Understanding the cytotoxicity or cytoprotective effects of biological and synthetic quinone derivatives by redox mechanism

Quinones represent an important class of biological compounds, but are also involved with toxicological intermediates and among their hazardous effects include cytotoxicity, immunotoxicity, and carcinogenesis. The structure–toxicity relationship for quinone derivatives has been used to cytotoxicity...

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Bibliographic Details
Published in:Journal of molecular modeling 2014-12, Vol.20 (12), p.2541, Article 2541
Main Authors: Borges, Rosivaldo S., Carneiro, Agnaldo S., Barros, Tainá G., Barros, Carlos A. L., Neto, Antonio M. J. Chaves, da Silva, Albérico B. F.
Format: Article
Language:English
Subjects:
Characterization and Evaluation of Materials
Chemistry
Chemistry and Materials Science
Computer Appl. in Life Sciences
Computer Applications in Chemistry
Cytoprotection
Drug Stability
Electrons
Energy Transfer
Free Radicals - chemistry
Isomerism
Models, Molecular
Molecular Medicine
Molecular Structure
Original Paper
Oxidation-Reduction
Quantum Theory
Quinones - chemical synthesis
Quinones - toxicity
Structure-Activity Relationship
Theoretical and Computational Chemistry
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Summary:Quinones represent an important class of biological compounds, but are also involved with toxicological intermediates and among their hazardous effects include cytotoxicity, immunotoxicity, and carcinogenesis. The structure–toxicity relationship for quinone derivatives has been used to cytotoxicity or cytoprotective effects by redox mechanism is determined using quantum chemical calculations through the density functional theory (DFT). According to our DFT study, the electron acceptance is related with LUMO, electron affinity, and stabilization energy values. The highest spin density distribution in the heteroatoms is more favored for the more cytotoxic compounds. The electrophilic capacities of these compounds have been related with LUMO values. The cytotoxic properties of quinones are related to the stabilization energy after electron accepting by redox mechanism. Electron affinity is the most relevant parameter related to toxicity mechanism. Regioisomers has different electrophilic capacity. The electrophilicity increases on molecules containing electron-withdrawing groups (EWG) and reduces on molecules containing electron-donating groups (EDG). These results explain the toxic difference between natural and synthetic quinone derivatives and can be used in the design and study of new drugs. Graphical Abstract Biological and synthetic ortho and para quinone derivatives
ISSN:1610-2940
0948-5023
DOI:10.1007/s00894-014-2541-9