Quinoid systems in chemistry and pharmacology

López, Juan José Marín; Cruz, Fabiola N. de la; Alcaraz, Yolanda; Delgado, Francisco; Vázquez, Miguel Á.

doi:10.1007/s00044-015-1412-y

Cited by 24 publications

(13 citation statements)

References 90 publications

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“…Naphthoquinones (naphthalenediones) form an important part of some pharmacophores in medicinal chemistry (Ló pez et al, 2015). During an exploration of antimalarial drugs, Fieser (Fieser & Fieser, 1935) indicated that aminoiminonaphthoquinones, although difficult to form, had interesting medicinal properties.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of (E)-2-(tert-butylamino)-4-(tert-butylimino)naphthalen-1(4H)-one

2018

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of (E)-2-(tert-butylamino)-4-(tert-butylimino)naphthalen-1(4H)-one

2018

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“…Naphthoquinone is a quinone-based, highly redox-active compound that can redox cycle with its semiquinone radical 14 . Quinone-based compounds may have one or more of the following functions: electron transport chain inhibition, oxidative phosphorylation uncoupling, DNA intercalation, reductive alkylation, and free radical generation 15 . Thus, naphthoquinone inhibits photosynthesis by disturbing photosynthetic electron transport in plants 16 , 17 .…”

Section: Introductionmentioning

confidence: 99%

Cyanobacteria-specific algicidal mechanism of bioinspired naphthoquinone derivative, NQ 2-0

Lee

Park

Joo

et al. 2018

Sci Rep

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To mitigate cyanobacterial blooms, the naphthoquinone derivative, NQ 2-0, which has selective algicidal activity against cyanobacteria, has been developed. However, due to a lack of information on its algicidal mechanisms, there are significant gaps in our understanding of how this substance is capable of selectively killing cyanobacteria. Here, we investigated the selective algicidal mechanisms of NQ 2-0 using target (Microcystis aeruginosa) and non-target (Cyclotella sp. and Selenastrum capricornutum) species. NQ 2-0 showed selective algicidal activity against only M. aeruginosa, and this activity was strongly light-dependent. This NQ compound has selectively reduced the oxygen evolution rate and photosystem II (PSII) efficiency of M. aeruginosa throughout blocking electron transfer from the photosynthetic electron transport system, and significantly (p ≤ 0.05) increased levels of reactive oxygen species (ROS), resulting in membrane damage through lipid peroxidation. In ultrastructural observations, thylakoid membranes were disintegrated within 12 h after NQ 2-0 treatment, and cytoplasmic vacuolation and disintegrated cellular membrane were observed at 24 h. These findings suggest that increased ROS levels following NQ 2-0 treatment may induce cell death. Interestingly, compared to non-target eukaryotic cells, M. aeruginosa showed relatively late antioxidant response to reduce the increased ROS level, this may enhance algicidal activity against this cyanobacterium.

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“…Quinoidal molecules have received particular attention from chemists, physicists and biochemists as building block in the fields of dyes chemistry, conducting organic materials, supramolecular chemistry and pharmacology [1][2][3][4][5][6]. Over the last three decades, they have also been strongly investigated as ligand, for the design of complexes that could be used in a wide range of applications ranging from catalysis and molecular electronics, to magnetism or optics [7][8][9][10].…”

Section: Introduction and Scopementioning

confidence: 99%

Benzoquinonediimine ligands: Synthesis, coordination chemistry and properties

Pascal

Siri

2017

Coordination Chemistry Reviews

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This review covers the synthesis and properties of 2,5-diamino-1,4-benzoquinonediimines (DABQDI), and their use as ligand in coordination chemistry. Although reported more than a century ago, these molecules emerged as highly versatile ligands only from 1998, and are so far used for the synthesis of numerous complexes with remarkable properties. This exceptional versatility results from the possible tuning of the N-substituents and the observation of an isomerization process upon coordination depending on the metal center. As such, these DABQDI can be also considered as ligands that combine the structural elements of ortho-and para-benzoquinonediimines (o-BQDI and p-BQDI) which are bidentate monotopic and monodentate ditopic ligands, respectively. These two classes of BQDI ligands are also reviewed in order to parallel their properties to those of the complexes based on DABQDI.

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Quinoid systems in chemistry and pharmacology

Cited by 24 publications

References 90 publications

Crystal structure of (E)-2-(tert-butylamino)-4-(tert-butylimino)naphthalen-1(4H)-one

Crystal structure of (E)-2-(tert-butylamino)-4-(tert-butylimino)naphthalen-1(4H)-one

Cyanobacteria-specific algicidal mechanism of bioinspired naphthoquinone derivative, NQ 2-0

Benzoquinonediimine ligands: Synthesis, coordination chemistry and properties

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