Home Other Building Blocks Methaneseleninic acid(6CI,8CI,9CI)

Methaneseleninic acid(6CI,8CI,9CI)

CAS No.:
28274-57-9
Catalog Number:
AG007L0F
Molecular Formula:
CH4O2Se
Molecular Weight:
127.0013
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Purity
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Product Description
Catalog Number:
AG007L0F
Chemical Name:
Methaneseleninic acid(6CI,8CI,9CI)
CAS Number:
28274-57-9
Molecular Formula:
CH4O2Se
Molecular Weight:
127.0013
MDL Number:
MFCD03093983
IUPAC Name:
methaneseleninic acid
InChI:
InChI=1S/CH4O2Se/c1-4(2)3/h1H3,(H,2,3)
InChI Key:
UEQANLFPOFICBH-UHFFFAOYSA-N
SMILES:
C[Se](=O)O
EC Number:
608-183-4
UNII:
9900C6V162
Properties
Complexity:
33  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
127.938g/mol
Formal Charge:
0
Heavy Atom Count:
4  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
127.012g/mol
Monoisotopic Mass:
127.938g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
37.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
Methylseleninic acid and sodium selenite induce severe ER stress and subsequent apoptosis through UPR activation in PEL cells. Chemico-biological interactions 20170325
Crucial role of macrophage selenoproteins in experimental colitis. Journal of immunology (Baltimore, Md. : 1950) 20141001
Methylseleninic acid potentiates multiple types of cancer cells to ABT-737-induced apoptosis by targeting Mcl-1 and Bad. Apoptosis : an international journal on programmed cell death 20120401
Targeting Werner syndrome protein sensitizes U-2 OS osteosarcoma cells to selenium-induced DNA damage response and necrotic death. Biochemical and biophysical research communications 20120330
Methylseleninic acid downregulates hypoxia-inducible factor-1α in invasive prostate cancer. International journal of cancer 20120315
Methylseleninic acid is a novel suppressor of aromatase expression. The Journal of endocrinology 20120201
Methylseleninic acid antagonizes the cytotoxic effect of bortezomib in mantle cell lymphoma cell lines through modulation of Bcl-2 family proteins. British journal of haematology 20120101
Methylseleninic acid enhances paclitaxel efficacy for the treatment of triple-negative breast cancer. PloS one 20120101
Prolyl hydroxylase 2 dependent and Von-Hippel-Lindau independent degradation of Hypoxia-inducible factor 1 and 2 alpha by selenium in clear cell renal cell carcinoma leads to tumor growth inhibition. BMC cancer 20120101
Comparison of different selenocompounds with respect to nutritional value vs. toxicity using liver cells in culture. The Journal of nutritional biochemistry 20111001
Lobe-specific lineages of carcinogenesis in the transgenic adenocarcinoma of mouse prostate and their responses to chemopreventive selenium. The Prostate 20110915
Methylseleninic acid inhibits HDAC activity in diffuse large B-cell lymphoma cell lines. Cancer chemotherapy and pharmacology 20110901
Selenoprotein-dependent up-regulation of hematopoietic prostaglandin D2 synthase in macrophages is mediated through the activation of peroxisome proliferator-activated receptor (PPAR) gamma. The Journal of biological chemistry 20110805
Capabilities of HPLC with APEX-Q nebulisation ICP-MS and ESI MS/MS to compare selenium uptake and speciation of non-malignant with different B cell lymphoma lines. Analytical and bioanalytical chemistry 20110201
Mouse prostate proteomes are differentially altered by supranutritional intake of four selenium compounds. Nutrition and cancer 20110101
Methaneseleninic acid is a substrate for truncated mammalian thioredoxin reductase: implications for the catalytic mechanism and redox signaling. Biochemistry 20101207
Selenium compounds activate ATM-dependent DNA damage response via the mismatch repair protein hMLH1 in colorectal cancer cells. The Journal of biological chemistry 20101022
Antioxidant and anticancer properties and mechanisms of inorganic selenium, oxo-sulfur, and oxo-selenium compounds. Cell biochemistry and biophysics 20100901
Proteomic profiling of potential molecular targets of methyl-selenium compounds in the transgenic adenocarcinoma of mouse prostate model. Cancer prevention research (Philadelphia, Pa.) 20100801
Telomerase as an important target of androgen signaling blockade for prostate cancer treatment. Molecular cancer therapeutics 20100701
Selenium compounds activate early barriers of tumorigenesis. The Journal of biological chemistry 20100416
Selenomethionine or methylseleninic acid inhibits mutagenesis of a reporter gene in mouse bone marrow. Anticancer research 20100201
Model mechanisms of sulfhydryl oxidation by methyl- and benzeneseleninic acid, inhibitors of zinc-finger transcription factors. Journal of inorganic biochemistry 20100101
Survivin gene silencing sensitizes prostate cancer cells to selenium growth inhibition. BMC cancer 20100101
Targeting the oncogenic protein beta-catenin to enhance chemotherapy outcome against solid human cancers. Molecular cancer 20100101
Thioredoxin reductase 1 ablation sensitizes colon cancer cells to methylseleninate-mediated cytotoxicity. Toxicology and applied pharmacology 20091215
Selenium modifies the osteoblast inflammatory stress response to bone metastatic breast cancer. Carcinogenesis 20091101
Negation of the cancer-preventive actions of selenium by over-expression of protein kinase Cepsilon and selenoprotein thioredoxin reductase. Carcinogenesis 20090901
In vivo molecular mediators of cancer growth suppression and apoptosis by selenium in mammary and prostate models: lack of involvement of gadd genes. Molecular cancer therapeutics 20090301
Chemotherapeutic sensitization by endoplasmic reticulum stress: increasing the efficacy of taxane against prostate cancer. Cancer biology & therapy 20090101
Locally generated methylseleninic acid induces specific inactivation of protein kinase C isoenzymes: relevance to selenium-induced apoptosis in prostate cancer cells. The Journal of biological chemistry 20081212
Prostate-derived Ets transcription factor as a favorable prognostic marker in ovarian cancer patients. International journal of cancer 20080915
Methylseleninic acid synergizes with tamoxifen to induce caspase-mediated apoptosis in breast cancer cells. Molecular cancer therapeutics 20080901
Preferential organ distribution of methylselenol source Se-methylselenocysteine relative to methylseleninic acid. Toxicology and applied pharmacology 20080215
Methylseleninic acid enhances taxane drug efficacy against human prostate cancer and down-regulates antiapoptotic proteins Bcl-XL and survivin. Clinical cancer research : an official journal of the American Association for Cancer Research 20080215
Kruppel-like factor 4 is a novel mediator of selenium in growth inhibition. Molecular cancer research : MCR 20080201
Methylation and demethylation of intermediates selenide and methylselenol in the metabolism of selenium. Toxicology and applied pharmacology 20080115
Methylseleninic acid inhibits microvascular endothelial G1 cell cycle progression and decreases tumor microvessel density. International journal of cancer 20080101
Vitamin E analog alpha-TEA, methylseleninic acid, and trans-resveratrol in combination synergistically inhibit human breast cancer cell growth. Nutrition and cancer 20080101
Novel potent organoselenium compounds as cytotoxic agents in prostate cancer cells. Bioorganic & medicinal chemistry letters 20071215
Chemosensitization of B-cell lymphomas by methylseleninic acid involves nuclear factor-kappaB inhibition and the rapid generation of other selenium species. Cancer research 20071115
Methylseleninic acid enhances the effect of etoposide to inhibit prostate cancer growth in vivo. International journal of cancer 20070915
Selenium inhibition of survivin expression by preventing Sp1 binding to its promoter. Molecular cancer therapeutics 20070901
Differential involvement of reactive oxygen species in apoptosis induced by two classes of selenium compounds in human prostate cancer cells. International journal of cancer 20070501
Methylseleninic acid inhibits PMA-stimulated pro-MMP-2 activation mediated by MT1-MMP expression and further tumor invasion through suppression of NF-kappaB activation. Carcinogenesis 20070401
Selenium sensitizes MCF-7 breast cancer cells to doxorubicin-induced apoptosis through modulation of phospho-Akt and its downstream substrates. Molecular cancer therapeutics 20070301
Selenomethionine induced transcriptional programs in human prostate cancer cells. The Journal of urology 20070201
Doxorubicin and selenium cooperatively induce fas signaling in the absence of Fas/Fas ligand interaction. Anticancer research 20070101
Availability and metabolism of 77Se-methylseleninic acid compared simultaneously with those of three related selenocompounds. Toxicology and applied pharmacology 20061115
Inhibition of androgen receptor signaling by selenite and methylseleninic acid in prostate cancer cells: two distinct mechanisms of action. Molecular cancer therapeutics 20060801
The activity of methylated and non-methylated selenium species in lymphoma cell lines and primary tumours. Annals of oncology : official journal of the European Society for Medical Oncology 20060501
Mechanisms of selenium down-regulation of androgen receptor signaling in prostate cancer. Molecular cancer therapeutics 20060401
Delineating the mechanism by which selenium deactivates Akt in prostate cancer cells. Molecular cancer therapeutics 20060201
Enhanced selenium effect on growth arrest by BiP/GRP78 knockdown in p53-null human prostate cancer cells. Oncogene 20060126
Neural network-based analysis of thiol proteomics data in identifying potential selenium targets. Preparative biochemistry & biotechnology 20060101
Endoplasmic reticulum stress signal mediators are targets of selenium action. Cancer research 20051001
PKB/AKT and ERK regulation of caspase-mediated apoptosis by methylseleninic acid in LNCaP prostate cancer cells. Carcinogenesis 20050801
Selenium disrupts estrogen receptor (alpha) signaling and potentiates tamoxifen antagonism in endometrial cancer cells and tamoxifen-resistant breast cancer cells. Molecular cancer therapeutics 20050801
Attenuation of estrogen receptor alpha (ERalpha) signaling by selenium in breast cancer cells via downregulation of ERalpha gene expression. Breast cancer research and treatment 20050801
Androgen receptor signaling intensity is a key factor in determining the sensitivity of prostate cancer cells to selenium inhibition of growth and cancer-specific biomarkers. Molecular cancer therapeutics 20050701
Selenium disrupts estrogen signaling by altering estrogen receptor expression and ligand binding in human breast cancer cells. Cancer research 20050415
Microarray Data Mining for Potential Selenium Targets in Chemoprevention of Prostate Cancer. Cancer genomics & proteomics 20050401
Methylseleninic acid potentiates apoptosis induced by chemotherapeutic drugs in androgen-independent prostate cancer cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20050315
Chemical forms of selenium for cancer prevention. Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS) 20050101
Methyl selenium metabolites decrease prostate-specific antigen expression by inducing protein degradation and suppressing androgen-stimulated transcription. Molecular cancer therapeutics 20040501
Diverse effects of methylseleninic acid on the transcriptional program of human prostate cancer cells. Molecular biology of the cell 20040201
Prostate specific antigen expression is down-regulated by selenium through disruption of androgen receptor signaling. Cancer research 20040101
Selenium compounds regulate p53 by common and distinctive mechanisms. Anticancer research 20040101
Delineation of the molecular basis for selenium-induced growth arrest in human prostate cancer cells by oligonucleotide array. Cancer research 20030101
Distinct effects of methylseleninic acid versus selenite on apoptosis, cell cycle, and protein kinase pathways in DU145 human prostate cancer cells. Molecular cancer therapeutics 20021001
Intracellular glutathione is a cofactor in methylseleninic acid-induced apoptotic cell death of human hepatoma HEPG(2) cells. Free radical biology & medicine 20020815
Induction of caspase-mediated apoptosis and cell-cycle G1 arrest by selenium metabolite methylselenol. Molecular carcinogenesis 20020701
Methylseleninate is a substrate rather than an inhibitor of mammalian thioredoxin reductase. Implications for the antitumor effects of selenium. The Journal of biological chemistry 20020322
Identification of molecular targets associated with selenium-induced growth inhibition in human breast cells using cDNA microarrays. Cancer research 20020201
Evidence of a field effect associated with mammary cancer chemoprevention by methylseleninic acid. Anticancer research 20020101
Antimitogenic and proapoptotic activities of methylseleninic acid in vascular endothelial cells and associated effects on PI3K-AKT, ERK, JNK and p38 MAPK signaling. Cancer research 20011001
Caspases as key executors of methyl selenium-induced apoptosis (anoikis) of DU-145 prostate cancer cells. Cancer research 20010401
Methylseleninic acid, a potent growth inhibitor of synchronized mouse mammary epithelial tumor cells in vitro. Biochemical pharmacology 20010201
Dimethyldiselenide and methylseleninic acid generate superoxide in an in vitro chemiluminescence assay in the presence of glutathione: implications for the anticarcinogenic activity of L-selenomethionine and L-Se-methylselenocysteine. Nutrition and cancer 20010101
Properties