NSC 77678 | CAS#21339-55-9 | IDO inhibitor

MedKoo Cat#: 464502 | Name: NSC 77678

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Description:

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

NSC 77678 is an inhibitor of indoleamine 2,3-dioxygenase (IDO; Ki = 19 µM). It inhibits kynurenine production from primary human monocyte-derived IDO-positive dendritic cells and increases T cell proliferation in an allogeneic mixed lymphocyte reaction (allo-MLR) when used at a concentration of 100 µM. NSC 77678 reverses depressive-like behavior in mice in a Bacillus Calmette-Guerin inflammation-induced model of depression. Unlike 1-methyl-D-tryptophan, NSC 77678 does not have an additive effect on survival induced by cyclophosphamide in an orthotopic murine mammary carcinoma model of 4T1 tumors when administered at a dose of 400 mg/kg twice per day.

Chemical Structure

NSC 77678

CAS#21339-55-9

Theoretical Analysis

MedKoo Cat#: 464502

Name: NSC 77678

CAS#: 21339-55-9

Chemical Formula: C12H14N2O2

Exact Mass: 218.1055

Molecular Weight: 218.26

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

Price and Availability

Size	Price	Availability	Quantity
1g	USD 350.00	2 Weeks
5g	USD 550.00	2 Weeks

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Related CAS #

No Data

Synonym

NSC 77678; NSC-77678; NSC77678;

IUPAC/Chemical Name

1-methyl-L-tryptophan

InChi Key

ZADWXFSZEAPBJS-JTQLQIEISA-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-/m0/s1

SMILES Code

OC([C@H](CC1=CN(C2=CC=CC=C12)C)N)=O

Appearance

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

(S)-Indoximod (1-Methyl-L-tryptophan) is an inhibitor of indoleamine 2,3-dioxygenase (IDO).

In vitro activity:

To investigate the role of IDO in immune regulation, an effective inhibitor 1-methyl-L-tryptophan (1-MT) was used to suppress its activity in DCs. The results showed that inhibition of IDO with 1-MT significantly decreased the expression of DC marker CD86. Treatment with 1-MT did not affect the phosphorylation of the MAPK pathway in DCs. Reference: Inflammation. 2020 Oct;43(5):1780-1788. https://pubmed.ncbi.nlm.nih.gov/32435912/

In vivo activity:

Importantly, 1-L-MT protected mice from azoxymethane (AOM)/dextran sodium sulfate (DSS)-induced colon carcinogenesis, with reduced mortality, tumor number and size. What is more, IDO1-/- mice exhibited fewer tumor burdens and reduced proliferation in the neoplastic epithelium, while, 1-L-MT did not exhibit any further protective effects on IDO-/- mice, confirming the critical role of IDO and the protective effect of 1-L-MT-mediated IDO inhibition in CRC. Furthermore, 1-L-MT also alleviated CRC in Rag1-/- mice, demonstrating the modulatory effects of IDO independent of its role in modulating adaptive immunity. Reference: Int J Cancer. 2018 Sep 15;143(6):1516-1529. https://pubmed.ncbi.nlm.nih.gov/29607498/

	Solvent	mg/mL	mM
Solubility
	Aqueous acid	10.0	45.00
	DMSO	5.0	22.91

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 218.26 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.

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. Zhang L, Huang Y, Cui X, Tan X, Zhu Y, Zhou W, Wang C, Yuan G, Cao Q, Su G, Kijlstra A, Yang P. Increased Expression of Indoleamine 2,3-Dioxygenase (IDO) in Vogt-Koyanagi-Harada (VKH) Disease May Lead to a Shift of T Cell Responses Toward a Treg Population. Inflammation. 2020 Oct;43(5):1780-1788. doi: 10.1007/s10753-020-01252-7. PMID: 32435912. 2. Yu J, Du W, Yan F, Wang Y, Li H, Cao S, Yu W, Shen C, Liu J, Ren X. Myeloid-derived suppressor cells suppress antitumor immune responses through IDO expression and correlate with lymph node metastasis in patients with breast cancer. J Immunol. 2013 Apr 1;190(7):3783-97. doi: 10.4049/jimmunol.1201449. Epub 2013 Feb 25. PMID: 23440412. 3. Liu X, Zhou W, Zhang X, Ding Y, Du Q, Hu R. 1-L-MT, an IDO inhibitor, prevented colitis-associated cancer by inducing CDC20 inhibition-mediated mitotic death of colon cancer cells. Int J Cancer. 2018 Sep 15;143(6):1516-1529. doi: 10.1002/ijc.31417. Epub 2018 Apr 17. PMID: 29607498. 4. Hanihara M, Kawataki T, Oh-Oka K, Mitsuka K, Nakao A, Kinouchi H. Synergistic antitumor effect with indoleamine 2,3-dioxygenase inhibition and temozolomide in a murine glioma model. J Neurosurg. 2016 Jun;124(6):1594-601. doi: 10.3171/2015.5.JNS141901. Epub 2015 Dec 4. PMID: 26636389.

In vitro protocol:

In vivo protocol:

1. Liu X, Zhou W, Zhang X, Ding Y, Du Q, Hu R. 1-L-MT, an IDO inhibitor, prevented colitis-associated cancer by inducing CDC20 inhibition-mediated mitotic death of colon cancer cells. Int J Cancer. 2018 Sep 15;143(6):1516-1529. doi: 10.1002/ijc.31417. Epub 2018 Apr 17. PMID: 29607498. 2. Hanihara M, Kawataki T, Oh-Oka K, Mitsuka K, Nakao A, Kinouchi H. Synergistic antitumor effect with indoleamine 2,3-dioxygenase inhibition and temozolomide in a murine glioma model. J Neurosurg. 2016 Jun;124(6):1594-601. doi: 10.3171/2015.5.JNS141901. Epub 2015 Dec 4. PMID: 26636389.

1: Zhang L, Huang Y, Cui X, Tan X, Zhu Y, Zhou W, Wang C, Yuan G, Cao Q, Su G, Kijlstra A, Yang P. Increased Expression of Indoleamine 2,3-Dioxygenase (IDO) in Vogt-Koyanagi-Harada (VKH) Disease May Lead to a Shift of T Cell Responses Toward a Treg Population. Inflammation. 2020 Oct;43(5):1780-1788. doi: 10.1007/s10753-020-01252-7. PMID: 32435912. 2: Shi J, Chen C, Ju R, Wang Q, Li J, Guo L, Ye C, Zhang D. Carboxyamidotriazole combined with IDO1-Kyn-AhR pathway inhibitors profoundly enhances cancer immunotherapy. J Immunother Cancer. 2019 Sep 11;7(1):246. doi: 10.1186/s40425-019-0725-7. PMID: 31511064; PMCID: PMC6740021. 3: Huang GL, Tao A, Miyazaki T, Khan T, Hong T, Nakagawa Y, Cabral H. PEG- Poly(1-Methyl-l-Tryptophan)-Based Polymeric Micelles as Enzymatically Activated Inhibitors of Indoleamine 2,3-Dioxygenase. Nanomaterials (Basel). 2019 May 9;9(5):719. doi: 10.3390/nano9050719. PMID: 31075929; PMCID: PMC6566635. 4: Gao W, He Y, Li F, Chai C, Zhang J, Guo J, Chen C, Wang J, Zhu H, Hu Z, Zhang Y. Antibacterial activity against drug-resistant microbial pathogens of cytochalasan alkaloids from the arthropod-associated fungus Chaetomium globosum TW1-1. Bioorg Chem. 2019 Mar;83:98-104. doi: 10.1016/j.bioorg.2018.10.020. Epub 2018 Oct 10. PMID: 30343206. 5: Oh JE, Shim KY, Lee JI, Choi SI, Baik SK, Eom YW. 1-Methyl-L-tryptophan promotes the apoptosis of hepatic stellate cells arrested by interferon-γ by increasing the expression of IFN-γRβ, IRF-1 and FAS. Int J Mol Med. 2017 Aug;40(2):576-582. doi: 10.3892/ijmm.2017.3043. Epub 2017 Jun 26. PMID: 28656203. 6: Li R, Li H, Sun Q, Liu L, Zhang C, Ren X. Indoleamine 2,3-dioxygenase regulates T cell activity through Vav1/Rac pathway. Mol Immunol. 2017 Jan;81:102-107. doi: 10.1016/j.molimm.2016.11.018. Epub 2016 Dec 5. PMID: 27930920. 7: Rana P, Sharma AK, Jain S, Deshmukh P, Bhattacharya SK, Banerjee BD, Mediratta PK. Comparison of fluoxetine and 1-methyl-L-tryptophan in treatment of depression-like illness in Bacillus Calmette-Guerin-induced inflammatory model of depression in mice. J Basic Clin Physiol Pharmacol. 2016 Nov 1;27(6):569-576. doi: 10.1515/jbcpp-2015-0120. PMID: 27508960.