QSAR of the free radical scavenging potency of selected hydroxyanthraquinones

Marković, Zoran; Filipović, Miloš R.; Manojlović, N.; Amić, Ana; Jeremić, Svetlana; Milenković, Dejan

doi:10.1007/s11696-018-0534-3

Cited by 12 publications

(9 citation statements)

References 53 publications

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“…These observations clearly indicated that classification of the individual OH-groups based on electronic parameters pertinent to them increased the accuracy and prediction quality of the regression models of antiradical assays studied. However, none of the models based on active group numbers has r 2 exceeding 0.9, while some multiple linear regression (MLR) models based on OH-group numbers (total or vicinal) plus BDE [ 17 , 18 , 20 , 32 ] or on EVA vector descriptors [ 50 ] are reported to possess r 2 higher than 0.9, thus suggesting the necessity for further optimization of the proposed models.…”

Section: Resultsmentioning

confidence: 99%

“…The regression QSAR models developed for antiradical capacity assays, in fact, almost always include the number of OH-groups in the (poly)phenol molecule as one of the descriptors in the regression equation [ 10 , 18 , 19 ], or the number of OH-groups identified as important in the antiradical reactions (e.g., vicinal OH-groups in catechol or pyrogallol moieties) [ 17 , 20 ]. In the models, where nOH is not among the regression parameters, a parameter strongly correlated with nOH is usually present, e.g., the sum of charges of hydroxyl group atoms [ 21 ] or cyclic voltammetry peak currents [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

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Hybrid Classification/Regression Approach to QSAR Modeling of Stoichiometric Antiradical Capacity Assays’ Endpoints

2022

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Quantitative structure–activity relationships (QSAR) are a widely used methodology allowing not only a better understanding of the mechanisms of chemical reactions, including radical scavenging, but also to predict the relevant properties of chemical compounds without their synthesis, isolation and experimental testing. Unlike the QSAR modeling of the kinetic antioxidant assays, modeling of the assays with stoichiometric endpoints depends strongly on the number of hydroxyl groups in the antioxidant molecule, as well as on some integral molecular descriptors characterizing the proportion of OH-groups able to enter and complete the radical scavenging reaction. In this work, we tested the feasibility of a “hybrid” classification/regression approach, consisting of explicit classification of individual OH-groups as involved in radical scavenging reactions, and using further the number of these OH-groups as a descriptor in simple-regression QSAR models of antiradical capacity assays with stoichiometric endpoints. A simple threshold classification based on the sum of trolox-equivalent antiradical capacity values was used, selecting OH-groups with specific radical stability- and reactivity-related electronic parameters or their combination as “active” or “inactive”. We showed that this classification/regression modeling approach provides a substantial improvement of the simple-regression QSAR models over those built on the number of total phenolic OH-groups only, and yields a statistical performance similar to that of the best reported multiple-regression QSARs for antiradical capacity assays with stoichiometric endpoints.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hybrid Classification/Regression Approach to QSAR Modeling of Stoichiometric Antiradical Capacity Assays’ Endpoints

2022

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“…Багато природних антрахінонів (хризопанол, емодін, алоеемодін, рейн, фізіоніт, обтузін, аурантіообтузин, руброфусарин, торахрисон і торалактон), виділених з рослин, проявляють антиоксидантні властивості 10,11 . Серед синтетичних похідних 9,10-антрахінону були виявлені сполуки з антиоксидантними властивостями 12,13,14 а деякі похідні досліджені одночасно на цитотоксичність та оксидативний стрес 15 . Також показано, що 9 Halenova T., Nikolaeva I., Nakonechna A., Lubenets V. Inhibition of human platelet aggregation by some newly synthesized S-esters of thiosulfonic acid.…”

Section: вступunclassified

Sulfur-containing derivatives of 9,10-anthraquinone as potential antithrombotic agents with antioxidant activity: in silico prediction and in vitro validation

Stasevych

Zvarych

2021

New Impulses for the Development of Natural Sciences in Ukraine and Eu Countries

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“…18 Many natural anthracenediones extracted from plants demonstrate antioxidant properties. [19][20][21] Among the synthetic derivatives of 9,10-anthracenedione were discovered compounds with antioxidant properties [22][23][24] and oxidative stress and cytotoxicity ability. 25 It was demonstrated that the amount and position of substituents in the anthracenedion's ring influence antioxidant properties.…”

Section: Introductionmentioning

confidence: 99%

N-(9,10-Dioxo-9,10-dihydroanthracen-1(2)-yl)-2-(R-thio) Acetamides: Synthesis, Antioxidant and Antiplatelet Activity

Stasevych¹,

Zvarych²,

Yaremkevych³

et al. 2022

ACSi

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The synthesis of new N-(9,10-dioxo-9,10-dihydroanthracen-1(2)-yl)-2-(R-thio) acetamides was carried out using reaction of 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracene-1(2)-yl)acetamides with functionalized thiols in the presence of potassium carbonate in N,N-dimethylformamide (DMF) at room temperature. Evaluation of the synthesized compounds on such indicators of radical scavenging activity as lipid peroxidation (LP) and oxidative modification of proteins (OMP) in vitro in rat liver homogenate was carried out. It was determined that the compounds with a substituent in the first position of anthracedione core showed better antioxidant properties than their isomers with a substituent in the second position. The compounds 6 and 7 with the best indicators of radical-scavenging activity were determined. Antioxidant effect in OMP processes was also determined for compound 10. The antiplatelet activity study in vitro revealed compound 10 with the inhibited effect of ADP-induced aggregation.

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QSAR of the free radical scavenging potency of selected hydroxyanthraquinones

Cited by 12 publications

References 53 publications

Hybrid Classification/Regression Approach to QSAR Modeling of Stoichiometric Antiradical Capacity Assays’ Endpoints

Hybrid Classification/Regression Approach to QSAR Modeling of Stoichiometric Antiradical Capacity Assays’ Endpoints

Sulfur-containing derivatives of 9,10-anthraquinone as potential antithrombotic agents with antioxidant activity: in silico prediction and in vitro validation

N-(9,10-Dioxo-9,10-dihydroanthracen-1(2)-yl)-2-(R-thio) Acetamides: Synthesis, Antioxidant and Antiplatelet Activity

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