L-Selenomethionine - 10mM in Water , CAS No.3211-76-5

CAS: 3211-76-5 Cat. No.: L423306 Peso molecular: 196.11 Beilstein Registry Number: 2410901 Número EC: 608-705-0

GRADE & PURITY 10mM in Water

Synonyms

L-(+)-Selenomethionine | L(+)-Selenomethionine | Megavite RX | CHEBI:30021 | Butanoic acid, 2-amino-4-(methylseleno)-, (S)- | SR-01000395830 | (2S)-2-amino-4-(methylseleno)butanoic acid | 2-Amino-4-(methylselenyl)butyrate | NCGC00181044-01 | Pharmakon1600

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

L-Selenomethionine displays antioxidant activity and has been shown to increase the activity of glutathione peroxidase in endothelial cells. Glutathione peroxidase protects cells from oxidative damage, such as DNA strand breaks, mutations and interference with protein tyrosine-based signaling and other protein functions due to formation of 3-nitrotyrosine, caused by excessive peroxynitrite. L-Selenomethionine administration to cancer cell lines (MCF-7/S breast carcinoma, DU-145 prostate cancer cells and UACC-375 melanoma) results in apoptotic cell death and aberrant mitosis. These human tumor cell lines exhibited dose-dependent growth inhibition by L-Selenomethionine in the micromolar range (45 to 130 μM), while growth inhibition of normal fibroblasts required 1 mM L-Selenomethionine.
A compound shown to increase expression of glutathione peroxidase

Specifications

Sinónimos

L-(+)-Selenomethionine | L(+)-Selenomethionine | Megavite RX | CHEBI:30021 | Butanoic acid, 2-amino-4-(methylseleno)-, (S)- | SR-01000395830 | (2S)-2-amino-4-(methylseleno)butanoic acid | 2-Amino-4-(methylselenyl)butyrate | NCGC00181044-01 | Pharmakon1600

Especificaciones y pureza

10mM in Water

Mecanismos bioquímicos y fisiológicos

Seleno-L-methionine displays antioxidant activity and has been shown to increase the activity of glutathione peroxidase in endothelial cells. Glutathione peroxidase protects cells from oxidative damage, such as DNA strand breaks, mutations and interferenc

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nombres e identificadores

• Sonrisas canónicas: C[Se]CCC(C(=O)O)N
• IUPAC Name: (2S)-2-amino-4-methylselanylbutanoic acid
• InChIKey: RJFAYQIBOAGBLC-BYPYZUCNSA-N
• INCHI: 1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
• Isómeros SMILES: C[Se]CC[C@@H](C(=O)O)N
• WGK Alemania: 3
• RTECS: EK7713840
• Peso molecular: 196.11
• Beilstein: 2410901
• Reaxy-Rn: 1758204
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1758204&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acids
              • Level8 L-alpha-amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
• Direct Parent: L-alpha-amino acids
• Alternative Parents: Fatty acids and conjugates Amino acids Selenoethers Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: L-alpha-amino acid - Fatty acid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Selenoether - Amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Primary amine - Organoselenium compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Primary aliphatic amine - Organic nitrogen compound - Carbonyl group - Aliphatic acyclic compound
• Descripción: This compound 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.
• External Descriptors: amino acid zwitterion

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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DU-145 (51482 Activities)

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HT-29 (80576 Activities)

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MCF7S (266 Activities)

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A549 (127892 Activities)

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UACC-375 (113 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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Objetivos asociados (no humanos)

Hdac6 Histone deacetylase 6 (222 Activities)

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Plasmodium falciparum (966862 Activities)

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V79 (1637 Activities)

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ddn Putative uncharacterized protein (49 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Heat and Moisture Sensitive
• Rotación específica [α]: 18° (C=0.5,2mol/L HCl)
• Punto de fusión (°C): 267 °C(dec.)
• Peso molecular: 196.120 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 196.995 Da
• Monoisotopic Mass: 196.995 Da
• Topological Polar Surface Area: 63.300 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 97.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

Referencias

1. Fei Yuxiang, Li Tao, Wu Ruoyu, Xu Xuejiao, Hu Sheng, Yang Ya, Jin Chenchen, Tang Wenlian, Zhang Xu, Du Qianming, Liu Chao.  (2023)  Se-(Methyl)-selenocysteine ameliorates blood-brain barrier disruption of focal cerebral ischemia mice via ferroptosis inhibition and tight junction upregulation in an Akt/GSK3β-dependent manner.  PSYCHOPHARMACOLOGY,      [PMID:38019326] [10.1007/s00213-023-06495-4]

2. Jingjing Sun, Changying Song, Dongying Ma, Shigang Shen, Shuying Huo.  (2021)  Expanding the Toolbox for Peptide Disulfide Bond Formation via l-Methionine Selenoxide Oxidation.  JOURNAL OF ORGANIC CHEMISTRY,      [PMID:33620221] [10.1021/acs.joc.0c02877]

3. Junjie Hu, Fei Liu, Nan Feng, Huangxian Ju.  (2019)  Selenium-isotopic signature toward mass spectrometric identification and enzyme activity assay.  ANALYTICA CHIMICA ACTA,      [PMID:30982506] [10.1016/j.aca.2019.03.045]

4. Haipeng He, Lei Chen, Jiaxin Peng, Jinyan Guo, Xue Xiao, Chaoxun Dou, Huining Chen, Songbiao Zhan, Xue Han, Weifeng Yao.  (2025)  ROS-responsive nanoparticles with Selenomethionine for ferroptosis modulation in abdominal aortic aneurysm.  iScience,      [PMID:40104069] [10.1016/j.isci.2025.111880]

5. Siyu Li, Zhaorong Ouyang, Mengjie Zhang, Shuai Guo, Biao Cai, Houli Liu.  (2024)  Selenomethionine-Conjugated Extracellular Vesicles for ROS-Mediated Cell Apoptosis.  ACS Applied Nano Materials,      [PMID:] [10.1021/acsanm.4c01793]

6. Huang Haoyang, Liu Shaowei, Xu Ligeng, Liang Hengrui, Wu Zihao, Chen Tianfeng, Wang Jinlin, Liu Jun.  (2025)  Translational selenium nanomedicine synergizes with nab-paclitaxel to enhance antitumor effects in esophageal squamous cell cancer via selenoprotein N-mediated ER stress.  JOURNAL OF NANOBIOTECHNOLOGY,  23  (1): (1-18).  [PMID:40229875] [10.1186/s12951-025-03356-4]

7. Xin Fu, Yuxiang Liu, Lixia Wang, Xiaolong Li, Rui Shu, Tiantian Yao, Jian Jiao, Xiaoyan Zhao, Jingjuan Li, Yihui Zhang, Jianwei Gao, Fengde Wang.  (2025)  Selenomethionine regulates flavonoid biosynthesis through the BroMYB34–BroCHSs module in kale (Brassica oleracea var. acephala).  Vegetable Research,  5  (1):   [PMID:] [10.48130/vegres-0025-0030]