1,4-Dithiothreitol (BioDeep_00000001728)
Secondary id: BioDeep_00000837572, BioDeep_00001892235
human metabolite Endogenous BioNovoGene_Lab2019
代谢物信息卡片
化学式: C4H10O2S2 (154.0122)
中文名称: DL-二硫苏糖醇(DTT), L-1,4-二硫代苏糖醇, 二硫代苏糖醇, 二硫苏糖醇, 1,4-二硫苏糖醇
谱图信息:
最多检出来源 Homo sapiens(blood) 3.35%
分子结构信息
SMILES: C(C(C(CS)O)O)S
InChI: InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2
描述信息
Dithiothreitol (DTT) is the common name for a small-molecule redox reagent known as Clelands reagent. DTTs formula is C4H10O2S2 and the molecular structure of its reduced form is shown at the right; its oxidized form is a disulfide-bonded 6-membered ring (shown below). Its name derives from the four-carbon sugar, threose. DTT has an epimeric (sister) compound, dithioerythritol. A common use of DTT is as a reducing or "deprotecting" agent for thiolated DNA. The terminal sulfur atoms of thiolated DNA have a tendency to form dimers in solution, especially in the presence of oxygen. Dimerization greatly lowers the efficiency of subsequent coupling reactions such as DNA immobilization on gold in biosensors. Typically DTT is mixed with a DNA solution and allowed to react, and then is removed by filtration (for the solid catalyst) or by chromatography (for the liquid form). The DTT removal procedure is often called "desalting.". DTT is frequently used to reduce the disulfide bonds of proteins and, more generally, to prevent intramolecular and intermolecular disulfide bonds from forming between cysteine residues of proteins. However, even DTT cannot reduce buried (solvent-inaccessible) disulfide bonds, so reduction of disulfide bonds is sometimes carried out under denaturing conditions (e.g., at high temperatures, or in the presence of a strong denaturant such as 6 M guanidinium hydrochloride, 8 M urea, or 1\\% sodium dodecylsulfate). Conversely, the solvent exposure of different disulfide bonds can be assayed by their rate of reduction in the presence of DTT. DTT can also be used as an oxidizing agent. Its principal advantage is that effectively no mixed-disulfide species are populated, in contrast to other agents such as glutathione. In very rare cases, a DTT adduct may be formed, i.e., the two sulfur atoms of DTT may form disulfide bonds to different sulfur atoms; in such cases, DTT cannot cyclize since it has no remaining free thiols. Due to air oxidation, DTT is a relatively unstable compound whose useful life can be extended by refrigeration and handling in an inert atmosphere. Since protonated sulfurs have lowered nucleophilicities, DTT becomes less potent as the pH lowers. Tris(2-carboxyethyl)phosphine HCl (TCEP hydrochloride) is an alternative which is more stable and works even at low pH.
Dithiothreitol (DTT) is the common name for a small-molecule redox reagent known as Clelands reagent. DTT has an epimeric compound, dithioerythritol.
COVID info from COVID-19 Disease Map
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
同义名列表
19 个代谢物同义名
DL-Threo-1,4-dimercapto-2,3-butanediol; (2R,3R)-1,4-disulfanylbutane-2,3-diol; L-Threo-1,4-dimercapto-2,3-butanediol; (2R,3R)-1,4-Dimercaptobutane-2,3-diol; Threo-1,4-dimercapto-2,3-butanediol; 2,3-DIHYDROXY-1,4-dithiobutane; D-1,4-dithiothreitol; 1,4-Dithiothreitol; Reagent, clelands; DL-Dithiothreitol; L-Dithiothreitol; Clelands reagent; Reagent, cleland; Cleland reagent; Dithiothreitol; Sputolysin; L-DTT; Dithiothreitol; 1,4-Dithiothreitol
数据库引用编号
28 个数据库交叉引用编号
- ChEBI: CHEBI:18320
- ChEBI: CHEBI:25189
- ChEBI: CHEBI:42106
- KEGG: C00265
- PubChem: 439196
- PubChem: 19001
- HMDB: HMDB0013593
- Metlin: METLIN4118
- DrugBank: DB04447
- ChEMBL: CHEMBL406270
- ChEMBL: CHEMBL47903
- Wikipedia: Dithiothreitol
- MeSH: Dithiothreitol
- foodb: FDB029593
- chemspider: 388336
- CAS: 27565-41-9
- CAS: 16096-97-2
- CAS: 7634-42-6
- CAS: 3483-12-3
- PMhub: MS000001066
- PubChem: 3563
- PDB-CCD: DTT
- NIKKAJI: J388.818E
- NIKKAJI: J64.633D
- LOTUS: LTS0226561
- wikidata: Q27104490
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-851
- KNApSAcK: 18320
分类词条
相关代谢途径
Reactome(0)
BioCyc(47)
- alkylnitronates degradation
- allantoin degradation to ureidoglycolate II (ammonia producing)
- allantoin degradation to glyoxylate III
- superpathway of demethylmenaquinol-8 biosynthesis I
- superpathway of N-acetylneuraminate degradation
- superpathway of hexitol degradation (bacteria)
- 2-carboxy-1,4-naphthoquinol biosynthesis
- superpathway of menaquinol-8 biosynthesis I
- superpathway of chorismate metabolism
- hordatine biosynthesis
- pyrimidine deoxyribonucleotides de novo biosynthesis III
- urea cycle
- superpathway of L-citrulline metabolism
- L-citrulline biosynthesis
- superpathway of pentose and pentitol degradation
- superpathway of glycolysis, pyruvate dehydrogenase, TCA, and glyoxylate bypass
- stachyose biosynthesis
- streptomycin biosynthesis
- superpathway of CMP-sialic acids biosynthesis
- superpathway of carotenoid biosynthesis in plants
- superpathway of L-lysine degradation
- L-lysine fermentation to acetate and butanoate
- superpathway of glycolysis and the Entner-Doudoroff pathway
- photosynthetic 3-hydroxybutanoate biosynthesis (engineered)
- gluconeogenesis I
- glycolysis II (from fructose 6-phosphate)
- glycolysis I (from glucose 6-phosphate)
- L-homomethionine biosynthesis
- allantoin degradation IV (anaerobic)
- sanguinarine and macarpine biosynthesis
- CMP-N-acetylneuraminate biosynthesis I (eukaryotes)
- pyrimidine deoxyribonucleotides de novo biosynthesis I
- patchoulol biosynthesis
- norspermidine biosynthesis
- superpathway of polyamine biosynthesis III
- GDP-mannose biosynthesis
- superpathway of GDP-mannose-derived O-antigen building blocks biosynthesis
- superpathway of penicillin, cephalosporin and cephamycin biosynthesis
- deacetylcephalosporin C biosynthesis
- isopenicillin N biosynthesis
- puromycin biosynthesis
- L-threonine degradation II
- ubiquinol-8 biosynthesis (prokaryotic)
- L-ascorbate biosynthesis IV
- superpathway of ubiquinol-8 biosynthesis (prokaryotic)
- superpathway of L-threonine metabolism
- pinitol biosynthesis II
PlantCyc(5)
代谢反应
5 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(1)
- @COVID-19 Disease
Map["name"]:
2-Methyl-3-acetoacetyl-CoA + Coenzyme A ⟶ Acetyl-CoA + Propanoyl-CoA
PathBank(4)
- Vitamin K Metabolism:
Carbon dioxide + Oxygen + Peptidyl-4-carboxyglutamate + Phylloquinol ⟶ Peptidyl-glutamate + Vitamin K1 2,3-epoxide + Water
- Vitamin K Metabolism:
Carbon dioxide + Oxygen + Reduced Vitamin K (phylloquinone) + Unknown ⟶ Unknown + Vitamin K1 2,3-epoxide + Water
- Vitamin K Metabolism:
Oxidized dithiothreitol + Vitamin K1 ⟶ 1,4-Dithiothreitol + Vitamin K1 2,3-epoxide
- Vitamin K Metabolism:
Oxidized dithiothreitol + Vitamin K1 ⟶ 1,4-Dithiothreitol + Vitamin K1 2,3-epoxide
PharmGKB(0)
2 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
- Xuemei Zhang, Chao Geng, Yang Fu, Zhen Lv, Zhonglin Wei, Hongda Wang, Shixue Wang. A Facile and Green Approach for the Preparation of Amine-Functionalized Poly(ethylene glycol) by Reducing Poly(ethylene glycol) Azide with Dithiothreitol.
Biomacromolecules.
2024 Mar; 25(3):1972-1977. doi:
10.1021/acs.biomac.3c01370
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Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.
2024 Feb; ?(?):. doi:
10.1007/s43630-023-00516-z
. [PMID: 38305951] - Meng Huang, Meng Li, Ying Zhang, Huan Gong, Yuju Zhou, Danping Zhu, Lingxi Li, Ning Ma, Yan Cui. Novel flavan-3-ol-dithiothreitol conjugates derived from the degradation of grape seed proanthocyanidins and their neuroprotective potential.
Food chemistry.
2023 Mar; 405(Pt A):134825. doi:
10.1016/j.foodchem.2022.134825
. [PMID: 36356360] - Song Li, Sheng-Jie Yue, Peng Huang, Tong-Tong Feng, Hong-Yan Zhang, Rui-Lian Yao, Wei Wang, Xue-Hong Zhang, Hong-Bo Hu. Comparative metabolomics and transcriptomics analyses provide insights into the high-yield mechanism of phenazines biosynthesis in Pseudomonas chlororaphis GP72.
Journal of applied microbiology.
2022 Nov; 133(5):2790-2801. doi:
10.1111/jam.15727
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The Plant cell.
2022 09; 34(10):4007-4027. doi:
10.1093/plcell/koac202
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Bioconjugate chemistry.
2022 05; 33(5):839-847. doi:
10.1021/acs.bioconjchem.2c00094
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Analytical chemistry.
2022 05; 94(17):6557-6565. doi:
10.1021/acs.analchem.2c00387
. [PMID: 35435658] - Gokul G, Jogender Singh. Dithiothreitol causes toxicity in C. elegans by modulating the methionine-homocysteine cycle.
eLife.
2022 04; 11(?):. doi:
10.7554/elife.76021
. [PMID: 35438636] - Karollyny Roger Pereira Lima, Francisco Lucas Pacheco Cavalcante, Stelamaris de Oliveira Paula-Marinho, Isabelle Mary Costa Pereira, Lineker de Sousa Lopes, João Victor Serra Nunes, Ítalo Antônio Cotta Coutinho, Enéas Gomes-Filho, Humberto Henrique de Carvalho. Metabolomic profiles exhibit the influence of endoplasmic reticulum stress on sorghum seedling growth over time.
Plant physiology and biochemistry : PPB.
2022 Jan; 170(?):192-205. doi:
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Cells.
2021 12; 10(12):. doi:
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Molecular and cellular biochemistry.
2021 Mar; 476(3):1467-1475. doi:
10.1007/s11010-020-04010-3
. [PMID: 33389495] - Lorenzo Ferroni, Andrea Colpo, Costanza Baldisserotto, Simonetta Pancaldi. In an ancient vascular plant the intermediate relaxing component of NPQ depends on a reduced stroma: Evidence from dithiothreitol treatment.
Journal of photochemistry and photobiology. B, Biology.
2021 Feb; 215(?):112114. doi:
10.1016/j.jphotobiol.2020.112114
. [PMID: 33385824] - Tony Tremblay, Donald R Branch, Lionel Loubaki. Daudi cell stroma: An alternative to dithiothreitol to resolve daratumumab interference in pretransfusion testing.
Transfusion.
2020 09; 60(9):2090-2096. doi:
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The Journal of molecular diagnostics : JMD.
2020 08; 22(8):1030-1040. doi:
10.1016/j.jmoldx.2020.04.211
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Cell biology and toxicology.
2020 08; 36(4):287-300. doi:
10.1007/s10565-019-09509-0
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Analytical chemistry.
2020 07; 92(13):8810-8818. doi:
10.1021/acs.analchem.0c00242
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The Plant cell.
2020 05; 32(5):1589-1609. doi:
10.1105/tpc.19.00797
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Analytica chimica acta.
2020 Mar; 1102(?):1-10. doi:
10.1016/j.aca.2020.01.025
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Transfusion.
2020 03; 60(3):488-497. doi:
10.1111/trf.15666
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Plant physiology and biochemistry : PPB.
2020 Feb; 147(?):223-234. doi:
10.1016/j.plaphy.2019.12.013
. [PMID: 31874339] - Heather A Walters, Brenda H Welter, William J Sullivan, Lesly A Temesvari. Phosphorylation of eukaryotic initiation factor-2α in response to endoplasmic reticulum and nitrosative stress in the human protozoan parasite, Entamoeba histolytica.
Molecular and biochemical parasitology.
2019 12; 234(?):111223. doi:
10.1016/j.molbiopara.2019.111223
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Annals of laboratory medicine.
2019 Nov; 39(6):572-576. doi:
10.3343/alm.2019.39.6.572
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Colloids and surfaces. B, Biointerfaces.
2019 Oct; 182(?):110355. doi:
10.1016/j.colsurfb.2019.110355
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Archives of biochemistry and biophysics.
2019 07; 669(?):87-95. doi:
10.1016/j.abb.2019.05.019
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Small (Weinheim an der Bergstrasse, Germany).
2019 07; 15(27):e1900860. doi:
10.1002/smll.201900860
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Journal of immunological methods.
2019 07; 470(?):40-45. doi:
10.1016/j.jim.2019.04.009
. [PMID: 31034879] - Xing Yu, Tanchun Wang, Meichen Zhu, Liting Zhang, Fengzhi Zhang, Enen Jing, Yongzhe Ren, Zhiqiang Wang, Zeyu Xin, Tongbao Lin. Transcriptome and physiological analyses for revealing genes involved in wheat response to endoplasmic reticulum stress.
BMC plant biology.
2019 May; 19(1):193. doi:
10.1186/s12870-019-1798-7
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Transfusion.
2019 05; 59(5):1827-1835. doi:
10.1111/trf.15202
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Phytochemistry.
2019 Mar; 159(?):159-171. doi:
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Transactions of the Royal Society of Tropical Medicine and Hygiene.
2019 02; 113(2):101-104. doi:
10.1093/trstmh/try116
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Analytical and bioanalytical chemistry.
2019 Feb; 411(6):1211-1218. doi:
10.1007/s00216-018-1552-2
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Immunohematology.
2018 Dec; 34(4):135-139. doi:
10.21307/immunohematology-2018-021
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Theriogenology.
2018 Sep; 117(?):34-39. doi:
10.1016/j.theriogenology.2018.05.023
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ACS applied materials & interfaces.
2018 May; 10(17):14399-14409. doi:
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Vox sanguinis.
2018 May; 113(4):397-399. doi:
10.1111/vox.12645
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Talanta.
2018 Apr; 180(?):36-46. doi:
10.1016/j.talanta.2017.11.063
. [PMID: 29332824] - Laura Martos, Luis Andrés Ramón, Julia Oto, Álvaro Fernández-Pardo, Santiago Bonanad, Ana Rosa Cid, Andras Gruber, John H Griffin, Francisco España, Silvia Navarro, Pilar Medina. α2-Macroglobulin Is a Significant In Vivo Inhibitor of Activated Protein C and Low APC:α2M Levels Are Associated with Venous Thromboembolism.
Thrombosis and haemostasis.
2018 04; 118(4):630-638. doi:
10.1055/s-0038-1629902
. [PMID: 29448296] - Reza Heidari, Vahid Ghanbarinejad, Hamidreza Mohammadi, Asrin Ahmadi, Athena Esfandiari, Negar Azarpira, Hossein Niknahad. Dithiothreitol supplementation mitigates hepatic and renal injury in bile duct ligated mice: Potential application in the treatment of cholestasis-associated complications.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2018 Mar; 99(?):1022-1032. doi:
10.1016/j.biopha.2018.01.018
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Transfusion clinique et biologique : journal de la Societe francaise de transfusion sanguine.
2018 Feb; 25(1):2-7. doi:
10.1016/j.tracli.2017.12.001
. [PMID: 29336950] - Ji-Hye Jang, Yun Shang, Hyun Kyung Kang, Sun Young Kim, Beg Hab Kim, Kyoung Hee Nam. Arabidopsis galactinol synthases 1 (AtGOLS1) negatively regulates seed germination.
Plant science : an international journal of experimental plant biology.
2018 Feb; 267(?):94-101. doi:
10.1016/j.plantsci.2017.11.010
. [PMID: 29362103] - Asmae Zerrouki, Sanae Ouadghiri, Nadia Benseffaj, Rachid Razine, Malika Essakalli. Reason and Resolution of High Negative Control Beads in Solid-Phase Immunoassay.
Experimental and clinical transplantation : official journal of the Middle East Society for Organ Transplantation.
2018 Feb; 16(1):38-43. doi:
10.6002/ect.2016.0239
. [PMID: 28540842] - Pingping Liang, Juan Canoura, Haixiang Yu, Obtin Alkhamis, Yi Xiao. Dithiothreitol-Regulated Coverage of Oligonucleotide-Modified Gold Nanoparticles To Achieve Optimized Biosensor Performance.
ACS applied materials & interfaces.
2018 Jan; 10(4):4233-4242. doi:
10.1021/acsami.7b16914
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Methods in enzymology.
2018; 603(?):129-150. doi:
10.1016/bs.mie.2018.02.007
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Molecular vision.
2018; 24(?):621-632. doi:
"
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European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2017 Dec; 110(?):77-86. doi:
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International journal of biological macromolecules.
2017 Nov; 104(Pt A):889-899. doi:
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Human immunology.
2017 Nov; 78(11-12):699-703. doi:
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Journal of virological methods.
2017 10; 248(?):1-6. doi:
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Journal of plant physiology.
2017 Sep; 216(?):52-57. doi:
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Clinical biochemistry.
2017 Sep; 50(13-14):777-783. doi:
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Plant, cell & environment.
2017 Aug; 40(8):1341-1355. doi:
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Talanta.
2017 Aug; 170(?):199-209. doi:
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The Journal of biological chemistry.
2017 07; 292(27):11230-11242. doi:
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BMC research notes.
2017 Jun; 10(1):237. doi:
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Biochemistry.
2017 05; 56(17):2251-2260. doi:
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Applied biochemistry and biotechnology.
2017 May; 182(1):181-196. doi:
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Neurotoxicity research.
2017 May; 31(4):545-559. doi:
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Acta crystallographica. Section F, Structural biology communications.
2017 04; 73(Pt 4):241-245. doi:
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Food & function.
2017 Mar; 8(3):1195-1203. doi:
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Sensors (Basel, Switzerland).
2017 Mar; 17(3):. doi:
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Animal science journal = Nihon chikusan Gakkaiho.
2017 Feb; 88(2):231-240. doi:
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HLA.
2017 02; 89(2):82-89. doi:
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Environmental toxicology.
2017 Jan; 32(1):17-27. doi:
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Methods in molecular biology (Clifton, N.J.).
2017; 1653(?):51-64. doi:
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American journal of physiology. Endocrinology and metabolism.
2017 01; 312(1):E48-E57. doi:
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PloS one.
2017; 12(9):e0184282. doi:
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Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology.
2017; 41(2):835-848. doi:
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Biochimica et biophysica acta.
2016 12; 1861(12 Pt A):1959-1967. doi:
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Journal of colloid and interface science.
2016 Dec; 483(?):201-210. doi:
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Transfusion.
2016 12; 56(12):2964-2972. doi:
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Journal of biochemical and molecular toxicology.
2016 Dec; 30(12):588-592. doi:
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Bioresource technology.
2016 Oct; 218(?):77-83. doi:
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Journal of the science of food and agriculture.
2016 Oct; 96(13):4345-50. doi:
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Journal of proteomics.
2016 08; 145(?):207-213. doi:
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Plant, cell & environment.
2016 Apr; 39(4):804-22. doi:
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Langmuir : the ACS journal of surfaces and colloids.
2016 Mar; 32(12):2963-74. doi:
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Chemical research in toxicology.
2016 Mar; 29(3):398-405. doi:
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Pharmaceutical research.
2016 Mar; 33(3):686-700. doi:
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The Plant journal : for cell and molecular biology.
2016 Jan; 85(1):83-95. doi:
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Renal failure.
2016; 38(1):137-41. doi:
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Journal of biotechnology.
2015 Oct; 211(?):12-9. doi:
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Journal of chromatography. A.
2015 Oct; 1415(?):100-7. doi:
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Molecular carcinogenesis.
2015 Oct; 54(10):1037-50. doi:
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International journal of biological macromolecules.
2015 Sep; 80(?):130-8. doi:
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Plant cell reports.
2015 Sep; 34(9):1629-46. doi:
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Journal of ethnopharmacology.
2015 Aug; 172(?):254-60. doi:
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The Journal of biological chemistry.
2015 Aug; 290(34):20841-20855. doi:
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Journal of cellular biochemistry.
2015 Aug; 116(8):1638-45. doi:
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Developmental and comparative immunology.
2015 Aug; 51(2):261-70. doi:
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Analytical biochemistry.
2015 Jun; 479(?):51-3. doi:
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Transfusion.
2015 Jun; 55(6 Pt 2):1545-54. doi:
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The journal of physical chemistry. B.
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Clinical and experimental medicine.
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Endocrine.
2015 Feb; 48(1):152-63. doi:
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PloS one.
2015; 10(4):e0122936. doi:
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Redox biology.
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PloS one.
2015; 10(7):e0132500. doi:
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