An antiproliferative and anti-inflammatory compound
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Fumarate hydratase-IN-1

Item No. 39275

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,3aS)-rel-1-([1,1′-biphenyl]-4-ylmethyl)-1,2,3,4,5,6-hexahydro-3-[2-(methylamino)-2-oxoethyl]-2-oxo-3aH-indole-3a-carboxylic acid, ethyl ester
CAS Number
1644060-37-6
Synonyms
  • Fumarate hydratase Inhibitor 1
Molecular Formula
C27H30N2O4
Formula Weight
446.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly soluble: 0.1-1 mg/mlDMSO: Sparingly soluble: 1-10 mg/ml
SMILES
O=C1[C@@H](CC(NC)=O)[C@@]2(C(OCC)=O)C(N1CC3=CC=C(C4=CC=CC=C4)C=C3)=CCCC2
InChi Code
InChI=1S/C27H30N2O4/c1-3-33-26(32)27-16-8-7-11-23(27)29(25(31)22(27)17-24(30)28-2)18-19-12-14-21(15-13-19)20-9-5-4-6-10-20/h4-6,9-15,22H,3,7-8,16-18H2,1-2H3,(H,28,30)/t22-,27-/m1/s1
InChi Key
VFGLXHHVYNTCPD-AJTFRIOCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Fumarate hydratase-IN-1 is an antiproliferative and anti-inflammatory compound.1 It inhibits proliferation of, and induces ATP depletion in, SW620 colorectal, ACHN kidney, HCT116 colorectal, PC3 prostate, and SK-MEL-28 melanoma cancer cells in the absence, but not in the presence, of glucose in a concentration-dependent manner. Fumarate hydratase-IN-1 reduces the oxygen consumption rate (OCR) in SW620 cells in the absence of glucose (IC50 = 2.2 µM). Preincubation with fumarate hydratase-IN-1 (25 µM) reduces secretion of Ifn-γ, Tnf-α, and granzyme B from mouse CD8+ T cells when co-cultured with B16-OVA melanoma cells expressing ovalbumin.2 In vivo, fumarate hydratase-IN-1 (25 mg/kg per day) increases tumor interstitial fluid levels of fumarate and the percentage of apoptotic tumor-associated CD8+ T cells, as well as reduces the levels of tumor-associated CD44+ CD8+ T cells and survival, in a B16-OVA murine melanoma model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takeuchi, T., Schumacker, P.T., and Kozmin, S.A. Identification of fumarate hydratase inhibitors with nutrient-dependent cytotoxicity. J. Am. Chem. Soc. 137(2), 564-567 (2015).

    2. Cheng, J., Yan, J., Liu, Y., et al. Cancer-cell-derived fumarate suppresses the anti-tumor capacity of CD8+ T cells in the tumor microenvironment. Cell Metab. 35(6), 961-978 (2023).