Arylated α- and β-dihydrofuran naphthoquinones: Electrochemical parameters, evaluation of antitumor activity and their correlation

Ferreira, Fabricia da Rocha; Ferreira, Sabrina Baptista; Araújo, Ana Jérsia; Filho, José Delano Barreto Marinho; Pessoa, Cláudia; Moraes, Manoel O. de; Costa-Lotufo, Letı́cia V.; Montenegro, Raquel Carvalho; Silva, Fernando de Carvalho da; Ferreira, Vı́tor F.; Costa, João Gomes da; Abreu, Fabiane Caxico de; Goulart, Marília Oliveira Fonseca

doi:10.1016/j.electacta.2013.04.148

Cited by 18 publications

(17 citation statements)

References 33 publications

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“…The addition of O 2 to the system Figure 10B), related to the generation of the semiquinone, which is dependent on O 2 concentration,a nd the disappearance of the corresponding anodic wave I a (Figure 10B), along with as light positive shift in the position of the first reduction peak potential( E p I c ), as observed previously for ortho-a nd para-quinones. [27,47,48] In the presenceo fO 2 ,t he complex reductions ystem of LQB-118 disappeared, which indicated the catalytic nature of the single-electron transfer process toward oxygen. It is also useful to note that the reactionw ithO 2 is reversiblea nd does not cause structuralm odification.T his was provedb yd eaerationw ith nitrogen and recovery of the original redox profile of LQB-118 (not shown).…”

Section: Reactivity With Oxygenmentioning

confidence: 97%

“…The parameters analyzed were the anodic shift in the potential of the first reduction wave (E p I c )a nd the current increase at the same peak (I p I c )o r decrease in the correspondent anodic peak (I p I a ). [27] Spectroelectrochemical experiments were performed in at hin-layer quartz electrochemical cell (path length 1mm, BASi)w ith at hreeelectrode arrangement that consisted of an optically transparent platinum minigrid as the working electrode, aP tw ire as the counter electrode, and Ag j AgCl j Cl À as the reference. The cell was paired with the already described potentiostat and spectra were obtained by using aH ewlett-Packard 8453 spectrophotometer.…”

Section: Reduction and Oxidationstudiesmentioning

confidence: 99%

“…Electrochemistry provides significant thermodynamic and kinetic information on the reaction of the semiquinone radical SQC À (generated after as ingle-electron transfer) with dioxygen to form the anion radical superoxide. [27,47,48] After the reduction of LQB-118, electrochemical experiments were carried out in the presence and absence of oxygen to verify the reactivity with oxygen, with positive results ( Figure 10A). The productso ft he electroreduction have been shownt or eact with oxygen.…”

Section: Reactivity With Oxygenmentioning

confidence: 99%

“…Studiesw ith CT-DNA biosensors [27,28] in buffered aqueous mediums howed as light interaction betweenL QB-118 and its reduction product with CT-DNA after 15 min of contact (not shown). The behavior was different in the presence of ssDNA in solution, in which current decreases were observed together with anodic potentials shifts ( Figure 12) under both conditions, that is, with originalL QB-118 ( Figure 12B) and with its reduction product ( Figure 12A).…”

Section: Studiesw Ith Dna Biosensorsmentioning

confidence: 99%

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Reactive Oxygen Species Release, Alkylating Ability, and DNA Interactions of a Pterocarpanquinone: A Test Case for Electrochemistry

et al. 2016

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The electrochemistry of a redox‐based bioactive pterocarpanquinone, designated as LQB‐118, and its precursor chromenquinone (CQ) was investigated in protic and aprotic media with a focus on the reduction mechanism in both media, the reactivity with oxygen, and the interaction with biological targets, such as DNA. UV/Vis spectroelectrochemistry clarified the proposed mechanism. The appearance of bands at λ=331, 400, and 600 nm suggests the generation of transient quinonemethides (QM). Electrochemical experiments revealed homogeneous electron transfer to oxygen. LQB‐118 itself interacts with calf‐thymus DNA and ssDNA in solution. It, and its electrogenerated intermediates, have been shown to decrease the diagnostic oxidation peaks of guanosine and adenosine residues. These results, together with electrochemical evidence for the formation of QMs and the reductive addition of thiols, partly explain the reported cytotoxic and parasiticidal effects of this quinone. Overall, the electrochemical methods do well to predict the molecular mechanism of the biological activity of the present class of compounds. As an additional competitive advantage, electrochemistry allows reductive cleavage in situ, the characterization of the generated intermediate, the calculation of the number of transferred electrons, and positively mimics in vitro and in vivo experiments.

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Section: Reactivity With Oxygenmentioning

confidence: 97%

Section: Reduction and Oxidationstudiesmentioning

confidence: 99%

Section: Reactivity With Oxygenmentioning

confidence: 99%

Section: Studiesw Ith Dna Biosensorsmentioning

confidence: 99%

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Reactive Oxygen Species Release, Alkylating Ability, and DNA Interactions of a Pterocarpanquinone: A Test Case for Electrochemistry

et al. 2016

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“…25 and inhibitor of four human tumor cell lines: HL-60 (leukemia), SF-295 (CNS), HCT-8 (colon) and MDA-MB435 (melanoma). 26 Recently, our group has published results on the interaction between serum albumin a d α-lapachone -a natural 1,4-naphthoquinone -by spectroscopic and molecular docking methods.…”

Section: Introductionmentioning

confidence: 99%

Drug-Protein Interaction: Spectroscopic and Theoretical Analysis on the Association between HSA and 1,4- Naphthoquinone Derivatives

Ferreira¹,

Chaves²,

Oliveira³

et al. 2018

Rev. Virtual Quim.

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Resumo: A interação entre albumina sérica humana (ASH) e dois derivados biologicamente ativos de 1,4-naftoquinona (FNP e FNP4Br) foi estudada por dicroísmo circular, fluorescência estacionária e fluorescência resolvida no tempo sob condições biológicas a 305 K, 310 K e 315 K. Para oferecer uma explicação a nível molecular, foram realizados cálculos de ancoramento molecular. Uma associação no estado estacionário entre a albumina e as amostras foi observada por estudos espectroscópicos. A ligação é espontânea, moderada, pode perturbar a estrutura secundária da albumina e aumentar a hidrofobicidade ao redor do resíduo Trp-214, isso provavelmente devido a efeitos hidrofóbicos. Parâmetros termodinâmicos e ancoramento molecular sugerem ligação de hidrogênio e interações eletrostáticas (dipolo-dipolo) como as principais forças para a associação ASH:FNP e ASH:FNP4Br.Palavras-chave: Albumina sérica humana; Derivados de 1,4-naftoquinona; Espectroscopia; Ancoramento molecular. AbstractThe interaction between human serum albumin (HSA) and two biologically active 1,4-naphthoquinone derivatives (FNP and FNP4Br) was studied by circular dichroism, steady-state and time-resolved fluorescence under biological conditions at 305 K, 310 K and 315 K. In order to offer a molecular level explanation, molecular docking calculations were carried out. A ground state association between albumin and the samples was observed by spectroscopic studies. The binding is spontaneous, moderate, can perturb the secondary structure of the albumin and increase the hydrophobicity around the Trp-214 residue, probably due the hydrophobic effect. Thermodynamic parameters and molecular docking results suggest hydrogen bonding and electrostatic interactions (dipole-dipole) as the main binding forces for the association HSA:FNP and HSA:FNP4Br.

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Advanced Routes in Synthesis and Reactions of Lawsone Molecules (2‐Hydroxynaphthalene‐1,4‐dione)

Hamama

Hassanien

Zoorob

2017

Journal of Heterocyclic Chem

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Arylated α- and β-dihydrofuran naphthoquinones: Electrochemical parameters, evaluation of antitumor activity and their correlation

Cited by 18 publications

References 33 publications

Reactive Oxygen Species Release, Alkylating Ability, and DNA Interactions of a Pterocarpanquinone: A Test Case for Electrochemistry

Reactive Oxygen Species Release, Alkylating Ability, and DNA Interactions of a Pterocarpanquinone: A Test Case for Electrochemistry

Drug-Protein Interaction: Spectroscopic and Theoretical Analysis on the Association between HSA and 1,4- Naphthoquinone Derivatives

Advanced Routes in Synthesis and Reactions of Lawsone Molecules (2‐Hydroxynaphthalene‐1,4‐dione)

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