Relevant bibliographies by topics / Quinone

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  1. Journal articles
  2. Dissertations / Theses
  3. Books
  4. Book chapters
  5. Conference papers
  6. Reports

Academic literature on the topic 'Quinone'

Author: Grafiati
Published: 4 June 2021
Last updated: 31 July 2024

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Journal articles on the topic "Quinone"

1

Weiss, Sophie A., and Lars J. C. Jeuken. "Electrodes modified with lipid membranes to study quinone oxidoreductases." Biochemical Society Transactions 37, no. 4 (July 22, 2009): 707–12. http://dx.doi.org/10.1042/bst0370707.

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Quinone oxidoreductases are a class of membrane enzymes that catalyse the oxidation or reduction of membrane-bound quinols/quinones. The conversion of quinone/quinol by these enzymes is difficult to study because of the hydrophobic nature of the enzymes and their substrates. We describe some biochemical properties of quinones and quinone oxidoreductases and then look in more detail at two model membranes that can be used to study quinone oxidoreductases in a native-like membrane environment with their native lipophilic quinone substrates. The results obtained with these model membranes are compared with classical enzyme assays that use water-soluble quinone analogues.
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Jensen,, Kenneth A., Zachary C. Ryan, Amber Vanden Wymelenberg, Daniel Cullen, and Kenneth E. Hammel. "An NADH:Quinone Oxidoreductase Active during Biodegradation by the Brown-Rot Basidiomycete Gloeophyllum trabeum." Applied and Environmental Microbiology 68, no. 6 (June 2002): 2699–703. http://dx.doi.org/10.1128/aem.68.6.2699-2703.2002.

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ABSTRACT The brown-rot basidiomycete Gloeophyllum trabeum uses a quinone redox cycle to generate extracellular Fenton reagent, a key component of the biodegradative system expressed by this highly destructive wood decay fungus. The hitherto uncharacterized quinone reductase that drives this cycle is a potential target for inhibitors of wood decay. We have identified the major quinone reductase expressed by G. trabeum under conditions that elicit high levels of quinone redox cycling. The enzyme comprises two identical 22-kDa subunits, each with one molecule of flavin mononucleotide. It is specific for NADH as the reductant and uses the quinones produced by G. trabeum (2,5-dimethoxy-1,4-benzoquinone and 4,5-dimethoxy-1,2-benzoquinone) as electron acceptors. The affinity of the reductase for these quinones is so high that precise kinetic parameters were not obtainable, but it is clear that k cat/Km for the quinones is greater than 108 M−1 s−1. The reductase is encoded by a gene with substantial similarity to NAD(P)H:quinone reductase genes from other fungi. The G. trabeum quinone reductase may function in quinone detoxification, a role often proposed for these enzymes, but we hypothesize that the fungus has recruited it to drive extracellular oxyradical production.
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Wang, Zhen-Hua, Xiao-Hui Fu, Qun Li, Yong You, Lei Yang, Jian-Qiang Zhao, Yan-Ping Zhang, and Wei-Cheng Yuan. "Recent Advances in the Domino Annulation Reaction of Quinone Imines." Molecules 29, no. 11 (May 24, 2024): 2481. http://dx.doi.org/10.3390/molecules29112481.

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Quinone imines are important derivatives of quinones with a wide range of applications in organic synthesis and the pharmaceutical industry. The attack of nucleophilic reagents on quinone imines tends to lead to aromatization of the quinone skeleton, resulting in both the high reactivity and the unique reactivity of quinone imines. The extreme value of quinone imines in the construction of nitrogen- or oxygen-containing heterocycles has attracted widespread attention, and remarkable advances have been reported recently. This review provides an overview of the application of quinone imines in the synthesis of cyclic compounds via the domino annulation reaction.
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Miseviciene, Lina, Zilvinas Anusevicius, Jonas Sarlauskas, Richard J. Harris, Nigel S. Scrutton, and Narimantas Cenas. "Two-electron reduction of quinones by Enterobacter cloacae PB2 pentaerythritol tetranitrate reductase: quantitative structure-activity relationships." Acta Biochimica Polonica 54, no. 2 (June 4, 2007): 379–85. http://dx.doi.org/10.18388/abp.2007_3260.

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In order to clarify the poorly understood mechanisms of two-electron reduction of quinones by flavoenzymes, we examined the quinone reductase reactions of a member of a structurally distinct old yellow enzyme family, Enterobacter cloacae PB2 pentaerythritol tetranitrate reductase (PETNR). PETNR catalyzes two-electron reduction of quinones according to a 'ping-pong' scheme. A multiparameter analysis shows that the reactivity of quinones increases with an increase in their single-electron reduction potential and pK(a) of their semiquinones (a three-step (e(-),H(+),e(-)) hydride transfer scheme), or with an increase in their hydride-transfer potential (E(7)(H(-))) (a single-step (H(-)) hydride transfer scheme), and decreases with a decrease in their van der Waals volume. However, the pH-dependence of PETNR reactivity is more consistent with a single-step hydride transfer. A comparison of X-ray data of PETNR, mammalian NAD(P)H : quinone oxidoreductase (NQO1), and Enterobacter cloacae nitroreductase, which reduce quinones in a two-electron way, and their reactivity revealed that PETNR is much less reactive, and much less sensitive to the quinone substrate steric effects than NQO1. This may be attributed to the lack of pi-pi stacking between quinone and the displaced aromatic amino acid in the active center, e.g., with Phe-178' in NQO1.
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Vienozinskis, J., A. Butkus, N. Cenas, and J. Kulys. "The mechanism of the quinone reductase reaction of pig heart lipoamide dehydrogenase." Biochemical Journal 269, no. 1 (July 1, 1990): 101–5. http://dx.doi.org/10.1042/bj2690101.

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The relationship between the NADH:lipoamide reductase and NADH:quinone reductase reactions of pig heart lipoamide dehydrogenase (EC 1.6.4.3) was investigated. At pH 7.0 the catalytic constant of the quinone reductase reaction (kcat.) is 70 s-1 and the rate constant of the active-centre reduction by NADH (kcat./Km) is 9.2 x 10(5) M-1.s-1. These constants are almost an order lower than those for the lipoamide reductase reaction. The maximal quinone reductase activity is observed at pH 6.0-5.5. The use of [4(S)-2H]NADH as substrate decreases kcat./Km for the lipoamide reductase reaction and both kcat. and kcat./Km for the quinone reductase reaction. The kcat./Km values for quinones in this case are decreased 1.85-3.0-fold. NAD+ is a more effective inhibitor in the quinone reductase reaction than in the lipoamide reductase reaction. The pattern of inhibition reflects the shift of the reaction equilibrium. Various forms of the four-electron-reduced enzyme are believed to reduce quinones. Simple and ‘hybrid ping-pong’ mechanisms of this reaction are discussed. The logarithms of kcat./Km for quinones are hyperbolically dependent on their single-electron reduction potentials (E1(7]. A three-step mechanism for a mixed one-electron and two-electron reduction of quinones by lipoamide dehydrogenase is proposed.
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Giulivi, C., and E. Cadenas. "One- and two-electron reduction of 2-methyl-1,4-naphthoquinone bioreductive alkylating agents: kinetic studies, free-radical production, thiol oxidation and DNA-strand-break formation." Biochemical Journal 301, no. 1 (July 1, 1994): 21–30. http://dx.doi.org/10.1042/bj3010021.

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The one- and two-electron enzymic reduction of the bioreductive alkylating agents 2-methylmethoxynaphthoquinone (quinone I) and 2-chloromethylnaphthoquinone (quinone II) was studied with purified NADPH-cytochrome P-450 reductase and DT-diaphorase respectively, and characterized in terms of kinetic constants, oxyradical production, thiol oxidation and DNA-strand-break formation. The catalytic-centre activity values indicated that DT-diaphorase catalysed the reduction of quinone I far more efficiently than NADPH-cytochrome P-450 reductase, although the Km values of the two enzymes for this quinone were similar (1.2-3.0 microM). The one-electron-transfer flavoenzyme also catalysed the reduction of quinone II, but the behaviour of DT-diaphorase towards this quinone did not permit calculation of kinetic constants. A salient feature of the redox transitions caused by the one- and two-electron catalysis of these quinones was the different contributions of disproportionation and autoxidation reactions respectively. In the former case, about 26% of NADPH consumed was accounted for in terms of autoxidation (as H2O2 formation), whereas in the latter, the autoxidation component accounted for most (98%) of the NADPH consumed. This difference was abrogated by superoxide dismutase, which enhanced autoxidation during NADPH-cytochrome P-450 catalysis to a maximal value. E.s.r. analysis indicated the formation of superoxide radicals, the signal of which was suppressed by superoxide dismutase and unaffected by catalase. The one- and two-electron reduction of these quinones in the presence of GSH was accompanied by formation of thiyl radicals. Although superoxide dismutase suppressed the thiol radical e.s.r. signal in both instances, the enzyme enhanced GSSG accumulation during NADPH-cytochrome P-450 catalysis of quinone I, whereas it inhibited GSSG formation during reduction of the quinone by DT-diaphorase. One- and two-electron reduction of quinone I led to calf thymus DNA-strand-break formation, a process that (a) was substantially decreased in experiments performed with dialysed DNA and in the presence of desferal and (b) was partially sensitive to superoxide dismutase and/or catalase. These findings are rationalized in terms of the occurrence of metal ions ligated to DNA, protecting against the toxic effects of superoxide radicals generated during enzymic reduction of quinones.
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Breker, Johannes, Reinhard Schmutzler, Bernd Dorbath, and Markus Wieber. "Reaktionen von unsymmetrischen λ5P – λ3P-Diphosphorverbindungen und von Diphosphinen (λ3P – λ3P) mit o-Chinonen / Reactions of Unsymmetrical λ5Ρ – λ3Ρ Diphosphorus Compounds and of Diphosphines (λ3P – λ3P) with o-Quinones." Zeitschrift für Naturforschung B 45, no. 8 (August 1, 1990): 1177–86. http://dx.doi.org/10.1515/znb-1990-0812.

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The reaction of λ5Ρ – λ3Ρ diphosphorus compounds with o-quinones, e.g. tetrachloro-o-benzoquinone or 2,5-di-tert-butyl-o-benzoquinone, led not only to oxidative addition of the o-quinone to λ3Ρ but also to insertion of a further molecule of o-quinone into the P–P bond (i.e. λ5Ρ – λ3Ρ diphosphorus compound and o-quinone reacted in a molar ratio 1:2). In the course of these oxidative addition and insertion reactions the o-quinones were converted into the corresponding hydroquinones (i.e. catechols). The products of these reactions were characterized by NMR and mass spectrometric methods, and by elemental analysis. The hydrolysis of the 1:2 addition products proceeded with cleavage of a P–O–C (hydroquinone) bond and formation of mononuclear products, involving λ4Ρ and λ5Ρ, respectively. A mechanism of this hydrolysis is proposed and has been elucidated by independent synthesis of some products. Diphosphines, i.e. symmetrical λ3Ρ – λ3Ρ diphosphorus compounds, were found to react with o-quinones in the same fashion in a molar ratio 1:3, i.e. with oxidative addition of the o-quinone to both λ3P atoms and insertion of tetrachloro-o-catechol into the P–P bond.
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Monks, Terrence, and Douglas Jones. "The Metabolism and Toxicity of Quinones, Quinonimines, Quinone Methides, and Quinone-Thioethers." Current Drug Metabolism 3, no. 4 (August 1, 2002): 425–38. http://dx.doi.org/10.2174/1389200023337388.

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Flynn, Noah R., Michael D. Ward, Mary A. Schleiff, Corentine M. C. Laurin, Rohit Farmer, Stuart J. Conway, Gunnar Boysen, S. Joshua Swamidass, and Grover P. Miller. "Bioactivation of Isoxazole-Containing Bromodomain and Extra-Terminal Domain (BET) Inhibitors." Metabolites 11, no. 6 (June 15, 2021): 390. http://dx.doi.org/10.3390/metabo11060390.

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The 3,5-dimethylisoxazole motif has become a useful and popular acetyl-lysine mimic employed in isoxazole-containing bromodomain and extra-terminal (BET) inhibitors but may introduce the potential for bioactivations into toxic reactive metabolites. As a test, we coupled deep neural models for quinone formation, metabolite structures, and biomolecule reactivity to predict bioactivation pathways for 32 BET inhibitors and validate the bioactivation of select inhibitors experimentally. Based on model predictions, inhibitors were more likely to undergo bioactivation than reported non-bioactivated molecules containing isoxazoles. The model outputs varied with substituents indicating the ability to scale their impact on bioactivation. We selected OXFBD02, OXFBD04, and I-BET151 for more in-depth analysis. OXFBD’s bioactivations were evenly split between traditional quinones and novel extended quinone-methides involving the isoxazole yet strongly favored the latter quinones. Subsequent experimental studies confirmed the formation of both types of quinones for OXFBD molecules, yet traditional quinones were the dominant reactive metabolites. Modeled I-BET151 bioactivations led to extended quinone-methides, which were not verified experimentally. The differences in observed and predicted bioactivations reflected the need to improve overall bioactivation scaling. Nevertheless, our coupled modeling approach predicted BET inhibitor bioactivations including novel extended quinone methides, and we experimentally verified those pathways highlighting potential concerns for toxicity in the development of these new drug leads.
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Xu, Wei, William R. Dolbier, Jian-Xin Duan, Yian Zhai, Katsu Ogawa, Merle A. Battiste, and Ion Ghiviriga. "Octafluoro[2.2]paracyclophane (AF4) Quinone." Collection of Czechoslovak Chemical Communications 73, no. 12 (2008): 1764–76. http://dx.doi.org/10.1135/cccc20081764.

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Octafluoro[2.2]paracyclophane (AF4) has been oxidized by treatment with HIO3 in CF3CO2H to form the corresponding p-quinone along with a unique triketone. This quinone undergoes reduction to the respective hydroquinone as well as a Diels-Alder reaction with 1,3-cyclohexadiene. Its reduction potential was obtained by cyclic voltammetry and is discussed in the context of other quinones.
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Dissertations / Theses on the topic "Quinone"

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Oosthuizen, Francois Jacobus. "Syntheses of the enantiopure quinones A and A' and their C-1 epimers." Thesis, Oosthuizen, Francois Jacobus (2002) Syntheses of the enantiopure quinones A and A' and their C-1 epimers. PhD thesis, Murdoch University, 2002. https://researchrepository.murdoch.edu.au/id/eprint/234/.

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The 3,4-dihydro-1H-naphtho[2,3-c]pyran ring system is found in many natural products as the 5,10- or 6,9-quinones. These compounds have been synthesized by various research groups as a result of their wide range of biological activities. This thesis describes several investigations directed towards syntheses of compounds in this general area. Quinone A (16) and quinone A'(17), derived from the naturally occurring aphid insect pigments protoaphin-fb and protoaphin-sl respectively, were of particular interest. The first chapter describes the previous syntheses of some naphtho[c]pyrans including those relating to the aphid pigment derivatives, followed by the isolation and identification of the aphid pigments. Also described was the ability of these naphthopyranquinones to act as potential bioreductive alkylating or dealkylating agents. The latter part of the chapter deals with the syntheses of the racemates of the aphid pigment derivatives quinones A and A' and deoxyquinone as well as model studies toward the non-quinonoid cleavage product, glucoside B. The chapter concludes with the progress made towards the first asymmetric synthesis of these compounds. Chapter 2 reports the establishment of conditions which led to ortho or para regioselectivity in the intramolecular cyclisation of tethered lactaldehydes to form benzo[c]pyrans. This regioselectivity depended on whether either benzyl or tbutyldimethylsilyl was used as protecting group. This chapter also described a model for the control of stereochemistry leading to quinone A'. Chapter 3 describes the syntheses of naphthalenes as potential precursors to the naphthopyranquinones derived from the aphid insect pigments. This followed after problems were encountered in previous work with inappropriate protection in the oxidation of halogenated benzopyrans. Chapter 4 develops the first successful syntheses of enantiopure quinone A and quinine A' with the correct absolute stereochemistry. This involved the regioselective addition of 1,3-bis(trimethylsilyloxy)-1-methoxybuta-1,3-diene toselectively halogenated benzopyranquinones. The latter were obtained through complementary series of highly diastereoselective transformations based on 2,5- dihydroxyacetophenone as starting material and (R)-lactate from the chiral pool as the source of asymmetry.
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Oosthuizen, Francois Jacobus. "Syntheses of the Enantiopure Quinones A and A' and Their C-1 Epimers." Murdoch University, 2002. http://wwwlib.murdoch.edu.au/adt/browse/view/adt-MU20040820.123649.

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The 3,4-dihydro-1H-naphtho[2,3-c]pyran ring system is found in many natural products as the 5,10- or 6,9-quinones. These compounds have been synthesized by various research groups as a result of their wide range of biological activities. This thesis describes several investigations directed towards syntheses of compounds in this general area. Quinone A (16) and quinone A’(17), derived from the naturally occurring aphid insect pigments protoaphin-fb and protoaphin-sl respectively, were of particular interest. The first chapter describes the previous syntheses of some naphtho[c]pyrans including those relating to the aphid pigment derivatives, followed by the isolation and identification of the aphid pigments. Also described was the ability of these naphthopyranquinones to act as potential bioreductive alkylating or dealkylating agents. The latter part of the chapter deals with the syntheses of the racemates of the aphid pigment derivatives quinones A and A’ Œ and deoxyquinone as well as model studies toward the non-quinonoid cleavage product, glucoside B. The chapter concludes with the progress made towards the first asymmetric synthesis of these compounds. Chapter 2 reports the establishment of conditions which led to ortho or para regioselectivity in the intramolecular cyclisation of tethered lactaldehydes to form benzo[c]pyrans. This regioselectivity depended on whether either benzyl or tbutyldimethylsilyl was used as protecting group. This chapter also described a model for the control of stereochemistry leading to quinone A’. Chapter 3 describes the syntheses of naphthalenes as potential precursors to the naphthopyranquinones derived from the aphid insect pigments. This followed after problems were encountered in previous work with inappropriate protection in the oxidation of halogenated benzopyrans. Chapter 4 develops the first successful syntheses of enantiopure quinone A and quinine A’ with the correct absolute stereochemistry. This involved the regioselective addition of 1,3-bis(trimethylsilyloxy)-1-methoxybuta-1,3-diene toselectively halogenated benzopyranquinones. The latter were obtained through complementary series of highly diastereoselective transformations based on 2,5- dihydroxyacetophenone as starting material and (R)-lactate from the chiral pool as the source of asymmetry.
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Cassagnes, Laure-Estelle. "Cycle redox quinone-quinone réductase 2 et conséquences sur la production d'espèces oxygénées réactives dans le contexte cellulaire." Thesis, Toulouse 3, 2015. http://www.theses.fr/2015TOU30148/document.

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La quinone réductase 2 ou QR2 est une enzyme qui, comme son homologue QR1, joue un rôle de détoxification des quinones, molécules fortement réactives, en les réduisant en hydroquinones. Cependant, il a été observé au niveau cellulaire et tissulaire que l'activité de cette flavoprotéine pouvait avoir des effets délétères en déclenchant une surproduction d'espèces réactives de l'oxygène (ROS). D'autre part, on observe une surexpression ou une sous expression de QR2 dans certaines maladies neurodégénératives comme la maladie de Parkinson et la maladie d'Alzheimer. Dans ce contexte, ce travail a porté sur l'étude des espèces oxygénées réactives produites lors du cycle redox quinone / QR2 et leurs variations en fonction de la nature de la quinone, sur protéine purifiée et sur modèles cellulaires comparativement à QR1. Les propriétés d'oxydo-réduction des substrats, co-substrats et inhibiteurs de QR2 étudiées par électrochimie ont permis de les classer en fonction de leur capacité à être réduits. L'activité enzymatique de la protéine, qu'elle soit purifiée ou intracellulaire, a été suivie par différentes méthodologies (résonance paramagnétique électronique, spectroscopie UV-visible et de fluorescence, U(H)PLC-MS, microscopie confocale de fluorescence). La production du radical superoxyde est observée en présence de lignées cellulaires surexprimant ou non QR1 et QR2. Les quinones sont réduites enzymatiquement pour donner des hydroquinones via l'activité des quinones réductases (QR1 et QR2) et des semiquinones via l'activité de réductases à un électron (CytP540 réductase par exemple). La réoxydation de ces produits est responsable d'une production plus ou moins forte de radicaux superoxydes selon la structure initiale de la quinone et l'affinité pour les différentes réductases. La ménadione provoque une production cellulaire de superoxyde plus importante en l'absence de QR1 et QR2. Ces analyses ont également démontré que, comme son homologue QR1, QR2 est capable de réduire les ortho-quinones dont certaines catécholquinones (aminochrome, dopachrome, adrénochrome) reconnues pour leur toxicité neuronale
Quinone reductase 2 or QR2 is an enzyme that, like its counterpart QR1, plays a role in detoxification of the highly reactives quinones by reducing them into hydroquinones. On one hand, it has been observed at the cellular and tissue level that the activity of this flavoprotein could have deleterious effects by triggering an overproduction of reactive oxygen species (ROS). On the other hand, overexpression or under expression of QR2 has been observed in some neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease. In this context, this work focused on the study of reactive oxygen species produced during the quinone / QR2 redox cycle and their variations depending on the nature of the quinone, on both purified protein and cell models, in comparison to QR1. The redox properties of the substrates, co-substrates and inhibitors ok QR2 studied by electrochemistry allowed to classify them according to their capacity to be reduced. The enzymatic activity of the protein, either purified or intracellular, was followed by various methodologies (electron paramagnetic resonance, UV-visible and fluorescence spectroscopy, U(H)PLC-MS, confocal fluorescence microscopy). Production of superoxide radical is observed in the presence of cell lines overexpressing or not QR1 and QR2. Quinones are reduced enzymatically to form hydroquinones via the activity of quinone reductase (QR1 and QR2) and semiquinone via the activity of one electron reductases (e.g. CytP540 reductase). Reoxidation of these products is responsible for a greater or lesser production of the superoxide radical, according to the initial structure of the quinone and the affinity for different reductases. Menadione causes a higher production of cellular superoxide in the absence of QR1 and QR2. These analyzes have also shown that, like its counterpart QR1, QR2 is capable of reducing ortho-quinones including catecholquinones (aminochrome, dopachrome, adrenochrome) known for their neuronal toxicity
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Minhas, Gurdeep Singh. "Interaction of quinone and quinone-like inhibitors with Thermus thermophilus complex I." Thesis, University of Cambridge, 2014. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.707994.

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Chauncey, Marek Anthony. "Reactions heterocyclic quinone methides." Thesis, University of Ulster, 1988. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.328193.

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Chhour, Monivan. "Etude de la métabolisation intracellulaire de quinones, du stress oxydant généré et des processus de détoxification associés." Thesis, Toulouse 3, 2020. http://www.theses.fr/2020TOU30004.

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Les quinones sont des composés ubiquitaires naturels indispensables aux organismes vivants. Cependant leur métabolisation est considérée comme toxique en raison de leur réactivité élevée. Les quinones sont en effet facilement réductibles à un ou deux électrons. La métabolisation intracellulaire de ces quinones par des réductases à un électron telles que le cytochrome P450 réductase ou d'autres flavoprotéines génèrent des semiquinones instables à l'origine de la production de radicaux libres conduisant à un stress oxydant. Les quinones-réductases 1 et 2 (QR1 et QR2) catalysent leur réduction à deux électrons pour former des hydroquinones chimiquement plus stables. Cette propriété est à l'origine du caractère détoxifiant généralement associé aux quinone-réductases. Cependant des analyses antérieures ont montré que ce caractère détoxifiant était remis en cause pour certains types de quinones et dépendait, notamment, du type de cellules. Ainsi afin de mieux comprendre les mécanismes conduisant à la génération d'espèces réactives et compte tenu du lien évoqué dans la littérature entre QR2 et neurodégénérescence, des études ont été menées sur des neurones primaires et des neuroblastomes génétiquement modifiés pour surexprimer QR2. Ces études ont mis en évidence, par diverses techniques analytiques telles que la résonance paramagnétique électronique ou la LC-MS, une augmentation de la toxicité de la ménadione mais également de l'adrénochrome en présence de la quinone-réductase 2. Afin d'expliquer les caractères contradictoires de QR2 d'une cellule à l'autre nous avons proposé l'hypothèse qu'une coopération avec une enzyme de conjugaison pouvant réagir avec la forme réduite instable et empêcher sa réoxydation soit nécessaire pour effectivement détoxifier les quinones. Des analyses complémentaires (RPE, LCMS, fluorescence) menées sur des neuroblastomes surexprimant à la fois QR2 et une enzyme de conjugaison spécifique des para-hydroquinone (UGT) ont en effet mis en évidence une diminution du stress oxydant lorsque les deux enzymes sont co-exprimées
Quinones are ubiquitous compounds in nature. They are also one of the essential elements in living organisms. However, their metabolisms are considered as toxic because there are highly reactive. Their structure is easily reduced by one or two electrons. The intracellular metabolism of these quinones via one-electron reduction such as cytochrome P450 reductase or others flavoproteins generates an unstable semiquinones which leads to a burst of free radical production that results in oxidative stress. On the other hand, quinone-reductases 1 and 2 (QR1 and QR2) catalyze quinone reduction via two electrons to form hydroquinones that chemically more stable. This property is well-known as the detoxifying character of quinone-reductase enzymes. However, previous analyses have shown that this detoxifying effect was appeared only for certain types of quinones and depended, in particular, on the type of cells. Thus, in order to better understand the mechanisms leading to the generation of reactive species and in consideration to those links that were mentioned in the literature between QR2 and neurodegeneration, studies were conducted on primary neurons and neuroblastoma cells genetically modified to overexpress in QR2. These studies have shown, by various analytical techniques such as electron paramagnetic resonance or LC-MS, an increase in the toxicity of menadione but also of adrenochrome in the presence of quinone- reductase 2. In order to explain the contradictory characteristics of QR2 from one cell to another, we proposed a hypothesis that a cooperation with another conjugating enzyme, which could react with the unstable reduced form that prevent its reoxidation, is needed to effectively detoxify quinones. Additional analyses (RPE, LCMS, fluorescence) conducted on neuroblastoma cells overexpressing both QR2 and a para-hydroquinone specific conjugation enzyme (UGT) have shown a decrease in oxidative stress when both enzymes are co-expressed
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Colucci, Marie A. "Quinone based inhibitors of NQ01." Thesis, University of Nottingham, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.478964.

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Sunassee, Suthananda Naidu. "Studies in marine quinone chemistry." Thesis, Rhodes University, 2011. http://hdl.handle.net/10962/d1005020.

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This thesis is divided into two parts and the rationale of the research conducted is based on the cytotoxicity of the prenylated quinones 1.24-1.29, isolated from the South African nudibranch Leminda millecra, against oesophageal cancer cells. The first part (Chapters 2 and 3) of the thesis initially documents the distribution of cytotoxic and antioxidant prenylated quinones and hydroquinones in the marine environment. We have been able to show, for the first time, that these compounds can be divided into eight structural classes closely related to their phyletic distribution. Secondly, we attempted to synthesize the two marine natural products 1.24 and 1.26 in an effort to contribute to an ongoing collaborative search with the Division of Medical Biochemistry at the University of Cape Town for new compounds with anti-oesophageal cancer activity. Accordingly, we followed the published synthetic procedure for 1.26 and, although we were unable to reproduce the reported results, we have generated five new prenylated quinone analogues 3.53-3.55, 3.63 and 3.71, which are a potentially viable addition to our ongoing structure-activity relationship (SAR) studies. Moreover, we embarked on a 7Li NMR mechanistic study for the synthesis of 3.2 from 3.1 which rewarded us with an improved and reproducible methodology for this crucial reaction that is detailed in Chapter 3. The second part of this thesis (Chapters 4 and 5) is concerned with a synthetic, structural, electrochemical and biological exploration of the 1,4-naphthoquinone nucleus as a primary pharmacophore in our search for new chemical entities which can induce apoptosis in oesophageal cancer cells, thus contributing to our overall ongoing SAR study in this class of compounds. Seven new naphthoquinone derivatves (4.19, 4.30, 4.31, 4.33 and 4.46-4.48) of the natural products 2-deoxylapachol (2.44), lapachol (4.1) and β-lapachone (5.2) were synthesized and 2-(1`-hydroxy-`-phenylmethyl)-1,4-naphthoquinone (4.29) was found to be the most cytotoxic (IC50 1.5 μM) against the oesophageal cancer cell line WHCO1, while 5.2, which is currently in phase II clinical trials as an anticancer drug, was found to be similarly active (IC50 1.6 μM). Electrochemical investigations of the redox properties of the benzylic alcohol derivatives 4.29-4.31 indicated a higher reduction potential compared to their oxidized counterparts 4.45-4.48, and this finding has been correlated to the increased activity of 4.29-4.31 against the WHCO1 cell line. Additionally, 4.29 is synthetically more accessible than either 1.26 or 5.2 and potentially a lead compound in our search for new and more effective chemotherapeutic agents against oesophageal cancer
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Ferreira, Janaina Gomes. "Estudo de compostos quinônicos com potencial atividade contra a doença de Chagas." Universidade de São Paulo, 2008. http://www.teses.usp.br/teses/disponiveis/75/75131/tde-23062008-163355/.

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Este trabalho apresenta as estruturas determinadas por difração de raio X de dois compostos naftoquinônicos, 3,4-diidro-[2,2-dimetil]-2H-nafto[1,2-b]pirano-5,6-diona (β-lapachona) e dimetil-1,4-naftoquinona. A estrutura cristalina destes compostos mostrou que estes são estabilizados por ligações de hidrogênio do tipo C-H...O, formando estruturas supramoleculares. Dos compostos derivados da β-lapachona, os naftoimidazóis têm-se mostrado muito ativos contra o T. cruzi, agente causador da doença de Chagas. Partindo das estruturas modeladas de 29 compostos naftoimidazólicos, propriedades eletrônicas, geométricas e topológicas foram calculadas para análise estatística por mínimos quadrados parciais (PLS). Após a análise e redução das variáveis foram selecionados os descritores Morp17p, X4a, piPC09, RDF065v, BELp6, RDF060p, R4u, RDF035m e RCI que foram utilizados para a construção um modelo de regressão com o método de PLS. Para o modelo, o menor erro de validação foi obtido com 3 fatores e os coeficientes de correlação R= 0,71 e Q= 0,82. O estudo de docking de alguns compostos naftoquinônicos e naftoimidazólicos mostrou que, do ponto de vista energético e de complementaridade química, estes compostos possuem pouca probabilidade de se ligarem no sítio ativo da tripanotiona redutase (TR), uma enzima essencial para o metabolismo do T. cruzi, bem como no sítio ativo da enzima humana glutationa redutase (GR), homóloga a TR. Há, no entanto, uma tendência geral destes compostos se ligarem no sítio da interface, sobretudo, de se ligarem neste sítio da enzima humana.
This work presents the structure determined by X-ray analyses for two naphthoquinone compounds 3,4-dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6- dione and dimethyl-1,4-naphthoquinone. The crystal packing of these compounds showed the existence of intermolecular hydrogen bonds of the type CH...0. These intermolecular forces are responsible for the self-assembly in three-dimensional supramolecular structure. A set of 29 naphthoimidazoles, derived from β-lapachone, that has shown activity against T. cruzi, the agent of Chagas disease, were modeled. From these structures electronic, geometric, topological, etc, properties were calculated to be used in the investigation by statistic analysis, using the partial least squares method (PLS). After reduction of the number of variables, the best PLS model found was the one obtained with the following variables: Morp17p, X4a, piPC09, RDF065v, BELp6, RDF060p, R4u, RDF035m and RCI. For the PLS model, the lower error of validation was obtained using 3 factors with the coefficients R=0.71 and Q=0.82. Two sets of compounds, naphtoquinones and naphthoimidazoles, were studied by docking method. The results showed that, for both, naphtoquinones and naphthoimidazoles and both trypanothione and glutathione reductase, the compounds have low probability to bind in the active site, and are more likely to bind in the interface site, especially in the interface site of the human protein.
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Cardoso, Mariana Filomena do Carmo. "Síntese de derivados 5-amino-1H-pirazólicos da nor-β-lapachona com potencial perfil anticancerígeno." Niterói, 2017. https://app.uff.br/riuff/handle/1/3283.

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Submitted by Biblioteca da Faculdade de Farmácia (bff@ndc.uff.br) on 2017-04-04T18:00:06Z No. of bitstreams: 1 Cardoso, Mariana Filomena do Carmo [Dissertação, 2012].pdf: 7461706 bytes, checksum: 1ba99c29719229ef773ca5d72b10c91f (MD5)
Made available in DSpace on 2017-04-04T18:00:06Z (GMT). No. of bitstreams: 1 Cardoso, Mariana Filomena do Carmo [Dissertação, 2012].pdf: 7461706 bytes, checksum: 1ba99c29719229ef773ca5d72b10c91f (MD5)
Esse trabalho descreve uma nova metodologia sintética de novos derivados pirazólicos análogos a 2,2-dimetil-2,3-di-hidronafto[1,2-b]furan-4,5-diona (nor-β-lapachona), através da inserção do núcleo pirazólico a posição C-3 da nor-β-lapachona. Nesta dissertação foram sintetizados 16 (dezesseis) substâncias inéditas, sendo oito da família 3-pirazolil-2,2-dimetil-2,3-di-hidronafto[1,2-b]furan-4,5-diona contendo o núcleo pirazólico acoplado à naftoquinona os quais foram submetidos a testes biológicos para avaliação de suas atividades citotóxicas in vitro contra quatro linhagens de células tumorais humanas e uma linhagem de células normais humanas. Todas as amostras mostraram-se ativas para as linhagens tumorais e não apresentaram hemólise. A metodologia clássica para a substituição nucleofílica no carbono 3 da nor-β-lapachona desenvolvida pelo nosso grupo de pesquisa mostrou-se pouco eficaz, levando a baixos rendimentos com formação de vários produtos colaterais. Desta forma, realizou-se um estudo metodológico a fim de se viabilizar a síntese de uma família de 3-pirazolil-nor-β-lapachonas com rendimentos satisfatórios. Assim, após várias modificações nos parâmetros reacionais, observou-se que o melhor intermediário sintético era o 3-hidroxi-2,2-dimetil-2,3-di-hidronafto[1,2-b]furan-4,5-diona
This paper describes a new synthetic methodology to new pyrazole derivatives analogous to the 2,2-dimethyl-2,3-dihidronaphtho-[1,2-b]-furan-4 ,5-dione (nor-β-lapachone) by inserting the core pyrazolic on the C-3 position of the nor-β-lapachone. In this essay were synthesized 16 (sixteen) new compounds, being eight 3-pyrazolyl-2,2-dimethyl-2,3-dihidronaphtho [1,2-b]-furan-4 ,5-dione family containing core pyrazolic naphthoquinone attached to which were submitted to biological tests to evaluate their in vitro cytotoxic activities against four human tumor cell lines and normal human cell line. All samples were active for tumor cell lines and showed no hemolysis. The classical methodology for the nucleophilic substitution at carbon 3 of the nor-β-lapachone developed by our research group proved to be ineffective, leading to low yields with the formation of various side products. Thus, there was a methodological study in order to facilitate the synthesis of a family of 3-pyrazolyl-nor-β-lapachones with satisfactory yields. Then, after the various modifications on the reaction parameters, it was found that the better synthetic intermediate was the 3-hydroxy-2,2-dimethyl-2,3-dihidronaphtho-[1,2-b]-furan-4 ,5-dione
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Books on the topic "Quinone"

1

1942-, Sies H., and Packer Lester, eds. Quinones and quinone enzymes. Amsterdam: Elsevier Academic Press, 2004.

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Rokita, Steven E., ed. Quinone Methides. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2009. http://dx.doi.org/10.1002/9780470452882.

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Chauncey, Mark Anthony. Reactions of heterocyclic quinone methides. [s.l: The Author], 1988.

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Robertson, Peter K. J. Photoelectrochemical reductions using quinone radical anions. [s.l: The Author], 1989.

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Thomson, R. H. Naturally occurring quinones III: Recent advances. 3rd ed. London: Chapman and Hall, 1987.

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Kleef, Mario van. The biosynthesis of the cofactor pyrroloquinoline quinone. Meppel: Drucker:] Krips Repro, 1988.

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L, Ernster, and Kungl Svenska vetenskapsakademien, eds. DT diaphorase: A quinone reductase with special functions in cell metabolism and detoxication : proceedings of an international conference held at the Arrhenius Laboratory, University of Stockholm, 1-4 June, 1986. Cambridge: Published on behalf of the Royal Swedish Academy of Sciences by Cambridge University Press, 1987.

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Thomson, R. H. Naturally occurring quinones IV: Recent advances. 4th ed. London: Blackie Academic & Professional, 1997.

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Thomson, R. H. Naturally occurring quinones IV: Recent advances. 4th ed. London: Blackie Academic & Professional, 1997.

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DeLuca, Dan A. The optimal production of the enzyme cofactor pyrroloquinoline quinone (PQQ) by different species of pseudomonas. Sudbury, Ont: Laurentian University, 1993.

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Book chapters on the topic "Quinone"

1

Schomburg, Dietmar, and Ida Schomburg. "quinate dehydrogenase (quinone) 1.1.5.8." In Class 1 Oxidoreductases, 155–59. Berlin, Heidelberg: Springer Berlin Heidelberg, 2013. http://dx.doi.org/10.1007/978-3-642-36265-1_24.

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Schomburg, Dietmar, and Dörte Stephan. "Quinate dehydrogenase (pyrroloquinoline-quinone)." In Enzyme Handbook 10, 603–5. Berlin, Heidelberg: Springer Berlin Heidelberg, 1995. http://dx.doi.org/10.1007/978-3-642-57756-7_154.

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Gooch, Jan W. "Quinone." In Encyclopedic Dictionary of Polymers, 604. New York, NY: Springer New York, 2011. http://dx.doi.org/10.1007/978-1-4419-6247-8_9709.

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Gooch, Jan W. "Quinone." In Encyclopedic Dictionary of Polymers, 919. New York, NY: Springer New York, 2011. http://dx.doi.org/10.1007/978-1-4419-6247-8_14632.

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Davidson, Victor L. "Quinone Cofactors." In Encyclopedia of Biophysics, 1–4. Berlin, Heidelberg: Springer Berlin Heidelberg, 2018. http://dx.doi.org/10.1007/978-3-642-35943-9_46-1.

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Matsuoka, Masaru. "Quinone Dyes." In Infrared Absorbing Dyes, 35–43. Boston, MA: Springer US, 1990. http://dx.doi.org/10.1007/978-1-4899-2046-1_4.

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Davidson, Victor L. "Quinone Cofactors." In Encyclopedia of Biophysics, 2166–68. Berlin, Heidelberg: Springer Berlin Heidelberg, 2013. http://dx.doi.org/10.1007/978-3-642-16712-6_46.

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Schomburg, Dietmar, and Dörte Stephan. "Cellobiose dehydrogenase (quinone)." In Enzyme Handbook 10, 496–99. Berlin, Heidelberg: Springer Berlin Heidelberg, 1995. http://dx.doi.org/10.1007/978-3-642-57756-7_130.

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Schomburg, D., M. Salzmann, and D. Stephan. "NADH dehydrogenase (quinone)." In Enzyme Handbook 7, 403–5. Berlin, Heidelberg: Springer Berlin Heidelberg, 1994. http://dx.doi.org/10.1007/978-3-642-78521-4_78.

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Schomburg, D., M. Salzmann, and D. Stephan. "NADPH dehydrogenase (quinone)." In Enzyme Handbook 7, 407–9. Berlin, Heidelberg: Springer Berlin Heidelberg, 1994. http://dx.doi.org/10.1007/978-3-642-78521-4_79.

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Conference papers on the topic "Quinone"

1

Rangel-Rojo, Raul, Hiro Matsuda, K. Kimura, Miguel A. Mendez-Rojas, and William H. Watson. "Wavelength-resolved nonlinearity on triazole-quinone derivatives." In Optical Science and Technology, SPIE's 48th Annual Meeting, edited by Mark G. Kuzyk, Manfred Eich, and Robert A. Norwood. SPIE, 2003. http://dx.doi.org/10.1117/12.502502.

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Rangel-Rojo, Raul, L. Stranges, Ajoy K. Kar, M. A. Mendez-Rojas, and W. H. Watson. "Near-resonance nonlinearities in triazole-quinone derivatives." In IV Iberoamerican Meeting of Optics and the VII Latin American Meeting of Optics, Lasers and Their Applications, edited by Vera L. Brudny, Silvia A. Ledesma, and Mario C. Marconi. SPIE, 2001. http://dx.doi.org/10.1117/12.437064.

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Pooja, Harish Mudila, and Anil Kumar. "Quinone based conducting materials for efficient energy storage." In THE FOURTH SCIENTIFIC CONFERENCE FOR ELECTRICAL ENGINEERING TECHNIQUES RESEARCH (EETR2022). AIP Publishing, 2023. http://dx.doi.org/10.1063/5.0162875.

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Jerrg-Li Liang and D. E. Nikles. "Amine-Quinone Polyurethanes As Binders For Metal Particle Tape." In 1993 Digests of International Magnetics Conference. IEEE, 1993. http://dx.doi.org/10.1109/intmag.1993.642050.

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Bezsonova, E., M. Dubar, D. Melekhina, К. Evdokimov, V. Klochkov, and E. Sokolova. "3-ARYLIDENE-2-OXINDOLES AS QUINONE REDUCTASE II INHIBITORS." In MedChem-Russia 2021. 5-я Российская конференция по медицинской химии с международным участием «МедХим-Россия 2021». Издательство Волгоградского государственного медицинского университета, 2021. http://dx.doi.org/10.19163/medchemrussia2021-2021-392.

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Yoshimura, Motomu, Tetsuya Nishimura, Eiji Yagyu, Noriaki Tsukada, and Tetsu Takeyama. "Hole Multiplexing in Quinone Derivative Photochemical Hole Burning Systems." In Persistent Spectral Hole Burning: Science and Applications. Washington, D.C.: Optica Publishing Group, 1991. http://dx.doi.org/10.1364/pshb.1991.the9.

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We have been interested in PHB mechanism1,2 in the quinone derivatives. The substituent effects of the guest molecules are examined on the hole multiplexing3, hole formation wavelength range and electric field effect4. We especially intend to know how densely multiple holes can be formed by wavelength tuning and Stark tuning.
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Budiawan, B., S. Handayani, I. C. Dani, R. Bakri, S. Hannaa, and F. Irawati. "In vitro study of DNA adduct 8-hidroxy-2’-deoxyguanosine (8-OHdG) formation through Fenton-like reaction with butylated hydroxytoluene quinone (BHT quinone)." In PROCEEDINGS OF THE 3RD INTERNATIONAL SYMPOSIUM ON CURRENT PROGRESS IN MATHEMATICS AND SCIENCES 2017 (ISCPMS2017). Author(s), 2018. http://dx.doi.org/10.1063/1.5064057.

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Xiao Hong Yin, K. Kobayashi, T. Kawai, M. Ozaki, K. Yoshino, and Qingquan Lei. "Electrical properties of polymer composites: conducting polymerpolyacene quinone radical polymer." In International Conference on Science and Technology of Synthetic Metals. IEEE, 1994. http://dx.doi.org/10.1109/stsm.1994.835422.

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Yang, XuePeng, Panpan Li, Fangfang Wang, Jianbin Ye, Ke Ma, and Duobin Mao. "An Efficient Separation of Pyrroloquinoline Quinone Using Chemical Complexation Extraction." In International Conference on Chemical,Material and Food Engineering. Paris, France: Atlantis Press, 2015. http://dx.doi.org/10.2991/cmfe-15.2015.20.

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Yano, J., Y. Matsufuji, and K. Ogura. "Multicolor-expressible ECD materials consisted of polyanilines, and an anionic quinone." In International Conference on Science and Technology of Synthetic Metals. IEEE, 1994. http://dx.doi.org/10.1109/stsm.1994.836068.

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Reports on the topic "Quinone"

1

Waite, J. H. Polymerization of Quinone-Crosslinked Marine Bioadhesive Protein. Fort Belvoir, VA: Defense Technical Information Center, October 1988. http://dx.doi.org/10.21236/ada200224.

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Cordingley, John S. The Molecular and Cellular Mechanisms of Quinone Tanning of Proteins. Fort Belvoir, VA: Defense Technical Information Center, June 1994. http://dx.doi.org/10.21236/ada303501.

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Galleguillos, R., M. Litt, and S. E. Rickert. Friedel Craft's synthesis and characterization of some acene quinone compounds. Office of Scientific and Technical Information (OSTI), January 1987. http://dx.doi.org/10.2172/6631885.

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Clark, Catherine D. Examining the Role of Quinone Moieties in the Photochemistry of Colored Dissolved Organic Matter in Coastal Waters. Fort Belvoir, VA: Defense Technical Information Center, September 2002. http://dx.doi.org/10.21236/ada628919.

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Clark, Catherine D. Examining the Role of Quinone Moieties in the Photochemistry of Colored Dissolved Organic Matter in Coastal Waters. Fort Belvoir, VA: Defense Technical Information Center, August 2001. http://dx.doi.org/10.21236/ada627292.

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Gust, D., and T. A. Moore. Artificial photosynthesis using chlorophyll based carotenoid quinone triads: A brief synopsis of research progress as of 31 December 1986. Office of Scientific and Technical Information (OSTI), December 1986. http://dx.doi.org/10.2172/5693588.

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Hanson, D. K., and M. Schiffer. Symmetry-related mutants in the quinone binding sites of the reaction center -- The effects of changes in charge distribution. Office of Scientific and Technical Information (OSTI), September 1997. http://dx.doi.org/10.2172/563250.

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Steele, W., and R. Chirico. Thermodynamics of the hydrodenitrogenation of quinoline. Office of Scientific and Technical Information (OSTI), June 1990. http://dx.doi.org/10.2172/6958305.

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Gunsaru, Bornface. Simplified Reversed Chloroquines to Overcome Malaria Resistance to Quinoline-based Drugs. Portland State University Library, January 2000. http://dx.doi.org/10.15760/etd.400.

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Wang, Hong, Eric Wolfe, Edgar Lara-Curzio, Marco Martinez, and Tracie Lowe. Study on Electrostatic Separation of Quinoline Insolubles from Coal Tar Pitch. Office of Scientific and Technical Information (OSTI), March 2023. http://dx.doi.org/10.2172/1960688.

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