Methionine sulfoxide (BioDeep_00000001378)

 

Secondary id: BioDeep_00000177895, BioDeep_00000398709, BioDeep_00000402858, BioDeep_00000838380

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


α-amino-γ-(methylsulfinyl)-Butyric acid

化学式: C5H11NO3S (165.046)
中文名称: DL-蛋氨酸亚砜, L-蛋氨酸亚砜, 蛋氨酸亚砜
谱图信息: 最多检出来源 Homo sapiens(feces) 19.5%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Methionine sulfoxide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/methionine_sulfoxide (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001378). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CS(=O)CCC(C(=O)O)N
InChI: InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

描述信息

Methionine sulfoxide belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Methionine sulfoxide exists in all living species, ranging from bacteria to humans. Within humans, methionine sulfoxide participates in a number of enzymatic reactions. In particular, methionine sulfoxide can be biosynthesized from L-methionine through its interaction with the enzyme methionine-R-sulfoxide reductase B3. In addition, methionine sulfoxide can be biosynthesized from L-methionine through the action of the enzyme methionine-R-sulfoxide reductase b2, mitochondrial. In humans, methionine sulfoxide is involved in the metabolic disorder called hypermethioninemia.
Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species via 2-electron-dependent mechanism. Such oxidants can be generated from activated neutrophils; therefore, methionine sulfoxide can be regarded as a biomarker of oxidative stress in vivo. (PMID 12576054) [HMDB]. Methionine sulfoxide is found in many foods, some of which are romaine lettuce, white cabbage, dill, and yellow bell pepper.
L-Methionine sulfoxide (H-Met(O)-OH), a metabolite of Methionine, induces M1/classical macrophage polarization, and modulates oxidative stress and purinergic signaling parameters[1].
Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species and can be regarded as a biomarker of oxidative stress in vivo.
Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species and can be regarded as a biomarker of oxidative stress in vivo.

同义名列表

26 个代谢物同义名

α-amino-γ-(methylsulfinyl)-Butyric acid; Methionine sulfoxide, 35S-labeled, (+-)-isomer; (2S)-2-amino-4-methanesulfinylbutanoic acid; Butanoic acid, 2-amino-4-(methylsulfinyl)-; Methionine sulfoxide, (R-(r*,s*))-isomer; 2-amino-4-(Methylsulfinyl)-butanoic acid; Methionine sulfoxide, (S-(r*,s*))-isomer; 2-amino-4-methylsulfinyl-butanoic acid; 2-amino-4-(Methylsulfinyl)-butanoate; Methionine sulfoxide, (+-)-isomer; Methionine sulfoxide, (2R)-isomer; Methionine sulfoxide, (2S)-isomer; L-Methionine (S)-S-oxide; L-Methionine sulphoxide; DL-Methionine sulfoxide; L-Methionine sulfoxide; Methionine sulphoxide; L-Methionine S-oxide; L-Methionine R-oxide; Methionine sulfoxide; S-Oxide-methionine; Methionine S-oxide; H-Met(O)-OH; Methionine sulfoxide; L-Methionine S-oxide; L-methionine sulfoxide



数据库引用编号

30 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

28 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(25)

PharmGKB(0)

15 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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 CASP3, CAT, ELANE, GLUL, GPX1, HPGDS, MICAL1, MSRA, MSRB1, MSRB3, TXN
Peripheral membrane protein 2 ACHE, HSD17B6
Endosome membrane 1 MICAL1
Nucleus 7 ACHE, CASP3, GLRX, GLUL, MPO, MSRB1, TXN
cytosol 13 APOA1, CASP3, CAT, ELANE, GLRX, GLUL, GPX1, HPGDS, MICAL1, MSRA, MSRB1, MSRB3, TXN
phagocytic vesicle 1 ELANE
nucleoplasm 6 CASP3, HPGDS, MPO, MSRA, MSRB1, TXN
Cell membrane 2 ACHE, GLUL
Lipid-anchor 2 GLUL, MSRA
Early endosome membrane 1 HSD17B6
Synapse 1 ACHE
cell surface 2 ACHE, ELANE
glutamatergic synapse 1 CASP3
Golgi apparatus 2 ACHE, SERPINA1
Golgi membrane 1 INS
neuromuscular junction 1 ACHE
neuronal cell body 1 CASP3
Cytoplasm, cytosol 1 GLUL
Lysosome 1 MPO
plasma membrane 5 ACHE, APOA1, GLUL, MICAL1, MSRA
Membrane 3 ACHE, CAT, MSRA
extracellular exosome 10 APOA1, CAT, ELANE, GLRX, GLUL, MPO, MSRA, SERPINA1, TXN, VWF
Lumenal side 1 HSD17B6
endoplasmic reticulum 5 GLUL, HSD17B6, MSRB3, SERPINA1, VWF
extracellular space 8 ACHE, APOA1, ELANE, IL6, INS, MPO, SERPINA1, VWF
perinuclear region of cytoplasm 1 ACHE
mitochondrion 5 CAT, GLUL, GPX1, MSRA, MSRB3
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 6 CAT, HPGDS, HSD17B6, MPO, MSRA, SERPINA1
Microsome membrane 1 HSD17B6
postsynaptic density 1 CASP3
Secreted 6 ACHE, APOA1, IL6, INS, TXN, VWF
extracellular region 10 ACHE, APOA1, CAT, ELANE, IL6, INS, MPO, SERPINA1, TXN, VWF
mitochondrial matrix 2 CAT, GPX1
Extracellular side 1 ACHE
Extracellular vesicle 1 APOA1
Secreted, extracellular space, extracellular matrix 1 VWF
chylomicron 1 APOA1
high-density lipoprotein particle 1 APOA1
low-density lipoprotein particle 1 APOA1
very-low-density lipoprotein particle 1 APOA1
actin cytoskeleton 3 MICAL1, MSRA, MSRB1
cytoplasmic vesicle 1 APOA1
midbody 2 MICAL1, MSRA
Early endosome 1 APOA1
COPII-coated ER to Golgi transport vesicle 1 SERPINA1
Cytoplasm, cytoskeleton 2 MICAL1, MSRB1
focal adhesion 1 CAT
extracellular matrix 1 VWF
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 4 APOA1, ELANE, SERPINA1, VWF
secretory granule 2 ELANE, MPO
intermediate filament 1 MICAL1
cytoskeleton 2 MICAL1, MSRB1
actin filament 1 MICAL1
blood microparticle 1 APOA1
Lipid-anchor, GPI-anchor 1 ACHE
intercellular bridge 1 MICAL1
endosome lumen 1 INS
cell body 1 GLUL
side of membrane 1 ACHE
azurophil granule 1 MPO
platelet alpha granule 1 VWF
Microsome 1 GLUL
ficolin-1-rich granule lumen 2 CAT, SERPINA1
secretory granule lumen 3 APOA1, CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 APOA1, IL6, INS, SERPINA1
transcription repressor complex 1 ELANE
platelet alpha granule lumen 2 SERPINA1, VWF
specific granule lumen 1 ELANE
endocytic vesicle 1 APOA1
transport vesicle 1 INS
azurophil granule lumen 2 ELANE, MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 INS, SERPINA1
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 ACHE
death-inducing signaling complex 1 CASP3
Cytoplasmic vesicle, phagosome 1 ELANE
spherical high-density lipoprotein particle 1 APOA1
glial cell projection 1 GLUL
endocytic vesicle lumen 1 APOA1
catalase complex 1 CAT
Weibel-Palade body 1 VWF
interleukin-6 receptor complex 1 IL6
[Isoform H]: Cell membrane 1 ACHE
hippocampal mossy fiber expansion 1 MICAL1


文献列表

  • Ewa Marzena Kalemba, Kris Gevaert, Francis Impens, Sara Dufour, Anna Czerwoniec. The association of protein-bound methionine sulfoxide with proteomic basis for aging in beech seeds. BMC plant biology. 2024 May; 24(1):377. doi: 10.1186/s12870-024-05085-6. [PMID: 38714916]
  • Darren Leahy, Cameron Grant, Alex Jackson, Alex Duff, Nicholas Tardiota, Jessica Van Haeften, Xingchen Chen, Jonathan M Peake, Michael D Kruppa, Eliot T Smith, David A Johnson, William B Lott, Jonathan M Harris. Discrimination of Methionine Sulfoxide and Sulfone by Human Neutrophil Elastase. Molecules (Basel, Switzerland). 2021 Sep; 26(17):. doi: 10.3390/molecules26175344. [PMID: 34500777]
  • Natalia Wojciechowska, Shirin Alipour, Ewelina Stolarska, Karolina Bilska, Pascal Rey, Ewa M Kalemba. Involvement of the MetO/Msr System in Two Acer Species That Display Contrasting Characteristics during Germination. International journal of molecular sciences. 2020 Dec; 21(23):. doi: 10.3390/ijms21239197. [PMID: 33276642]
  • Su H Chu, Jing Cui, Jeffrey A Sparks, Bing Lu, Sara K Tedeschi, Cameron B Speyer, LauraKay Moss, Marie L Feser, Lindsay B Kelmenson, Elizabeth A Mewshaw, Jess D Edison, Kevin D Deane, Clary Clish, Jessica Lasky-Su, Elizabeth W Karlson, Karen H Costenbader. Circulating plasma metabolites and risk of rheumatoid arthritis in the Nurses' Health Study. Rheumatology (Oxford, England). 2020 11; 59(11):3369-3379. doi: 10.1093/rheumatology/keaa125. [PMID: 32310291]
  • Tiffany Thomas, Davide Stefanoni, Julie A Reisz, Travis Nemkov, Lorenzo Bertolone, Richard O Francis, Krystalyn E Hudson, James C Zimring, Kirk C Hansen, Eldad A Hod, Steven L Spitalnik, Angelo D'Alessandro. COVID-19 infection alters kynurenine and fatty acid metabolism, correlating with IL-6 levels and renal status. JCI insight. 2020 07; 5(14):. doi: 10.1172/jci.insight.140327. [PMID: 32559180]
  • Thaís S Franceschi, Mayara S P Soares, Nathalia S Pedra, Natália P Bona, Luiza Spohr, Fernanda C Teixeira, Carlus A T do Couto, Roselia M Spanevello, Marion Deon, Carmen R Vargas, Elizandra Braganhol, Francieli M Stefanello. Characterization of macrophage phenotype, redox, and purinergic response upon chronic treatment with methionine and methionine sulfoxide in mice. Amino acids. 2020 Apr; 52(4):629-638. doi: 10.1007/s00726-020-02841-4. [PMID: 32246211]
  • Kristine B Holte, Mona Svanteson, Kristian F Hanssen, Kari Anne Sveen, Ingebjørg Seljeflot, Svein Solheim, David R Sell, Vincent M Monnier, Tore Julsrud Berg. Collagen methionine sulfoxide and glucuronidine/LW-1 are markers of coronary artery disease in long-term survivors with type 1 diabetes. The Dialong study. PloS one. 2020; 15(5):e0233174. doi: 10.1371/journal.pone.0233174. [PMID: 32401813]
  • Maurizio Bruschi, Andrea Petretto, Laura Santucci, Augusto Vaglio, Federico Pratesi, Paola Migliorini, Roberta Bertelli, Chiara Lavarello, Martina Bartolucci, Giovanni Candiano, Marco Prunotto, Gian Marco Ghiggeri. Neutrophil Extracellular Traps protein composition is specific for patients with Lupus nephritis and includes methyl-oxidized αenolase (methionine sulfoxide 93). Scientific reports. 2019 05; 9(1):7934. doi: 10.1038/s41598-019-44379-w. [PMID: 31138830]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Mayara Sandrielly Pereira Soares, Marcelo Zanusso Costa, Tatiane Morgana da Silva, Marta Gazal, Carlus Augustu Tavares do Couto, Gabriela Nogueira Debom, Rodrigo Rodrigues, Juliana Hofstätter Azambuja, Emerson André Casali, Cesar Eduardo Jacintho Moritz, Marta Frescura Duarte, Elizandra Braganhol, Francieli Moro Stefanello, Roselia Maria Spanevello. Methionine and/or Methionine Sulfoxide Alter Ectoenzymes Activities in Lymphocytes and Inflammatory Parameters in Serum from Young Rats: Acute and Chronic Effects. Cell biochemistry and biophysics. 2018 Jun; 76(1-2):243-253. doi: 10.1007/s12013-017-0815-4. [PMID: 28726179]
  • Ákos Kenéz, Tobias Warnken, Karsten Feige, Korinna Huber. Lower plasma trans-4-hydroxyproline and methionine sulfoxide levels are associated with insulin dysregulation in horses. BMC veterinary research. 2018 May; 14(1):146. doi: 10.1186/s12917-018-1479-z. [PMID: 29716602]
  • Maria-Armineh Tossounian, Inge Van Molle, Khadija Wahni, Silke Jacques, Kris Gevaert, Frank Van Breusegem, Didier Vertommen, David Young, Leonardo Astolfi Rosado, Joris Messens. Disulfide bond formation protects Arabidopsis thaliana glutathione transferase tau 23 from oxidative damage. Biochimica et biophysica acta. General subjects. 2018 03; 1862(3):775-789. doi: 10.1016/j.bbagen.2017.10.007. [PMID: 29031766]
  • Juraj Koska, Aramesh Saremi, Scott Howell, Gideon Bahn, Barbora De Courten, Henry Ginsberg, Paul J Beisswenger, Peter D Reaven. Advanced Glycation End Products, Oxidation Products, and Incident Cardiovascular Events in Patients With Type 2 Diabetes. Diabetes care. 2018 03; 41(3):570-576. doi: 10.2337/dc17-1740. [PMID: 29208654]
  • Mayara Sandrielly Pereira Soares, Cassiana Macagnan Viau, Jenifer Saffi, Marcelo Zanusso Costa, Tatiane Morgana da Silva, Pathise Souto Oliveira, Juliana Hofstatter Azambuja, Alethéa Gatto Barschak, Elizandra Braganhol, Angela T S Wyse, Roselia Maria Spanevello, Francieli Moro Stefanello. Acute administration of methionine and/or methionine sulfoxide impairs redox status and induces apoptosis in rat cerebral cortex. Metabolic brain disease. 2017 10; 32(5):1693-1703. doi: 10.1007/s11011-017-0054-9. [PMID: 28676970]
  • Martina I Boxler, Matthias E Liechti, Yasmin Schmid, Thomas Kraemer, Andrea E Steuer. First Time View on Human Metabolome Changes after a Single Intake of 3,4-Methylenedioxymethamphetamine in Healthy Placebo-Controlled Subjects. Journal of proteome research. 2017 09; 16(9):3310-3320. doi: 10.1021/acs.jproteome.7b00294. [PMID: 28722422]
  • Rupesh Bommana, Olivier Mozziconacci, Y John Wang, Christian Schöneich. An Efficient and Rapid Method to Monitor the Oxidative Degradation of Protein Pharmaceuticals: Probing Tyrosine Oxidation with Fluorogenic Derivatization. Pharmaceutical research. 2017 Jul; 34(7):1428-1443. doi: 10.1007/s11095-017-2159-6. [PMID: 28421307]
  • Audrey S Vanhove, Saiyu Hang, Vidhya Vijayakumar, Adam Cn Wong, John M Asara, Paula I Watnick. Vibrio cholerae ensures function of host proteins required for virulence through consumption of luminal methionine sulfoxide. PLoS pathogens. 2017 Jun; 13(6):e1006428. doi: 10.1371/journal.ppat.1006428. [PMID: 28586382]
  • Guoxiang Jiang, Lu Xiao, Huiling Yan, Dandan Zhang, Fuwang Wu, Xuncheng Liu, Xinguo Su, Xinhong Dong, Jiasheng Wang, Xuewu Duan, Yueming Jiang. Redox regulation of methionine in calmodulin affects the activity levels of senescence-related transcription factors in litchi. Biochimica et biophysica acta. General subjects. 2017 May; 1861(5 Pt A):1140-1151. doi: 10.1016/j.bbagen.2017.02.004. [PMID: 28188859]
  • Lien M Dos Santos, Tatiane M da Silva, Juliana H Azambuja, Priscila T Ramos, Pathise S Oliveira, Elita F da Silveira, Nathalia S Pedra, Kennia Galdino, Carlus A T do Couto, Mayara S P Soares, Rejane G Tavares, Roselia M Spanevello, Francieli M Stefanello, Elizandra Braganhol. Methionine and methionine sulfoxide treatment induces M1/classical macrophage polarization and modulates oxidative stress and purinergic signaling parameters. Molecular and cellular biochemistry. 2017 Jan; 424(1-2):69-78. doi: 10.1007/s11010-016-2843-6. [PMID: 27752805]
  • Mayara Sandrielly Pereira Soares, Pathise Souto Oliveira, Gabriela Nogueira Debom, Bruna da Silveira Mattos, Carla Roberta Polachini, Jucimara Baldissarelli, Vera Maria Morsch, Maria Rosa Chitolina Schetinger, Rejane Giacomelli Tavares, Francieli Moro Stefanello, Roselia Maria Spanevello. Chronic administration of methionine and/or methionine sulfoxide alters oxidative stress parameters and ALA-D activity in liver and kidney of young rats. Amino acids. 2017 01; 49(1):129-138. doi: 10.1007/s00726-016-2340-y. [PMID: 27718024]
  • Satoko Suzuki, Yoshio Kodera, Tatsuya Saito, Kazumi Fujimoto, Akari Momozono, Akinori Hayashi, Yuji Kamata, Masayoshi Shichiri. Methionine sulfoxides in serum proteins as potential clinical biomarkers of oxidative stress. Scientific reports. 2016 12; 6(?):38299. doi: 10.1038/srep38299. [PMID: 27929071]
  • Nathan J White, Yi Wang, Xiaoyun Fu, Jessica C Cardenas, Erika J Martin, Donald F Brophy, Charles E Wade, Xu Wang, Alexander E St John, Esther B Lim, Susan A Stern, Kevin R Ward, José A López, Dominic Chung. Post-translational oxidative modification of fibrinogen is associated with coagulopathy after traumatic injury. Free radical biology & medicine. 2016 07; 96(?):181-9. doi: 10.1016/j.freeradbiomed.2016.04.023. [PMID: 27105953]
  • Johannes Wüst, Monika Pischetsrieder. Methionine sulfoxide profiling of milk proteins to assess the influence of lipids on protein oxidation in milk. Food & function. 2016 Jun; 7(6):2526-36. doi: 10.1039/c5fo01550b. [PMID: 26927981]
  • Sara Samino, Maria Vinaixa, Marta Díaz, Antoni Beltran, Miguel A Rodríguez, Roger Mallol, Mercedes Heras, Anna Cabre, Lorena Garcia, Nuria Canela, Francis de Zegher, Xavier Correig, Lourdes Ibáñez, Oscar Yanes. Metabolomics reveals impaired maturation of HDL particles in adolescents with hyperinsulinaemic androgen excess. Scientific reports. 2015 Jun; 5(?):11496. doi: 10.1038/srep11496. [PMID: 26099471]
  • Silke Jacques, Bart Ghesquière, Pieter-Jan De Bock, Hans Demol, Khadija Wahni, Patrick Willems, Joris Messens, Frank Van Breusegem, Kris Gevaert. Protein Methionine Sulfoxide Dynamics in Arabidopsis thaliana under Oxidative Stress. Molecular & cellular proteomics : MCP. 2015 May; 14(5):1217-29. doi: 10.1074/mcp.m114.043729. [PMID: 25693801]
  • G Sartore, R Seraglia, S Burlina, A Bolis, R Marin, E Manzato, E Ragazzi, P Traldi, A Lapolla. High-density lipoprotein oxidation in type 2 diabetic patients and young patients with premature myocardial infarction. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2015 Apr; 25(4):418-25. doi: 10.1016/j.numecd.2014.12.004. [PMID: 25636381]
  • Yong Li, Sridhar A Malkaram, Jie Zhou, Janos Zempleni. Lysine biotinylation and methionine oxidation in the heat shock protein HSP60 synergize in the elimination of reactive oxygen species in human cell cultures. The Journal of nutritional biochemistry. 2014 Apr; 25(4):475-82. doi: 10.1016/j.jnutbio.2013.12.008. [PMID: 24582286]
  • Paul J Beisswenger, Scott K Howell, Greg Russell, Michael E Miller, Stephen S Rich, Michael Mauer. Detection of diabetic nephropathy from advanced glycation endproducts (AGEs) differs in plasma and urine, and is dependent on the method of preparation. Amino acids. 2014 Feb; 46(2):311-9. doi: 10.1007/s00726-013-1533-x. [PMID: 24036985]
  • Jackob Moskovitz. Detection and localization of methionine sulfoxide residues of specific proteins in brain tissue. Protein and peptide letters. 2014; 21(1):52-5. doi: 10.2174/09298665113209990068. [PMID: 24354771]
  • Joung Sug Kim, Hyang-Mi Park, Songhwa Chae, Tae-Ho Lee, Duk-Ju Hwang, Sung-Dug Oh, Jong-Sug Park, Dae-Geun Song, Cheol-Ho Pan, Doil Choi, Yul-Ho Kim, Baek Hie Nahm, Yeon-Ki Kim. A pepper MSRB2 gene confers drought tolerance in rice through the protection of chloroplast-targeted genes. PloS one. 2014; 9(3):e90588. doi: 10.1371/journal.pone.0090588. [PMID: 24614245]
  • Marcelo Zanusso Costa, Tatiane Morgana da Silva, Natália Porto Flores, Felipe Schmitz, Emilene Barros da Silva Scherer, Cassiana Macagnan Viau, Jenifer Saffi, Alethéa Gatto Barschak, Angela Terezinha de Souza Wyse, Roselia Maria Spanevello, Francieli Moro Stefanello. Methionine and methionine sulfoxide alter parameters of oxidative stress in the liver of young rats: in vitro and in vivo studies. Molecular and cellular biochemistry. 2013 Dec; 384(1-2):21-8. doi: 10.1007/s11010-013-1777-5. [PMID: 23963990]
  • Silke Jacques, Bart Ghesquière, Frank Van Breusegem, Kris Gevaert. Plant proteins under oxidative attack. Proteomics. 2013 Mar; 13(6):932-40. doi: 10.1002/pmic.201200237. [PMID: 23172756]
  • Roberta Seraglia, Giovanni Sartore, Raffaella Marin, Silvia Burlina, Enzo Manzato, Eugenio Ragazzi, Pietro Traldi, Annunziata Lapolla. An effective and rapid determination by MALDI/TOF/TOF of methionine sulphoxide content of ApoA-I in type 2 diabetic patients. Journal of mass spectrometry : JMS. 2013 Jan; 48(1):105-10. doi: 10.1002/jms.3113. [PMID: 23303753]
  • Dung Tien Le, Lionel Tarrago, Yasuko Watanabe, Alaattin Kaya, Byung Cheon Lee, Uyen Tran, Rie Nishiyama, Dmitri E Fomenko, Vadim N Gladyshev, Lam-Son Phan Tran. Diversity of plant methionine sulfoxide reductases B and evolution of a form specific for free methionine sulfoxide. PloS one. 2013; 8(6):e65637. doi: 10.1371/journal.pone.0065637. [PMID: 23776515]
  • Fatima Bouchenak, Patricia Henri, Fatma-Zohra Benrebiha, Pascal Rey. Differential responses to salinity of two Atriplex halimus populations in relation to organic solutes and antioxidant systems involving thiol reductases. Journal of plant physiology. 2012 Oct; 169(15):1445-53. doi: 10.1016/j.jplph.2012.06.009. [PMID: 22840322]
  • Surabhi Bhatia, Bianca Knoch, Jenny Wong, Woojin S Kim, Paul L Else, Aaron J Oakley, Brett Garner. Selective reduction of hydroperoxyeicosatetraenoic acids to their hydroxy derivatives by apolipoprotein D: implications for lipid antioxidant activity and Alzheimer's disease. The Biochemical journal. 2012 Mar; 442(3):713-21. doi: 10.1042/bj20111166. [PMID: 22150111]
  • John M Ringman, Andrew T Fithian, Karen Gylys, Jeffrey L Cummings, Giovanni Coppola, David Elashoff, Domenico Pratico, Jackob Moskovitz, Gal Bitan. Plasma methionine sulfoxide in persons with familial Alzheimer's disease mutations. Dementia and geriatric cognitive disorders. 2012; 33(4):219-25. doi: 10.1159/000338546. [PMID: 22584618]
  • Veselin Dimitrov Petrov, Frank Van Breusegem. Hydrogen peroxide-a central hub for information flow in plant cells. AoB PLANTS. 2012; 2012(?):pls014. doi: 10.1093/aobpla/pls014. [PMID: 22708052]
  • Daniel Laporte, Ema Olate, Paula Salinas, Marcela Salazar, Xavier Jordana, Loreto Holuigue. Glutaredoxin GRXS13 plays a key role in protection against photooxidative stress in Arabidopsis. Journal of experimental botany. 2012 Jan; 63(1):503-15. doi: 10.1093/jxb/err301. [PMID: 21963612]
  • Somayyeh Fahiminiya, Valérie Labas, Stéphane Roche, Jean-Louis Dacheux, Nadine Gérard. Proteomic analysis of mare follicular fluid during late follicle development. Proteome science. 2011 Sep; 9(?):54. doi: 10.1186/1477-5956-9-54. [PMID: 21923925]
  • Andrzej Kozik, Anna Golda, Pawel Mak, Piotr Suder, Jerzy Silberring, Anna Barbasz, Maria Rapala-Kozik. Myeloperoxidase-catalyzed oxidative inactivation of human kininogens: the impairment of kinin-precursor and prekallikrein-binding functions. Biological chemistry. 2011 Mar; 392(3):263-74. doi: 10.1515/bc.2011.021. [PMID: 21194373]
  • Harriet Mörtstedt, Marina C Jeppsson, Giovanni Ferrari, Bo A G Jönsson, Monica H Kåredal, Christian H Lindh. Strategy for identification and detection of multiple oxidative modifications within proteins applied on persulfate-oxidized hemoglobin and human serum albumin. Rapid communications in mass spectrometry : RCM. 2011 Jan; 25(2):327-40. doi: 10.1002/rcm.4867. [PMID: 21192028]
  • Lisa A Brennan, Wanda Lee, Marc Kantorow. TXNL6 is a novel oxidative stress-induced reducing system for methionine sulfoxide reductase a repair of α-crystallin and cytochrome C in the eye lens. PloS one. 2010 Nov; 5(11):e15421. doi: 10.1371/journal.pone.0015421. [PMID: 21079812]
  • Wayne Chris Hawkes, Zeynep Alkan. Regulation of redox signaling by selenoproteins. Biological trace element research. 2010 Jun; 134(3):235-51. doi: 10.1007/s12011-010-8656-7. [PMID: 20306235]
  • Sarah Green, David J Studholme, Bridget E Laue, Federico Dorati, Helen Lovell, Dawn Arnold, Joan E Cottrell, Stephen Bridgett, Mark Blaxter, Edgar Huitema, Richard Thwaites, Paul M Sharp, Robert W Jackson, Sophien Kamoun. Comparative genome analysis provides insights into the evolution and adaptation of Pseudomonas syringae pv. aesculi on Aesculus hippocastanum. PloS one. 2010 Apr; 5(4):e10224. doi: 10.1371/journal.pone.0010224. [PMID: 20419105]
  • Nicolas Rouhier. Plant glutaredoxins: pivotal players in redox biology and iron-sulphur centre assembly. The New phytologist. 2010 Apr; 186(2):365-72. doi: 10.1111/j.1469-8137.2009.03146.x. [PMID: 20074091]
  • Iván Iglesias-Baena, Sergio Barranco-Medina, Alfonso Lázaro-Payo, Francisco Javier López-Jaramillo, Francisca Sevilla, Juan-José Lázaro. Characterization of plant sulfiredoxin and role of sulphinic form of 2-Cys peroxiredoxin. Journal of experimental botany. 2010 Mar; 61(5):1509-21. doi: 10.1093/jxb/erq016. [PMID: 20176891]
  • Edith Laugier, Lionel Tarrago, Christina Vieira Dos Santos, Françoise Eymery, Michel Havaux, Pascal Rey. Arabidopsis thaliana plastidial methionine sulfoxide reductases B, MSRBs, account for most leaf peptide MSR activity and are essential for growth under environmental constraints through a role in the preservation of photosystem antennae. The Plant journal : for cell and molecular biology. 2010 Jan; 61(2):271-82. doi: 10.1111/j.1365-313x.2009.04053.x. [PMID: 19874542]
  • Kanti Bhooshan Pandey, Syed Ibrahim Rizvi. Markers of oxidative stress in erythrocytes and plasma during aging in humans. Oxidative medicine and cellular longevity. 2010 Jan; 3(1):2-12. doi: 10.4161/oxim.3.1.10476. [PMID: 20716923]
  • F Lahnsteiner. The role of free amino acids in semen of rainbow trout Oncorhynchus mykiss and carp Cyprinus carpio. Journal of fish biology. 2009 Sep; 75(4):816-33. doi: 10.1111/j.1095-8649.2009.02317.x. [PMID: 20738581]
  • Derek B Oien, Tamar Canello, Ruth Gabizon, Maria Gasset, Brandi L Lundquist, Jeff M Burns, Jackob Moskovitz. Detection of oxidized methionine in selected proteins, cellular extracts and blood serums by novel anti-methionine sulfoxide antibodies. Archives of biochemistry and biophysics. 2009 May; 485(1):35-40. doi: 10.1016/j.abb.2009.01.020. [PMID: 19388147]
  • Xiao Suo Wang, Baohai Shao, Michael N Oda, Jay W Heinecke, Stephen Mahler, Roland Stocker. A sensitive and specific ELISA detects methionine sulfoxide-containing apolipoprotein A-I in HDL. Journal of lipid research. 2009 Mar; 50(3):586-594. doi: 10.1194/jlr.d800042-jlr200. [PMID: 18832772]
  • Dong Ju Lee, Jong Wha Park, Han Woo Lee, Jungmook Kim. Genome-wide analysis of the auxin-responsive transcriptome downstream of iaa1 and its expression analysis reveal the diversity and complexity of auxin-regulated gene expression. Journal of experimental botany. 2009; 60(13):3935-57. doi: 10.1093/jxb/erp230. [PMID: 19654206]
  • Byung Cheon Lee, Dung Tien Le, Vadim N Gladyshev. Mammals reduce methionine-S-sulfoxide with MsrA and are unable to reduce methionine-R-sulfoxide, and this function can be restored with a yeast reductase. The Journal of biological chemistry. 2008 Oct; 283(42):28361-9. doi: 10.1074/jbc.m805059200. [PMID: 18697736]
  • Stephan Good, Martin A Walter, Beatrice Waser, Xuejuan Wang, Jan Müller-Brand, Martin P Béhé, Jean-Claude Reubi, Helmut R Maecke. Macrocyclic chelator-coupled gastrin-based radiopharmaceuticals for targeting of gastrin receptor-expressing tumours. European journal of nuclear medicine and molecular imaging. 2008 Oct; 35(10):1868-77. doi: 10.1007/s00259-008-0803-4. [PMID: 18509636]
  • Xing-Hai Zhang, Herbert Weissbach. Origin and evolution of the protein-repairing enzymes methionine sulphoxide reductases. Biological reviews of the Cambridge Philosophical Society. 2008 Aug; 83(3):249-57. doi: 10.1111/j.1469-185x.2008.00042.x. [PMID: 18557976]
  • Jonathan W C Brock, Alicia J Jenkins, Timothy J Lyons, Richard L Klein, Eunsil Yim, Maria Lopes-Virella, Rickey E Carter, Suzanne R Thorpe, John W Baynes. Increased methionine sulfoxide content of apoA-I in type 1 diabetes. Journal of lipid research. 2008 Apr; 49(4):847-55. doi: 10.1194/jlr.m800015-jlr200. [PMID: 18202432]
  • Maurizio Bruschi, Andrea Petretto, Giovanni Candiano, Luca Musante, Ezio Movilli, Laura Santucci, Andrea Urbani, Rosanna Gusmano, Enrico Verrina, Giovanni Cancarini, Francesco Scolari, Gian Marco Ghiggeri. Determination of the oxido-redox status of plasma albumin in hemodialysis patients. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Mar; 864(1-2):29-37. doi: 10.1016/j.jchromb.2008.01.035. [PMID: 18262857]
  • L Bermúdez, U Urias, D Milstein, L Kamenetzky, R Asis, A R Fernie, M A Van Sluys, F Carrari, M Rossi. A candidate gene survey of quantitative trait loci affecting chemical composition in tomato fruit. Journal of experimental botany. 2008; 59(10):2875-90. doi: 10.1093/jxb/ern146. [PMID: 18552354]
  • Ryuichiro Tanaka. New polar constituents of the pupae of the silkworm Bombyx mori L. I. Isolation and identification of methionine sulfoxide, methionine sulfone, and gamma-cyclic di-L-glutamate. Bioscience, biotechnology, and biochemistry. 2007 Dec; 71(12):3055-62. doi: 10.1271/bbb.70457. [PMID: 18071251]
  • A D Simonović, M D Anderson. Analysis of methionine oxides and nitrogen-transporting amino acids in chilled and acclimated maize seedlings. Amino acids. 2007 Nov; 33(4):607-13. doi: 10.1007/s00726-007-0503-6. [PMID: 17334901]
  • Mario A Moscarello, Fabrizio G Mastronardi, D Denise Wood. The role of citrullinated proteins suggests a novel mechanism in the pathogenesis of multiple sclerosis. Neurochemical research. 2007 Feb; 32(2):251-6. doi: 10.1007/s11064-006-9144-5. [PMID: 17031564]
  • Jonathan W C Brock, Jennifer M Ames, Suzanne R Thorpe, John W Baynes. Formation of methionine sulfoxide during glycoxidation and lipoxidation of ribonuclease A. Archives of biochemistry and biophysics. 2007 Jan; 457(2):170-6. doi: 10.1016/j.abb.2006.10.029. [PMID: 17141728]
  • Joseph T Dever, Adnan A Elfarra. In vivo metabolism of L-methionine in mice: evidence for stereoselective formation of methionine-d-sulfoxide and quantitation of other major metabolites. Drug metabolism and disposition: the biological fate of chemicals. 2006 Dec; 34(12):2036-43. doi: 10.1124/dmd.106.012104. [PMID: 16963488]
  • Daniel Nagore, Begoña Sanz, Javier Soria, Marta Llarena, María J Llama, Juan J Calvete, Juan L Serra. The nitrate/nitrite ABC transporter of Phormidium laminosum: phosphorylation state of NrtA is not involved in its substrate binding activity. Biochimica et biophysica acta. 2006 Feb; 1760(2):172-81. doi: 10.1016/j.bbagen.2005.12.011. [PMID: 16442736]
  • J W C Brock, W C Cotham, J M Ames, S R Thorpe, J W Baynes. Proteomic method for the quantification of methionine sulfoxide. Annals of the New York Academy of Sciences. 2005 Jun; 1043(?):284-9. doi: 10.1196/annals.1333.035. [PMID: 16037250]
  • Philipp O Tsvetkov, Benjamin Ezraty, Jennifer K Mitchell, François Devred, Vincent Peyrot, Peter J Derrick, Frédéric Barras, Alexander A Makarov, Daniel Lafitte. Calorimetry and mass spectrometry study of oxidized calmodulin interaction with target and differential repair by methionine sulfoxide reductases. Biochimie. 2005 May; 87(5):473-80. doi: 10.1016/j.biochi.2004.11.020. [PMID: 15820754]
  • Ute Panzenböck, Roland Stocker. Formation of methionine sulfoxide-containing specific forms of oxidized high-density lipoproteins. Biochimica et biophysica acta. 2005 Jan; 1703(2):171-81. doi: 10.1016/j.bbapap.2004.11.003. [PMID: 15680225]
  • Wesley G Taylor, Daniel H Sutherland, Douglas J H Olson, Andrew R S Ross, Paul G Fields. Insecticidal components from field pea extracts: sequences of some variants of pea albumin 1b. Journal of agricultural and food chemistry. 2004 Dec; 52(25):7499-506. doi: 10.1021/jf030807l. [PMID: 15675795]
  • Christian Lherbet, Christian Gravel, Jeffrey W Keillor. Synthesis of S-alkyl L-homocysteine analogues of glutathione and their kinetic studies with gamma-glutamyl transpeptidase. Bioorganic & medicinal chemistry letters. 2004 Jul; 14(13):3451-5. doi: 10.1016/j.bmcl.2004.04.072. [PMID: 15177451]
  • N Ahmed, P J Thornalley. Quantitative screening of protein biomarkers of early glycation, advanced glycation, oxidation and nitrosation in cellular and extracellular proteins by tandem mass spectrometry multiple reaction monitoring. Biochemical Society transactions. 2003 Dec; 31(Pt 6):1417-22. doi: 10.1042/bst0311417. [PMID: 14641078]
  • Abuduaini Abulimiti, Xiaolei Qiu, Jing Chen, Yang Liu, Zengyi Chang. Reversible methionine sulfoxidation of Mycobacterium tuberculosis small heat shock protein Hsp16.3 and its possible role in scavenging oxidants. Biochemical and biophysical research communications. 2003 May; 305(1):87-93. doi: 10.1016/s0006-291x(03)00685-5. [PMID: 12732200]
  • Ryuichi Mashima, Takako Nakanishi-Ueda, Yorihiro Yamamoto. Simultaneous determination of methionine sulfoxide and methionine in blood plasma using gas chromatography-mass spectrometry. Analytical biochemistry. 2003 Feb; 313(1):28-33. doi: 10.1016/s0003-2697(02)00537-7. [PMID: 12576054]
  • Magdalena Nieziołek, Marcin Kot, Krzysztof Pyka, Paweł Mak, Andrzej Kozik. Properties of chemically oxidized kininogens. Acta biochimica Polonica. 2003; 50(3):753-63. doi: 035003753. [PMID: 14515155]
  • Niklas Gustavsson, Bas P A Kokke, Ulrika Härndahl, Maria Silow, Ulrike Bechtold, Zaruhi Poghosyan, Denis Murphy, Wilbert C Boelens, Cecilia Sundby. A peptide methionine sulfoxide reductase highly expressed in photosynthetic tissue in Arabidopsis thaliana can protect the chaperone-like activity of a chloroplast-localized small heat shock protein. The Plant journal : for cell and molecular biology. 2002 Mar; 29(5):545-53. doi: 10.1046/j.1365-313x.2002.029005545.x. [PMID: 11874568]
  • Sema Sentürker, Richard Tschirret-Guth, Jason Morrow, Rod Levine, Emily Shacter. Induction of apoptosis by chemotherapeutic drugs without generation of reactive oxygen species. Archives of biochemistry and biophysics. 2002 Jan; 397(2):262-72. doi: 10.1006/abbi.2001.2681. [PMID: 11795881]
  • C J van Dalen, A J Kettle. Substrates and products of eosinophil peroxidase. The Biochemical journal. 2001 Aug; 358(Pt 1):233-9. doi: 10.1042/0264-6021:3580233. [PMID: 11485572]
  • H Sakagami, H Arakawa, M Maeda, K Satoh, T Kadofuku, K Fukuchi, K Gomi. Production of hydrogen peroxide and methionine sulfoxide by epigallocatechin gallate and antioxidants. Anticancer research. 2001 Jul; 21(4A):2633-41. doi: . [PMID: 11724332]
  • I Petropoulos, J Mary, M Perichon, B Friguet. Rat peptide methionine sulphoxide reductase: cloning of the cDNA, and down-regulation of gene expression and enzyme activity during aging. The Biochemical journal. 2001 May; 355(Pt 3):819-25. doi: 10.1042/bj3550819. [PMID: 11311146]
  • E Issakidis-Bourguet, N Mouaheb, Y Meyer, M Miginiac-Maslow. Heterologous complementation of yeast reveals a new putative function for chloroplast m-type thioredoxin. The Plant journal : for cell and molecular biology. 2001 Jan; 25(2):127-35. doi: 10.1046/j.0960-7412.2000.00943.x. [PMID: 11169189]
  • U Panzenböck, L Kritharides, M Raftery, K A Rye, R Stocker. Oxidation of methionine residues to methionine sulfoxides does not decrease potential antiatherogenic properties of apolipoprotein A-I. The Journal of biological chemistry. 2000 Jun; 275(26):19536-44. doi: 10.1074/jbc.m000458200. [PMID: 10751387]
  • M Kalic, J Lauterwein, G Büsselmann, G Kamp. Assignment of overlapping (1)H NMR signals in carp seminal plasma by proton-detected 2D C,H correlation spectroscopy. Biochemical and biophysical research communications. 2000 Mar; 269(1):76-80. doi: 10.1006/bbrc.2000.2250. [PMID: 10694480]
  • R Mashima, S Yoshimura, Y Yamamoto. Reduction of lipid hydroperoxides by apolipoprotein B-100. Biochemical and biophysical research communications. 1999 May; 259(1):185-9. doi: 10.1006/bbrc.1999.0739. [PMID: 10334937]
  • T Kornfelt, E Persson, L Palm. Oxidation of methionine residues in coagulation factor VIIa. Archives of biochemistry and biophysics. 1999 Mar; 363(1):43-54. doi: 10.1006/abbi.1998.1071. [PMID: 10079116]
  • H Sun, J Gao, D A Ferrington, H Biesiada, T D Williams, T C Squier. Repair of oxidized calmodulin by methionine sulfoxide reductase restores ability to activate the plasma membrane Ca-ATPase. Biochemistry. 1999 Jan; 38(1):105-12. doi: 10.1021/bi981295k. [PMID: 9890888]
  • J O Konz, J King, C L Cooney. Effects of oxygen on recombinant protein expression. Biotechnology progress. 1998 May; 14(3):393-409. doi: 10.1021/bp980021l. [PMID: 9622520]
  • B Garner, P K Witting, A R Waldeck, J K Christison, M Raftery, R Stocker. Oxidation of high density lipoproteins. I. Formation of methionine sulfoxide in apolipoproteins AI and AII is an early event that accompanies lipid peroxidation and can be enhanced by alpha-tocopherol. The Journal of biological chemistry. 1998 Mar; 273(11):6080-7. doi: 10.1074/jbc.273.11.6080. [PMID: 9497325]
  • A Z Haghighi, K R Maples. On the mechanism of the inhibition of glutamine synthetase and creatine phosphokinase by methionine sulfoxide. Journal of neuroscience research. 1996 Jan; 43(1):107-11. doi: 10.1002/jnr.490430114. [PMID: 8838581]
  • Q F Gan, G L Witkop, D L Sloane, K M Straub, E Sigal. Identification of a specific methionine in mammalian 15-lipoxygenase which is oxygenated by the enzyme product 13-HPODE: dissociation of sulfoxide formation from self-inactivation. Biochemistry. 1995 May; 34(21):7069-79. doi: 10.1021/bi00021a019. [PMID: 7766617]
  • A von Eckardstein, M Walter, H Holz, A Benninghoven, G Assmann. Site-specific methionine sulfoxide formation is the structural basis of chromatographic heterogeneity of apolipoproteins A-I, C-II, and C-III. Journal of lipid research. 1991 Sep; 32(9):1465-76. doi: 10.1016/s0022-2275(20)41914-5. [PMID: 1753217]
  • F Parrot, D Fontan, M Besson-Léaud. [A case of urinary elimination of methionine sulfoxide without hypermethioninemia]. Annales de biologie clinique. 1991; 49(7):405-6. doi: NULL. [PMID: 1763844]
  • R J Truscott, F Martin. The reaction of proteins with 3-hydroxyanthranilic acid as a possible model for senile nuclear cataract in man. Experimental eye research. 1989 Dec; 49(6):927-40. doi: 10.1016/s0014-4835(89)80017-x. [PMID: 2515071]
  • M W Swaim, S V Pizzo. Methionine sulfoxide and the oxidative regulation of plasma proteinase inhibitors. Journal of leukocyte biology. 1988 Apr; 43(4):365-79. doi: 10.1002/jlb.43.4.365. [PMID: 2450941]
  • L D Stegink, E F Bell, L J Filer, E E Ziegler, D W Andersen, F H Seligson. Effects of equimolar doses of L-methionine, D-methionine and L-methionine-dl-sulfoxide on plasma and urinary amino acid levels in normal adult humans. The Journal of nutrition. 1986 Jul; 116(7):1185-92. doi: 10.1093/jn/116.7.1185. [PMID: 3746457]
  • H K Nielsen, P A Finot, R F Hurrell. Reactions of proteins with oxidizing lipids. 2. Influence on protein quality and on the bioavailability of lysine, methionine, cyst(e)ine and tryptophan as measured in rat assays. The British journal of nutrition. 1985 Jan; 53(1):75-86. doi: 10.1079/bjn19850012. [PMID: 3933548]
  • A Aksnes. Studies on the in vivo utilisation and the in vitro enzymatic reduction of methionine sulphoxide in rats and rat tissues. Annals of nutrition & metabolism. 1984; 28(5):288-96. doi: 10.1159/000176818. [PMID: 6486721]
  • V Ganapathy, F H Leibach. Transport and utilization of methionine sulfoxide in the rabbit. Biochimica et biophysica acta. 1982 Dec; 693(2):305-14. doi: 10.1016/0005-2736(82)90436-9. [PMID: 7159581]
  • L R Njaa, A Aksnes. The nitrogen-sparing effect of methionine sulphoxide and some other sulphur-containing amino acids. The British journal of nutrition. 1982 Nov; 48(3):565-70. doi: 10.1079/bjn19820141. [PMID: 7171541]