; RFP: red fluorescentprotein;ROS: reactive oxygen species; TBA: thiobarbituricacid; TBARS: thiobarbituric acid reactive substances; TEM:transmission electron microscopy.

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Section: Methods For Monitoring Autophagy-dependent Ferroptosismentioning

confidence: 99%

International consensus guidelines for the definition, detection, and interpretation of autophagy-dependent ferroptosis

Chen,

Tsvetkov,

Shen

et al. 2024

Autophagy

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“…Following previous studies on modeled chemical structures [30,[34][35][36][37][38], the use of chemical drawn, and molecular modeling software allowed to analyze and illustrate the structure of some boron-containing agents. Chemical structures with formal double bonds were drawn with ChemDraw Ultra v12.0 software.…”

Section: Methodsmentioning

confidence: 99%

Molecular Modeling of Phenyl-Boronic Acids and Catechol-Borate Esters: A Mechanistic Rationale for Boron Binding to Melanin Catechols, Regarding the 10Boron Neutron-Capture Therapy of Melanoma

Stockert

2022

ARR

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The 10 boron neutron-capture therapy (BNCT) is an emerging anti-tumor therapy based on the accumulation of a 10 B isotope within the tumor followed by irradiation with low-energy neutrons. The nuclear fission process produces 7 lithium, 4 helium, and λ rays within the tumor tissue, inducing specific tumor cell damage and death. 10 B can be delivered either as simple B-containing agents or as B clusters. In the first case, boronic acid derivatives such as 4-borono-phenylalanine (BPA) are currently applied for BNCT of melanoma and other tumors. Although it can be assumed that BPA would act as a precursor metabolite for melanin biosynthesis, the precise action mechanism is not yet clear. Direct binding of this boronic acid to a target substrate, namely the catechol groups from already synthesized melanin, could be an alternative mechanism. In keeping with this, high affinity for melanin would explain the action mode of boronic acids as melanoma seekers. DOPA-and dopamine-borate esters are also potential B-carrier candidates for BNCT, and they could be incorporated as melanin precursors or binding reagents. In this work, molecular modeling methods have been applied to analyze the structure of boronic acid and borate ester derivatives, as well as their interaction and binding mode with the recently proposed catechol-porphycene model for the melanin polymer. Interestingly, remarkable structural features drawn from chemical geometry, and also molecular orbital calculations, support the possibility that boronic acids and borate esters could be reactive agents for direct binding to melanin catechols.

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“…Examples of inner-salt colorants and fluorochromes (zwitterionic phenol blue, indophenol blue, merocyanine 540, Nile red, rhodols, Bodipy dyes, etc.) are also known [36,57,58]. However, the relations between chemical structure, pH, and fluorescence features are intriguing, and no structures of the reaction product are expected to be fluorescent.…”

Section: Bzpopy Fluorochromes From Fluorescaminementioning

confidence: 99%

“…Examples of inner-salt colorants and fluorochromes (zwitterionic phenol blue, indophenol blue, merocyanine 540, Nile red, rhodols, Bodipy dyes, etc.) are also known [36,57,58].…”

Section: Bzpopy Fluorochromes From Fluorescaminementioning

confidence: 99%

Diphenyl-Furanones and Diphenyl-Oxopyrrole Derivatives: From Analytical Reagents for Amino Groups to New Fluorochromes for Cytochemical Staining of Chromatin DNA and Chromosomes: Proposal for Intercalative Binding and Fluorescence Mechanism

et al. 2023

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Diaryl-furanones are specific analytical reagents for the biochemical detection of primary amines by fluorescence techniques. Well-known reagents are fluorescamine (Fluram) and 2-methoxy-2,4-diphenyl-3(2H)-furanone (MDPF), yielding fluorescent products with λem at 480–490 nm. Although the reaction products claim to be pyrrolinones, recent studies show that they are really 3-oxopyrrole (pyrrolone) derivatives. Both reagents have been used for the cytochemical demonstration of primary amines. In this work, we have applied the fluorescent products of MDPF with amines (n-butylamine, BA; glucosamine, GA; and spermine, Sp), which showed interesting fluorescence reactions with chromatin DNA. 2,4-diphenyl-3-oxopyrrole products (diPOPy) can be easily synthesized according to well-known procedures, by mixing solutions of MDPF in acetone with water at pH 9 containing the amino compounds. DiPOPy derivatives of BA, GA, and Sp were used for spectroscopic, microscopic, and molecular modeling studies, showing a bright and selective blue–green fluorescence on DNA substrates, mainly chromatin, kinetoplast DNA, and stretched chromatin fibers. The cationic diPOPy fluorophore is planar, with a high partial positive charge in the N atom, and suitable for intercalative binding to DNA. A mechanism of fluorescamine fluorescence due to an inner-salt isomeric form is proposed, and an astonishing correlation between adenine–thymine-rich centromeric heterochromatin in mouse metaphase chromosomes after reaction of the fluorescamine reagent with protein amino groups is also discussed.

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Lipid Peroxidation Assay Using BODIPY-Phenylbutadiene Probes: A Methodological Overview

Cited by 6 publications

References 72 publications

International consensus guidelines for the definition, detection, and interpretation of autophagy-dependent ferroptosis

International consensus guidelines for the definition, detection, and interpretation of autophagy-dependent ferroptosis

Molecular Modeling of Phenyl-Boronic Acids and Catechol-Borate Esters: A Mechanistic Rationale for Boron Binding to Melanin Catechols, Regarding the 10Boron Neutron-Capture Therapy of Melanoma

Diphenyl-Furanones and Diphenyl-Oxopyrrole Derivatives: From Analytical Reagents for Amino Groups to New Fluorochromes for Cytochemical Staining of Chromatin DNA and Chromosomes: Proposal for Intercalative Binding and Fluorescence Mechanism

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