☆ 4.6 Article

A small molecule that mimics the metabolic activity of copper-containing amine oxidases (CuAOs) toward physiological mono- and polyamines

ORGANIC & BIOMOLECULAR CHEMISTRY (2010)

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY

卷 8, 期 16, 页码 3796-3800

出版社

ROYAL SOC CHEMISTRY

DOI: 10.1039/c004501b

关键词

-

类别

Chemistry, Organic

向作者/读者索取更多资源

Protocol

Reagent

摘要

Primary aliphatic biogenic amines have been successfully oxidized using a quinonoid species that mimics the metabolic activity of copper-containing amine oxidase (CuAO) enzymes. Especially, high catalytic performances were observed with aminoacetone, a threonine catabolite, and methylamine, a metabolite of adrenaline, and with the primary amino groups of putrescine and spermidine which are both decarboxylation products of ornithine and S-adenosyl-methionine. Furthermore, contrary to flavine adenine dinucleotide (FAD)-dependent amine oxidase enzymes, no activity was found toward secondary and tertiary amines.

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.6

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Agronomy

Inhibiting Copper Amine Oxidase Using L-Aminoguanidine Induces Cultivar and Age-Dependent Alterations of Polyamine Catabolism in Tomato Seedlings

Agnes Szepesi, Laszlo Bakacsy, Henrietta Kovacs, Arpad Szilagyi, Zoltan Marton Kohler

Summary: This study explores the role of CuAO in different tomato genotypes at different stages of seedling development. The results indicate that there is genotype dependence in the degradation of Put, and inhibition of CuAO activity leads to a long-term shift in PA catabolism by altering the activity of PAO.

AGRICULTURE-BASEL (2022)

添加到收藏夹

Article Cell Biology

A New Player in Jasmonate-Mediated Stomatal Closure: The Arabidopsis thaliana Copper Amine Oxidase β

Ilaria Fraudentali, Chiara Pedalino, Paraskevi Tavladoraki, Riccardo Angelini, Alessandra Cona

Summary: Plant defence responses to adverse environmental conditions involve various stress signalling pathways, with the modulation of stomatal aperture being a common and effective response. AtCuAO beta in Arabidopsis thaliana plays a crucial role in stomatal closure induced by MeJA, involving H2O2 production. Mutants of AtCuAO beta show compromised response to MeJA and reduced H2O2 production in guard cells.

CELLS (2021)

添加到收藏夹

Review Biochemistry & Molecular Biology

Plant Copper Amine Oxidases: Key Players in Hormone Signaling Leading to Stress-Induced Phenotypic Plasticity

Ilaria Fraudentali, Renato A. Rodrigues-Pousada, Riccardo Angelini, Sandip A. Ghuge, Alessandra Cona

Summary: Polyamines are essential compounds in living organisms, and copper amine oxidases play a key role in oxidizing them to aminoaldehydes. CuAOs participate in the response to various stresses by modulating multilevel phenotypic plasticity expression in different plant species, particularly in Arabidopsis thaliana. Studies have focused on the involvement of CuAOs in the IAA/JA/ABA signal transduction pathways mediating stress-induced phenotypic plasticity events.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

L-Aminoguanidine Induces Imbalance of ROS/RNS Homeostasis and Polyamine Catabolism of Tomato Roots after Short-Term Salt Exposure

Agnes Szepesi, Laszlo Bakacsy, Attila Feher, Henrietta Kovacs, Peter Palfi, Peter Poor, Reka Szollosi, Orsolya Kinga Gondor, Tibor Janda, Gabriella Szalai, Christian Lindermayr, Laszlo Szabados, Laura Zsigmond

Summary: Polyamine catabolism mediated by amine oxidases is important for regulating polyamine homeostasis and related mechanisms during salt stress. The effects of L-aminoguanidine (AG), an inhibitor of copper amine oxidases, on tomato roots exposed to short-term salt stress were studied. AG treatment alleviated the increase in reactive oxygen and nitrogen species caused by salt stress, suggesting its possible antioxidant effect.

ANTIOXIDANTS (2023)

添加到收藏夹

Article Biochemistry & Molecular Biology

Novel Facet of an Old Dietary Molecule? Direct Influence of Caffeine on Glucose and Biogenic Amine Handling by Human Adipocytes

Wiem Haj Ahmed, Nathalie Boulet, Anais Briot, Barry J. Ryan, Gemma K. Kinsella, Jeffrey O'Sullivan, Francisco Les, Josep Mercader-Barcelo, Gary T. M. Henehan, Christian Carpene

Summary: Caffeine has direct inhibitory effects on glucose transport and lipogenesis in adipocytes. The findings suggest the potential of caffeine in the treatment or prevention of obesity complications.

MOLECULES (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Semicarbazide-Sensitive Amine Oxidase (SSAO) and Lysyl Oxidase (LOX) Association in Rat Aortic Vascular Smooth Muscle Cells

Vesna Manasieva, Shori Thakur, Lisa A. Lione, Jessal Patel, Anwar Baydoun, John Skamarauskas

Summary: The study demonstrates the relationship between SSAO and LOX in VSMCs, showing that increased SSAO activity and decreased LOX activity are associated with pathological changes in the vascular wall. Silencing the LOX gene leads to a reduction in SSAO activity, protein expression, and mRNA levels in VSMCs. These findings suggest that LOX acts as a regulator of SSAO activity and expression in early passage rat aortic VSMCs.

BIOMOLECULES (2022)

添加到收藏夹

Article Biochemistry & Molecular Biology

Effects of Chemical Structures Interacting with Amine Oxidases on Glucose, Lipid and Hydrogen Peroxide Handling by Human Adipocytes

Christian Carpene, Penelope Viana, Zsuzsa Iffiu-Soltesz, Pal Tapolcsanyi, Anna Agota Foldi, Peter Matyus, Petra Dunkel

Summary: Benzylamine, a natural molecule found in food and edible plants, has been found to activate hexose uptake and inhibit lipolysis in human fat cells. These effects rely on the oxidation of benzylamine by amine oxidases in adipocytes, leading to the production of hydrogen peroxide, which exhibits insulin-like actions. The study identified compounds that interact with highly expressed amine oxidases in human adipocytes and showed that they have similar metabolic effects to benzylamine, making them potential candidates for the treatment of obesity and diabetes.

MOLECULES (2022)

添加到收藏夹

Article Biochemistry & Molecular Biology

Obesity of mice lacking VAP-1/SSAO byAoc3gene deletion is reproduced in mice expressing a mutated vascular adhesion protein-1 (VAP-1) devoid of amine oxidase activity

Valentin Jargaud, Sandy Bour, Francois Terce, Xavier Collet, Philippe Valet, Anne Bouloumie, Jean-Claude Guillemot, Pascale Mauriege, Sirpa Jalkanen, Craig Stolen, Marko Salmi, David J. Smith, Christian Carpene

Summary: The study compared the endocrine-metabolic phenotypes of mice lacking the AOC3 gene and mice expressing a mutated VAP-1, finding that both types of mice exhibited obesity, glucose and lipid handling disorders, as well as certain common adipocyte changes. The results suggest that modulation of SSAO activity could be a potential target for treating cardiometabolic diseases, particularly obesity with low-grade inflammation.

JOURNAL OF PHYSIOLOGY AND BIOCHEMISTRY (2021)

添加到收藏夹

Article Fisheries

Transcriptomic and physiological analyses of hepatopancreas reveal the key metabolic changes in response to dietary copper level in Pacific white shrimp Litopenaeus vannamei

Bo Shi, Ye Yuan, Min Jin, Monica B. Betancor, Douglas R. Tocher, Lefei Jiao, Dongying Song, Qicun Zhou

Summary: This study investigates the metabolic changes in Litopenaeus vannamei in response to dietary copper supplementation. Shrimp fed with copper supplemented diets showed higher weight gain and Cu concentration, increased levels of essential and non-essential amino acids, and impacts on amino acid and glycerophospholipid metabolism. Additionally, pathways related to the immune system were identified in shrimp fed with specific copper diets.

AQUACULTURE (2021)

添加到收藏夹

Article Engineering, Environmental

Effects of copper sulfate algaecide on the cell growth, physiological characteristics, the metabolic activity of Microcystis aeruginosa and raw water application

Hanyan Liu, Shengnan Chen, Haihan Zhang, Na Wang, Ben Ma, Xiang Liu, Limin Niu, Fan Yang, Yue Xu, Xiaoli Zhang

Summary: Harmful cyanobacteria blooms (HCBs) are a significant scientific challenge. Copper sulfate (CuSO4) was found to effectively inhibit the growth and photosynthetic capacity of Microcystis aeruginosa, as well as alter its metabolic profiles. The application of CuSO4 also showed potential in controlling algal growth and community structure in site-collected water. These findings contribute to understanding the mechanisms behind algae control and the impact on carbon cycling in aquatic ecosystems.

JOURNAL OF HAZARDOUS MATERIALS (2023)

添加到收藏夹

Article Biochemical Research Methods

Serial femtosecond X-ray crystallography of an anaerobically formed catalytic intermediate of copper amine oxidase

Takeshi Murakawa, Mamoru Suzuki, Kenji Fukui, Tetsuya Masuda, Michihiro Sugahara, Kensuke Tono, Tomoyuki Tanaka, So Iwata, Eriko Nango, Takato Yano, Katsuyuki Tanizawa, Toshihide Okajima

Summary: Recent progress in understanding the mechanisms by which enzymes promote catalytic reactions efficiently through their structural changes has been made using serial femtosecond X-ray crystallography and mix-and-inject serial crystallography techniques. In this study, researchers successfully observed the structural changes associated with ongoing enzymic reactions using a liquid-jet system. The results indicate that anaerobic conditions were maintained throughout the measurements, preventing interference with the catalytic intermediates.

ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Bioinspired Catalytic Aerobic Oxidative CH Functionalization of Primary Aliphatic Amines: Synthesis of 1,2-Disubstituted Benzimidazoles

Khac Minh Huy Nguyen, Martine Largeron

CHEMISTRY-A EUROPEAN JOURNAL (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Metalloenzyme-Like Catalytic System for the Chemoselective Oxidative Cross-Coupling of Primary Amines to Imines under Ambient Conditions

Martine Largeron, Maurice-Bernard Fleury

CHEMISTRY-A EUROPEAN JOURNAL (2015)

添加到收藏夹

Article Plant Sciences

Polycyclic Polyprenylated Xanthones from Symphonia globulifera: Isolation and Biomimetic Electrosynthesis

Kevin Cottet, Anne Neudoerffer, Marina Kritsanida, Sylvie Michel, Marie-Christine Lallemand, Martine Largeron

JOURNAL OF NATURAL PRODUCTS (2015)

添加到收藏夹

Article Chemistry, Organic

Regiospecific synthesis of neuroprotective 1,4-benzoxazine derivatives through a tandem oxidation-Diels-Alder reaction

Khac Minh Huy Nguyen, Leslie Schwendimann, Pierre Gressens, Martine Largeron

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

添加到收藏夹

Article Chemistry, Organic

Catalytic Oxidative Coupling of Primary Amines under Air: A Flexible Route to Benzimidazole Derivatives

Khac Minh Huy Nguyen, Martine Largeron

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

添加到收藏夹

Review Chemistry, Organic

Aerobic catalytic systems inspired by copper amine oxidases: recent developments and synthetic applications

Martine Largeron

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

添加到收藏夹

Review Chemistry, Organic

Recent Advances in the Synthesis of Benzimidazole Derivatives from the Oxidative Coupling of Primary Amines

Martine Largeron, Khac Minh Huy Nguyen

SYNTHESIS-STUTTGART (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Biologically Inspired CuI/Topaquinone-Like Co-Catalytic System for the Highly Atom-Economical Aerobic Oxidation of Primary Amines to Imines

Martine Largeron, Maurice-Bernard Fleury

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis and Neurotoxicity Profile of 2,4,5-Trihydroxymethamphetamine and Its 6-(N-Acetylcystein-S-yl) Conjugate

Anne Neudoerffer, Melanie Mueller, Claire-Marie Martinez, Annis Mechan, Una McCann, George A. Ricaurte, Martine Largeron

CHEMICAL RESEARCH IN TOXICOLOGY (2011)

添加到收藏夹

Review Chemistry, Organic

Protocols for the Catalytic Oxidation of Primary Amines to Imines

Martine Largeron

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Organic

A convenient biomimetic synthesis of optically active putative neurotoxic metabolites of MDMA (ecstasy) from R-(-)- and S-(+)-N-methyl-α-methyldopamine precursors

Claire-Marie Martinez, Anne Neudoerffer, Martine Largeron

ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

添加到收藏夹

Editorial Material Multidisciplinary Sciences

Bioinspired Oxidation Catalysts

Martine Largeron, Maurice-Bernard Fleury

SCIENCE (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Aerobic catalytic systems inspired by copper amine oxidases

Martine Largeron

PURE AND APPLIED CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

A dual biomimetic process for the selective aerobic oxidative coupling of primary amines using pyrogallol as a precatalyst. Isolation of the [5+2] cycloaddition redox intermediates

Martine Largeron, Patrick Deschamps, Karim Hammad, Maurice-Bernard Fleury

GREEN CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Bioinspired Organocatalytic Cascade for the Selective Oxidation of Amines under Air

Martine Largeron, Maurice-Bernard Fleury

CHEMISTRY-A EUROPEAN JOURNAL (2017)

添加到收藏夹

Article Chemistry, Organic

Catalyst-free photo-induced aerobic radical synthesis of lactams from N-alkenyl trichloroacetamides in 2-methyltetrahydrofuran as the radical initiator under violet light

Faiza Diaba, Gisela Trenchs

Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

添加到收藏夹

Article Chemistry, Organic

Synthesis of mixed phosphorotrithioates via thiol coupling with bis(diisopropylamino)chlorophosphine and sulphenyl chloride

Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed

Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

添加到收藏夹

Article Chemistry, Organic

Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Hyunjin Oh, Ikyon Kim

Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

添加到收藏夹

Article Chemistry, Organic

Synthesis of sulfinamides via photocatalytic alkylation or arylation of sulfinylamine

Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li

Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

添加到收藏夹

Article Chemistry, Organic

Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts

Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst

Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

添加到收藏夹

Article Chemistry, Organic

Conversion of amino-terephthalonitriles to multi-substituted single benzene fluorophores with utility in bioimaging

Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar

Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

添加到收藏夹

Review Chemistry, Organic

Microbial alcohol dehydrogenases: recent developments and applications in asymmetric synthesis

Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan

Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.