Quinone-based molecular electrochemistry and their contributions to medicinal chemistry: A look at the present and future

Silva, Thaissa L.; Azevedo, Maria de Lourdes S.G. de; Ferreira, Fabricia da Rocha; Santos, Danyelle Cândido; Amatore, Christian; Goulart, Marília Oliveira Fonseca

doi:10.1016/j.coelec.2020.06.011

Cited by 26 publications

(12 citation statements)

References 46 publications

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“…Nowadays, the application of quinone-based molecules as efficient electron carriers in biological processes, in energy storage, and in CO 2 reduction − devices and their pharmacological activity in different diseases are extensively investigated. Quinones’ key role in the aforementioned applications is mainly due to their facile and highly tailorable redox chemistry.…”

Section: Introductionmentioning

confidence: 99%

Unveiling KuQuinone Redox Species: An Electrochemical and Computational Cross Study

et al. 2021

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The study of the electrochemical properties of variegated quinones is a fascinating topic in chemistry. In fact, redox reactions occurring with quinoid scaffolds are essential for most of their applications in biological systems, in photoelectrochemical devices, and in many other fields. In this paper, a detailed investigation of KuQuinones’ redox behavior is presented. The distinctiveness of such molecules is the presence in the structure of two condensed naphthoquinone units, which implies the possibility to undergo multiple one-electron reduction processes. Solvent, supporting electrolyte, and hydrogen bond donor species effects have been elucidated. Changing the experimental parameters provoked significant shift of the redox potential for each reduction process. In particular, additions of 2,2,2-trifluoroethanol as a hydrogen bond donor in solution as well as Lewis acid coordination were crucial to obtain important shifts of the redox potentials toward more favorable values. UV–vis–NIR spectroelectrochemical experiments and DFT calculations are also presented to clarify the nature of the reduced species in solution.

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Section: Introductionmentioning

confidence: 99%

Unveiling KuQuinone Redox Species: An Electrochemical and Computational Cross Study

et al. 2021

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“…A set of compounds derived from 1,4-NQ and 1,2-NQ were studied ( Figure 1 ) to evaluate the viability of an alternative MA protocol for their synthesis, their biological potential, and the impact of the association of these moieties in the same molecule. Aliphatic amines and substituted anilines with electron donor and acceptor groups have been used as nucleophilic partners since it is known that the electronic nature and position of the substituents in the NQ aromatic rings affect their redox potential and, consequently, the associated biological activities [ 6 ].…”

Section: Resultsmentioning

confidence: 99%

“…These heterocyclic compounds are known to exhibit a diverse range of biological properties, such as antimicrobials, antitumoral, antioxidants, antimalarial, and neuroprotectants, among others [ 1 , 2 , 3 ]. Their mechanisms of action are often related to their redox properties, as most have the capacity to accept one or two electrons to generate highly reactive radical species capable of interacting with biological molecules such as DNA, enzymes, and other proteins [ 4 , 5 , 6 ]. The electrochemical behavior of these compounds seems to be related to the biological activity and quinone scaffold, with multiple redox functionalities, justifying the continuous interest and efforts to find derivatives with different functionalization and screening for potential biological properties [ 6 , 7 , 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Sustainable Synthesis, Antiproliferative and Acetylcholinesterase Inhibition of 1,4- and 1,2-Naphthoquinone Derivatives

et al. 2023

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This work describes the design, sustainable synthesis, evaluation of electrochemical and biological properties against HepG2 cell lines, and AChE enzymes of different substituted derivatives of 1,4- and 1,2-naphthoquinones (NQ). A microwave-assisted protocol was optimized with success for the synthesis of the 2-substituted-1,4-NQ series and extended to the 4-substituted-1,2-NQ family, providing an alternative and more sustainable approach to the synthesis of naphthoquinones. The electrochemical properties were studied by cyclic voltammetry, and the redox potentials related to the molecular structural characteristics and the biological properties. Compounds were tested for their potential anti-cancer activity against a hepatocellular carcinoma cell line, HepG2, using MTT assay, and 1,2-NQ derivatives were found to be more active than their 1,4-NQ homologues (3a–f), with the highest cytotoxic potential found for compound 4a (EC50 = 3 μM). The same trend was found for the inhibitory action against acetylcholinesterase, with 1,2-NQ derivatives showing higher inhibition50µM than their 1,4-NQ homologues, with 4h being the most potent compound (Inhibition50µM = 85%). Docking studies were performed for the 1,2-NQ derivatives with the highest inhibitions, showing dual binding interactions with both CAS and PAS sites, while the less active 1,4-NQ derivatives showed interactions with PAS and the mid-gorge region.

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“…Molecular electrochemistry now is closely interfaced with medicinal chemistry, especially in the case of quinones [72]. Voltammetry allows obtaining additional information about the properties of nanosystems as encapsulated into (co)polymer electrochemical active compounds [44,45,53,57,73], especially if their free (molecular) and encapsulated forms differ substantially with energetic characteristics, see, e.g., [45,52,57].…”

Section: Cyclic Voltammetry Of the Free Dox And Being Encapsulated In...mentioning

confidence: 99%

New Nanosized Systems Doxorubicin—Amphiphilic Copolymers of N-Vinylpyrrolidone and (Di)methacrylates with Antitumor Activity

et al. 2022

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Nanosized systems of DOX with antitumor activity on the base of micelle-like particles of amphiphilic thermosensitive copolymers of N-vinylpyrrolidone (VP) with triethylene glycol dimethacrylate (TEGDM), and N-vinylpyrrolidone and methacrylic acid (MAA) with TEGDM were explored. They were investigated in aqueous solutions by electron absorption spectroscopy, dynamic light scattering and cyclic voltammetry. Experimental data and quantum-chemical modeling indicated the formation of a hydrogen bond between oxygen-containing groups of monomer units of the copolymers and H-atoms of OH and NH2 groups of DOX; the energies and H-bond lengths in the considered structures were calculated. A simulation of TDDFT spectra of DOX and its complexes with the VP and TEGDM units was carried out. Electrochemical studies in PBS have demonstrated that the oxidation of encapsulated DOX appeared to be easier than that of the free one, and its reduction was somewhat more difficult. The cytotoxicity of VP-TEGDM copolymer compositions containing 1, 5 and 15 wt% DOX was studied in vitro on HeLa cells, and the values of IC50 doses were determined at 24 and 72 h of exposure. The copolymer compositions containing 5 and 15 wt% DOX accumulated actively in cell nuclei and did not cause visual changes in cell morphology.

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Quinone-based molecular electrochemistry and their contributions to medicinal chemistry: A look at the present and future

Cited by 26 publications

References 46 publications

Unveiling KuQuinone Redox Species: An Electrochemical and Computational Cross Study

Unveiling KuQuinone Redox Species: An Electrochemical and Computational Cross Study

Sustainable Synthesis, Antiproliferative and Acetylcholinesterase Inhibition of 1,4- and 1,2-Naphthoquinone Derivatives

New Nanosized Systems Doxorubicin—Amphiphilic Copolymers of N-Vinylpyrrolidone and (Di)methacrylates with Antitumor Activity

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