The inhibition of lipoperoxidation by mesoionic compound MI-D: A relationship with its uncoupling effect and scavenging activity

Méndez‐Sánchez, Stelia C.; Martinez, Gláucia Regina; Romão, Sílvia; Echevarrı́a, Aurea; Silva, Edson Fernandes; Rocha, Maria Eliane Merlin; Noleto, Guilhermina Rodrigues; Carnieri, Eva Gunilla Skare; Cadena, Sílvia Maria Suter Correia; Oliveira, Maria Benigna Martinelli de

doi:10.1016/j.cbi.2008.11.016

Cited by 8 publications

(2 citation statements)

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“…This water-soluble azo compound is widely used as a model reagent to mimic oxidative stress due to its ability to generate peroxyl radicals at a constant rate at physiological temperatures (Niki 1990). It is used to induce oxidative stress in various in vivo and in vitro biological systems, such as rat lungs (Gomes et al 2016), zebrafishes (Wang et al 2018), chicken embryos (He et al 2013), human erythrocytes (Zou et al 2001) and to induce peroxidation of low-density lipoproteins (Yoshida et al 2004) and of phosphatidylcholine liposomes (Mendez-Sanchez et al 2009). It is also used in ORAC (oxygen radical absorbance capacity) assays to evaluate the antioxidant capacity of different compounds to protect target molecules (e.g., phycoerythrine, fluorescine, pyrogallol red) against peroxyl radicals (Prior et al 2005).…”

Section: Introductionmentioning

confidence: 99%

Uncoupling effect of lipid peroxidation in spinach thylakoids exposed to peroxyl radicals generated by 2,2′-azobis (2-amidinopropane) dihydrochloride

Yergeau

Samson

2021

Botany

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In this study, we characterized how lipid peroxidation alters the functionality of spinach thylakoids exposed to peroxyl radicals generated by the azo compound 2,2-azobis(2-amidinopropane) dihydrochloride (AAPH). Incubation of thylakoids in presence of different concentrations (0 to 200 mM) of AAPH inhibited the formation of ΔpH (IC50 ≈ 1.5 mM) estimated by the quenching of 9-aminoacridine fluorescence (Q9-AA). The Q9-AA inhibition was correlated (R2=0.98) to the extent of lipid peroxidation determined by the accumulation of thiobarbituric acid reactive substances (TBARS). Much higher AAPH concentrations were required to inhibit the maximum (Fv/Fm) and effective (ΔF/Fm’) photochemical efficiencies of photosystem II (IC50 ≈ 120 mM and 50 mM respectively), indicating that moderate lipid peroxidation caused the uncoupling of spinach thylakoids. This was confirmed by the 62 % stimulation of the O2 uptake rates measured without the artificial uncoupler NH4Cl when the AAPH concentrations increased from 0 to at 20 mM, reaching similar values to the rates measured in presence of NH4Cl. Above 20 mM AAPH, the O2 uptake rates measured with and without NH4Cl declined similarly to the decrease of ΔF/Fm’. These results suggest that the increased H+-leakiness of thylakoid membranes could be one of the primary effects of oxidative stress.

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Section: Introductionmentioning

confidence: 99%

Uncoupling effect of lipid peroxidation in spinach thylakoids exposed to peroxyl radicals generated by 2,2′-azobis (2-amidinopropane) dihydrochloride

Yergeau

Samson

2021

Botany

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“…In our previous studies with 1,3,4-thiadiazolium salts (mesoionic compounds) containing a substituted styryl moiety, important results for in vitro cytotoxic activity in various types of tumor cells, including leukemias [23,[32][33][34], and in vivo antitumor effects have been observed [35,36]. Besides, results on the antiviral activity of 1,3,4-thiadiazole derivatives against HIV-1 [37][38][39][40], which also belong to the same Retroviridae family, have also been reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

Synthetic (E)-3-Phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium Chloride Derivatives as Promising Chemotherapy Agents on Cell Lines Infected with HTLV-1

et al. 2020

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Synthesis of four compounds belonging to mesoionic class, (E)-3-phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium chloride derivatives (5a–d) and their biological evaluation against MT2 and C92 cell lines infected with human T-cell lymphotropic virus type-1 (HTLV-1), which causes adult T-cell leukemia/lymphoma (ATLL), and non-infected cell lines (Jurkat) are reported. The compounds were obtained by convergent synthesis under microwave irradiation and the cytotoxicity was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays. Results showed IC50 values of all compounds in the range of 1.51–7.70 μM in HTLV-1-infected and non-infected cells. Furthermore, it was observed that 5b could induce necrosis after 24 h for Jurkat and MT2 cell lines. The experimental (fluorimetric method) and theoretical (molecular docking) results suggested that the mechanism of action for 5b could be related to its capacity to intercalate into DNA. Moreover, the preliminary pharmacokinetic profile of the studied compounds (5a–d) was obtained through human serum albumin (HSA) binding affinity using multiple spectroscopic techniques (circular dichroism, steady-state and time-resolved fluorescence), zeta potential and molecular docking calculations. The interaction HSA:5a–d is spontaneous and moderate (Ka ~ 104 M−1) via a ground-state association, without significantly perturbing both the secondary and surface structures of the albumin in the subdomain IIA (site I), indicating feasible biodistribution in the human bloodstream.

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Type A mesoionic compounds (1980–2020)

Ramsden

Dumitraşcu

2022

Advances in Heterocyclic Chemistry

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The inhibition of lipoperoxidation by mesoionic compound MI-D: A relationship with its uncoupling effect and scavenging activity

Cited by 8 publications

References 35 publications

Uncoupling effect of lipid peroxidation in spinach thylakoids exposed to peroxyl radicals generated by 2,2′-azobis (2-amidinopropane) dihydrochloride

Uncoupling effect of lipid peroxidation in spinach thylakoids exposed to peroxyl radicals generated by 2,2′-azobis (2-amidinopropane) dihydrochloride

Synthetic (E)-3-Phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium Chloride Derivatives as Promising Chemotherapy Agents on Cell Lines Infected with HTLV-1

Type A mesoionic compounds (1980–2020)

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