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Journal articles on the topic 'Novel reactive intermediates'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Hemberger, Patrick, Jeroen A. van Bokhoven, Javier Pérez-Ramírez, and Andras Bodi. "New analytical tools for advanced mechanistic studies in catalysis: photoionization and photoelectron photoion coincidence spectroscopy." Catalysis Science & Technology 10, no. 7 (2020): 1975–90. http://dx.doi.org/10.1039/c9cy02587a.

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2

Damsten, Micaela C., Jon S. B. de Vlieger, Wilfried M. A. Niessen, Hubertus Irth, Nico P. E. Vermeulen, and Jan N. M. Commandeur. "Trimethoprim: Novel Reactive Intermediates and Bioactivation Pathways by Cytochrome P450s." Chemical Research in Toxicology 21, no. 11 (November 17, 2008): 2181–87. http://dx.doi.org/10.1021/tx8002593.

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3

Kessar, S. V. "Lewis acid complexed azacarbanions: Novel reactive intermediates of wide synthetic utility." Pure and Applied Chemistry 68, no. 3 (January 1, 1996): 509–14. http://dx.doi.org/10.1351/pac199668030509.

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4

Hansel, Colleen M., Timothy G. Ferdelman, and Bradley M. Tebo. "Cryptic Cross-Linkages Among Biogeochemical Cycles: Novel Insights from Reactive Intermediates." Elements 11, no. 6 (November 30, 2015): 409–14. http://dx.doi.org/10.2113/gselements.11.6.409.

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5

Green, Justin L., and Gregory A. Reed. "Benzo[a]pyrene bay-region sulfonates, a novel class of reactive intermediates." Chemical Research in Toxicology 3, no. 1 (January 1990): 59–64. http://dx.doi.org/10.1021/tx00013a010.

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6

Thome, Ulrich, Ahmed Lazrak, Lan Chen, Marion C. Kirk, Michael J. Thomas, Henry Jay Forman, and Sadis Matalon. "Novel SIN-1 reactive intermediates modulate chloride secretion across murine airway cells." Free Radical Biology and Medicine 35, no. 6 (September 2003): 662–75. http://dx.doi.org/10.1016/s0891-5849(03)00392-7.

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7

Attwa, Mohamed W., Adnan A. Kadi, and Hany W. Darwish. "Belizatinib: Novel reactive intermediates and bioactivation pathways characterized by LC–MS/MS." Journal of Pharmaceutical and Biomedical Analysis 171 (July 2019): 132–47. http://dx.doi.org/10.1016/j.jpba.2019.04.006.

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8

Groves, John T. "Cytochrome P450 enzymes: understanding the biochemical hieroglyphs." F1000Research 4 (July 1, 2015): 178. http://dx.doi.org/10.12688/f1000research.6314.1.

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Cytochrome P450 (CYP) enzymes are the primary proteins of drug metabolism and steroid biosynthesis. These crucial proteins have long been known to harbor a cysteine thiolate bound to the heme iron. Recent advances in the field have illuminated the nature of reactive intermediates in the reaction cycle. Similar intermediates have been observed and characterized in novel heme-thiolate proteins of fungal origin. Insights from these discoveries have begun to solve the riddle of how enzyme biocatalyst design can afford a protein that can transform substrates that are more difficult to oxidize than the surrounding protein architecture.

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9

He, Chao, Galiya R. Galimova, Yuheng Luo, Long Zhao, André K. Eckhardt, Rui Sun, Alexander M. Mebel, and Ralf I. Kaiser. "A chemical dynamics study on the gas-phase formation of triplet and singlet C5H2carbenes." Proceedings of the National Academy of Sciences 117, no. 48 (November 16, 2020): 30142–50. http://dx.doi.org/10.1073/pnas.2019257117.

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Since the postulation of carbenes by Buchner (1903) and Staudinger (1912) as electron-deficient transient species carrying a divalent carbon atom, carbenes have emerged as key reactive intermediates in organic synthesis and in molecular mass growth processes leading eventually to carbonaceous nanostructures in the interstellar medium and in combustion systems. Contemplating the short lifetimes of these transient molecules and their tendency for dimerization, free carbenes represent one of the foremost obscured classes of organic reactive intermediates. Here, we afford an exceptional glance into the fundamentally unknown gas-phase chemistry of preparing two prototype carbenes with distinct multiplicities—triplet pentadiynylidene (HCCCCCH) and singlet ethynylcyclopropenylidene (c-C5H2) carbene—via the elementary reaction of the simplest organic radical—methylidyne (CH)—with diacetylene (HCCCCH) under single-collision conditions. Our combination of crossed molecular beam data with electronic structure calculations and quasi-classical trajectory simulations reveals fundamental reaction mechanisms and facilitates an intimate understanding of bond-breaking processes and isomerization processes of highly reactive hydrocarbon intermediates. The agreement between experimental chemical dynamics studies under single-collision conditions and the outcome of trajectory simulations discloses that molecular beam studies merged with dynamics simulations have advanced to such a level that polyatomic reactions with relevance to extreme astrochemical and combustion chemistry conditions can be elucidated at the molecular level and expanded to higher-order homolog carbenes such as butadiynylcyclopropenylidene and triplet heptatriynylidene, thus offering a versatile strategy to explore the exotic chemistry of novel higher-order carbenes in the gas phase.

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10

Kotuniak, Radosław, and Wojciech Bal. "Kinetics of Cu(ii) complexation by ATCUN/NTS and related peptides: a gold mine of novel ideas for copper biology." Dalton Transactions 51, no. 1 (2022): 14–26. http://dx.doi.org/10.1039/d1dt02878b.

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The aim of this perspective is to help revive studies of the kinetics of formation and exchange in Cu(ii)–peptide complexes. Such studies have the power to reveal novel reactive intermediates and set timeframes for actual physiological processes.

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11

Derevianko, A., T. Graeber, and H. Simms. "REACTIVE OXYGEN INTERMEDIATES (ROI) - A NOVEL ROLE AS SECOND MESSENGERS IN CYTOKINE STIMULATED PMN." Shock 5 (June 1996): 49. http://dx.doi.org/10.1097/00024382-199606002-00157.

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12

Scheer, Manfred, Eva Leiner, Peter Kramkowski, Michael Schiffer, and Gerhard Baum. "A Novel Synthetic Approach to Highly Reactive Intermediates Containing a Metal-Phosphorus Triple Bond." Chemistry - A European Journal 4, no. 10 (October 2, 1998): 1917–23. http://dx.doi.org/10.1002/(sici)1521-3765(19981002)4:10<1917::aid-chem1917>3.0.co;2-9.

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13

AlRabiah, Haitham, Adnan A. Kadi, Mohamed W. Attwa, Ali S. Abdelhameed, and Gamal A. E. Mostafa. "Reactive intermediates in copanlisib metabolism identified by LC-MS/MS: phase I metabolic profiling." RSC Advances 9, no. 11 (2019): 6409–18. http://dx.doi.org/10.1039/c8ra10322d.

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14

Ruan, Jia, Gregory St. John, Sabine Ehrt, Lee Riley, and Carl Nathan. "noxR3, a Novel Gene fromMycobacterium tuberculosis, Protects Salmonella typhimurium from Nitrosative and Oxidative Stress." Infection and Immunity 67, no. 7 (July 1, 1999): 3276–83. http://dx.doi.org/10.1128/iai.67.7.3276-3283.1999.

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ABSTRACT Reactive oxygen intermediates (ROI) and reactive nitrogen intermediates (RNI) produced by activated macrophages participate in host defense against the facultative intracellular pathogensMycobacterium tuberculosis and Salmonella typhimurium. To survive within macrophages, such pathogens may have evolved ROI and RNI resistance mechanisms. ROI resistance pathways have been intensively studied. Much less is known about the mechanisms of resistance to RNI. To identify possible RNI resistance genes inM. tuberculosis, a mycobacterial library was expressed inS. typhimurium and subjected to selection by exposure to the NO donor S-nitrosoglutathione (GSNO) in concentrations sufficient to kill the vast majority of nontransformed salmonellae. Among the rare surviving recombinants was a clone expressingnoxR3, a novel and previously anonymous M. tuberculosis gene predicted to encode a small, basic protein. Expression of noxR3 protected S. typhimuriumnot only from GSNO and acidified nitrite but also from H2O2. noxR3 is the third gene cloned from M. tuberculosis that has been shown to protect heterologous cells from both RNI and ROI. This suggests diversity in the repertoire of mechanisms that help pathogens resist the oxidative and nitrosative defenses of the host.

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15

Schneider, Thomas, Michael Keim, Bianca Seitz, and Gerhard Maas. "Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes." Beilstein Journal of Organic Chemistry 16 (August 24, 2020): 2064–72. http://dx.doi.org/10.3762/bjoc.16.173.

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3-Aryl-1-(trifluoromethyl)prop-2-yn-1-iminium triflate salts represent a novel, highly reactive class of acetylenic iminium salts. Herein we present several reactions which are based on the electron-poor acetylenic bond and on the high electrophilicity of the CF3-substituted iminium group. These salts were found to be highly reactive dienophiles in Diels–Alder reactions with cyclopentadiene, 2,3-dimethylbutadiene and even anthracene. At higher temperature, the cycloadducts undergo an intramolecular SE(Ar) reaction leading to condensed carbocycles incorporating a 1-(trifluoromethyl)-1-(dimethylamine)indene ring system. With styrenes and some substituted styrenes, cascade reactions take place, which likely include cyclobutene and several cationic intermediates and mainly yield 2-(1-phenylvinyl)indenes. In a similar reaction cascade, a fulvene derivative was obtained with 1,4-diphenylbutadiene as the substrate.

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16

Chen, Mei, Guoyan Zhang, Xiao Liang, Wanshu Zhang, Le Zhou, Baofeng He, Ping Song, et al. "Thermally stable transparent sol–gel based active siloxane–oligomer materials with tunable high refractive index and dual reactive groups." RSC Advances 6, no. 75 (2016): 70825–31. http://dx.doi.org/10.1039/c6ra13164f.

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17

Ray, César, Andrés García-Sampedro, Christopher Schad, Edurne Avellanal-Zaballa, Florencio Moreno, María J. Ortiz, Jorge Bañuelos, et al. "Alkynyl N-BODIPYs as Reactive Intermediates for the Development of Dyes for Biophotonics." Chemistry Proceedings 3, no. 1 (November 14, 2020): 15. http://dx.doi.org/10.3390/ecsoc-24-08374.

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A new approach for the rapid multi-functionalization of BODIPY dyes towards biophotonics is reported. It is based on novel N-BODIPYs, through reactive intermediates with alkynyl groups to be further derivatized by click chemistry. This approach has been exemplified by the development of new dyes for cell bio-imaging, which have proven to successfully internalize into pancreatic cancer cells and accumulate in the mitochondria. The in vitro suitability for photodynamic therapy (PDT) was also analyzed and confirmed our compounds to be promising PDT candidates for the treatment of pancreatic cancer.

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18

Orhan, Hilmi, and Nico P.E. Vermeulen. "Conventional and Novel Approaches in Generating and Characterization of Reactive Intermediates from Drugs/Drug Candidates." Current Drug Metabolism 12, no. 4 (May 1, 2011): 383–94. http://dx.doi.org/10.2174/138920011795202974.

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19

Ong, Voon, Grayson Hough, Michael Schlosser, Ken Bartizal, James M. Balkovec, Kenneth D. James, and B. Radha Krishnan. "Preclinical Evaluation of the Stability, Safety, and Efficacy of CD101, a Novel Echinocandin." Antimicrobial Agents and Chemotherapy 60, no. 11 (September 12, 2016): 6872–79. http://dx.doi.org/10.1128/aac.00701-16.

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ABSTRACTFungal infections pose a significant public health burden with high morbidity and mortality. CD101 is a novel echinocandin under development for the treatment and prevention of systemicCandidainfections. Preclinical studies were conducted to evaluate the metabolic stability, plasma protein binding, pharmacokinetics, toxicity, and efficacy of CD101 at various dose levels. CD101 was stable to biotransformation in rat, monkey, and human liver microsomes and rat, monkey, dog, and human hepatocytes.In vitrostudies suggest minimal interaction with recombinant cytochrome P450 enzymes (50% inhibitory concentrations [IC50s] of >10 μM). Similar to anidulafungin, CD101 bound avidly (>98%) to human, mouse, rat, and primate plasma proteins. In a 2-week repeat-dose comparison study, CD101 was well tolerated in rats (no effects on body weight, hematology, coagulation, or urinalysis). In contrast, administration of anidulafungin (at comparable exposure levels) resulted in reduced body weight, decreases in red blood cell, hemoglobin, hematocrit, mean cell volume, mean corpuscular hemoglobin, platelet, and reticulocyte counts, increases in neutrophil and eosinophil counts, polychromasia, and decreased activated partial thromboplastin time. Elevated plasma transaminases, total bilirubin, cholesterol, and globulin, dark and enlarged spleens, and single-cell hepatocyte necrosis were also observed for anidulafungin but not CD101. Hepatotoxicity may be due to the inherent chemical lability of anidulafungin generating potentially reactive intermediates. A glutathione trapping experiment confirmed the formation of a reactive species from anidulafungin, whereas CD101 did not exhibit instability or reactive intermediates. CD101 showed antifungal activity againstCandidaandAspergillusinfections in neutropenic mice. These preclinical studies demonstrated that CD101 is chemically and metabolically stable, well tolerated with no hepatotoxicity, and efficacious as an antifungal agent.

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20

Chen, Lu Yi, Jian Gang Chen, Xin Hui Ruan, Su Xin Xu, Yi Qi Yang, and Bi Jia Wang. "Sustainable Reactive Dyeing of Cotton Fabric in Green Non-Aqueous Medium: A Density Function Theory (DFT) Modeling Study." Key Engineering Materials 671 (November 2015): 139–48. http://dx.doi.org/10.4028/www.scientific.net/kem.671.139.

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Sustainable reactive dyeing of cotton in green non-nucleophilic solvents was investigated. Dye fixation in the new medium was modeled using DFT calculations with the aim of understanding the role of organic bases. The novel procedure uses non-nucleophilic green solvents instead of water to eliminate the dye hydrolysis. All residuals in the spent dye bath could be conveniently recycled and reused. The three major stages in cotton reactive dyeing, cellulose swelling, dye adsorption and dye fixation were optimized respectively. Two organic bases and potassium carbonate were studied for dye fixation. The mechanisms of the amine-promoted dye fixation were modeled using density function theory (DFT) calculations. The formation of the amine-dye intermediate was elucidated and analyzed using high performance liquid chromatography (HPLC) analysis. The quaternary ammonium catalysis effect on intermediates forming was observed. A 10-cycle repeated dyeing sequence was demonstrated using Reactive orange 5 to give consistently high shade buildup, excellent colorfastness and dramatic reduction in resource consumption. The results have implications for better understanding the new hydrolysis-free and recyclable solvent dyeing process.

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21

Ehrt, Sabine, Michael U. Shiloh, Jia Ruan, Michael Choi, Stuart Gunzburg, Carl Nathan, Qiao-wen Xie, and Lee W. Riley. "A Novel Antioxidant Gene from Mycobacterium tuberculosis." Journal of Experimental Medicine 186, no. 11 (December 1, 1997): 1885–96. http://dx.doi.org/10.1084/jem.186.11.1885.

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Among the major antimicrobial products of macrophages are reactive intermediates of the oxidation of nitrogen (RNI) and the reduction of oxygen (ROI). Selection of recombinants in acidified nitrite led to the cloning of a novel gene, noxR1, from a pathogenic clinical isolate of Mycobacterium tuberculosis. Expression of noxR1 conferred upon Escherichia coli and Mycobacterium smegmatis enhanced ability to resist RNI and ROI, whether the bacteria were exposed to exogenous compounds in medium or to endogenous products in macrophages. These studies provide the first identification of an RNI resistance mechanism in mycobacteria, point to a new mechanism for resistance to ROI, and raise the possibility that inhibition of the noxR1 pathway might enhance the ability of macrophages to control tuberculosis.

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22

Zhiqiang, Wang, Hwang Seung Hwan, and Lim Soon Sung. "Effect of Novel Synthesised Policosanyl Phenolates on Lipid Oxidation." Czech Journal of Food Sciences 34, No. 5 (November 1, 2016): 414–21. http://dx.doi.org/10.17221/530/2015-cjfs.

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Lipophilic derivatisation of phenolic acids could greatly improve their antioxidant activities and solubility in hydrophobic environments, broadening their applications in food, pharmaceutical, and cosmetic industries. In this study, we conducted enzymatic lipophilisation of eight phenolates with policosanols. Vinyl phenolates were used as intermediates to improve the efficiency of enzymatic lipophilisation; and the yields of policosanyl phenolates were in the range of 1.32–20.58%. The antioxidant activities of the resulting phenolipids were compared using 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assay and linoleic acid peroxidation ferric thiocyanate assay. The synthesised policosanyl phenolates showed lower ABTS radical scavenging capacities (IC<sub>50</sub>s > 15 mM); whereas they showed high lipid peroxidation inhibitory activities (IC<sub>50</sub>s of peroxidation value < 0.25 mM). The lipid oxidation inhibitory activities of policosanol phenolates were further evaluated using the total oxidation value in a linoleic acid model system and the thiobarbituric acid reactive substances value in a cooked pork model system. Finally, policosanyl 4-hydroxybenzoate, policosanyl syringate, and policosanyl 4-hydroxyphenylacetate showed the highest inhibition effects on lipid oxidation and a potential for use as lipid antioxidants.

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23

Abdelhameed, Ali S., Mohamed W. Attwa, and Adnan A. Kadi. "Liquid chromatography–tandem mass spectrometry metabolic profiling of nazartinib reveals the formation of unexpected reactive metabolites." Royal Society Open Science 6, no. 8 (August 2019): 190852. http://dx.doi.org/10.1098/rsos.190852.

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Nazartinib (EGF816, NZB) is a promising third-generation human epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor. This novel irreversible mutant-selective EGFR inhibitor targets EGFR containing both the resistance mutation (T790M) and the activating mutations (L858R and Del19), while it does not affect wild-type EGFR. However, the metabolic pathway and bioactivation mechanisms of NZB are still unexplored. Thus, using liquid chromatography–tandem mass spectrometry, we screened for products of NZB metabolism formed in vitro by human liver microsomal preparations and investigated the formation of reactive intermediates using potassium cyanide as a nucleophile trap. Unexpectedly, the azepane ring was not bioactivated. Instead, the carbon atom between the aliphatic linear tertiary amine and electron-withdrawing system (butenoyl amide group) was bioactivated, generating iminium intermediates as reactive species. Six NZB phase I metabolites, formed by hydroxylation, oxidation and N -demethylation, were characterized. Moreover, two reactive iminium ions were characterized and their corresponding bioactivation mechanisms were proposed. Based on our results, we speculate that bioactivation of NZB can be blocked by small sterically hindering groups, isosteric replacement or a spacer. This approach might reduce the toxicity of NZB by avoiding the generation of reactive species.

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24

Petrič, Andrej, Tatjana Špes, and Jorge R. Barrio. "Novel Fluorescent Reactive Dyes as Intermediates for the Preparation of UV and Vis Wavelength Fluorescent Probes." Monatshefte für Chemie / Chemical Monthly 129, no. 8-9 (September 1998): 777–86. http://dx.doi.org/10.1007/pl00013476.

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25

Adams, Nicholas J., Joachim Bargon, John M. Brown, Edward J. Farrington, Erwan Galardon, Ralf Giernoth, Hanjo Heinrich, Benjamin D. John, and Kenji Maeda. "Interplay of synthesis and mechanism in asymmetric homogeneous catalysis." Pure and Applied Chemistry 73, no. 2 (January 1, 2001): 343–46. http://dx.doi.org/10.1351/pac200173020343.

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Asymmetric homogeneous catalysis forms one of the main planks of modern organic synthesis. It has developed rapidly and largely through the application of novel ligands, whose design is very much based on insight and intuition. At the same time, a better understanding of catalytic reaction mechanisms can contribute to further progress, since it can identify the intimate relationship between ligand structure and successful applications. The presentation will concentrate on the author's research with complexes of the late transition metals and include the search for superior methodologies in hydroboration, as well as ventures into the chemistry of reactive intermediates. The latter will be exemplified from work with rhodium and palladium catalysts.

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26

Skariah, Sini, Robert B. Bednarczyk, Matthew K. McIntyre, Gregory A. Taylor, and Dana G. Mordue. "Discovery of a Novel Toxoplasma gondii Conoid-Associated Protein Important for Parasite Resistance to Reactive Nitrogen Intermediates." Journal of Immunology 188, no. 7 (March 2, 2012): 3404–15. http://dx.doi.org/10.4049/jimmunol.1101425.

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27

PETRIC, A., T. SPES, and J. R. BARRIO. "ChemInform Abstract: Novel Fluorescent Reactive Dyes as Intermediates for the Preparation of UV and Vis Wavelength Fluorescent Probes." ChemInform 29, no. 52 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199852214.

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28

Ye, Jianhuai, Jonathan P. D. Abbatt, and Arthur W. H. Chan. "Novel pathway of SO<sub>2</sub> oxidation in the atmosphere: reactions with monoterpene ozonolysis intermediates and secondary organic aerosol." Atmospheric Chemistry and Physics 18, no. 8 (April 24, 2018): 5549–65. http://dx.doi.org/10.5194/acp-18-5549-2018.

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Abstract. Ozonolysis of monoterpenes is an important source of atmospheric biogenic secondary organic aerosol (BSOA). While enhanced BSOA formation has been associated with sulfate-rich conditions, the underlying mechanisms remain poorly understood. In this work, the interactions between SO2 and reactive intermediates from monoterpene ozonolysis were investigated under different humidity conditions (10 % vs. 50 %). Chamber experiments were conducted with ozonolysis of α-pinene or limonene in the presence of SO2. Limonene SOA formation was enhanced in the presence of SO2, while no significant changes in SOA yields were observed during α-pinene ozonolysis. Under dry conditions, SO2 primarily reacted with stabilized Criegee intermediates (sCIs) produced from ozonolysis, but at 50 % RH heterogeneous uptake of SO2 onto organic aerosol was found to be the dominant sink of SO2, likely owing to reactions between SO2 and organic peroxides. This SO2 loss mechanism to organic peroxides in SOA has not previously been identified in experimental chamber studies. Organosulfates were detected and identified using an electrospray ionization–ion mobility spectrometry–high-resolution time-of-flight mass spectrometer (ESI-IMS-TOF) when SO2 was present in the experiments. Our results demonstrate the synergistic effects between BSOA formation and SO2 oxidation through sCI chemistry and SO2 uptake onto organic aerosol and illustrate the importance of considering the chemistry of organic and sulfur-containing compounds holistically to properly account for their reactive sinks.

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29

Spotte-Smith, Evan Walter Clark, Samuel M. Blau, and Kristin A. Persson. "GPS for the SEI: Charting Electrochemical Mechanisms with Reaction Networks." ECS Meeting Abstracts MA2022-01, no. 4 (July 7, 2022): 518. http://dx.doi.org/10.1149/ma2022-014518mtgabs.

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An electrolyte is placed under an applied potential - what happens next? This question of electrochemical reactivity seems simple on its surface. However, the answer of what intermediates, products, and byproducts will form, as well as how they will form, is immensely challenging to predict. Traditional theoretical methods have either used intuitively guided mechanistic calculations (e.g. density functional theory) that abstract away competition between reactions or dynamical simulations (e.g. ab initio molecular dynamics) that are computationally intractable beyond extremely short time scales. Recently, we have taken a new approach: using data-driven reaction networks to automatically explore electrochemical reactive landscapes. In this talk, we will present an end-to-end methodology to answer questions of reactivity in complex environments. Drawing from recent studies of solid electrolyte interphase (SEI) formation in lithium-ion batteries, we will describe how to generate and analyze reaction networks, leading to insights regarding both formation mechanisms of experimentally identified products as well as the prediction of novel SEI components. We will then illustrate how individual mechanisms obtained via reaction networks can be combined to understand reactive competition using kinetic Monte Carlo simulations. The methodology that we describe has potential not just to expand our understanding of battery chemistry, but of electrochemical reactivity in general.

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Guo, Shuang, Xiwen Cheng, Jun-Hee Lim, Yu Liu, and Hung-Ying Kao. "Control of antioxidative response by the tumor suppressor protein PML through regulating Nrf2 activity." Molecular Biology of the Cell 25, no. 16 (August 15, 2014): 2485–98. http://dx.doi.org/10.1091/mbc.e13-11-0692.

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Oxidative stress is a consequence of an imbalance between reactive oxygen species (ROS) production and the ability of the cytoprotective system to detoxify the reactive intermediates. The tumor suppressor promyelocytic leukemia protein (PML) functions as a stress sensor. Loss of PML results in impaired mitochondrial complex II activity, increased ROS, and subsequent activation of nuclear factor erythroid 2–related factor 2 (Nrf2) antioxidative pathway. We also demonstrate that sulforaphane (SFN), an antioxidant, regulates Nrf2 activity by controlling abundance and subcellular distribution of PML and that PML is essential for SFN-mediated ROS increase, Nrf2 activation, antiproliferation, antimigration, and antiangiogenesis. Taking the results together, we have uncovered a novel antioxidative mechanism by which PML regulates cellular oxidant homeostasis by controlling complex II integrity and Nrf2 activity and identified PML as an indispensable mediator of SFN activity.

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31

Katayev, Evgeny A., Herman V. Lavrov, and Victor N. Khrustalev. "Deprotonation induced dioxygen activation and ligand oxidation by dipyrromethane-palladium complexes." Journal of Porphyrins and Phthalocyanines 12, no. 11 (November 2008): 1137–45. http://dx.doi.org/10.1142/s1088424608000509.

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Novel palladium(II) complexes with α,α'-bis(phenylimino)- and α,α'-bis(picolyl)-substituted meso- H -dipyrromethanes have been prepared. The complexes are able to react with dioxygen upon activation with potassium tert-butoxide. Reactions with dioxygen afford C - N or C - C self-bond cleavage producing α-pyrrole-carboxylate or α-hydroxypyrrole residues, respectively. According to DFT calculations the deprotonation of meso-hydrogen leads to the redistribution of electron density between ligand and metal, thus formally forming dipyrromethene-palladium(0) anionic complex. Possible reactive oxygen-containing intermediates have been suggested on the basis of calculations.

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32

Barton, Derek H. R., and Shyamal I. Parekh. "Novel selenium-oxygen and silane-nitrogen bond metatheses. Mechanistic probes, spectroscopic studies, and structural evidence for reactive oligomeric selenoazyl intermediates." Journal of the American Chemical Society 115, no. 3 (February 1993): 948–55. http://dx.doi.org/10.1021/ja00056a019.

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33

Shen, Chieh-Yu, Cheng-Hsun Lu, Cheng-Han Wu, Ko-Jen Li, Yu-Min Kuo, Song-Chou Hsieh, and Chia-Li Yu. "The Development of Maillard Reaction, and Advanced Glycation End Product (AGE)-Receptor for AGE (RAGE) Signaling Inhibitors as Novel Therapeutic Strategies for Patients with AGE-Related Diseases." Molecules 25, no. 23 (November 27, 2020): 5591. http://dx.doi.org/10.3390/molecules25235591.

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Advanced glycation end products (AGEs) are generated by nonenzymatic modifications of macromolecules (proteins, lipids, and nucleic acids) by saccharides (glucose, fructose, and pentose) via Maillard reaction. The formed AGE molecules can be catabolized and cleared by glyoxalase I and II in renal proximal tubular cells. AGE-related diseases include physiological aging, neurodegenerative/neuroinflammatory diseases, diabetes mellitus (DM) and its complications, autoimmune/rheumatic inflammatory diseases, bone-degenerative diseases, and chronic renal diseases. AGEs, by binding to receptors for AGE (RAGEs), alter innate and adaptive immune responses to induce inflammation and immunosuppression via the generation of proinflammatory cytokines, reactive oxygen species (ROS), and reactive nitrogen intermediates (RNI). These pathological molecules cause vascular endothelial/smooth muscular/connective tissue-cell and renal mesangial/endothelial/podocytic-cell damage in AGE-related diseases. In the present review, we first focus on the cellular and molecular bases of AGE–RAGE axis signaling pathways in AGE-related diseases. Then, we discuss in detail the modes of action of newly discovered novel biomolecules and phytochemical compounds, such as Maillard reaction and AGE–RAGE signaling inhibitors. These molecules are expected to become the new therapeutic strategies for patients with AGE-related diseases in addition to the traditional hypoglycemic and anti-hypertensive agents. We particularly emphasize the importance of “metabolic memory”, the “French paradox”, and the pharmacokinetics and therapeutic dosing of the effective natural compounds associated with pharmacogenetics in the treatment of AGE-related diseases. Lastly, we propose prospective investigations for solving the enigmas in AGE-mediated pathological effects.

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Mus, Florence, Hsin-Hua Wu, Alexander B. Alleman, Krista A. Shisler, Oleg A. Zadvornyy, Brian Bothner, Jennifer L. Dubois, and John W. Peters. "Insights into the unique carboxylation reactions in the metabolism of propylene and acetone." Biochemical Journal 477, no. 11 (June 4, 2020): 2027–38. http://dx.doi.org/10.1042/bcj20200174.

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Alkenes and ketones are two classes of ubiquitous, toxic organic compounds in natural environments produced in several biological and anthropogenic processes. In spite of their toxicity, these compounds are utilized as primary carbon and energy sources or are generated as intermediate metabolites in the metabolism of other compounds by many diverse bacteria. The aerobic metabolism of some of the smallest and most volatile of these compounds (propylene, acetone, isopropanol) involves novel carboxylation reactions resulting in a common product acetoacetate. Propylene is metabolized in a four-step pathway involving five enzymes where the penultimate step is a carboxylation reaction catalyzed by a unique disulfide oxidoreductase that couples reductive cleavage of a thioether linkage with carboxylation to produce acetoacetate. The carboxylation of isopropanol begins with conversion to acetone via an alcohol dehydrogenase. Acetone is converted to acetoacetate in a single step by an acetone carboxylase which couples the hydrolysis of MgATP to the activation of both acetone and bicarbonate, generating highly reactive intermediates that are condensed into acetoacetate at a Mn2+ containing the active site. Acetoacetate is then utilized in central metabolism where it is readily converted to acetyl-coenzyme A and subsequently converted into biomass or utilized in energy metabolism via the tricarboxylic acid cycle. This review summarizes recent structural and biochemical findings that have contributed significant insights into the mechanism of these two unique carboxylating enzymes.

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Colussi, Agustín, and Shinichi Enami. "Detecting Intermediates and Products of Fast Heterogeneous Reactions on Liquid Surfaces via Online Mass Spectrometry." Atmosphere 10, no. 2 (January 26, 2019): 47. http://dx.doi.org/10.3390/atmos10020047.

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One of the research priorities in atmospheric chemistry is to advance our understanding of heterogeneous reactions and their effect on the composition of the troposphere. Chemistry on aqueous surfaces is particularly important because of their ubiquity and expanse. They range from the surfaces of oceans (360 million km2), cloud and aerosol drops (estimated at ~10 trillion km2) to the fluid lining the human lung (~150 m2). Typically, ambient air contains reactive gases that may affect human health, influence climate and participate in biogeochemical cycles. Despite their importance, atmospheric reactions between gases and solutes on aqueous surfaces are not well understood and, as a result, generally overlooked. New, surface-specific techniques are required that detect and identify the intermediates and products of such reactions as they happen on liquids. This is a tall order because genuine interfacial reactions are faster than mass diffusion into bulk liquids, and may produce novel species in low concentrations. Herein, we review evidence that validates online pneumatic ionization mass spectrometry of liquid microjets exposed to reactive gases as a technique that meets such requirements. Next, we call attention to results obtained by this approach on reactions of gas-phase ozone, nitrogen dioxide and hydroxyl radicals with various solutes on aqueous surfaces. The overarching conclusion is that the outermost layers of aqueous solutions are unique media, where most equilibria shift and reactions usually proceed along new pathways, and generally faster than in bulk water. That the rates and mechanisms of reactions at air-aqueous interfaces may be different from those in bulk water opens new conceptual frameworks and lines of research, and adds a missing dimension to atmospheric chemistry.

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36

Yang, Xiaojuan, Jing Song, and Liang-Jun Yan. "Chronic Inhibition of Mitochondrial Dihydrolipoamide Dehydrogenase (DLDH) as an Approach to Managing Diabetic Oxidative Stress." Antioxidants 8, no. 2 (February 2, 2019): 32. http://dx.doi.org/10.3390/antiox8020032.

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Mitochondrial dihydrolipoamide dehydrogenase (DLDH) is a redox enzyme involved in decarboxylation of pyruvate to form acetyl-CoA during the cascade of glucose metabolism and mitochondrial adenine triphosphate (ATP) production. Depending on physiological or pathophysiological conditions, DLDH can either enhance or attenuate the production of reactive oxygen species (ROS) and reactive nitrogen species. Recent research in our laboratory has demonstrated that inhibition of DLDH induced antioxidative responses and could serve as a protective approach against oxidative stress in stroke injury. In this perspective article, we postulated that chronic inhibition of DLDH could also attenuate oxidative stress in type 2 diabetes. We discussed DLDH-involving mitochondrial metabolic pathways and metabolic intermediates that could accumulate upon DLDH inhibition and their corresponding roles in abrogating oxidative stress in diabetes. We also discussed a couple of DLDH inhibitors that could be tested in animal models of type 2 diabetes. It is our belief that DLDH inhibition could be a novel approach to fighting type 2 diabetes.

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37

Rahman, Md Motiar, Mst Gulshan Ara, Md Sohanur Rahman, Md Sahab Uddin, May N. Bin-Jumah, and Mohammed M. Abdel-Daim. "Recent Development of Catalytic Materials for Ethylbenzene Oxidation." Journal of Nanomaterials 2020 (February 25, 2020): 1–20. http://dx.doi.org/10.1155/2020/7532767.

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Catalysts are well-known to convert alkylbenzenes at high thermal condition to a number of useful products. However, the current schemes of transformation are not suitable for the hazard-free industrial applications because their reactive intermediates are transformed to a variety of side products that often retard the optimum yield and cause environmental pollutions. It is also observed that the formation of products depends on a wide range of parameters which are extremely difficult to control and often incur extra cost. Recently, heterogeneous catalysts have received huge commercial interests for the oxidation of alkylbenzene into carbonyl compounds which are platform chemicals in various synthetics and fine chemicals. This review is an up-to-date documentary on various catalysts used for the oxidation of alkyl-substituted benzenes along with their reaction condition and selectivity profiles. This work updates our knowledge for the selection and/or design of novel catalysts for the chemists and engineers in the industrial and academic settings.

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38

Kassaee, M. Z., S. M. Musavi, M. Ghambarian, and M. R. Khalili Zanjani. "Switching of global minima of novel germylenic reactive intermediates via halogens (X): C2GeH2 vs. C2GeHX at ab initio and DFT levels." Journal of Organometallic Chemistry 691, no. 13 (June 2006): 2933–44. http://dx.doi.org/10.1016/j.jorganchem.2006.02.038.

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39

Yin, Guochuan, Andrew M. Danby, David Kitko, John D. Carter, William M. Scheper, and Daryle H. Busch. "Olefin Epoxidation by Alkyl Hydroperoxide with a Novel Cross-Bridged Cyclam Manganese Complex: Demonstration of Oxygenation by Two Distinct Reactive Intermediates." Inorganic Chemistry 46, no. 12 (June 2007): 5125–26. http://dx.doi.org/10.1021/ic700886v.

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40

Zhang, Xini, and Peter Ulrich. "Directed approaches to reactive maillard intermediates: Formation of a novel 3-alkylamino-2-hydroxy-4-hydroxymethyl-2-cyclopenten-1-one (“Cypentodine”)." Tetrahedron Letters 37, no. 27 (July 1996): 4667–70. http://dx.doi.org/10.1016/0040-4039(96)00959-8.

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41

Yin, Guochuan, Andrew M. Danby, David Kitko, John D. Carter, William M. Scheper, and Daryle H. Busch. "Olefin Epoxidation by Alkyl Hydroperoxide with a Novel Cross-Bridged Cyclam Manganese Complex: Demonstration of Oxygenation by Two Distinct Reactive Intermediates." Inorganic Chemistry 46, no. 6 (March 2007): 2173–80. http://dx.doi.org/10.1021/ic061957r.

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42

Atiakshin, Dmitry A., Victoria Shishkina, Dmitry I. Esaulenko, Evgeniy S. Ovsyannikov, Lyubov N. Antakova, Olga A. Gerasimova, Tatiana V. Samoilenko, Pavel Yu Andreev, Sara T. Magerramova, and Sofia A. Budnevskaya. "Mast Cells as the Target of the Biological Effects of Molecular Hydrogen in the Specific Tissue Microenvironment." International Journal of Biomedicine 12, no. 2 (June 5, 2022): 183–87. http://dx.doi.org/10.21103/article12(2)_ra2.

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Mast cells (MCs) as key players in the development of both physiological and pathological processes in the organism can form a specific tissue microenvironment. Having a rich secretion of biologically active substances, MCs can secrete tryptase and/or chymase and thereby participate in the regulation of processes such as inflammation, neoangiogenesis, allergic reactions, and oncogenesis. Reactive oxygen intermediates (ROI) play an essential role in regulation of MC degranulation, shown in vitro and in vivo models. Application of molecular hydrogen as a substance with antioxidant characteristics pathogenically appears to be an important mechanism decreasing MC secretory activity, and, as a consequence, a novel option to reduce an inflammatory background in the specific tissue microenvironment.

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43

Wang, Xuefeng, Lester Andrews, and Gary P. Kushto. "ChemInform Abstract: Infrared Spectra of the Novel Ge2H2 and Ge2H4 Species and the Reactive GeH1,2,3 Intermediates in Solid Neon, Deuterium and Argon." ChemInform 33, no. 37 (September 17, 2002): no. http://dx.doi.org/10.1002/chin.200237002.

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Wang, Xuefeng, Lester Andrews, George V. Chertihin, and P. F. Souter. "ChemInform Abstract: Infrared Spectra of the Novel Sn2H2 Species and the Reactive SnH1,2,3 and PbH1,2,3 Intermediates in Solid Neon, Deuterium, and Argon." ChemInform 33, no. 39 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200239005.

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45

Hasanpour, Fatemeh, Javad Saien, and Omid Norouzi. "Catalytic Activation of Hydrogen Peroxide Using Highly Porous Hydrothermally Modified Manganese Catalysts for Removal of Azithromycin Antibiotic from Aqueous Solution." Catalysts 13, no. 1 (December 30, 2022): 77. http://dx.doi.org/10.3390/catal13010077.

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Hydrogen peroxide catalytic activation holds great promise in the treatment of persistent pollutants. In this study, the novel Mn-Acacair/Al, Mn-Acacarg/Al and Mn-BTCarg/Al catalysts, supported on Al2O3, were applied for rapid hydrogen peroxide activation and azithromycin antibiotic removal. The catalysts were prepared by the calcination-hydrothermal method under air or argon atmosphere. The characterization confirmed that the modification of manganese with acetylacetonate and benzene-1,3,5-tricarboxylic acid (H3BTC) O-donor ligands highly improves the catalyst porosity, amorphousity, and abundance of coordinately unsaturated sites, which facilitate the generation of reactive oxygen species. The hydrogen peroxide activation and azithromycin removal reached 98.4% and 99.3% after 40 min using the Mn-BTCarg/Al catalyst with incredible stability and reusability. Only a 5.2% decrease in activity and less than 2% manganese releasing in solutions were detected after five regeneration cycles under the optimum operating conditions. The removal intermediates were identified by LC-MS/MS analysis, and the pathways were proposed. The hydroxylation and decarboxylation reactions play a key role in the degradation reaction.

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Thompson, David M., Jason McLeod, and Michael C. Baird. "New methods for the synthesis of transition-metal fullerene complexes." Pure and Applied Chemistry 73, no. 2 (January 1, 2001): 287–89. http://dx.doi.org/10.1351/pac200173020287.

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Buckminsterfullerene, C60, is readily reduced on exposure to solutions of strongly reducing transition-metal carbonylate anions to give the radical anion fulleride C60- and the corresponding highly reactive, 17-electron neutral compounds. Three secondary reaction paths have been identified, depending on the nature of the reactants and the reaction conditions. (1) With Na+ and PPN+ salts of [Mn (CO) 5]-, thermal substitution of a CO on the metal radical by the C60-results in formation of the anionic, h2-fullerene complex [Mn (C60) (CO) 4]- . (2) With salts of [Co (CO) 4]-, the thermal reaction results in formation of a novel transition-metal fulleride NaCoC60 while (3) with Na[CpFe (CO) 2] and [CpM (CO) 3]- (M = Mo, W) , the 17-electron intermediates couple to form the 18-electron dimers, [CpFe (CO) 2]2 and [CpM (CO) 3]2. In contrast, photochemical reactions of C60 with salts of [Mn (CO) 5]-, [Co (CO) 4]-, and [CpM (CO) 3]- result in excellent yields of the complexes [Mn (C60) (CO) 4]- , [Co (C60) (CO) 3]- and [CpM (C60) (CO) 2]- , respectively; analogous complexes of C70 may be made similarly. The new complexes have been characterized crystallographically, by IR, 13C NMR, and/or Raman spectroscopy and by electrospray mass spectrometry.

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Thorsell, Annika, Emre Isin, and Ulrik Jurva. "Characterization of peptide adducts formed via novel reactive intermediates of the CB1 antagonist rimonabant in a model electrochemical system and human liver microsomes." Toxicology Letters 229 (September 2014): S248. http://dx.doi.org/10.1016/j.toxlet.2014.06.835.

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48

ZHANG, X., and P. ULRICH. "ChemInform Abstract: Directed Approaches to Reactive Maillard Intermediates: Formation of a Novel 3-Alkylamino-2-hydroxy-4-hydroxymethyl-2-cyclopenten-1-one (“ Cypentodine”)." ChemInform 27, no. 41 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199641079.

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49

Saito, A., and H. Sinohara. "Rabbit α-1-antiproteinase E: a novel recombinant serpin which does not inhibit proteinases." Biochemical Journal 307, no. 2 (April 15, 1995): 369–75. http://dx.doi.org/10.1042/bj3070369.

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A cDNA coding for the E isoform of alpha-1-antiproteinase (also called alpha-1-antitrypsin or alpha-1-proteinase inhibitor) was isolated by oligonucleotide hybridization following immunochemical screening of the rabbit liver cDNA library. The deduced amino acid sequence of the E isoform showed 96.4% identity in 413 residues of the F and S-1 isoforms of rabbit alpha-1-antiproteinase. The N-terminal half of the amino acid residues of the three isoforms was almost identical, but the putative reactive-site loop structure (P8-P′8) was significantly different in the various forms, the P1 site of the E form being glutamic acid. Interaction of the recombinant E form with the various proteinases was investigated by SDS/PAGE, followed by immunoblot analysis. The recombinant protein and trypsin formed a 62 kDa equimolar complex, which gradually became graded to the 37 kDa fragment through several intermediates. The E form also formed a complex of a similar size with elastase and became degraded to the 31 kDa fragment. Several proteinases which cleaved the E form without forming a detectable complex on SDS/PAGE are chymotrypsin, protease V8, pancreas kallikrein, thermolysin, papain and ficin. Other proteinases, with a stringent substrate specificity, such as thrombin, factor Xa, plasmin, plasma kallikrein and cathepsin G, did not attack the E form. Unlike the F and S-1 forms of rabbit plasma alpha-1-antiproteinase, the recombinant E form did not inhibit the amidolytic and proteolytic activities of trypsin. Neither elastase nor protease V8 was inhibited by the E form. Thus the change in the amino acid residues in the reactive-site loop, probably in the P1 site, is responsible for the loss of inhibitory activity of rabbit alpha-1-antiproteinase E. The novel character of the E form could provide a new insight into the interaction of serpin and proteinases.

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Pan, Yi, Kyle D. Mansfield, Cara C. Bertozzi, Viktoriya Rudenko, Denise A. Chan, Amato J. Giaccia, and M. Celeste Simon. "Multiple Factors Affecting Cellular Redox Status and Energy Metabolism Modulate Hypoxia-Inducible Factor Prolyl Hydroxylase Activity In Vivo and In Vitro." Molecular and Cellular Biology 27, no. 3 (November 13, 2006): 912–25. http://dx.doi.org/10.1128/mcb.01223-06.

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ABSTRACT Prolyl hydroxylation of hypoxible-inducible factor alpha (HIF-α) proteins is essential for their recognition by pVHL containing ubiquitin ligase complexes and subsequent degradation in oxygen (O2)-replete cells. Therefore, HIF prolyl hydroxylase (PHD) enzymatic activity is critical for the regulation of cellular responses to O2 deprivation (hypoxia). Using a fusion protein containing the human HIF-1α O2-dependent degradation domain (ODD), we monitored PHD activity both in vivo and in cell-free systems. This novel assay allows the simultaneous detection of both hydroxylated and nonhydroxylated PHD substrates in cells and during in vitro reactions. Importantly, the ODD fusion protein is regulated with kinetics identical to endogenous HIF-1α during cellular hypoxia and reoxygenation. Using in vitro assays, we demonstrated that the levels of iron (Fe), ascorbate, and various tricarboxylic acid (TCA) cycle intermediates affect PHD activity. The intracellular levels of these factors also modulate PHD function and HIF-1α accumulation in vivo. Furthermore, cells treated with mitochondrial inhibitors, such as rotenone and myxothiazol, provided direct evidence that PHDs remain active in hypoxic cells lacking functional mitochondria. Our results suggest that multiple mitochondrial products, including TCA cycle intermediates and reactive oxygen species, can coordinate PHD activity, HIF stabilization, and cellular responses to O2 depletion.

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