Home Other Building Blocks 26046-90-2
26046-90-2,MFCD00800565
Catalog No.:AA002RF8

26046-90-2 | 3-(Methylseleno)-l-alanine

Pack Size
Purity
Availability
Price(USD)
Quantity
  
100mg
98%
in stock  
$56.00   $39.00
- +
250mg
98%
in stock  
$129.00   $90.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002RF8
Chemical Name:
3-(Methylseleno)-l-alanine
CAS Number:
26046-90-2
Molecular Formula:
C4H9NO2Se
Molecular Weight:
182.0798
MDL Number:
MFCD00800565
SMILES:
C[Se]C[C@@H](C(=O)O)N
Properties
Properties
 
BP:
327.976°C at 760 mmHg  
Form:
Solid  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
86.1  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
3  

Downstream Synthesis Route
seleno-L-cystine 
  74-88-4    26046-90-2 

[1]Andreadou;Menge;Commandeur;Worthington;Vermeulen[JournalofMedicinalChemistry,1996,vol.39,#10,p.2040-2046]

67-56-1    26046-90-2   
Se-methyl-L-methylselenocysteinatehydrochloride 

[1]Block,Eric;Birringer,Marc;Jiang,Weiqin;Nakahodo,Tsukasa;Thompson,HenryJ.;Toscano,PaulJ.;Uzar,Horst;Zhang,Xing;Zhu,Zongjian[JournalofAgriculturalandFoodChemistry,2001,vol.49,#1,p.458-470]

[1]Rooseboom;Vermeulen;VanHemert;Commandeur[ChemicalResearchinToxicology,2001,vol.14,#8,p.996-1005]

[1]CurrentPatentAssignee:SAMILABSLIMITED-US2008/26017,2008,A1Locationinpatent:Page/Pagecolumn7

None 
  6486-05-1    26046-90-2 

[1]CurrentPatentAssignee:PHARMASE-EP1205471,2002,A1Locationinpatent:Page6

Literature

Title: Molecular mechanisms involved in the protective effect of selenocystine against methylmercury-induced cell death in human HepG2 cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20130901

Title: A reliable solid phase microextraction-gas chromatography-triple quadrupole mass spectrometry method for the assay of selenomethionine and selenomethylselenocysteine in aqueous extracts: difference between selenized and not-enriched selenium potatoes.

Journal: Analytica chimica acta 20121017

Title: Methylselenocysteine treatment leads to diselenide formation in human cancer cells: evidence from X-ray absorption spectroscopy studies.

Journal: Biochemistry 20120124

Title: Analysis of selenomethylselenocysteine and selenomethionine by LC-ESI-MS/MS with diethyl ethoxymethylenemalonate derivatization.

Journal: The Analyst 20111221

Title: Augmented therapeutic efficacy of irinotecan is associated with enhanced drug accumulation.

Journal: Cancer letters 20111208

Title: Selenium is a modulator of circadian clock that protects mice from the toxicity of a chemotherapeutic drug via upregulation of the core clock protein, BMAL1.

Journal: Oncotarget 20111201

Title: Chemical form of selenium affects its uptake, transport, and glutathione peroxidase activity in the human intestinal Caco-2 cell model.

Journal: Biological trace element research 20111101

Title: Methyl selenocysteine: single-dose pharmacokinetics in men.

Journal: Cancer prevention research (Philadelphia, Pa.) 20111101

Title: Biofortification of tomato (Solanum lycopersicum) fruit with the anticancer compound methylselenocysteine using a selenocysteine methyltransferase from a selenium hyperaccumulator.

Journal: Journal of agricultural and food chemistry 20111026

Title: Lobe-specific lineages of carcinogenesis in the transgenic adenocarcinoma of mouse prostate and their responses to chemopreventive selenium.

Journal: The Prostate 20110915

Title: Distribution of Se and its species in Myriophyllum spicatum and Ceratophyllum demersum growing in water containing Se (VI).

Journal: Chemosphere 20110901

Title: The von Hippel-Lindau (VHL) tumor-suppressor gene is down-regulated by selenium deficiency in Caco-2 cells and rat colon mucosa.

Journal: Biological trace element research 20110801

Title: Interventions that induce modifications in the tumor microenvironment.

Journal: Cancer radiotherapie : journal de la Societe francaise de radiotherapie oncologique 20110801

Title: Methylselenocysteine: a promising antiangiogenic agent for overcoming drug delivery barriers in solid malignancies for therapeutic synergy with anticancer drugs.

Journal: Expert opinion on drug delivery 20110601

Title: Anti-hemolytic and peroxyl radical scavenging activity of organoselenium compounds: an in vitro study.

Journal: Biological trace element research 20110501

Title: Se-methylselenocysteine inhibits lipopolysaccharide-induced NF-κB activation and iNOS induction in RAW 264.7 murine macrophages.

Journal: Molecular nutrition & food research 20110501

Title: Metabolic and bioprocess engineering for production of selenized yeast with increased content of seleno-methylselenocysteine.

Journal: Metabolic engineering 20110501

Title: Uptake, distribution, and speciation of selenoamino acids by human cancer cells: X-ray absorption and fluorescence methods.

Journal: Biochemistry 20110315

Title: Magnetic resonance and fluorescence-protein imaging of the anti-angiogenic and anti-tumor efficacy of selenium in an orthotopic model of human colon cancer.

Journal: Anticancer research 20110201

Title: Mouse prostate proteomes are differentially altered by supranutritional intake of four selenium compounds.

Journal: Nutrition and cancer 20110101

Title: Selenium compounds activate ATM-dependent DNA damage response via the mismatch repair protein hMLH1 in colorectal cancer cells.

Journal: The Journal of biological chemistry 20101022

Title: Se-methylselenocysteine sensitizes hypoxic tumor cells to irinotecan by targeting hypoxia-inducible factor 1alpha.

Journal: Cancer chemotherapy and pharmacology 20101001

Title: Simultaneous analysis of mercury and selenium species including chiral forms of selenomethionine in human urine and serum by HPLC column-switching coupled to ICP-MS.

Journal: The Analyst 20101001

Title: Differential apoptotic response of human cancer cells to organoselenium compounds.

Journal: Cancer chemotherapy and pharmacology 20100801

Title: Proteomic profiling of potential molecular targets of methyl-selenium compounds in the transgenic adenocarcinoma of mouse prostate model.

Journal: Cancer prevention research (Philadelphia, Pa.) 20100801

Title: Interleukin-10 delivery via mesenchymal stem cells: a novel gene therapy approach to prevent lung ischemia-reperfusion injury.

Journal: Human gene therapy 20100601

Title: Methylselenocysteine resets the rhythmic expression of circadian and growth-regulatory genes disrupted by nitrosomethylurea in vivo.

Journal: Cancer prevention research (Philadelphia, Pa.) 20100501

Title: Selenium compounds activate early barriers of tumorigenesis.

Journal: The Journal of biological chemistry 20100416

Title: Selenium, but not lycopene or vitamin E, decreases growth of transplantable dunning R3327-H rat prostate tumors.

Journal: PloS one 20100101

Title: Survivin gene silencing sensitizes prostate cancer cells to selenium growth inhibition.

Journal: BMC cancer 20100101

Title: Selenium hyperaccumulation offers protection from cell disruptor herbivores.

Journal: BMC ecology 20100101

Title: Combination of methylselenocysteine with tamoxifen inhibits MCF-7 breast cancer xenografts in nude mice through elevated apoptosis and reduced angiogenesis.

Journal: Breast cancer research and treatment 20091101

Title: Speciation analysis of selenium metabolites in urine and breath by HPLC- and GC-inductively coupled plasma-MS after administration of selenomethionine and methylselenocysteine to rats.

Journal: Chemical research in toxicology 20091101

Title: In vitro radioprotection studies of organoselenium compounds: differences between mono- and diselenides.

Journal: Radiation and environmental biophysics 20091101

Title: Speciation of selenium dietary supplements; formation of S-(methylseleno)cysteine and other selenium compounds.

Journal: Analytica chimica acta 20091012

Title: Dietary supplementation with selenomethylselenocysteine produces a differential proteomic response.

Journal: The Journal of nutritional biochemistry 20091001

Title: Antiproliferative effects of selenium compounds in colon cancer cells: comparison of different cytotoxicity assays.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20091001

Title: Inhibition of colon cancer growth by methylselenocysteine-induced angiogenic chemomodulation is influenced by histologic characteristics of the tumor.

Journal: Clinical colorectal cancer 20090701

Title: Accumulation of an organic anticancer selenium compound in a transgenic Solanaceous species shows wider applicability of the selenocysteine methyltransferase transgene from selenium hyperaccumulators.

Journal: Transgenic research 20090601

Title: Separation and determination of seleno amino acids using gas chromatography hyphenated with inductively coupled plasma mass spectrometry after hollow fiber liquid phase microextraction.

Journal: Journal of mass spectrometry : JMS 20090501

Title: Se-methylselenocysteine sensitized TRAIL-mediated apoptosis via down-regulation of Bcl-2 expression.

Journal: International journal of oncology 20090501

Title: Methyl-selenium compounds inhibit prostate carcinogenesis in the transgenic adenocarcinoma of mouse prostate model with survival benefit.

Journal: Cancer prevention research (Philadelphia, Pa.) 20090501

Title: Selenium metabolism in rats with long-term ingestion of Se-methylselenocysteine using enriched stable isotopes.

Journal: The Journal of toxicological sciences 20090401

Title: Differential action of methylselenocysteine in control and alloxan-diabetic rabbits.

Journal: Chemico-biological interactions 20090127

Title: Differential sensitivity of various human tumour-derived cell types to apoptosis by organic derivatives of selenium.

Journal: The British journal of nutrition 20090101

Title: Organic and inorganic selenium compounds produce different protein patterns in the blood plasma of rats.

Journal: Biological research 20090101

Title: Selenium supplementation improves antioxidant capacity in vitro and in vivo in patients with coronary artery disease The SElenium Therapy in Coronary Artery disease Patients (SETCAP) Study.

Journal: American heart journal 20081201

Title: Se-methylselenocysteine alters collagen gene and protein expression in human prostate cells.

Journal: Cancer letters 20080928

Title: Long exposure of non-cytotoxic concentrations of methylselenol suppresses the invasive potential of B16F10 melanoma.

Journal: Oncology reports 20080901

Title: Hypoxia-specific drug tirapazamine does not abrogate hypoxic tumor cells in combination therapy with irinotecan and methylselenocysteine in well-differentiated human head and neck squamous cell carcinoma a253 xenografts.

Journal: Neoplasia (New York, N.Y.) 20080801

Title: Chemopreventive doses of methylselenocysteine alter circadian rhythm in rat mammary tissue.

Journal: Cancer prevention research (Philadelphia, Pa.) 20080701

Title: Tumor vascular maturation and improved drug delivery induced by methylselenocysteine leads to therapeutic synergy with anticancer drugs.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080615

Title: Subchronic oral toxicity studies of Se-methylselenocysteine, an organoselenium compound for breast cancer prevention.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080301

Title: Preferential organ distribution of methylselenol source Se-methylselenocysteine relative to methylseleninic acid.

Journal: Toxicology and applied pharmacology 20080215

Title: [Effects of Se-methylselenocysteine on biological behavior of and matrix metalloproteinase-2 expression in human breast cancer MDA-MB-231 cells].

Journal: Ai zheng = Aizheng = Chinese journal of cancer 20080201

Title: Elemental selenium at nano size (Nano-Se) as a potential chemopreventive agent with reduced risk of selenium toxicity: comparison with se-methylselenocysteine in mice.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20080101

Title: Selenium methylselenocysteine protects human hepatoma HepG2 cells against oxidative stress induced by tert-butyl hydroperoxide.

Journal: Analytical and bioanalytical chemistry 20071201

Title: Efficacy of increasing the therapeutic index of irinotecan, plasma and tissue selenium concentrations is methylselenocysteine dose dependent.

Journal: Biochemical pharmacology 20070501

Title: Selenium accumulation protects plants from herbivory by Orthoptera via toxicity and deterrence.

Journal: The New phytologist 20070101

Title: Mechanism for proliferation inhibition by various selenium compounds and selenium-enriched broccoli extract in rat glial cells.

Journal: Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine 20061201

Title: Metabolism of 76Se-methylselenocysteine compared with that of 77Se-selenomethionine and 82Se-selenite.

Journal: Toxicology and applied pharmacology 20061201

Title: Selenium-tolerant diamondback moth disarms hyperaccumulator plant defense.

Journal: Current biology : CB 20061121

Title: The mechanism of methylselenocysteine and docetaxel synergistic activity in prostate cancer cells.

Journal: Molecular cancer therapeutics 20061001

Title: Monomethylated selenium inhibits growth of LNCaP human prostate cancer xenograft accompanied by a decrease in the expression of androgen receptor and prostate-specific antigen (PSA).

Journal: The Prostate 20060701

Title: Potentiation of irinotecan sensitivity by Se-methylselenocysteine in an in vivo tumor model is associated with downregulation of cyclooxygenase-2, inducible nitric oxide synthase, and hypoxia-inducible factor 1alpha expression, resulting in reduced angiogenesis.

Journal: Oncogene 20060420

Title: Se-methylselenocysteine enhances PMA-mediated CD11c expression via phospholipase D1 activation in U937 cells.

Journal: Immunobiology 20060101

Title: [Effects of selenium and B-27 supplements on viability and differentiation of neural stem cell in newborn rat].

Journal: Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20050901

Title: Selenium protects against toxicity induced by anticancer drugs and augments antitumor activity: a highly selective, new, and novel approach for the treatment of solid tumors.

Journal: Clinical colorectal cancer 20050701

Title: Molecular and biochemical characterization of the selenocysteine Se-methyltransferase gene and Se-methylselenocysteine synthesis in broccoli.

Journal: Plant physiology 20050501

Title: Irinotecan pharmacokinetic and pharmacogenomic alterations induced by methylselenocysteine in human head and neck xenograft tumors.

Journal: Molecular cancer therapeutics 20050501

Title: Se-methylselenocysteine inhibits phosphatidylinositol 3-kinase activity of mouse mammary epithelial tumor cells in vitro.

Journal: Breast cancer research : BCR 20050101

Title: Chemical forms of selenium for cancer prevention.

Journal: Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS) 20050101

Title: Insight into the polar reactivity of the onium chalcogen analogues of S-adenosyl-L-methionine.

Journal: Biochemistry 20041026

Title: Enhanced 7-ethyl-10-hydroxycamptothecin (SN-38) lethality by methylselenocysteine is associated with Chk2 phosphorylation at threonine-68 and down-regulation of Cdc6 expression.

Journal: Molecular pharmacology 20040701

Title: Identification and synthesis of a novel selenium-sulfur amino acid found in selenized yeast: Rapid indirect detection NMR methods for characterizing low-level organoselenium compounds in complex matrices.

Journal: Journal of agricultural and food chemistry 20040616

Title: Overexpression of selenocysteine methyltransferase in Arabidopsis and Indian mustard increases selenium tolerance and accumulation.

Journal: Plant physiology 20040501

Title: Selective modulation of the therapeutic efficacy of anticancer drugs by selenium containing compounds against human tumor xenografts.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040401

Title: Methioninase and selenomethionine but not Se-methylselenocysteine generate methylselenol and superoxide in an in vitro chemiluminescent assay: implications for the nutritional carcinostatic activity of selenoamino acids.

Journal: Biochemical pharmacology 20040201

Title: Production of Se-methylselenocysteine in transgenic plants expressing selenocysteine methyltransferase.

Journal: BMC plant biology 20040101

Title: Osteopontin is a potential target gene in mouse mammary cancer chemoprevention by Se-methylselenocysteine.

Journal: Breast cancer research : BCR 20040101

Title: Induction of apoptosis by Se-MSC in U937 human leukemia cells through release of cytochrome c and activation of caspases and PKC-delta: mutual regulation between caspases and PKC-delta via a positive feedback mechanism.

Journal: International journal of molecular medicine 20031101

Title: Characteristics of selenazolidine prodrugs of selenocysteine: toxicity and glutathione peroxidase induction in V79 cells.

Journal: Journal of medicinal chemistry 20030717

Title: Incorporation of selenomethionine into proteins through selenohomocysteine-mediated ligation.

Journal: Angewandte Chemie (International ed. in English) 20030525

Title: Se-methylselenocysteine induces apoptosis through caspase activation and Bax cleavage mediated by calpain in SKOV-3 ovarian cancer cells.

Journal: Cancer letters 20020808

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Se-methylselenocysteine induces apoptosis mediated by reactive oxygen species in HL-60 cells.

Journal: Free radical biology & medicine 20010815

Title: Se-methylselenocysteine induces apoptosis through caspase activation in HL-60 cells.

Journal: Carcinogenesis 20010401

Title: Characterization of the biological activity of gamma-glutamyl-Se-methylselenocysteine: a novel, naturally occurring anticancer agent from garlic.

Journal: Cancer research 20010401

Title: Characterization of the zinc sites in cobalamin-independent and cobalamin-dependent methionine synthase using zinc and selenium X-ray absorption spectroscopy.

Journal: Biochemistry 20010130

Title: Methylselenocysteine modulates proliferation and apoptosis biomarkers in premalignant lesions of the rat mammary gland.

Journal: Anticancer research 20010101

Title: Se-methylselenocysteine activates caspase-3 in mouse mammary epithelial tumor cells in vitro.

Journal: BioFactors (Oxford, England) 20010101

Title: Chemistry and biological activity of novel selenium-containing compounds.

Journal: Advances in experimental medicine and biology 20010101

Title: Se-methylselenocysteine: a new compound for chemoprevention of breast cancer.

Journal: Nutrition and cancer 20010101

Title: 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.

Journal: Nutrition and cancer 20010101

Title: Effects of methylselenocysteine on PKC activity, cdk2 phosphorylation and gadd gene expression in synchronized mouse mammary epithelial tumor cells.

Journal: Cancer letters 19991115

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Related Products of 26046-90-2
Tags:26046-90-2 Molecular Formula|26046-90-2 MDL|26046-90-2 SMILES|26046-90-2 3-(Methylseleno)-l-alanine