Relevant bibliographies by topics / Quinones

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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 'Quinones'

Author: Grafiati
Published: 4 June 2021
Last updated: 25 January 2025

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Journal articles on the topic "Quinones"

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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Gutiérrez, Isela, Sonia G. Bertolotti, M. A. Biasutti, Arnaldo T. Soltermann, and Norman A. García. "Quinones and hydroxyquinones as generators and quenchers of singlet molecular oxygen." Canadian Journal of Chemistry 75, no. 4 (April 1, 1997): 423–28. http://dx.doi.org/10.1139/v97-048.

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The role of quinones and hydroxyquinones as sensitizers and as quenchers in Type II photooxygenations has been examined. The second aspect is discussed here, through a systematic study, for the first time in the open literature. Quinonic compounds are excellent generators of O2(1Δg) in aprotic solvents (excluding those quinones possessing substituents in positions adjacent to the carbonyl groups, in the case of anthraquinone derivatives). Benzoquinones, anthraquinones, and hydroxy derivatives are good O2(1Δg) quenchers upon dye-sensitized photoirradiation. The excited oxygen species is deactivated with rate constants in the range 106–107 M−1 s−1 depending on the solvent employed. The quenching process deactivates O2(1Δg) without further destruction of the quinone. The main interaction with O2(1Δg) is driven by the quinone moiety, in spite of the presence of potentially active nuclear substituents. The quenching mechanism could involve a reversible charge transfer intermediate, with the quinonic compound acting as an electron donor. Keywords: photooxidation, quenching, quinones, rose bengal, singlet oxygen.
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Wengryniuk, Sarah E., and Xiao Xiao. "Recent Advances in the Selective Oxidative Dearomatization of Phenols to o-Quinones and o-Quinols with Hypervalent Iodine Reagents." Synlett 32, no. 08 (January 14, 2021): 752–62. http://dx.doi.org/10.1055/s-0037-1610760.

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Abstract ortho-Quinones are valuable molecular frameworks with diverse applications across biology, materials, organic synthesis, catalysis, and coordination chemistry. Despite their broad utility, their synthesis remains challenging, in particular via the direct oxidation of readily accessible phenols, due to the need to affect regioselective ortho oxidation coupled with the sensitivity of the resulting o-quinone products. The perspective looks at the emergence of I(V) hypervalent iodine reagents as an effective class of oxidants for regioselective o-quinone synthesis. The application of these reagents in regioselective phenol oxidation to both o-quinones and o-quinols will be discussed, including a recent report from our laboratory on the first method for the oxidation of electron-deficient phenols using a novel nitrogen-ligated I(V) reagent. Also included are select examples of total syntheses utilizing this methodology as well as recent advancements in chiral I(V) reagent design for asymmetric phenol dearomatization.1 Introduction2 I(V): Hypervalent Iodine Reagents3 I(V)-Mediated Dearomatization to o-Quinones4 Bisnitrogen-Ligated I(V) Reagents: ortho Dearomatization of Electron-Poor Phenols5 I(V)-Mediated Dearomatization to o-Quinols6 Conclusion and Outlook
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Becker, James Y. "Electrochemistry of Diquinonyl Amines with an Internal Proton Source." ECS Meeting Abstracts MA2024-01, no. 41 (August 9, 2024): 2340. http://dx.doi.org/10.1149/ma2024-01412340mtgabs.

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It is well established that quinones play an important role in various biological systems. Studying electrochemical properties of quinones affords fundamental knowledge of semi-quinone radicals formation in vivo and in vitro in different media. Following our previous work on electrochemical properties of various quinonyl amines [1], Scheme 1 below describes seven diquinonyl amines. Noteworthy that six of them (1-6) contain an internal proton donor (‘NH’) except for the seventh one (7), in which both quinone moieties are attached to ‘NMe’ group. Their redox potentials were measured by cyclic voltammetry in dichloromethane [2]. The results show a strong dependence of the nature of substituent on the first reduction potentials, and that protonation of diquinonyl amines is feasible by internal proton source even in a non-polar medium. References [1] S. Bittner, S. Gorohovsky, O. Paz-Tal (Levi), J.Y. Becker, Amino Acids, 2002, 22, 71-93 [2] G. Temtsin-Krayz, S. Bittner, A. Dhiman and J.Y. Becker, "Electrochemistry of Quinones with Respect to their Role in Biomedical Chemistry", Chem. Rec., 2021, 21. Figure 1
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Ito, Shosuke, Manickam Sugumaran, and Kazumasa Wakamatsu. "Chemical Reactivities of ortho-Quinones Produced in Living Organisms: Fate of Quinonoid Products Formed by Tyrosinase and Phenoloxidase Action on Phenols and Catechols." International Journal of Molecular Sciences 21, no. 17 (August 24, 2020): 6080. http://dx.doi.org/10.3390/ijms21176080.

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Tyrosinase catalyzes the oxidation of phenols and catechols (o-diphenols) to o-quinones. The reactivities of o-quinones thus generated are responsible for oxidative browning of plant products, sclerotization of insect cuticle, defense reaction in arthropods, tunichrome biochemistry in tunicates, production of mussel glue, and most importantly melanin biosynthesis in all organisms. These reactions also form a set of major reactions that are of nonenzymatic origin in nature. In this review, we summarized the chemical fates of o-quinones. Many of the reactions of o-quinones proceed extremely fast with a half-life of less than a second. As a result, the corresponding quinone production can only be detected through rapid scanning spectrophotometry. Michael-1,6-addition with thiols, intramolecular cyclization reaction with side chain amino groups, and the redox regeneration to original catechol represent some of the fast reactions exhibited by o-quinones, while, nucleophilic addition of carboxyl group, alcoholic group, and water are mostly slow reactions. A variety of catecholamines also exhibit side chain desaturation through tautomeric quinone methide formation. Therefore, quinone methide tautomers also play a pivotal role in the fate of numerous o-quinones. Armed with such wide and dangerous reactivity, o-quinones are capable of modifying the structure of important cellular components especially proteins and DNA and causing severe cytotoxicity and carcinogenic effects. The reactivities of different o-quinones involved in these processes along with special emphasis on mechanism of melanogenesis are discussed.
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Ellis, Jessie, Xueyan Fu, J. Philip Karl, Patrick Radcliffe, Jason Soares, Laurel Doherty, Christopher Hernandez, Joel Mason, Angela Oliverio, and Sarah Booth. "Investigation of Vitamin K Quinone Metabolism by Human Gut Bacteria." Current Developments in Nutrition 4, Supplement_2 (May 29, 2020): 392. http://dx.doi.org/10.1093/cdn/nzaa045_025.

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Abstract Objectives Vitamin K (VK) is a family of structurally-related quinones, phylloquinone (PK) and menaquinones (MKn, n = prenyl units in side chain), that share a common napthoquinone ring (menadione, MD). VK quinones function as an essential dietary nutrient for humans. MD is considered a pro-vitamin form of VK. Plants and bacteria that produce VK quinones (PK and MKn, respectively) use them as an electron carrier in energy production. Little is known about the interaction of dietary VK quinones with gut bacteria, which may be bi-directional. The objective of this study was to investigate the influence of VK quinones and MD on human gut bacteria composition and MKn production. Methods Stool from 5 healthy male donors was pooled and inoculated in bioreactors under conditions mimicking the colon (anaerobic, pH 6.8, 37°C) for 48 h. Bioreactors were treated with deuterium (2H)-labeled quinones (2H-PK, 2H-MK4, 2H-MK9 or 2H-MD); no quinones (cell controls); or 2H-quinone treatment with no stool (cell-free controls). Culture aliquots were collected at 0, 5, 10, 24, and 48 h, and separated into pellet and supernatant fractions. Experiments were conducted in triplicate. All fractions were analyzed for VK quinone content using LC-MS. DNA from 0 and 24 h pellet fractions was extracted and amplified for paired-end 16S sequencing on an Illumina MiSeq 2500. Differences in bacterial composition were assessed using PERMANOVA. Results Supplemented 2H-quinones accumulated in the pellet fraction over time. This was not observed in cell-free controls and was thus not a function of culture media solubility. Endogenous (unlabeled) production of MKn was unaffected by supplementation of 2H-quinones. Generated 2H-MKn (2H-MK4, 2H-MK9, 2H-MK10, and 2H-MK11) were only detected in 2H-MD supplemented vessels. Community-wide bacterial composition significantly differed between 0 h and 24 h (r2 = 0.85, P = 0.001), but not by quinone treatment. Conclusions PK and MKn, dietary viamin K quinones, were not transformed by gut microbes to MKn in vitro, whereas the pro-vitamin quinone MD was transformed to MKn of multiple side chain lengths. Although no quinone induced community-wide changes in bacteria composition, additional analyses are needed to assess species-specific growth promotion. Funding Sources USDA ARS and DOD Health Program.
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MacDonald, Michael J. "Stimulation of insulin release from pancreatic islets by quinones." Bioscience Reports 11, no. 3 (June 1, 1991): 165–70. http://dx.doi.org/10.1007/bf01182485.

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Coenzyme Q (CoQ0) and other quinones were shown to be potent insulin secretagogues in the isolated pancreatic islet. The order of potency was CoQ0≅benzoquinone≅hydroquinonemenadione. CoQ6 and CoQ10 (ubiquinone), duroquinone and durohydroquinone did not stimulate insulin release. CoQ0's insulinotropism was enhanced in calcium-free medium and CoQ0 appeared to stimulate only the second phase of insulin release. CoQ0 inhibited inositol mono-, bis- and trisphosphate formation. Inhibitors of mitochondrial respiration (rotenone, antimycin A, FCCP and cyanide) and the calcium channel blocker verapamil, did not inhibit CoQ0-induced insulin release. Dicumarol, an inhibitor of quinone reductase, did not inhibit CoQ0-induced insulin release, but it did inhibit glucose-induced insulin release suggesting that the enzyme and quinones play a role in glucose-induced insulin release. Quinones may stimulate insulin release by mimicking physiologically-occuring quinones, such as CoQ10, by acting on the plasma membrane or in the cytosol. Exogenous quinones may bypass the quinone reductase reaction, as well as many reactions important for exocytosis.
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Li, Zhi, and Xiao-Long Xu. "Deciphering the Redox Chain Mechanism in the Catalytic Alkylation of Quinones." Synlett 29, no. 14 (May 14, 2018): 1807–13. http://dx.doi.org/10.1055/s-0037-1610125.

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Alkylation of p-quinones with allylic and benzylic esters is achieved by using a strong Lewis acid as the catalyst. This transformation likely follows an unusual redox chain mechanism. In this mechanism, quinone undergoes a sequence of reactions: it is reduced to ­hydroquinone (HQ), functionalized in a Lewis acid-catalyzed Friedel–Crafts alkylation, and then oxidized back to quinone. The last step is concurrent with the first step of a second quinone molecule, which is reduced to new HQ and functionalized, and thus propagates the redox chain reaction. The autoinitiation mechanism of the redox chain is not well understood, but additive HQ or Hantzsch ester can serve as effective initiators. The likelihood of this mechanism was elaborated by ­kinetic studies and various control experiments.1 Introduction2 Discovery of Catalytic Alkylation Reactions of Quinones3 Proposed Redox Chain Reaction Mechanism and Experimental Evidence4 Substrate Scope5 Conclusion
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Begleiter, Asher. "The contribution of alkylation to the activity of quinone antitumor agents." Canadian Journal of Physiology and Pharmacology 64, no. 5 (May 1, 1986): 581–85. http://dx.doi.org/10.1139/y86-096.

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Studies have shown that the quinone group can produce tumor cell kill by a mechanism involving active oxygen species. This cytotoxic activity can be correlated with the induction of DNA double strand breaks and is enhanced by the ability of the quinone compound to bind to DNA by alkylation. The cytotoxic activity and the production of DNA damage by model quinone antitumor agents were compared in L5178Y cells, sensitive and resistant to alkylating agents, to assess the contribution of alkylation to the activity of these agents. The resistant L5178Y/HN2 cells were found to be two fold and six fold more resistant to the alkylating quinones, benzoquinone mustard and benzoquinone dimustard, respectively, than parent L5178Y cells. In contrast, the L5178 Y/HN2 cells showed no resistance to the nonalkylating quinones, hydrolyzed benzoquinone mustard and bis(dimethylamino)benzoquinone. The alkylating quinones produced approximately two fold less cross-linking in L5178Y/HN2 cells compared with L5178Y sensitive cells. DNA double strand break formation by hydrolyzed benzoquinone mustard and bis(dimethylamino)benzoquinone was not significantly different in sensitive and resistant cells. However, the induction of double strand breaks by the alkylating quinones benzoquinone mustard and benzoquinone dimustard was reduced by 5-fold and 15-fold, respectively, in L5178Y/HN2 cells. These results show that the alkylating activity of the alkylating quinones cannot directly explain all of the enhanced cytotoxic activity of these agents. Furthermore, they provide strong evidence that the enhanced formation of DNA double strand breaks by alkylating quinone agents is directly related to the ability of these agents to bind to DNA. This increased formation of strand breaks may account for the enhanced cytotoxic activity of the alkylating quinones.
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Juliasih, Ni Luh Gede Ratna, Lee Chang Yuan, Yuki Sago, Yoichi Atsuta, and Hiroyuki Daimon. "Supercritical Fluid Extraction of Quinones from Compost for Microbial Community Analysis." Journal of Chemistry 2015 (2015): 1–7. http://dx.doi.org/10.1155/2015/717616.

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Supercritical fluid extraction (SFE) was used to extract quinones from compost to monitor the microbial community dynamics during composting. The 0.3 g of dried compost was extracted using 3 mL min−1of carbon dioxide (90%) and methanol (10%) at 45°C and 25 MPa for a 30 min extraction time. The extracted quinones were analysed using ultra performance liquid chromatography (UPLC) with 0.3 mL min−1of methanol mobile phase for a 50 min chromatographic run time. A comparable detected amount of quinones was obtained using the developed method and an organic solvent extraction method, being 36.06 μmol kg−1and 34.54 μmol kg−1, respectively. Significantly low value of dissimilarity index (D) between the two methods (0.05) indicated that the quinone profile obtained by both methods was considered identical. The developed method was then applied to determine the maturity of the compost by monitoring the change of quinone during composting. The UQ-9 and MK-7 were predominant quinones in the initial stage of composting. The diversity of quinone became more complex during the cooling and maturation stages. This study showed that SFE had successfully extracted quinones from a complex matrix with simplification and rapidity of the analysis that is beneficial for routine analysis.
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Dissertations / Theses on the topic "Quinones"

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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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Rafipoor, Fereshteh. "Synthesis of oxindole quinones and carboline quinones." Thesis, Brunel University, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.292445.

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Kitagawa, Rodrigo Rezende [UNESP]. "Avaliação da atividade biológica de uma nova naftoquinona extraída de Paepalanthus latipes." Universidade Estadual Paulista (UNESP), 2008. http://hdl.handle.net/11449/100749.

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Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
Quinonas são substâncias orgânicas amplamente distribuídas na natureza, encontradas em plantas, fungos e bactérias, associadas à atividade antitumoral e antimicrobiana. Recentemente, uma quinona (5-metoxi-3,4-diidroxantomegnina), estruturalmente semelhante à 1,4-naftoquinona, foi isolada dos capítulos de Paepalanthus latipes. O objetivo desse estudo foi avaliar atividades biológicas dessa quinona visando possível aplicação terapêutica. A 5-metoxi-3,4-diidroxantomegnina apresentou concentração inibitória mínima para Staphylococcus aureus e Enterococcus faecalis (197µM), mas não para Escherichia coli. Essa quinona demonstrou significativo índice citotóxico para células McCoy quando comparado ao da cisplatina. Nos ensaios utilizando linhagens tumorais de adenocarcinoma de pulmão (LP07) e mama (LM2), a maior citotoxicidade da 5-metoxi-3,4-diidroxantomegnina foi para a linhagem LP07. A associação com ácido ascórbico aumentou a citotoxicidade da 5-metoxi-3,4-diidroxantomegnina para células McCoy, LM2 e LP07 devido a um redox cílcico com formação de peróxido de hidrogênio. Visto que alguns antineoplásicos somente apresentam efeito citotóxico após biotransformação, a citotoxicidade da 5-metoxi-3,4-diidroxantomegnina na presença do sistema microssomal S9 foi avaliada e constatou-se que esse sistema de ativação metabólica não altera o potencial citotóxico da quinona. Óxido nítrico (NO) e fator de necrose tumoral-a (TNF-a) não foram detectados nos sobrenadantes de culturas de macrófagos tratados com 5-metoxi-3,4-diidroxantomegnina, portanto seu efeito tóxico, nesse sistema celular, não está relacionado com a produção desses mediadores. Entretanto, macrófagos tratados com essa quinona aumentaram significativamente a liberação de peróxido de hidrogênio. Nos testes de inibição dos...
Quinones are organic substances widely distributed in nature, found in plants, fungi and bacteria, associated with antitumoral and antimicrobial activities. Recently, a quinone (5-methoxy-3,4-dehydroxanthomegnin), structurally similar to 1,4-naphthoquinone, was isolated of the capitula of Paepalanthus latipes. The objective of this study was to evaluate biological activities of this quinone aiming a possible therapeutical application. The 5-methoxy-3,4-dehydroxanthomegnin showed minimal inhibitory concentration for Staphylococcus aureus and Enterococcus faecalis (197µM), but not for Escherichia coli. This quinone showed significative cytotoxic index for McCoy cells when compared with cisplatin. In the assays using tumoral cell lines of adenocarcinoma of lung (LP07) and breast (LM2), the largest cytotoxicity of the 5-methoxy-3,4-dehydroxanthomegnin was for LP07 line. The association with ascorbic acid increased the cytotoxicity of the 5-methoxy-3,4-dehydroxanthomegnin for McCoy cells, LM2 and LP07 due to redox cycling with hydrogen peroxide formation. Since some antineoplastic only present cytotoxic effect after biotransformation, the cytotoxicity of the 5-methoxy-3,4-dehydroxanthomegnin in the presence of the microssomal system S9 was evaluated and it was found that this system does not change the cytotoxic potential of the quinone. Nitric oxide (NO) and tumoral necrosis factor- α (TNF-α) were not detected in supernatants of macrophages treated with 5-methoxy-3,4-dehydroxanthomegnin, therefore its toxic effect, in this cell system, is not related to the production these mediators. However, macrophages treated with 5-methoxy-3,4-dehydroxanthomegnin increased hydrogen peroxide liberation significantly. The tests of inhibition of the mediators NO and TNF-α demonstrated that the 5-methoxy-3,4-dehydroxanthomegnin inhibits the release... (Complete abstract click electronic access below)
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Chilloux, Aurelie Amelia. "Synthesis of anticancer heterocyclic quinones." Thesis, University of Nottingham, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.537637.

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Jacob, Aouregan Michèle Marguerite Simone. "Synthesis of naturally occurring quinones." Thesis, University of Nottingham, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.437087.

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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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Eralp, Tugce. "Synthesis Of Ferrocenyl Quinones And Polyquinanes." Master's thesis, METU, 2005. http://etd.lib.metu.edu.tr/upload/3/12606205/index.pdf.

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ABSTRACT SYNTHESIS OF FERROCENYL QUINONES AND POLYQUINANES Eralp, Tugç
e M.S., Department of Chemistry Supervisor: Assoc. Prof. Dr. Metin Zora June 2005, 79 pages With the discovery of antitumor activity of ferrocene derivatives, research on new ferrocene derivatives have gained importance. For this purpose, we have investigated the synthesis of ferrocenyl quinones starting from squaric acid. Several quinone derivatives are known to have antitumor and antibiotic activities. In this research, by combining ferrocene and quinone moieties, we have targeted ferrocenyl quinones which are supposed to have enhanced potential antitumor activity. Thermolysis of ferrocenyl-substituted 4-alkynyl cyclobutenones, which have been prepared from ferrocenyl cyclobutenediones and alkynyllithiums, leads to the formation of ferrocenyl quinones and besides also cyclopentendiones are observed. Ferrocenyl cyclobutenediones have been prepared from known cyclobutenediones by nucleophilic addition of ferrocenyllithium followed by hydrolysis. A mechanism for the formation of ferrocenyl substituted quinones, involving first electrocyclic ring opening of alkynyl substituted cyclobutenone to ketene intermediate and then ring closure, has been proposed. Polyquinanes are widely found in nature and proved to have biological activity such as antibiotic activity. For the synthesis of ferrocenyl polyquinanes, starting from squaric acid, ferrocenyl substituted cyclobutenediones were prepared and reacted with alkenyllithium, and hydrolyzed to afford ferrocenyl substituted polyquinanes. A mechanism has been proposed that involves first the formation of cis- and trans-divinyl substituted cyclobutenes that produce cyclooctatriene-dienolate, upon hydrolysis of this dienolate, aldol-type transannular ring closure reaction takes place, producing polyquinanes.
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Nielsen, Linda Birgitta. "Synthesis of some naturally occurring quinones." University of Western Australia. School of Biomedical, Biomolecular and Chemical Sciences, 2008. http://theses.library.uwa.edu.au/adt-WU2009.0067.

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Naturally occurring quinones have attracted considerable interest due to their widespread occurrence, structural diversity and often potent biological activities. The research outlined in this thesis involves the development of synthetic approaches to two novel naphthoquinone derivatives, both of which were discovered during investigations into the bioactive constituents of tropical plant species. Chapter 1 introduces the family of quinonoid compounds and also considers the important role that natural product synthesis can play in structural confirmation and in providing an adequate supply of compounds for further research. Chapter 2 describes the synthesis of elecanacin 36, an unusual cyclobuta-fused naphthalene-1,4-dione derivative which has been isolated from the bulbs of the iris Eleutherine americana Merr. et Heyne (Iridaceae), along with the isomeric and well-known pyranonaphthoquinones eleutherin 38 and isoeleutherin 39. Chapter 3 focuses on an approach to 3-hydroxymethylfuro[3,2-b]naphtho[2,3-d]furan-5,10-dione 37, which has been isolated from the wood of the tropical tree Crescentia cujete L. (Bignoniaceae) and incorporates a rare fully aromatic furofuran moiety.
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Visconti, Andrea. "Synthesis of quinones with anticancer activity." Thesis, University of Nottingham, 2012. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.574662.

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Quinones attract the attention of chemists and biologists because of their unique structure and biological properties. Cancer is a leading cause of death worldwide, killing millions of people every year. Several antitumour agents, frequently employed in the treatment of different forms of cancer, contain in their structure the quinone motif, discovered to have marked cytotoxic effects. Chapter 1 presents an overview of the unique properties of quinones, with particular emphasis on their anticancer activity. Bioactivation of quinones by cellular reductive enzymes generates reactive oxygen species and/or alkylating species responsible for the cytotoxic effects of these compounds. Chapter 2 discusses the synthetic approaches to the novel quinone-containing natural product (+ )-terreusinone, recently isolated from the marine algicolous fungus Aspergillus terreus. Although the total synthesis of the natural product could not be accomplished, an innovative and efficient symmetric strategy, with a double Claisen rearrangement as the key step, led to the formation of the dipyrrolobenzoquinone core of ( + )-terreusinone. Chapter 3 describes the design, the synthesis and the biological evaluation of novel 2-unsubstituted indolequinones based on the structure of the indolequinones, previously synthesised in our group, that showed growth inhibitory activity against human pancreatic cancer cells in vitro and in vivo. Human thioredoxin reductase 1, a selenium-containing enzyme, was identified as the molecular target of these indolequinones. All the novel indolequinones made were tested for their anticancer activity in vitro against human pancreatic cancer and some of them were found very potent compounds at inducing inhibition of growth in human pancreatic cancer cells, confirming the potential use of these indolequinone-based compounds as a therapeutic approach to pancreatic cancer.
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Books on the topic "Quinones"

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

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A, Pedersen Jens, ed. CRC handbook of EPR spectra from quinones and quinols. Boca Raton, Fla: CRC Press, 1985.

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Thomson, R. H. Naturally Occurring Quinones IV. Dordrecht: Springer Netherlands, 1996. http://dx.doi.org/10.1007/978-94-009-1551-0.

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Thomson, R. H. Naturally occurring quinones III: Recent advances. 3rd ed. London: Chapman and Hall, 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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Thomas, R. D. Synthetic studies using quinones and related compounds. Norwich: University of East Anglia, 1987.

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Rafipoor, Fereshteh. Synthesis of oxindole quionones and carboline quinones. Uxbridge: Brunel University, 1991.

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Quinones, Lee. Lee Quinones, new horizons: Riverside Studios, 15 May-16 June 1985. London: The Studios, 1985.

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1952-, Davidson Victor L., ed. Principles and applications of quinoproteins. New York: M. Dekker, 1993.

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Book chapters on the topic "Quinones"

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Thomson, R. H. "Diterpenoid quinones." In Naturally Occurring Quinones IV, 650–710. Dordrecht: Springer Netherlands, 1997. http://dx.doi.org/10.1007/978-94-009-1551-0_6.

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Thomson, R. H. "Miscellaneous quinones." In Naturally Occurring Quinones IV, 711–24. Dordrecht: Springer Netherlands, 1997. http://dx.doi.org/10.1007/978-94-009-1551-0_7.

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Thomson, R. H. "Other polycyclic quinones." In Naturally Occurring Quinones IV, 484–582. Dordrecht: Springer Netherlands, 1997. http://dx.doi.org/10.1007/978-94-009-1551-0_4.

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Thomson, R. H. "N-Heterocyclic quinones." In Naturally Occurring Quinones IV, 583–649. Dordrecht: Springer Netherlands, 1997. http://dx.doi.org/10.1007/978-94-009-1551-0_5.

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Bensasson, R. v., E. J. Land, and T. G. Truscott. "Cancer: chemotherapy." In Excited States and Free Radicals in Biology and Medicine, 306–21. Oxford University PressOxford, 1993. http://dx.doi.org/10.1093/oso/9780198555605.003.0011.

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Abstract The first compound tested for antitumour activity by the National Cancer Institute of the USA was the simple quinone, 2-methyl-p-benzoquinone. Since 1955 over 1500potential drugs have been screened for antitumour activity, the majority of which are quinones.
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Lenaz, Giorgio, and Maria Luisa Genova. "Quinones." In Reference Module in Life Sciences. Elsevier, 2020. http://dx.doi.org/10.1016/b978-0-12-809633-8.21410-6.

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Lenaz, G., and M. L. Genova. "Quinones." In Encyclopedia of Biological Chemistry, 722–29. Elsevier, 2013. http://dx.doi.org/10.1016/b978-0-12-378630-2.00204-8.

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"Quinones." In Encyclopedia of Parasitology, 2303–4. Berlin, Heidelberg: Springer Berlin Heidelberg, 2016. http://dx.doi.org/10.1007/978-3-662-43978-4_2642.

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Itoh, Akichika. "Quinones." In Photoorganocatalysis in Organic Synthesis, 39–70. WORLD SCIENTIFIC (EUROPE), 2019. http://dx.doi.org/10.1142/9781786346056_0002.

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Unger, Thomas A. "Quinones." In Pesticide Synthesis Handbook, 965. Elsevier, 1996. http://dx.doi.org/10.1016/b978-081551401-5.50748-6.

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Conference papers on the topic "Quinones"

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Bende, Attila. "First Principle Study of Dopamine O-Quinone Photochemistry Behavior." In 2024 International Conference on Advanced Scientific Computing (ICASC), 1–5. IEEE, 2024. https://doi.org/10.1109/icasc63229.2024.10785243.

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Carneiro, Paula F., Alice S. B. Rocha, Guilherme C. Lechuga, Samara B. Nascimento, Maria do Carmo F. R. Pinto, Saulo C. Bourguignon, and Vitor F. Ferreira. "Synthesis of oxirane from quinones against T. cruzi." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013820205350.

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Oelgemo¨ller, Michael, Christian Jung, Ju¨rgen Ortner, Jochen Mattay, Christian Schiel, and Elmar Zimmermann. "“Back to the Roofs”: The Solarchemical Production of Fine Chemicals With Sunlight." In ASME 2004 International Solar Energy Conference. ASMEDC, 2004. http://dx.doi.org/10.1115/isec2004-65021.

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Three photochemical reactions were performed successfully under solar irradiation conditions: the photoacylation of quinones with aldehydes and the rose bengal sensitized photooxygenations of citronellol or 1,5-dihydroxynaphthalene. All reactions were easily performed on multigram to kilogram scales using cheap and commercially available starting materials, and yielded important key-intermediates for industrial applications.
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Birau, Maria. "Conjugated quinones and fluorenes as novel materials for use in semiconductors and optoelectronics." In Opto-Canada: SPIE Regional Meeting on Optoelectronics, Photonics, and Imaging, edited by John C. Armitage. SPIE, 2017. http://dx.doi.org/10.1117/12.2283840.

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SAGUN, E. I., A. A. YAROVOI, A. M. SHULGA, V. N. KNYUKSHTO, A. P. STUPAK, and E. I. ZENKEVICH. "PHOTOINDUCED ELECTRON TRANSFER IN HETEROCOMPOSITES BASED ON SEMICONDUCTOR CdSe QUANTUM DOTS AND QUINONES." In Proceedings of the International Conference on Nanomeeting 2009. WORLD SCIENTIFIC, 2009. http://dx.doi.org/10.1142/9789814280365_0035.

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Love, Charlotte, Hye-Young Kim, Keri Tallman, Ned Porter, Phillip Clapp, and Ilona Jaspers. "Vaping-derived Δ8-THC quinones form cysteine adducts and alter the respiratory epithelium transcriptome." In ERS International Congress 2023 abstracts. European Respiratory Society, 2023. http://dx.doi.org/10.1183/13993003.congress-2023.oa4237.

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VETROVA, EV, and NS KUDRYASHEVA. "MECHANISM OF INFLUENCE OF QUINONES ON BIOLUMINESCENT ENZYME SYSTEM NAD(P)H: FMN-OXIDOREDUCTASE-LUCIFERASE." In Bioluminescence and Chemiluminescence - Progress and Current Applications - 12th International Symposium on Bioluminescence (BL) and Chemiluminescence (CL). WORLD SCIENTIFIC, 2002. http://dx.doi.org/10.1142/9789812776624_0022.

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Speck, M., M. Senge, and H. Kurreck. "Synthesis and Characterization of Porphyrin-o-Quinones - A New Group of Model Compounds for Photosynthesis." In The 4th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2000. http://dx.doi.org/10.3390/ecsoc-4-01923.

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Hidayat, Aulia Fikri, Taufik Muhammad Fakih, and Mentari Luthfika Dewi. "Investigation of tyrosinase inhibitory activity of thymol and quinones of Nigella sativa using molecular docking." In 24TH TOPICAL CONFERENCE ON RADIO-FREQUENCY POWER IN PLASMAS. AIP Publishing, 2023. http://dx.doi.org/10.1063/5.0158239.

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Hussein, Yasser H. A., Velautham Sivakumar, Karuppasamy Ganesh, and Gary Hastings. "Computational Calculation of Midpoint Potential of Quinones in the A1 Binding Site of the Photosystem I." In Qatar Foundation Annual Research Conference Proceedings. Hamad bin Khalifa University Press (HBKU Press), 2016. http://dx.doi.org/10.5339/qfarc.2016.ictpp2024.

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Reports on the topic "Quinones"

1

Steffens, John, Eithan Harel, and Alfred Mayer. Coding, Expression, Targeting, Import and Processing of Distinct Polyphenoloxidases in Tissues of Higher Plants. United States Department of Agriculture, November 1994. http://dx.doi.org/10.32747/1994.7613008.bard.

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Polyphenol oxidase (PPO) catalyzes the oxidation of phenols to quinones at the expense of O2. PPOs are ubiquitous in higer plants, and their role in oxidative browning of plant tissues causes large annual losses to food production. Despite the importance of PPOs to agriculture, the function(s) of PPOs in higher plants are not understood. Among other roles, PPOs have been proposed to participate in aspects of chloroplast metabolism, based on their occurrence in plastids and high Km for O2. Due to the ability of PPO to catalyze formation of highly reactive quinones, PPOs have also been proposed to be involved in a wide array of defensive interactions with insect, bacterial, and fungal pests. Physiological and biochemical studies of PPO have provided few answers to the major problems of PPO function, subcellular localization, and biochemical properties. This proposal achieved the following major objectives: cloning of PPO cDNAs in potato and tomato; characterization of the tomato PPO gene family; antisense downregulation of the tomato PPO gene family; and reduction in post-harvest enzymic browning of potato through expression of antisense PPO genes under the control of tuber-specific promoters. In addition, we established the lumenal localization of PPO, characterized and clarified the means by which PPOs are imported and processed by chloroplasts, and provided insight into the factors which control localization of PPOs. This proposal has thereby provided fundamental advances in the understanding of this enzyme and the control of its expression.
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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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Chaudhuri, Shubham, Pinelopi Goldberg, and Panle Jia. Estimating the Effects of Global Patent Protection in Pharmaceuticals: A Case Study of Quinolones in India. Cambridge, MA: National Bureau of Economic Research, December 2003. http://dx.doi.org/10.3386/w10159.

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Ross, Peter, Samantha Scott, Marie Noel, and Jenn Blancard. Anderson Creek watershed: Water quality report for the 2023/24 wet season. Raincoast Conservation Foundation, November 2024. http://dx.doi.org/10.70766/126.498.

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Water is essential for life, and steps are needed to understand, protect and restore its health in fish habitat throughout British Columbia. The Raincoast Healthy Waters program was launched in 2023 to establish community-oriented water pollution monitoring in select BC watersheds. Two Healthy Waters sampling events take place every year in each watershed – the first in the dry season (summer), and the second being in the wet season (winter). This report highlights results from the first wet (winter) season sampling carried out with the support and participation of the Pender Harbour Ocean Discovery Station (PODS). Briefly, the Healthy Waters team collected water samples on January 16, 2024, from five water categories, including source water (3 samples), river water (3 samples), road runoff (3 samples), tap water (10 samples) and marine water (3 samples). Samples were then pooled by water category and analysed for coliform, metals, nutrients and physical parameters at ALS Environmental, and analysed for pesticides, polycyclic aromatic hydrocarbons (PAHs), pharmaceuticals and personal care products (PPCPs), polychlorinated biphenyls (PCBs), alkylphenol ethoxylates, bisphenols, per- and poly-fluoroalkyl substances (PFAS), and sucralose at SGS Axys Analytical and for 6PPD Quinone at DFO’s Institute of Ocean Science. Overall, the Anderson Creek watershed had relatively good water quality in the wet season, but additional sampling and analysis will provide further insight into contamination impacts from forest fires, domestic wastewater, industrial chemicals and road runoff on the health of this valued watershed.
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