Indoximod
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MedKoo CAT#: 206160

CAS#: 110117-83-4

Description: 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

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Indoximod
CAS# 110117-83-4

Theoretical Analysis

MedKoo Cat#: 206160
Name: Indoximod
CAS#: 110117-83-4
Chemical Formula: C12H14N2O2
Exact Mass: 218.10553
Molecular Weight: 218.25
Elemental Analysis: C, 66.04; H, 6.47; N, 12.84; O, 14.66

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200.0mg USD 150.0 Same day
500.0mg USD 250.0 Same day
1.0g USD 450.0 Same day
5.0g USD 950.0 Same day
10.0g USD 1450.0 Same day
20.0g USD 1950.0 Same day
50.0g USD 3450.0 Same day
100.0g USD 5450.0 2 weeks
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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

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.55 2.52
Water 5.0 22.91
Methanol 0.1 0.46
Acetic Acid 1.0 4.58
5% TFA 3.02 13.84

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.

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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.

Indoximod

200.0mg / USD 150.0


Additional Information