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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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100 μG
CN¥4,472.02

CN¥4,472.02

Available to ship onApril 14, 2025Details

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100 μG
CN¥4,472.02

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

CN¥4,472.02

Available to ship onApril 14, 2025Details

Request a Bulk Order

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

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peptide cleavage

no cleavage

peptide cleavage

no cleavage

peptide cleavage

no cleavage

peptide cleavage

no cleavage

origin of replication

pUC (500 copies)

origin of replication

pUC (500 copies)

origin of replication

pUC (500 copies)

origin of replication

pUC (500 copies)

bacteria selection

ampicillin

bacteria selection

ampicillin

bacteria selection

ampicillin

bacteria selection

kanamycin

form

buffered aqueous solution

form

buffered aqueous solution

form

buffered aqueous solution

form

buffered aqueous solution

mol wt

size 2686 bp

mol wt

size 4310 bp

mol wt

size 4309 bp

mol wt

size 7694 bp

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 is an inihbitor of Lactate dehydrogenase-A (LDH-A, LDHA).
NHI-2 possesses highr cell permeability.[1]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000440310
    0000209094
    0000209094
    0000098455
    0000056592

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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
    Maxime Alessandri et al.
    iScience, 27(5), 109679-109679 (2024-04-24)
    Epilepsy affects millions globally with a significant portion exhibiting pharmacoresistance. Abnormal neuronal activity elevates brain lactate levels, which prompted the exploration of its receptor, the hydroxycarboxylic acid receptor 1 (HCAR1) known to downmodulate neuronal activity in physiological conditions. This study

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