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CN

SML1327

Glutaminase Inhibitor 968

≥98% (HPLC)

Synonym(s):

5-(3-Bromo-4-(dimethylamino)phenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one

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About This Item

Empirical Formula (Hill Notation):
C27H27BrN2O
CAS Number:
311795-38-7
Molecular Weight:
475.42
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Glutaminase Inhibitor 968, ≥98% (HPLC)

SMILES string

Brc1c(ccc(c1)C2Nc3c(c5c(cc3)cccc5)C4=C2C(=O)CC(C4)(C)C)N(C)C

InChI

1S/C27H27BrN2O/c1-27(2)14-19-24-18-8-6-5-7-16(18)9-11-21(24)29-26(25(19)23(31)15-27)17-10-12-22(30(3)4)20(28)13-17/h5-13,26,29H,14-15H2,1-4H3

InChI key

NVFRRJQWRZFDLM-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

Glutaminase inhibitor 968 has been used to study the role of glutamine metabolism in macrophage activation.

Biochem/physiol Actions

Glutaminase Inhibitor 968 is an allosteric inihibitor of the mitochondrial enzyme glutaminase C (GAC), which is overexpressed in a number of cancer cell lines. Glutaminase Inhibitor 968 shows 21% inhibition at 10 μM, 94% at 25 μM. Glutaminase Inhibitor 968 blocked human cancer cell proliferation in culture, and in inhibited tumor formation in mouse xenograft models.
Glutaminase Inhibitor 968 is an allosteric inihibitor of the mitochondrial enzyme glutaminase C (GAC).
Variation in the 3-bromo-4-(dimethylamino)phenyl ring of glutaminase inhibitor 968, leads to loss of its inhibitory activity. Glutaminase catalysed glutamine metabolism maintains intracellular pH of cancer cells. Inhibition by glutaminase inhibitor 968 is known to hinder cell proliferation as a consequences of low intracellular pH.

General description

Glutaminase Inhibitor 968 belongs to the benzophenanthridinone family.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000132066
0000132067
0000123025
0000071120
0000051502

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Dibenzophenanthridines as Inhibitors of Glutaminase C and Cancer Cell Proliferation
Katt W P, et al.
Molecular Cancer Therapeutics, 11(6) (2012)
Glutaminase: a hot spot for regulation of cancer cell metabolism?.
Erickson J W and Cerione R A
Oncotarget, 1(8), 734-734 (2010)
Glutaminase regulation in cancer cells: a druggable chain of events.
Katt W P and Cerione R A
Drug Discovery Today, 19(4), 450-457 (2014)
α-ketoglutarate orchestrates macrophage activation through metabolic and epigenetic reprogramming.
Liu P S, et al.
Nature Immunology, 18(9), 985-985 (2017)
Shuting Han et al.
Theranostics, 11(17), 8464-8479 (2021-08-11)
As glutamine plays a central role in cancer metabolism, inhibition of glutaminolysis has become an ideal anticancer therapeutic target. However, glutaminolysis inhibition leads to activation of autophagy, which compromises its antitumor effect. Hence, we investigated the mechanism underlying glutaminolysis inhibition-induced
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