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SML1463

Sigma-Aldrich

NHI-2

≥98% (HPLC)

Synonym(s):

1-Hydroxy-6-phenyl-4-(trifluoromethyl)-1H-Indole-2-carboxylic acid methyl ester, Methyl 1-hydroxy-6-phenyl-4-(trifluoromethyl)-1H-indole-2-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C17H12F3NO3
CAS Number:
1269802-97-2
Molecular Weight:
335.28
UNSPSC Code:
12352200
PubChem Substance ID:
329825897
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

ON(C(C(OC)=O)=C1)C2=C1C(C(F)(F)F)=CC(C3=CC=CC=C3)=C2

InChI

1S/C17H12F3NO3/c1-24-16(22)15-9-12-13(17(18,19)20)7-11(8-14(12)21(15)23)10-5-3-2-4-6-10/h2-9,23H,1H3

InChI key

YPPFWRWCZNXINO-UHFFFAOYSA-N

Biochem/physiol Actions

NHI-2 is an inihbitor of Lactate dehydrogenase-A (LDH-A, LDHA), a key enzyme necessary to sustain glycolysis, the major pathway used by many cancer cells for cell growth and proliferation (the Warburg effect). NHI-2 has anti-glycolytic activity against a variety of cancer cells. NHI-2 inhibited cell growth of pancreatic cancer LPC006 and PANC-1 cells and enhanced the antiproliferative effects of Gemcitabine and caused apoptosis in colon cancer HCT116 cells.
NHI-2 possesses highr cell permeability.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Carlotta Granchi et al.
Organic & biomolecular chemistry, 11(38), 6588-6596 (2013-08-30)
A head-to-head study of representative examples of N-hydroxyindole-2-carboxylates (NHI) and malonic derivatives (Mal) as LDH-A inhibitors was conducted, comparing the enzyme inhibition potency, cellular uptake, reduction of lactate production in cancer cells and anti-proliferative activity. Among the compounds tested, methyl

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