Nitroxyl (BioDeep_00000013746)
代谢物信息卡片
Nitroxyl
化学式: HNO (31.0058)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: N=O
InChI: InChI=1S/HNO/c1-2/h1H
描述信息
D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents
D020011 - Protective Agents > D000975 - Antioxidants
同义名列表
1 个代谢物同义名
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:84879
- KEGG: C20937
- PubChem: 945
- ChEMBL: CHEMBL1234765
- CAS: 14332-28-6
- PMhub: MS000028281
- PubChem: 254741399
- PDB-CCD: NO
分类词条
相关代谢途径
Reactome(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Vipul Mishra, Durgesh Kumar Tripathi, Francisco J Corpas, Ravi Gupta, Vijay Pratap Singh. Nitroxyl, the 'prodigal son' of the NO family.
Plant cell reports.
2024 Mar; 43(4):91. doi:
10.1007/s00299-024-03190-2. [PMID: 38466458] - Shoko Okazaki. [Mechanistic Analysis of Oxidative Stress-related Diseases Using Nitroxyl Radicals and Electron Spin Resonance].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2024; 144(4):339-344. doi:
10.1248/yakushi.23-00141. [PMID: 38556304] - Grzegorz Bartosz, Natalia Pieńkowska, Kacper Kut, Bogumił Cieniek, Ireneusz Stefaniuk, Izabela Sadowska-Bartosz. Effect of Low Concentration of Nitroxides on SH-SY5Y Cells Transfected with the Tau Protein.
International journal of molecular sciences.
2023 Nov; 24(23):. doi:
10.3390/ijms242316675. [PMID: 38069000] - Laura Morbiato, Celeste Quaggia, Luca Menilli, Chiara Dalla Torre, Antonio Barbon, Marta De Zotti. Synthesis, Conformational Analysis and Antitumor Activity of the Naturally Occurring Antimicrobial Medium-Length Peptaibol Pentadecaibin and Spin-Labeled Analogs Thereof.
International journal of molecular sciences.
2023 Aug; 24(17):. doi:
10.3390/ijms241713396. [PMID: 37686199] - Stella Bujak-Pietrek, Anna Pieniazek, Krzysztof Gwozdzinski, Lukasz Gwozdzinski. The Effect of Piperidine Nitroxides on the Properties of Metalloproteins in Human Red Blood Cells.
Molecules (Basel, Switzerland).
2023 Aug; 28(16):. doi:
10.3390/molecules28166174. [PMID: 37630426] - Jolanta Floryszak-Wieczorek, Ewa Sobieszczuk-Nowicka, Magdalena Arasimowicz-Jelonek. Endogenous plant nitroxyl, a new component of nitric oxide biology.
Trends in biochemical sciences.
2023 Jun; ?(?):. doi:
10.1016/j.tibs.2023.05.010. [PMID: 37331830] - Takumi Udo, Yuta Matsuoka, Masatomo Takahashi, Yoshihiro Izumi, Kota Saito, Kaho Tazoe, Moe Tanaka, Hideto Naka, Takeshi Bamba, Ken-Ichi Yamada. Structural Analysis of Intracellular Lipid Radicals by LC/MS/MS Using a BODIPY-Based Profluorescent Nitroxide Probe.
Analytical chemistry.
2023 03; 95(10):4585-4591. doi:
10.1021/acs.analchem.2c04950. [PMID: 36847588] - Sophie Ketter, Benesh Joseph. Gd3+-Trityl-Nitroxide Triple Labeling and Distance Measurements in the Heterooligomeric Cobalamin Transport Complex in the Native Lipid Bilayers.
Journal of the American Chemical Society.
2023 01; 145(2):960-966. doi:
10.1021/jacs.2c10080. [PMID: 36599418] - M Arasimowicz-Jelonek, J Floryszak-Wieczorek, S Suarez, F Doctorovich, E Sobieszczuk-Nowicka, S Bruce King, G Milczarek, T Rębiś, J Gajewska, P Jagodzik, M Żywicki. Discovery of endogenous nitroxyl as a new redox player in Arabidopsis thaliana.
Nature plants.
2023 01; 9(1):36-44. doi:
10.1038/s41477-022-01301-z. [PMID: 36564632] - Natalia Pieńkowska, Margaret Fahnestock, Crystal Mahadeo, Izabela Zaborniak, Paweł Chmielarz, Grzegorz Bartosz, Izabela Sadowska-Bartosz. Induction of Oxidative Stress in SH-SY5Y Cells by Overexpression of hTau40 and Its Mitigation by Redox-Active Nanoparticles.
International journal of molecular sciences.
2022 Dec; 24(1):. doi:
10.3390/ijms24010359. [PMID: 36613801] - Ruijun Jian, Xue Zhao, Qiaohong Lin, Yu Xia. Profiling of branched-chain fatty acids via nitroxide radical-directed dissociation integrated on an LC-MS/MS workflow.
The Analyst.
2022 May; 147(10):2115-2123. doi:
10.1039/d2an00266c. [PMID: 35471208] - Fabio Mollica, Rosa Lucernati, Riccardo Amorati. Expanding the spectrum of polydopamine antioxidant activity by nitroxide conjugation.
Journal of materials chemistry. B.
2021 12; 9(48):9980-9988. doi:
10.1039/d1tb02154k. [PMID: 34873604] - Xiaoming Wang, Shiwei Guo, Zhiqian Li, Qiang Luo, Yan Dai, Hu Zhang, Yun Ye, Qiyong Gong, Kui Luo. Amphiphilic branched polymer-nitroxides conjugate as a nanoscale agent for potential magnetic resonance imaging of multiple objects in vivo.
Journal of nanobiotechnology.
2021 Jul; 19(1):205. doi:
10.1186/s12951-021-00951-z. [PMID: 34243760] - Nathan J Martin, Belal Chami, Abigail Vallejo, Albaraa A Mojadadi, Paul K Witting, Gulfam Ahmad. Efficacy of the Piperidine Nitroxide 4-MethoxyTEMPO in Ameliorating Serum Amyloid A-Mediated Vascular Inflammation.
International journal of molecular sciences.
2021 Apr; 22(9):. doi:
10.3390/ijms22094549. [PMID: 33925294] - Risa Azuma, Toshihide Yamasaki, Kohei Sano, Masayuki Munekane, Yuta Matsuoka, Ken-Ichi Yamada, Takahiro Mukai. A radioiodinated nitroxide probe with improved stability against bioreduction for in vivo detection of lipid radicals.
Free radical biology & medicine.
2021 02; 163(?):297-305. doi:
10.1016/j.freeradbiomed.2020.12.028. [PMID: 33359688] - Yuta Matsuoka. [Developments of Profluorescent Nitroxide Probes for Highly Sensitive and Selective Detection of Biological Redox Molecules].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2021; 141(12):1297-1304. doi:
10.1248/yakushi.21-00149. [PMID: 34853201] - Michael J Barnes, Alexander J Robson, Javad Naderi, Robert D Short, James W Bradley. Plasma polymerization of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl in a collisional, capacitively coupled radio frequency discharge.
Biointerphases.
2020 11; 15(6):061007. doi:
10.1116/6.0000662. [PMID: 33218222] - Jan Czepas, Karolina Matczak, Aneta Koceva-Chyła, Bartłomiej Grobelski, Zofia Jóźwiak, Krzysztof Gwoździński. Doxyl Nitroxide Spin Probes Can Modify Toxicity of Doxorubicin towards Fibroblast Cells.
Molecules (Basel, Switzerland).
2020 Nov; 25(21):. doi:
10.3390/molecules25215138. [PMID: 33158261] - Thomas Danny Michl, Dung Thuy Thi Tran, Kilian Böttle, Hannah Frederike Kuckling, Aigerim Zhalgasbaikyzy, Barbora Ivanovská, Alex Anthony Cavallaro, Maria Antonia Araque Toledo, Patrick James Sherman, Sameer A Al-Bataineh, Krasimir Vasilev. To be a radical or not to be one? The fate of the stable nitroxide radical TEMPO [(2,2,6,6-Tetramethylpiperidin-1-yl)oxyl] undergoing plasma polymerization into thin-film coatings.
Biointerphases.
2020 06; 15(3):031015. doi:
10.1116/6.0000259. [PMID: 32590900] - Monika Pichla, Grzegorz Bartosz, Natalia Pieńkowska, Izabela Sadowska-Bartosz. Possible artefacts of antioxidant assays performed in the presence of nitroxides and nitroxide-containing nanoparticles.
Analytical biochemistry.
2020 05; 597(?):113698. doi:
10.1016/j.ab.2020.113698. [PMID: 32222539] - Yusuke Okuno, Attila Szabo, G Marius Clore. Quantitative Interpretation of Solvent Paramagnetic Relaxation for Probing Protein-Cosolute Interactions.
Journal of the American Chemical Society.
2020 05; 142(18):8281-8290. doi:
10.1021/jacs.0c00747. [PMID: 32286812] - Linlin Jing, Jin Shao, Wei Sun, Ting Lan, Zhengping Jia, Huiping Ma, Haibo Wang. Protective effects of two novel nitronyl nitroxide radicals on heart failure induced by hypobaric hypoxia.
Life sciences.
2020 May; 248(?):116481. doi:
10.1016/j.lfs.2019.05.037. [PMID: 31102744] - Sergey Dobrynin, Sergei Kutseikin, Denis Morozov, Olesya Krumkacheva, Anna Spitsyna, Yurii Gatilov, Vladimir Silnikov, Goran Angelovski, Michael K Bowman, Igor Kirilyuk, Alexey Chubarov. Human Serum Albumin Labelled with Sterically-Hindered Nitroxides as Potential MRI Contrast Agents.
Molecules (Basel, Switzerland).
2020 Apr; 25(7):. doi:
10.3390/molecules25071709. [PMID: 32276437] - Zhuofu Wu, Sitong Zhang, Xiaojun Wang, Can Cai, Guang Chen, Li Ma. Nitroxide-Modified Protein-Incorporated Nanoflowers with Dual Enzyme-Like Activities.
International journal of nanomedicine.
2020; 15(?):263-273. doi:
10.2147/ijn.s220718. [PMID: 32021179] - Sybille Tachon, Eugénie Fournier, Christophe Decroos, Pascal Mansuelle, Emilien Etienne, Marc Maresca, Marlène Martinho, Valérie Belle, Thierry Tron, Ariane Jalila Simaan. Chemical Modification of 1-Aminocyclopropane Carboxylic Acid (ACC) Oxidase: Cysteine Mutational Analysis, Characterization, and Bioconjugation with a Nitroxide Spin Label.
Molecular biotechnology.
2019 Sep; 61(9):650-662. doi:
10.1007/s12033-019-00191-5. [PMID: 31201604] - G Michael Felker, Maria Borentain, John G Cleland, Mary M DeSouza, Paul D Kessler, Christopher M O'Connor, Dietmar Seiffert, John R Teerlink, Adriaan A Voors, John J V McMurray. Rationale and design for the development of a novel nitroxyl donor in patients with acute heart failure.
European journal of heart failure.
2019 08; 21(8):1022-1031. doi:
10.1002/ejhf.1504. [PMID: 31168885] - Mingwang Yang, Jiangli Fan, Wen Sun, Jianjun Du, Saran Long, Kun Shao, Xiaojun Peng. A nitroxyl-responsive near-infrared fluorescent chemosensor for visualizing H2S/NO crosstalk in biological systems.
Chemical communications (Cambridge, England).
2019 Jul; 55(59):8583-8586. doi:
10.1039/c9cc04060a. [PMID: 31274135] - Douglas Cowart, Robert P Venuti, Kim Lynch, Jeffrey T Guptill, Robert J Noveck, Shi Yin Foo. A Phase 1 Randomized Study of Single Intravenous Infusions of the Novel Nitroxyl Donor BMS-986231 in Healthy Volunteers.
Journal of clinical pharmacology.
2019 05; 59(5):717-730. doi:
10.1002/jcph.1364. [PMID: 30703258] - Janine Wegner, Gabriele Valora, Karin Halbmair, Annemarie Kehl, Brigitte Worbs, Marina Bennati, Ulf Diederichsen. Semi-Rigid Nitroxide Spin Label for Long-Range EPR Distance Measurements of Lipid Bilayer Embedded β-Peptides.
Chemistry (Weinheim an der Bergstrasse, Germany).
2019 Feb; 25(9):2203-2207. doi:
10.1002/chem.201805880. [PMID: 30500095] - Babita Shashni, Yukio Nagasaki. Nitroxide radical-containing nanoparticles attenuate tumorigenic potential of triple negative breast cancer.
Biomaterials.
2018 09; 178(?):48-62. doi:
10.1016/j.biomaterials.2018.05.042. [PMID: 29908344] - V Meenakumari, Hideo Utsumi, A Jawahar, A Milton Franklin Benial. Concentration dependence of nitroxyl spin probes in liposomal solution: electron spin resonance and overhauser-enhanced magnetic resonance studies.
Journal of liposome research.
2018 Jun; 28(2):87-96. doi:
10.1080/08982104.2016.1264960. [PMID: 27892752] - Taiming Liu, Meijuan Zhang, Michael H Terry, Hobe Schroeder, Sean M Wilson, Gordon G Power, Qian Li, Trent E Tipple, Dan Borchardt, Arlin B Blood. Hemodynamic Effects of Glutathione-Liganded Binuclear Dinitrosyl Iron Complex: Evidence for Nitroxyl Generation and Modulation by Plasma Albumin.
Molecular pharmacology.
2018 05; 93(5):427-437. doi:
10.1124/mol.117.110957. [PMID: 29476040] - M Zareba, J Widomska, J M Burke, W K Subczynski. Nitroxide free radicals protect macular carotenoids against chemical destruction (bleaching) during lipid peroxidation.
Free radical biology & medicine.
2016 12; 101(?):446-454. doi:
10.1016/j.freeradbiomed.2016.11.012. [PMID: 27840316] - Benesh Joseph, Victor M Tormyshev, Olga Yu Rogozhnikova, Dmitry Akhmetzyanov, Elena G Bagryanskaya, Thomas F Prisner. Selective High-Resolution Detection of Membrane Protein-Ligand Interaction in Native Membranes Using Trityl-Nitroxide PELDOR.
Angewandte Chemie (International ed. in English).
2016 09; 55(38):11538-42. doi:
10.1002/anie.201606335. [PMID: 27511025] - S Raschke, S Spickermann, T Toncian, M Swantusch, J Boeker, U Giesen, G Iliakis, O Willi, F Boege. Ultra-short laser-accelerated proton pulses have similar DNA-damaging effectiveness but produce less immediate nitroxidative stress than conventional proton beams.
Scientific reports.
2016 08; 6(?):32441. doi:
10.1038/srep32441. [PMID: 27578260] - Till Hauenschild, Jörg Reichenwallner, Volker Enkelmann, Dariush Hinderberger. Characterizing Active Pharmaceutical Ingredient Binding to Human Serum Albumin by Spin-Labeling and EPR Spectroscopy.
Chemistry (Weinheim an der Bergstrasse, Germany).
2016 Aug; 22(36):12825-38. doi:
10.1002/chem.201601810. [PMID: 27460503] - Daniela T Longhi-Balbinot, Ana C Rossaneis, Felipe A Pinho-Ribeiro, Mariana M Bertozzi, Fernando Q Cunha, José C Alves-Filho, Thiago M Cunha, Jean P S Peron, Katrina M Miranda, Rubia Casagrande, Waldiceu A Verri. The nitroxyl donor, Angeli's salt, reduces chronic constriction injury-induced neuropathic pain.
Chemico-biological interactions.
2016 Aug; 256(?):1-8. doi:
10.1016/j.cbi.2016.06.009. [PMID: 27287419] - Adam N Smith, Umar T Twahir, Thierry Dubroca, Gail E Fanucci, Joanna R Long. Molecular Rationale for Improved Dynamic Nuclear Polarization of Biomembranes.
The journal of physical chemistry. B.
2016 08; 120(32):7880-8. doi:
10.1021/acs.jpcb.6b02885. [PMID: 27434371] - Long Binh Vong, Yukio Nagasaki. Combination Treatment of Murine Colon Cancer with Doxorubicin and Redox Nanoparticles.
Molecular pharmaceutics.
2016 Feb; 13(2):449-55. doi:
10.1021/acs.molpharmaceut.5b00676. [PMID: 26605906] - Ken-Ichi Yamada. Development of a Functional Contrast Agent for Targeting Lipid-derived Radicals.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2016; 136(8):1093-100. doi:
10.1248/yakushi.15-00234-4. [PMID: 27477723] - Hinako Eto, Fuminori Hyodo, Nutavutt Kosem, Ryoma Kobayashi, Keiji Yasukawa, Motonao Nakao, Mamoru Kiniwa, Hideo Utsumi. Redox imaging of skeletal muscle using in vivo DNP-MRI and its application to an animal model of local inflammation.
Free radical biology & medicine.
2015 Dec; 89(?):1097-104. doi:
10.1016/j.freeradbiomed.2015.10.418. [PMID: 26505925] - Rita Guzzi, Rosa Bartucci. Electron spin resonance of spin-labeled lipid assemblies and proteins.
Archives of biochemistry and biophysics.
2015 Aug; 580(?):102-11. doi:
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Biointerphases.
2015 Jun; 10(2):029514. doi:
10.1116/1.4919709. [PMID: 25934074] - M C Emoto, M Yamato, H Sato-Akaba, K Yamada, Y Matsuoka, H G Fujii. Brain imaging in methamphetamine-treated mice using a nitroxide contrast agent for EPR imaging of the redox status and a gadolinium contrast agent for MRI observation of blood-brain barrier function.
Free radical research.
2015; 49(8):1038-47. doi:
10.3109/10715762.2015.1040787. [PMID: 25968953] - Maxim A Voinov, Alex I Smirnov. Ionizable Nitroxides for Studying Local Electrostatic Properties of Lipid Bilayers and Protein Systems by EPR.
Methods in enzymology.
2015; 564(?):191-217. doi:
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Biofizika.
2015 Jan; 60(1):88-94. doi:
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The Journal of biological chemistry.
2014 Dec; 289(51):35570-81. doi:
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Rapid communications in mass spectrometry : RCM.
2014 Aug; 28(15):1683-90. doi:
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Journal of drug targeting.
2014 Aug; 22(7):638-47. doi:
10.3109/1061186x.2014.928716. [PMID: 24955616] - Nicole Bye, Oliver E Hutt, Tracey M Hinton, Durga P Acharya, Lynne J Waddington, Bradford A Moffat, David K Wright, Hong X Wang, Xavier Mulet, Benjamin W Muir. Nitroxide-loaded hexosomes provide MRI contrast in vivo.
Langmuir : the ACS journal of surfaces and colloids.
2014 Jul; 30(29):8898-906. doi:
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Journal of magnetic resonance (San Diego, Calif. : 1997).
2014 Jul; 244(?):98-106. doi:
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Chemical communications (Cambridge, England).
2014 Jun; 50(43):5790-2. doi:
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Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2014 Apr; 124(?):322-7. doi:
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Redox biology.
2014; 2(?):91-8. doi:
10.1016/j.redox.2013.12.006. [PMID: 25460723] - Toru Yoshitomi, Yuki Ozaki, Sindhu Thangavel, Yukio Nagasaki. Redox nanoparticle therapeutics to cancer--increase in therapeutic effect of doxorubicin, suppressing its adverse effect.
Journal of controlled release : official journal of the Controlled Release Society.
2013 Nov; 172(1):137-143. doi:
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Chemico-biological interactions.
2013 Nov; 206(2):262-71. doi:
10.1016/j.cbi.2013.09.019. [PMID: 24121186] - Rumiana Bakalova, Zhivko Zhelev, Ichio Aoki, Tsuneo Saga. Tissue redox activity as a hallmark of carcinogenesis: from early to terminal stages of cancer.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2013 May; 19(9):2503-17. doi:
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Biophysical journal.
2013 Jan; 104(1):106-16. doi:
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Free radical biology & medicine.
2012 Nov; 53(10):1942-53. doi:
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Free radical biology & medicine.
2012 Jul; 53(2):328-36. doi:
10.1016/j.freeradbiomed.2012.04.026. [PMID: 22579576] - Benjamin W Muir, Durga P Acharya, Danielle F Kennedy, Xavier Mulet, Richard A Evans, Suzanne M Pereira, Kim L Wark, Ben J Boyd, Tri-Hung Nguyen, Tracey M Hinton, Lynne J Waddington, Nigel Kirby, David K Wright, Hong X Wang, Gary F Egan, Bradford A Moffat. Metal-free and MRI visible theranostic lyotropic liquid crystal nitroxide-based nanoparticles.
Biomaterials.
2012 Mar; 33(9):2723-33. doi:
10.1016/j.biomaterials.2011.12.018. [PMID: 22209558] - Toru Yoshitomi, Aki Hirayama, Yukio Nagasaki. The ROS scavenging and renal protective effects of pH-responsive nitroxide radical-containing nanoparticles.
Biomaterials.
2011 Nov; 32(31):8021-8. doi:
10.1016/j.biomaterials.2011.07.014. [PMID: 21816462] - Atsuyuki Tomizawa, George Hadjidekov, Itsuko Ishii, Rumiana Bakalova, Zhivko Zhelev, Ichio Aoki, Tsuneo Saga, Mitsukazu Kitada. Nitroxide derivatives for imaging of hypercholesterolemia-induced kidney dysfunction and assessing the effectiveness of antilipidemic drugs.
Molecular pharmaceutics.
2011 Oct; 8(5):1962-9. doi:
10.1021/mp200087v. [PMID: 21744874] - Marcelo J Berardi, William M Shih, Stephen C Harrison, James J Chou. Mitochondrial uncoupling protein 2 structure determined by NMR molecular fragment searching.
Nature.
2011 Jul; 476(7358):109-13. doi:
10.1038/nature10257. [PMID: 21785437] - Toshihide Yamasaki, Yuko Ito, Fumiya Mito, Kana Kitagawa, Yuta Matsuoka, Mayumi Yamato, Ken-ichi Yamada. Structural concept of nitroxide as a lipid peroxidation inhibitor.
The Journal of organic chemistry.
2011 May; 76(10):4144-8. doi:
10.1021/jo200361p. [PMID: 21500796] - Pennapa Chonpathompikunlert, Toru Yoshitomi, Junkyu Han, Kazuko Toh, Hiroko Isoda, Yukio Nagasaki. Chemical nanotherapy: nitroxyl radical-containing nanoparticle protects neuroblastoma SH-SY5Y cells from Abeta-induced oxidative stress.
Therapeutic delivery.
2011 May; 2(5):585-97. doi:
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