Home Other Building Blocks 1-Methyl-D-tryptophan

1-Methyl-D-tryptophan

CAS No.:
110117-83-4
Catalog Number:
AG0032T7
Molecular Formula:
C12H14N2O2
Molecular Weight:
218.2518
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
97%
In Stock USA
United States
$113
- +
5g
97%
In Stock USA
United States
$400
- +
Product Description
Catalog Number:
AG0032T7
Chemical Name:
1-Methyl-D-tryptophan
CAS Number:
110117-83-4
Molecular Formula:
C12H14N2O2
Molecular Weight:
218.2518
MDL Number:
MFCD00274271
IUPAC Name:
(2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid
InChI:
InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)/t10-/m1/s1
InChI Key:
ZADWXFSZEAPBJS-SNVBAGLBSA-N
SMILES:
OC(=O)[C@@H](Cc1cn(c2c1cccc2)C)N
UNII:
TX5CYN1KMZ
NSC Number:
721782
Properties
Complexity:
270  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
218.106g/mol
Formal Charge:
0
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
218.256g/mol
Monoisotopic Mass:
218.106g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
68.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.3  
Literature
Title Journal
IDO2 is critical for IDO1-mediated T-cell regulation and exerts a non-redundant function in inflammation. International immunology 20140701
Indoleamine 2,3-dioxygenase 2 (IDO2) and the kynurenine pathway: characteristics and potential roles in health and disease. Amino acids 20131201
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. Arthritis and rheumatism 20120701
Effects of indoleamine 2,3-dioxygenases in carbon tetrachloride-induced hepatitis model of rats. Cell biochemistry and function 20120601
Suppression of azoxymethane-induced colonic preneoplastic lesions in rats by 1-methyltryptophan, an inhibitor of indoleamine 2,3-dioxygenase. Cancer science 20120501
The role of indoleamine 2, 3 dioxygenase in regulating host immunity to leishmania infection. Journal of biomedical science 20120101
Modulation of tumor tolerance in primary central nervous system malignancies. Clinical & developmental immunology 20120101
Targeting multiple-myeloma-induced immune dysfunction to improve immunotherapy outcomes. Clinical & developmental immunology 20120101
Altered tryptophan metabolism as a paradigm for good and bad aspects of immune privilege in chronic inflammatory diseases. Frontiers in immunology 20120101
Purification and kinetic characterization of human indoleamine 2,3-dioxygenases 1 and 2 (IDO1 and IDO2) and discovery of selective IDO1 inhibitors. Biochimica et biophysica acta 20111201
Novel action of 3,4-DAA ameliorating acute liver allograft injury. Cell biochemistry and function 20111201
Imatinib potentiates antitumor T cell responses in gastrointestinal stromal tumor through the inhibition of Ido. Nature medicine 20110901
The role of indoleamine 2, 3-dioxygenase in lepromatous leprosy immunosuppression. Clinical and experimental immunology 20110801
Contribution of dehydroepiandrosterone sulfate and progesterone to in vitro regulation of tolerogenic activity of IFN-α-induced dendritic cells. Bulletin of experimental biology and medicine 20110601
Vascular expression, activity and function of indoleamine 2,3-dioxygenase-1 following cerebral ischaemia-reperfusion in mice. Naunyn-Schmiedeberg's archives of pharmacology 20110501
Expression of indoleamine 2,3-dioxygenase in acute myeloid leukemia and the effect of its inhibition on cultured leukemia blast cells. Medical oncology (Northwood, London, England) 20110301
Interferon-γ regulates the proliferation and differentiation of mesenchymal stem cells via activation of indoleamine 2,3 dioxygenase (IDO). PloS one 20110101
The indoleamine-2,3-dioxygenase (IDO) inhibitor 1-methyl-D-tryptophan upregulates IDO1 in human cancer cells. PloS one 20110101
Vascular endothelial expression of indoleamine 2,3-dioxygenase 1 forms a positive gradient towards the feto-maternal interface. PloS one 20110101
Suppression of humoral immune response to hepatitis B surface antigen vaccine in BALB/c mice by 1-methyl-tryptophan co-administration. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences 20110101
Indoleamine 2,3-dioxygenase-expressing leukemic dendritic cells impair a leukemia-specific immune response by inducing potent T regulatory cells. Haematologica 20101201
Mesenchymal stem cells inhibit complement activation by secreting factor H. Stem cells and development 20101101
Ability of IDO to attenuate liver injury in alpha-galactosylceramide-induced hepatitis model. Journal of immunology (Baltimore, Md. : 1950) 20101015
Inhibitor of indoleamine-2,3-dioxygenase 1-methyl-D-tryptophan can stimulate the growth of immunogenic tumors. Bulletin of experimental biology and medicine 20101001
Biochemical characteristics and inhibitor selectivity of mouse indoleamine 2,3-dioxygenase-2. Amino acids 20100701
A combination of the metabolic enzyme inhibitor APO866 and the immune adjuvant L-1-methyl tryptophan induces additive antitumor activity. Experimental biology and medicine (Maywood, N.J.) 20100701
Rational design of indoleamine 2,3-dioxygenase inhibitors. Journal of medicinal chemistry 20100211
The role of indoleamine 2,3-dioxygenase in retinal pigment epithelial cell-mediated immune modulation. Ocular immunology and inflammation 20100101
Melanoma: a model for testing new agents in combination therapies. Journal of translational medicine 20100101
Divergent modulation of Chlamydia pneumoniae infection cycle in human monocytic and endothelial cells by iron, tryptophan availability and interferon gamma. Immunobiology 20100101
Psychological stress-induced, IDO1-dependent tryptophan catabolism: implications on immunosuppression in mice and humans. PloS one 20100101
Role of the immunosuppressive enzyme indoleamine 2,3-dioxygenase in the progression of ovarian carcinoma. Gynecologic oncology 20091101
IDO and outcomes in ovarian cancer. Gynecologic oncology 20091101
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. Cancer research 20090701
Lipopolysaccharide-induced depressive-like behavior is mediated by indoleamine 2,3-dioxygenase activation in mice. Molecular psychiatry 20090501
Allostimulatory activity of bone marrow-derived plasmacytoid dendritic cells is independent of indoleamine dioxygenase but regulated by inducible costimulator ligand expression. Human immunology 20090501
Combined effect of antiretroviral therapy and blockade of IDO in SIV-infected rhesus macaques. Journal of immunology (Baltimore, Md. : 1950) 20090401
Indoleamine 2,3-dioxygenase-2; a new enzyme in the kynurenine pathway. The international journal of biochemistry & cell biology 20090301
Expression of indoleamine 2,3-dioxygenase in nasopharyngeal carcinoma impairs the cytolytic function of peripheral blood lymphocytes. BMC cancer 20090101
Overexpression of indoleamine 2,3-dioxygenase in human endometrial carcinoma cells induces rapid tumor growth in a mouse xenograft model. Clinical cancer research : an official journal of the American Association for Cancer Research 20081115
The indoleamine 2,3-dioxygenase pathway is essential for human plasmacytoid dendritic cell-induced adaptive T regulatory cell generation. Journal of immunology (Baltimore, Md. : 1950) 20081015
Interaction of tryptophan derivatives with SLC6A14 (ATB0,+) reveals the potential of the transporter as a drug target for cancer chemotherapy. The Biochemical journal 20080915
Indoleamine 2,3-dioxygenase expression promotes renal ischemia-reperfusion injury. American journal of physiology. Renal physiology 20080701
Antimicrobial and immunoregulatory effects mediated by human lung cells: role of IFN-gamma-induced tryptophan degradation. FEMS immunology and medical microbiology 20080301
Levo- but not dextro-1-methyl tryptophan abrogates the IDO activity of human dendritic cells. Blood 20080215
Increased striatal serotonin synthesis following cortical resection in children with intractable epilepsy. Epilepsy research 20080201
Toxicology and pharmacokinetics of 1-methyl-d-tryptophan: absence of toxicity due to saturating absorption. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080101
Abatacept modulates human dendritic cell-stimulated T-cell proliferation and effector function independent of IDO induction. Clinical immunology (Orlando, Fla.) 20080101
HIV-induced type I interferon and tryptophan catabolism drive T cell dysfunction despite phenotypic activation. PloS one 20080101
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. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20071101
Nitric oxide and indoleamine 2,3-dioxygenase mediate CTLA4Ig-induced survival in heart allografts in rats. Transplantation 20071027
Proapoptotic activity of indoleamine 2,3-dioxygenase expressed in renal tubular epithelial cells. American journal of physiology. Renal physiology 20070901
Novel tryptophan catabolic enzyme IDO2 is the preferred biochemical target of the antitumor indoleamine 2,3-dioxygenase inhibitory compound D-1-methyl-tryptophan. Cancer research 20070801
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. Zhongguo shi yan xue ye xue za zhi 20070601
Synovial autoreactive T cells in rheumatoid arthritis resist IDO-mediated inhibition. Journal of immunology (Baltimore, Md. : 1950) 20061201
Indoleamine 2,3-dioxygenase participates in the interferon-gamma-induced cell death process in cultured bovine luteal cells. Biology of reproduction 20060301
Inhibition of indoleamine 2,3-dioxygenase (IDO) enhances elimination of virus-infected macrophages in an animal model of HIV-1 encephalitis. Blood 20051001
Temperature-sensitive polymer-conjugated IFN-gamma induces the expression of IDO mRNA and activity by fibroblasts populated in collagen gel (FPCG). Journal of cellular physiology 20041001
Expression of indoleamine 2,3-dioxygenase by plasmacytoid dendritic cells in tumor-draining lymph nodes. The Journal of clinical investigation 20040715
Properties