Home Amines 26988-72-7
26988-72-7,MFCD00005803
Catalog No.:AA0037DS

26988-72-7 | 2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid

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Purity
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250mg
98%(HPLC)
in stock  
$178.00   $125.00
- +
1g
98%(HPLC)
in stock  
$496.00   $347.00
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5g
97%
in stock  
$2,416.00   $1,692.00
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0037DS
Chemical Name:
2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
CAS Number:
26988-72-7
Molecular Formula:
C12H14N2O2
Molecular Weight:
218.2518
MDL Number:
MFCD00005803
SMILES:
OC(=O)C(Cc1cn(c2c1cccc2)C)N
Properties
Properties
 
BP:
429.3°C at 760 mmHg  
Form:
Solid  
MP:
250 °C  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
270  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
3  
Undefined Atom Stereocenter Count:
1  
XLogP3:
-1.3  

Literature

Title: Indoleamine 2,3-dioxygenase mediates anhedonia and anxiety-like behaviors caused by peripheral lipopolysaccharide immune challenge.

Journal: Hormones and behavior 20120801

Title: Addition of an indoleamine 2,3,-dioxygenase inhibitor to B cell-depletion therapy blocks autoreactive B cell activation and recurrence of arthritis in K/BxN mice.

Journal: Arthritis and rheumatism 20120701

Title: Induction of prolonged asthma tolerance by IL-10-differentiated dendritic cells: differential impact on airway hyperresponsiveness and the Th2 immunoinflammatory response.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20120701

Title: Effects of indoleamine 2,3-dioxygenases in carbon tetrachloride-induced hepatitis model of rats.

Journal: Cell biochemistry and function 20120601

Title: Suppression of azoxymethane-induced colonic preneoplastic lesions in rats by 1-methyltryptophan, an inhibitor of indoleamine 2,3-dioxygenase.

Journal: Cancer science 20120501

Title: Novel Cβ-Cγ bond cleavages of tryptophan-containing peptide radical cations.

Journal: Journal of the American Society for Mass Spectrometry 20120201

Title: Activated CD69+ T cells foster immune privilege by regulating IDO expression in tumor-associated macrophages.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20120201

Title: IDO and regulatory T cell support are critical for cytotoxic T lymphocyte-associated Ag-4 Ig-mediated long-term solid organ allograft survival.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20120101

Title: The indoleamine 2,3-dioxygenase inhibitor 1-methyl-tryptophan suppresses mitochondrial function, induces aerobic glycolysis and decreases interleukin-10 production in human lymphocytes.

Journal: Immunological investigations 20120101

Title: M. tuberculosis induces potent activation of IDO-1, but this is not essential for the immunological control of infection.

Journal: PloS one 20120101

Title: Immunological and nonimmunological effects of indoleamine 2,3-dioxygenase on breast tumor growth and spontaneous metastasis formation.

Journal: Clinical & developmental immunology 20120101

Title: Amelioration of 2,4,6-trinitrobenzene sulfonic acid-induced colitis in mice by immunoregulatory dendritic cells.

Journal: Journal of gastroenterology 20111201

Title: Indoleamine 2,3-dioxygenase expression in human cancers: clinical and immunologic perspectives.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20111115

Title: Structure-activity relationship and enzyme kinetic studies on 4-aryl-1H-1,2,3-triazoles as indoleamine 2,3-dioxygenase (IDO) inhibitors.

Journal: European journal of medicinal chemistry 20111101

Title: The role of indoleamine 2, 3-dioxygenase in lepromatous leprosy immunosuppression.

Journal: Clinical and experimental immunology 20110801

Title: Contribution of dehydroepiandrosterone sulfate and progesterone to in vitro regulation of tolerogenic activity of IFN-α-induced dendritic cells.

Journal: Bulletin of experimental biology and medicine 20110601

Title: Structure and reaction mechanism in the heme dioxygenases.

Journal: Biochemistry 20110412

Title: Expression of indoleamine 2,3-dioxygenase in acute myeloid leukemia and the effect of its inhibition on cultured leukemia blast cells.

Journal: Medical oncology (Northwood, London, England) 20110301

Title: A biological pathway linking inflammation and depression: activation of indoleamine 2,3-dioxygenase.

Journal: Neuropsychiatric disease and treatment 20110101

Title: Peripheral anti-inflammatory effects explain the ginsenosides paradox between poor brain distribution and anti-depression efficacy.

Journal: Journal of neuroinflammation 20110101

Title: Cnidarians as a source of new marine bioactive compounds--an overview of the last decade and future steps for bioprospecting.

Journal: Marine drugs 20110101

Title: Suppression of humoral immune response to hepatitis B surface antigen vaccine in BALB/c mice by 1-methyl-tryptophan co-administration.

Journal: Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences 20110101

Title: Indoleamine 2,3-dioxygenase-expressing leukemic dendritic cells impair a leukemia-specific immune response by inducing potent T regulatory cells.

Journal: Haematologica 20101201

Title: Novel 1-alkyl-tryptophan derivatives downregulate IDO1 and IDO2 mRNA expression induced by interferon-gamma in dendritic cells.

Journal: Molecular and cellular biochemistry 20100901

Title: Induction of indoleamine 2,3-dioxygenase by interferon-gamma in human lens epithelial cells: apoptosis through the formation of 3-hydroxykynurenine.

Journal: The international journal of biochemistry & cell biology 20100901

Title: A combination of the metabolic enzyme inhibitor APO866 and the immune adjuvant L-1-methyl tryptophan induces additive antitumor activity.

Journal: Experimental biology and medicine (Maywood, N.J.) 20100701

Title: The role of indoleamine 2,3-dioxygenase in retinal pigment epithelial cell-mediated immune modulation.

Journal: Ocular immunology and inflammation 20100101

Title: Discrepancy between the in vitro and in vivo effects of murine mesenchymal stem cells on T-cell proliferation and collagen-induced arthritis.

Journal: Arthritis research & therapy 20100101

Title: Role of 4-1BB receptor in the control played by CD8(+) T cells on IFN-gamma production by Mycobacterium tuberculosis antigen-specific CD4(+) T Cells.

Journal: PloS one 20100101

Title: Divergent modulation of Chlamydia pneumoniae infection cycle in human monocytic and endothelial cells by iron, tryptophan availability and interferon gamma.

Journal: Immunobiology 20100101

Title: Psychological stress-induced, IDO1-dependent tryptophan catabolism: implications on immunosuppression in mice and humans.

Journal: PloS one 20100101

Title: Therapeutic potential of human umbilical cord mesenchymal stem cells in the treatment of rheumatoid arthritis.

Journal: Arthritis research & therapy 20100101

Title: Role of the immunosuppressive enzyme indoleamine 2,3-dioxygenase in the progression of ovarian carcinoma.

Journal: Gynecologic oncology 20091101

Title: IDO and outcomes in ovarian cancer.

Journal: Gynecologic oncology 20091101

Title: Neuronal damage and protection in the pathophysiology and treatment of psychiatric illness: stress and depression.

Journal: Dialogues in clinical neuroscience 20090901

Title: Efficacy of levo-1-methyl tryptophan and dextro-1-methyl tryptophan in reversing indoleamine-2,3-dioxygenase-mediated arrest of T-cell proliferation in human epithelial ovarian cancer.

Journal: Cancer research 20090701

Title: Soluble mediators from mesenchymal stem cells suppress T cell proliferation by inducing IL-10.

Journal: Experimental & molecular medicine 20090531

Title: Lipopolysaccharide-induced depressive-like behavior is mediated by indoleamine 2,3-dioxygenase activation in mice.

Journal: Molecular psychiatry 20090501

Title: Allostimulatory activity of bone marrow-derived plasmacytoid dendritic cells is independent of indoleamine dioxygenase but regulated by inducible costimulator ligand expression.

Journal: Human immunology 20090501

Title: Indoleamine 2,3 dioxygenase-mediated tryptophan catabolism regulates accumulation of Th1/Th17 cells in the joint in collagen-induced arthritis.

Journal: Arthritis and rheumatism 20090501

Title: Induction of IDO by bacille Calmette-Guérin is responsible for development of murine depressive-like behavior.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20090301

Title: Substrate promiscuity of the cyclic dipeptide prenyltransferases from Aspergillus fumigatus ( section sign).

Journal: Journal of natural products 20090101

Title: Kynurenine pathway metabolites in humans: disease and healthy States.

Journal: International journal of tryptophan research : IJTR 20090101

Title: Interaction of tryptophan derivatives with SLC6A14 (ATB0,+) reveals the potential of the transporter as a drug target for cancer chemotherapy.

Journal: The Biochemical journal 20080915

Title: Synthesis of indoleamine 2,3-dioxygenase inhibitory analogues of the sponge alkaloid exiguamine A.

Journal: Journal of medicinal chemistry 20080508

Title: Indoleamine 2,3-dioxygenase-dependent tryptophan metabolites contribute to tolerance induction during allergen immunotherapy in a mouse model.

Journal: The Journal of allergy and clinical immunology 20080401

Title: Antimicrobial and immunoregulatory effects mediated by human lung cells: role of IFN-gamma-induced tryptophan degradation.

Journal: FEMS immunology and medical microbiology 20080301

Title: Levo- but not dextro-1-methyl tryptophan abrogates the IDO activity of human dendritic cells.

Journal: Blood 20080215

Title: Increased striatal serotonin synthesis following cortical resection in children with intractable epilepsy.

Journal: Epilepsy research 20080201

Title: Uveal melanoma expression of indoleamine 2,3-deoxygenase: establishment of an immune privileged environment by tryptophan depletion.

Journal: Experimental eye research 20071101

Title: Effect of Kidney-replenishing herb on the indoleamine 2,3-dioxygenase of human syncytiotrophoblasts cultured in vitro and the balance of helper T-cell cytokines.

Journal: Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20071101

Title: Nitric oxide and indoleamine 2,3-dioxygenase mediate CTLA4Ig-induced survival in heart allografts in rats.

Journal: Transplantation 20071027

Title: The blockade of T-cell co-stimulation as a therapeutic stratagem for immunosuppression: Focus on belatacept.

Journal: Biologics : targets & therapy 20070901

Title: Indoleamine 2, 3-dioxygenase expression in cells of human acute monocyte leukemia (M(5)) and acute lymphocyte leukemia and therapeutic effect of its inhibitor 1-methyl tryptophan.

Journal: Zhongguo shi yan xue ye xue za zhi 20070601

Title: IL-8 and IDO expression by human gingival fibroblasts via TLRs.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20070115

Title: Indoleamine 2,3-dioxygenase (IDO) is involved in promoting the development of anterior chamber-associated immune deviation.

Journal: Immunology letters 20061115

Title: Hydrophobic effect and hydrogen bonds account for the improved activity of a complement inhibitor, compstatin.

Journal: Journal of medicinal chemistry 20060727

Title: Inhibition of histidine ammonia lyase by heteroaryl-alanines and acrylates.

Journal: Chemistry & biodiversity 20060501

Title: Influenza-induced expression of indoleamine 2,3-dioxygenase enhances interleukin-10 production and bacterial outgrowth during secondary pneumococcal pneumonia.

Journal: The Journal of infectious diseases 20060115

Title: CD8 alpha+, but not CD8 alpha-, dendritic cells tolerize Th2 responses via contact-dependent and -independent mechanisms, and reverse airway hyperresponsiveness, Th2, and eosinophil responses in a mouse model of asthma.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20050801

Title: Inhibition of indoleamine 2,3-dioxygenase, an immunoregulatory target of the cancer suppression gene Bin1, potentiates cancer chemotherapy.

Journal: Nature medicine 20050301

Title: Interferon-gamma-modified dendritic cells suppress B cell function and ameliorate the development of experimental autoimmune myasthenia gravis.

Journal: Clinical and experimental immunology 20041101

Title: 4-1BB-mediated immunotherapy of rheumatoid arthritis.

Journal: Nature medicine 20041001

Title: Indoleamine 2,3-dioxygenase activity and L-tryptophan transport in human breast cancer cells.

Journal: Biochimica et biophysica acta 20040210

Title: Inhibition of indoleamine 2,3-dioxygenase suppresses NK cell activity and accelerates tumor growth.

Journal: Journal of experimental therapeutics & oncology 20030101

Title: IDO (indolamine 2,3-dioxygenase) expression and function in the CNS.

Journal: Advances in experimental medicine and biology 20030101

Title: Reproducing tna operon regulation in vitro in an S-30 system. Tryptophan induction inhibits cleavage of TnaC peptidyl-tRNA.

Journal: The Journal of biological chemistry 20010119

Title: 1-Methyl-DL-tryptophan, beta-(3-benzofuranyl)-DL-alanine (the oxygen analog of tryptophan), and beta-[3-benzo(b)thienyl]-DL-alanine (the sulfur analog of tryptophan) are competitive inhibitors for indoleamine 2,3-dioxygenase.

Journal: Archives of biochemistry and biophysics 19911201

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Tags:26988-72-7 Molecular Formula|26988-72-7 MDL|26988-72-7 SMILES|26988-72-7 2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid |Heterocyclic_Building_Blocks