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MedKoo Cat#: 206160 | Name: Indoximod
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Indoximod, also known as NLG8189 and D-1MT, is a methylated tryptophan with anti-immunosuppressive activity. 1-methyl-d-tryptophan inhibits the enzyme indoleamine 2,3-dioxygenase (IDO), which degrades the essential amino acid tryptophan, and may increase or maintain tryptophan levels important to T cell function. Tryptophan depletion is associated with immunosuppression involving T cell arrest and anergy.

Chemical Structure

Indoximod
Indoximod
CAS#110117-83-4

Theoretical Analysis

MedKoo Cat#: 206160

Name: Indoximod

CAS#: 110117-83-4

Chemical Formula: C12H14N2O2

Exact Mass: 218.1055

Molecular Weight: 218.25

Elemental Analysis: C, 66.04; H, 6.47; N, 12.84; O, 14.66

Price and Availability

Size Price Availability Quantity
200mg USD 90.00 Ready to ship
500mg USD 150.00 Ready to ship
1g USD 250.00 Ready to ship
2g USD 450.00 Ready to ship
5g USD 950.00 Ready to ship
10g USD 1,650.00 Ready to ship
20g USD 2,950.00 Ready to ship
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Related CAS #
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Synonym
Indoximod; NLG8189; NLG 8189; NLG-8189; D1MT; 1-methyl-D-tryptophan.
IUPAC/Chemical Name
(R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
InChi Key
ZADWXFSZEAPBJS-SNVBAGLBSA-N
InChi Code
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
SMILES Code
N[C@H](CC1=CN(C)C2=CC=CC=C12)C(O)=O
Appearance
White to off-white solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
        
Biological target:
Indoximod (1-Methyl-D-tryptophan; NLG-8189) is an indoleamine 2,3-dioxygenase (IDO) pathway inhibitor.
In vitro activity:
Pair-wise comparisons between 1-MT (indoximod) treatment and controls (main effect: Treatment) are presented in Table 1. Thereby, the concentrations of TRP were increased by 1-MT in Balb/C and IDO1−/− mice as well as in human blood. In both murine and human cell culture supernatants, the increased level of TRP concentration corresponded to decreased levels of KYN, and 5-HT indicating downregulation of TRP breakdown. The downstream TRP metabolite QUIN was reduced by 1-MT in mice but not in human blood, suggesting species-specific differences. The observation of a diminished degradation of TRP via KP was further supported by the results of KYN to TRP ratio, often used as a marker for IDO activity. This ratio was decreased by 1-MT at all time points both in mice and human cell cultures, indicating that 1-MT inhibited the activity of IDO. 1-MT induced an increase of KYNA in cell culture supernatants of murine splenocytes as well as in human blood, confirming studies in pigs and mice. Reference: Front Immunol. 2020; 11: 313. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7059861/
In vivo activity:
To elucidate the role of IDO in testicular immune regulation, the impact of inhibiting IDO during EAO induction was evaluated. As described in Materials and Methods, immunized rats were treated or not with a specific enzyme inhibitor 1-MT until euthanasia. Notably, rats treated with 1-MT during the immunization period developed orchitis with significantly increased severity (Fig. 8B). Testicular histopathology showed that vehicle group presented multifocal testicular damage characterized by mild infiltration of mononuclear cells and foci of ST with different degrees of germ cell sloughing. In contrast, most rats treated with 1-MT presented extended areas of severely damaged ST presenting aspermatogenesis (Fig. 8A). Epididymis of EAO rats treated with 1-MT compared to EAO vehicle group showed a higher degree of inflammation represented by interstitial immune cell infiltrates and similar sperm depletion in the tubular lumen (Fig. 8A). Reference: Sci Rep. 2019; 9: 15919. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6828782/
Solvent mg/mL mM comments
Solubility
DMSO 0.6 2.52
Water 5.0 22.91
Methanol 0.1 0.46
Acetic Acid 1.0 4.58
5% TFA 3.0 13.84
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 218.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Brincks EL, Adams J, Wang L, Turner B, Marcinowicz A, Ke J, Essmann M, Mautino LM, Allen CV, Kumar S, Vahanian N, Link C, Mautino MR. Indoximod opposes the immunosuppressive effects mediated by IDO and TDO via modulation of AhR function and activation of mTORC1. Oncotarget. 2020 Jun 23;11(25):2438-2461. doi: 10.18632/oncotarget.27646. PMID: 32637034; PMCID: PMC7321702. 2. Wirthgen E, Leonard AK, Scharf C, Domanska G. The Immunomodulator 1-Methyltryptophan Drives Tryptophan Catabolism Toward the Kynurenic Acid Branch. Front Immunol. 2020 Feb 28;11:313. doi: 10.3389/fimmu.2020.00313. PMID: 32180772; PMCID: PMC7059861. 3. Gualdoni GS, Jacobo PV, Sobarzo CM, Pérez CV, Matzkin ME, Höcht C, Frungieri MB, Hill M, Anegon I, Lustig L, Guazzone VA. Role of indoleamine 2,3-dioxygenase in testicular immune-privilege. Sci Rep. 2019 Nov 4;9(1):15919. doi: 10.1038/s41598-019- 52192-8. PMID: 31685866; PMCID: PMC6828782. 4. Wirthgen E, Otten W, Tuchscherer M, Tuchscherer A, Domanska G, Brenmoehl J, Günther J, Ohde D, Weitschies W, Seidlitz A, Scheuch E, Kanitz E. Effects of 1-Methyltryptophan on Immune Responses and the Kynurenine Pathway after Lipopolysaccharide Challenge in Pigs. Int J Mol Sci. 2018 Oct 2;19(10):3009. doi: 10.3390/ijms19103009. PMID: 30279361; PMCID: PMC6213023.
In vitro protocol:
1. Brincks EL, Adams J, Wang L, Turner B, Marcinowicz A, Ke J, Essmann M, Mautino LM, Allen CV, Kumar S, Vahanian N, Link C, Mautino MR. Indoximod opposes the immunosuppressive effects mediated by IDO and TDO via modulation of AhR function and activation of mTORC1. Oncotarget. 2020 Jun 23;11(25):2438-2461. doi: 10.18632/oncotarget.27646. PMID: 32637034; PMCID: PMC7321702. 2. Wirthgen E, Leonard AK, Scharf C, Domanska G. The Immunomodulator 1-Methyltryptophan Drives Tryptophan Catabolism Toward the Kynurenic Acid Branch. Front Immunol. 2020 Feb 28;11:313. doi: 10.3389/fimmu.2020.00313. PMID: 32180772; PMCID: PMC7059861.
In vivo protocol:
1. Gualdoni GS, Jacobo PV, Sobarzo CM, Pérez CV, Matzkin ME, Höcht C, Frungieri MB, Hill M, Anegon I, Lustig L, Guazzone VA. Role of indoleamine 2,3-dioxygenase in testicular immune-privilege. Sci Rep. 2019 Nov 4;9(1):15919. doi: 10.1038/s41598-019- 52192-8. PMID: 31685866; PMCID: PMC6828782. 2. Wirthgen E, Otten W, Tuchscherer M, Tuchscherer A, Domanska G, Brenmoehl J, Günther J, Ohde D, Weitschies W, Seidlitz A, Scheuch E, Kanitz E. Effects of 1-Methyltryptophan on Immune Responses and the Kynurenine Pathway after Lipopolysaccharide Challenge in Pigs. Int J Mol Sci. 2018 Oct 2;19(10):3009. doi: 10.3390/ijms19103009. PMID: 30279361; PMCID: PMC6213023.
1: Yim HS, Choi KM, Kim B, Jung ID, Park YM, Kang YK, Lee MG. Effect of 1-methyl-D-tryptophan and adoptive transfer of dendritic cells on polymicrobial sepsis induced by cecal content injection. Microbiol Immunol. 2013 Sep;57(9):633-9. doi: 10.1111/1348-0421.12081. PubMed PMID: 23841524. 2: Opitz CA, Litzenburger UM, Opitz U, Sahm F, Ochs K, Lutz C, Wick W, Platten M. The indoleamine-2,3-dioxygenase (IDO) inhibitor 1-methyl-D-tryptophan upregulates IDO1 in human cancer cells. PLoS One. 2011;6(5):e19823. doi: 10.1371/journal.pone.0019823. Epub 2011 May 20. PubMed PMID: 21625531; PubMed Central PMCID: PMC3098827. 3: Vasil'eva ED, Nikolin VP, Popova NA, Lushnikova EL, Kaledin VI. Inhibitor of indoleamine-2,3-dioxygenase 1-methyl-D-tryptophan can stimulate the growth of immunogenic tumors. Bull Exp Biol Med. 2010 Oct;149(5):625-7. PubMed PMID: 21165403. 4: Jia L, Schweikart K, Tomaszewski J, Page JG, Noker PE, Buhrow SA, Reid JM, Ames MM, Munn DH. Toxicology and pharmacokinetics of 1-methyl-d-tryptophan: absence of toxicity due to saturating absorption. Food Chem Toxicol. 2008 Jan;46(1):203-11. Epub 2007 Aug 10. PubMed PMID: 17868966; PubMed Central PMCID: PMC2744343.