NH 125

Names

[ Name ]:
NH 125

[Synonym ]:
1-Benzyl-3-cetyl-2-methylimidazolium iodide
NH125
1H-Imidazolium, 1-hexadecyl-2-methyl-3-(phenylmethyl)-, iodide (1:1)
eEF-2 Kinase Inhibitor,NH125
HMS3229F01
3-Benzyl-1-hexadecyl-2-methyl-1H-imidazol-3-ium iodide

Biological Activity

[Description]:

NH125 is a potent and selective inhibitor of eukaryotic elongation factor 2 kinase (eEF-2K/CaMKIII), also could induce eEF2 phosphorylation, with an IC50 of 60 nM for eEF-2K.

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> CaMK

Research Areas >> Cancer

[Target]

eEF-2K:60 nM (IC50)

[In Vitro]

NH125 inhibits eEF-2 kinase activity (IC50 = 60 nM) in vitro, blocks the phosphorylation of eEF-2 in intact cells, and shows relative selectivity over other protein kinases: protein kinase C (IC50 = 7.5 μM), protein kinase A (IC50 = 80 μM), and calmodulin-dependent kinase II (IC50 > 100 μM). NH125 decreases the viability of 10 cancer cell lines with IC50s ranging from 0.7 to 4.7 μM. Forced overexpression of eEF-2 kinase in a glioma cell line produces 10-fold resistance to NH125. In conclusion, these results suggest that identification of potent inhibitors of eEF-2 kinase may lead to the development of new types of anticancer drugs[1]. Anticancer effect of NH125 is not mediated through inhibition of eEF2K. Inhibition of cell growth correlates with induction of peEF2[2].

[References]

[1]. Arora S, et al. Identification and characterization of an inhibitor of eukaryotic elongation factor 2 kinase against human cancer cell lines. Cancer Res. 2003 Oct 15;63(20):6894-9.

[2]. Chen Z, et al. 1-Benzyl-3-cetyl-2-methylimidazolium iodide (NH125) induces phosphorylation of eukaryotic elongation factor-2 (eEF2): a cautionary note on the anticancer mechanism of an eEF2 kinase inhibitor. J Biol Chem. 2011 Dec 23;286(51):43951-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
88.2-94.9ºC

[ Molecular Formula ]:
C₂₇H₄₅IN₂

[ Molecular Weight ]:
524.564

[ Exact Mass ]:
524.262756

[ PSA ]:
8.81000

[ LogP ]:
4.61760

[ Appearance of Characters ]:
solid | white to off-white

[ Storage condition ]:
−20°C

[ Water Solubility ]:
DMSO: 20 mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Inhibition of AMP-activated protein kinase signaling alleviates impairments in hippocampal synaptic plasticity induced by amyloid β.

J. Neurosci. 34(36) , 12230-8, (2014)

The AMP-activated protein kinase (AMPK) is a Ser/Thr kinase that is activated in response to low-energy states to coordinate multiple signaling pathways to maintain cellular energy homeostasis. Dysreg...