Home Other Building Blocks L-MIMOSINE

L-MIMOSINE

CAS No.:
500-44-7
Catalog Number:
AG00DENI
Molecular Formula:
C8H10N2O4
Molecular Weight:
198.1760
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%(HPLC)
In Stock USA
United States
$87
- +
25mg
98%(HPLC)
In Stock USA
United States
$155
- +
100mg
98%(HPLC)
In Stock USA
United States
$433
- +
Product Description
Catalog Number:
AG00DENI
Chemical Name:
L-MIMOSINE
CAS Number:
500-44-7
Molecular Formula:
C8H10N2O4
Molecular Weight:
198.1760
MDL Number:
MFCD00075909
IUPAC Name:
(2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
InChI:
InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)/t5-/m0/s1
InChI Key:
WZNJWVWKTVETCG-YFKPBYRVSA-N
SMILES:
OC(=O)[C@H](Cn1ccc(=O)c(c1)O)N
EC Number:
207-905-1
UNII:
Z46B1LUI5N
Properties
Complexity:
321  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
198.064g/mol
Formal Charge:
0
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
198.178g/mol
Monoisotopic Mass:
198.064g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
104A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.5  
Literature
Title Journal
Endothelin-converting enzyme is a plausible target gene for hypoxia-inducible factor. Kidney international 20150401
Hypoxia regulates the expression of the neuromedin B receptor through a mechanism dependent on hypoxia-inducible factor-1α. PloS one 20130101
Productive performance and urinary excretion of mimosine metabolites by hair sheep grazing in a silvopastoral system with high densities of Leucaena leucocephala. Tropical animal health and production 20121201
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. Bioorganic & medicinal chemistry 20121115
Prolyl hydroxylase inhibitors increase the production of vascular endothelial growth factor in dental pulp-derived cells. Journal of endodontics 20121101
The balance of beneficial and deleterious effects of hypoxia-inducible factor activation by prolyl hydroxylase inhibitor in rat remnant kidney depends on the timing of administration. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20120801
Preparative scale isolation, purification and derivatization of mimosine, a non-proteinogenic amino acid. Amino acids 20120701
A comparative study on mimosine, 3,4-dihydroxy pyridone (3,4-DHP) and 2,3-dihydroxy pyridone (2,3-DHP), purine derivatives (PD) excretion in the urine, thyroid hormone and blood metabolites profiles of Thai swamp buffalo (Bubalus bubalis) and Murrah buffalo (Bubalus bubalis). Tropical animal health and production 20120401
Prolyl hydroxylase inhibitors increase the production of vascular endothelial growth factor by periodontal fibroblasts. Journal of periodontal research 20120401
L-Mimosine blocks cell proliferation via upregulation of B-cell translocation gene 2 and N-myc downstream regulated gene 1 in prostate carcinoma cells. American journal of physiology. Cell physiology 20120215
Mimosine arrests the cell cycle prior to the onset of DNA replication by preventing the binding of human Ctf4/And-1 to chromatin via Hif-1α activation in HeLa cells. Cell cycle (Georgetown, Tex.) 20120215
Mimosine-induced apoptosis in C6 glioma cells requires the release of mitochondria-derived reactive oxygen species and p38, JNK activation. Neurochemical research 20120201
Transient hypoxia-inducible factor activation in rat renal ablation and reduced fibrosis with L-mimosine. Nephrology (Carlton, Vic.) 20120101
HIF-independent regulation of thioredoxin reductase 1 contributes to the high levels of reactive oxygen species induced by hypoxia. PloS one 20120101
Polyphenols: key issues involved in chemoprevention of prostate cancer. Oxidative medicine and cellular longevity 20120101
Solid-phase synthesis of mimosine tetrapeptides and their inhibitory activities on neuraminidase and tyrosinase. Journal of agricultural and food chemistry 20111228
N-myc downstream regulated gene1/Cap43 overexpression suppresses tumor growth by hepatic cancer cells through cell cycle arrest at the G0/G1 phase. Cancer letters 20111101
Curcumin provides potential protection against the activation of hypoxia and prolyl 4-hydroxylase inhibitors on prostate-specific antigen expression in human prostate carcinoma cells. Molecular nutrition & food research 20111101
Upregulation of hypoxia-inducible factor 1 alpha in local vein wall is associated with enhanced venous thrombus resolution. Thrombosis research 20111001
Inhibitory effect of mimosine on polyphenoloxidase from cephalothoraxes of Pacific white shrimp (Litopenaeus vannamei). Journal of agricultural and food chemistry 20110928
Formation of dehydroalanine from mimosine and cysteine: artifacts in gas chromatography/mass spectrometry based metabolomics. Rapid communications in mass spectrometry : RCM 20110915
Pretreatment with intracoronary mimosine improves postischemic myocardial functional recovery. Surgery 20110801
Daboia russelli venom hyaluronidase: purification, characterization and inhibition by β-3-(3-hydroxy-4-oxopyridyl) α-amino-propionic Acid. Current topics in medicinal chemistry 20110101
Phosphorylation of AIB1 at mitosis is regulated by CDK1/CYCLIN B. PloS one 20110101
Tyrosinase inhibitory effect of benzoic acid derivatives and their structure-activity relationships. Journal of enzyme inhibition and medicinal chemistry 20101201
Hypoxia-inducible factor regulates osteoclast-mediated bone resorption: role of angiopoietin-like 4. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20101201
Hypoxia and upregulation of hypoxia-inducible factor 1{alpha} stimulate venous thrombus recanalization. Arteriosclerosis, thrombosis, and vascular biology 20101201
Compounds that target host cell proteins prevent varicella-zoster virus replication in culture, ex vivo, and in SCID-Hu mice. Antiviral research 20100601
Xanthine oxidase/tyrosinase inhibiting, antioxidant, and antifungal oxindole alkaloids from Isatis costata. Pharmaceutical biology 20100601
Transgenic Leucaena leucocephala expressing the Rhizobium gene pydA encoding a meta-cleavage dioxygenase shows reduced mimosine content. Plant physiology and biochemistry : PPB 20100401
Cytometry of chromatin bound Mcm6 and PCNA identifies two states in G1 that are separated functionally by the G1 restriction point. BMC cell biology 20100101
Prolyl hydroxylase inhibitors increase neoangiogenesis and callus formation following femur fracture in mice. Journal of orthopaedic research : official publication of the Orthopaedic Research Society 20091001
Aurora B kinase inhibition in mitosis: strategies for optimising the use of aurora kinase inhibitors such as AT9283. Cell cycle (Georgetown, Tex.) 20090615
Association of luteinizing hormone receptor gene expression with cell cycle progression in granulosa cells. American journal of physiology. Endocrinology and metabolism 20090601
Coat condition of ringtailed lemurs, Lemur catta, at Berenty Reserve, Madagascar: II. Coat and tail alopecia associated with Leucaena leucocepahala, 2001-2006. American journal of primatology 20090301
Synthesis of 4-pyridone-3-sulfate and an improved synthesis of 3-hydroxy-4-pyridone. Chemistry Central journal 20090101
Pyruvate carboxylase is involved in metabolism of mimosine by Rhizobium sp. strain TAL1145. Archives of microbiology 20081001
The cloned 1-aminocyclopropane-1-carboxylate (ACC) deaminase gene from Sinorhizobium sp. strain BL3 in Rhizobium sp. strain TAL1145 promotes nodulation and growth of Leucaena leucocephala. Systematic and applied microbiology 20080601
Centrosome duplication proceeds during mimosine-induced G1 cell cycle arrest. Journal of cellular physiology 20080401
Kinetic properties of catecholoxidase activity of tarantula hemocyanin. The FEBS journal 20080401
S-phase progression stimulates both the mutagenic KU-independent pathway and mutagenic processing of KU-dependent intermediates, for nonhomologous end joining. Oncogene 20080313
In search of novel agents for therapy of tropical diseases and human immunodeficiency virus. Journal of medicinal chemistry 20080124
Pharmacologic augmentation of hypoxia-inducible factor-1alpha with mimosine boosts the bactericidal capacity of phagocytes. The Journal of infectious diseases 20080115
A molecular mechanism for mimosine-induced apoptosis involving oxidative stress and mitochondrial activation. Apoptosis : an international journal on programmed cell death 20080101
Inhibition of hypoxia inducible factor hydroxylases protects against renal ischemia-reperfusion injury. Journal of the American Society of Nephrology : JASN 20080101
Kinetic properties of hexameric tyrosinase from the crustacean Palinurus elephas. Photochemistry and photobiology 20080101
Susceptibility of Autographa californica multiple nucleopolyhedrovirus to inhibitors of DNA replication. Journal of virological methods 20071201
Tyrosinase inhibitory pentacyclic triterpenes and analgesic and spasmolytic activities of methanol extracts of Rhododendron collettianum. Phytotherapy research : PTR 20071101
Cell cycle related modulations in Runx2 protein levels are independent of lymphocyte enhancer-binding factor 1 (Lef1) in proliferating osteoblasts. Journal of molecular histology 20071001
Mimosine mitigates oxidative stress in selenium deficient seedlings of Vigna radiata. Part II: mitochondrial uptake of 75selenium and mimosine. Biological trace element research 20070901
Phytotoxic effects of 21 plant secondary metabolites on Arabidopsis thaliana germination and root growth. Journal of chemical ecology 20070701
Mimosine mitigates oxidative stress in selenium deficient seedlings of Vigna radiata--Part I: Restoration of mitochondrial function. Biological trace element research 20070701
The pydA-pydB fusion gene produces an active dioxygenase-hydrolase that degrades 3-hydroxy-4-pyridone, an intermediate of mimosine metabolism. Applied microbiology and biotechnology 20070601
Prediction of tyrosinase inhibition activity using atom-based bilinear indices. ChemMedChem 20070401
Studies on cell-cycle synchronization in the asexual erythrocytic stages of Plasmodium falciparum. Parasitology 20070301
TOMOCOMD-CARDD descriptors-based virtual screening of tyrosinase inhibitors: evaluation of different classification model combinations using bond-based linear indices. Bioorganic & medicinal chemistry 20070201
Determination of growth inhibitory action point of interferon gamma on WISH cells in cell cycle progression and the window of responsiveness of the cells to the interferon. Cytokine 20070201
The mitotic manipulation of cytotrophoblast differentiation in vitro. Placenta 20070101
Expression and actions of HIF prolyl-4-hydroxylase in the rat kidneys. American journal of physiology. Renal physiology 20070101
Dragon method for finding novel tyrosinase inhibitors: Biosilico identification and experimental in vitro assays. European journal of medicinal chemistry 20070101
Plant secondary metabolites. Methods in molecular biology (Clifton, N.J.) 20070101
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. Journal of molecular graphics & modelling 20061101
Selective determination of mimosine and its dihydroxypyridinyl derivative in plant systems. Amino acids 20061001
Tyrosinase inhibition studies of cycloartane and cucurbitane glycosides and their structure-activity relationships. Bioorganic & medicinal chemistry 20060901
Oxazolones: new tyrosinase inhibitors; synthesis and their structure-activity relationships. Bioorganic & medicinal chemistry 20060901
G1/S phase synchronization using mimosine arrest. CSH protocols 20060901
Piperidones with activity against Plasmodium falciparum. Parasitology research 20060801
Distinctive activities of DNA polymerases during human DNA replication. The FEBS journal 20060701
Newt orthologue of Growth arrest-specific 6 (NvGas6) is implicated in stress response during newt forelimb regeneration. Developmental dynamics : an official publication of the American Association of Anatomists 20060301
Tyrosinase inhibitory cycloartane type triterpenoids from the methanol extract of the whole plant of Amberboa ramosa Jafri and their structure-activity relationship. Bioorganic & medicinal chemistry 20060215
Tetraketones: a new class of tyrosinase inhibitors. Bioorganic & medicinal chemistry 20060115
Antidermatophytic and bacterial activity of mimosine. Phytotherapy research : PTR 20051101
Goniothalamin induces cell cycle-specific apoptosis by modulating the redox status in MDA-MB-231 cells. European journal of pharmacology 20051017
Proteomic identification of insulin-like growth factor-binding protein-6 induced by sublethal H2O2 stress from human diploid fibroblasts. Molecular & cellular proteomics : MCP 20050901
Modulation of differentiation-related gene 1 expression by cell cycle blocker mimosine, revealed by proteomic analysis. Molecular & cellular proteomics : MCP 20050701
Tyrosinase inhibition studies of diterpenoid alkaloids and their derivatives: structure-activity relationships. Natural product research 20050701
Structure-activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues. Bioorganic & medicinal chemistry 20050516
Induction of hypoxia inducible factor-1 attenuates metabolic insults induced by 3-nitropropionic acid in rat C6 glioma cells. Journal of neurochemistry 20050501
Synthesis of methyl ether analogues of sildenafil (Viagra) possessing tyrosinase inhibitory potential. Chemistry & biodiversity 20050401
Iron-mediated H2O2 production as a mechanism for cell type-specific inhibition of tumor necrosis factor alpha-induced but not interleukin-1beta-induced IkappaB kinase complex/nuclear factor-kappaB activation. The Journal of biological chemistry 20050128
Mimosine attenuates serine hydroxymethyltransferase transcription by chelating zinc. Implications for inhibition of DNA replication. The Journal of biological chemistry 20050107
Inhibition of MCP-1 and MIP-2 chemokines in murine trichinellosis: effect of the anti-inflammatory compound L-mimosine. International journal of immunopathology and pharmacology 20050101
P-glycoprotein expression is induced in human pancreatic cancer xenografts during treatment with a cell cycle regulator, mimosine. Pathology oncology research : POR 20050101
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Rb regulates C/EBPbeta-DNA-binding activity during 3T3-L1 adipogenesis. American journal of physiology. Cell physiology 20040201
PPARgamma1 synthesis and adipogenesis in C3H10T1/2 cells depends on S-phase progression, but does not require mitotic clonal expansion. Journal of cellular biochemistry 20040201
p53-independent induction of p21(waf1/cip1) contributes to the activation of caspases in GTP-depletion-induced apoptosis of insulin-secreting cells. Cell death and differentiation 20040101
Cytotoxic activity of deferiprone, maltol and related hydroxyketones against human tumor cell lines. Anticancer research 20040101
Response of ADA and its isoenzymes in mice infected by Trichinella spiralis and treated with mimosine. International journal of immunopathology and pharmacology 20040101
Replication inhibitors modulate instability of an expanded trinucleotide repeat at the myotonic dystrophy type 1 disease locus in human cells. American journal of human genetics 20031101
Potential therapeutic applications of some antinutritional plant secondary metabolites. Journal of agricultural and food chemistry 20030910
Cell cycle synchronization of porcine granulosa cells in G1 stage with mimosine. Animal reproduction science 20030715
Activation of the hypoxia-inducible factor-pathway and stimulation of angiogenesis by application of prolyl hydroxylase inhibitors. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030601
Cell cycle inhibition mediated by the outer surface of the C/EBPalpha basic region is required but not sufficient for granulopoiesis. Oncogene 20030501
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Truffle thio-flavours reversibly inhibit truffle tyrosinase. FEMS microbiology letters 20030314
Spectroscopic characterization of the electronic changes in the active site of Streptomyces antibioticus tyrosinase upon binding of transition state analogue inhibitors. The Journal of biological chemistry 20030227
The mid genes of Rhizobium sp strain TAL1145 are required for degradation of mimosine into 3-hydroxy-4-pyridone and are inducible by mimosine. Microbiology (Reading, England) 20030201
Effect of the compound L-mimosine in an in vivo model of chronic granuloma formation induced by potassium permanganate (KMNO4). International journal of immunopathology and pharmacology 20030101
DNA breaks induction by mimosine. Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101
Mimosine, a plant-derived amino acid induces apoptosis in human pancreatic cancer xenografts. Anticancer research 20030101
Enantioseparation of chiral aromatic amino acids by capillary electrophoresis in neutral and charged cyclodextrin selector modes. Electrophoresis 20021201
Ultraviolet light-induced apoptosis is associated with S-phase in primary human fibroblasts. DNA repair 20021001
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Association between the cell cycle and neural crest delamination through specific regulation of G1/S transition. Developmental cell 20020901
Cell-cycle-dependent regulation of CNT1, a concentrative nucleoside transporter involved in the uptake of cell-cycle-dependent nucleoside-derived anticancer drugs. Biochemical and biophysical research communications 20020823
Mimosine prevents the death of glucose-deprived immunostimulated astrocytes by scavenging peroxynitrite. Glia 20020701
Inhibition of ultraviolet B (UVB) induced apoptosis in A431 cells by mimosine is not dependent on cell cycle arrest. Canadian journal of physiology and pharmacology 20020701
A novel association of the SMN protein with two major non-ribosomal nucleolar proteins and its implication in spinal muscular atrophy. Human molecular genetics 20020501
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
Modulation of intrinsic P-glycoprotein expression in multicellular prostate tumor spheroids by cell cycle inhibitors. Biochimica et biophysica acta 20020213
Survivin exists in immunochemically distinct subcellular pools and is involved in spindle microtubule function. Journal of cell science 20020201
Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53. Oncogene 20020117
Inhibition of MCP-1 and MIP-2 transcription and translation by mimosine in muscle tissue infected with the parasite Trichinella spiralis. Molecular and cellular biochemistry 20020101
The deoxyribo-mode expression of primase activities of the primase-alpha DNA polymerase enzyme complex associated with nucleoprotein complexes harboring an extrachromosomal DNA identical with avian myeloblastosis virus core-bound DNA: influencing by carbonyldiphosphonate, mimosine and butylphenyl deoxyguanosine-5'-triphosphate. Acta virologica 20020101
Lymphoblasts already in the DNA synthesis phase of the cell cycle can be reversibly arrested at the R/G transition. Chromosoma 20011201
Methylation of episomal plasmids as a barrier to transient gene expression via a synthetic delivery vector. Biomolecular engineering 20011031
A DNA polymerase epsilon inhibitor activates the ribo and deoxyribo modes of primase expression and induces a unique phenomenon of primer accumulation. FEBS letters 20010907
Characterization of homologous recombination induced by replication inhibition in mammalian cells. The EMBO journal 20010716
Selection of several classes of mimosine-degradation-defective Tn3Hogus-insertion mutants of Rhizobium sp. strain TAL1145 on the basis of mimosine-inducible GUS activity. Canadian journal of microbiology 20010601
Methods for synchronizing cells at specific stages of the cell cycle. Current protocols in cell biology 20010501
Cell cycle-related changes in regulatory volume decrease and volume-sensitive chloride conductance in mouse fibroblasts. Journal of cellular physiology 20010401
Anatomy of the primase-alpha DNA polymerase reaction accomplished by nucleoprotein complexes harboring an extrachromosomal DNA identical with avian myeloblastosis virus core-bound DNA: influencing by carbonyldiphosphonate, mimosine and butylphenyl deoxyguanosine-5'-triphosphate. Acta virologica 20010401
Kinetic analyses of mitochondrial 75selenium uptake in Trigonella foenum-graecum seedlings exposed to selenium and mimosine. Biological trace element research 20010301
MCM3AP, a novel acetyltransferase that acetylates replication protein MCM3. EMBO reports 20010215
Radiation sensitization of mammalian cells by metal chelators. Radiation research 20010201
Prevention of entrance into G2 cell cycle phase by mimosine decreases locomotion of cells from the tumor cell line SW480. Cancer letters 20010101
Uptake of 45Ca by mitochondria of Trigonella foenum-graecum as influenced by selenium and mimosine--detailed kinetic analyses. Biological trace element research 20010101
Modulation of cell cycle regulatory protein expression and suppression of tumor growth by mimosine in nude mice. International journal of oncology 20001001
Steroid hormone activity of flavonoids and related compounds. Breast cancer research and treatment 20000701
Mimosine arrests cells in G1 by enhancing the levels of p27(Kip1). Experimental cell research 20000110
Protection from oxidative stress-induced apoptosis in cortical neuronal cultures by iron chelators is associated with enhanced DNA binding of hypoxia-inducible factor-1 and ATF-1/CREB and increased expression of glycolytic enzymes, p21(waf1/cip1), and erythropoietin. The Journal of neuroscience : the official journal of the Society for Neuroscience 19991115
Inhibitory effect of mimosine on proliferation of human lung cancer cells is mediated by multiple mechanisms. Cancer letters 19991018
Antiretroviral effects of deoxyhypusyl hydroxylase inhibitors: a hypusine-dependent host cell mechanism for replication of human immunodeficiency virus type 1 (HIV-1). Biochemical pharmacology 19980601
Submicromolar paclitaxel induces apoptosis in human gastric cancer cells at early G1 phase. Anticancer research 19980101
The effect of administration of glycine and tyrosine on the growth depression caused by mimosine in rats. Zeitschrift fur Tierphysiologie, Tierernahrung und Futtermittelkunde 19830801
Properties