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About This Item

Empirical Formula (Hill Notation):
C27H45IN2
CAS Number:
278603-08-0
Molecular Weight:
524.56
MDL number:
MFCD07370143
UNSPSC Code:
12352200
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Quality Level

100

Assay

≥95% (NMR)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

white to yellow

solubility

DMSO: 20 mg/mL
70% ethanol: 5 mg/mL

storage temp.

2-8°C

SMILES string

[I-].[n+]2(c([n](cc2)CCCCCCCCCCCCCCCC)C)Cc1ccccc1

InChI

1S/C27H45N2.HI/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-28-23-24-29(26(28)2)25-27-20-17-16-18-21-27;/h16-18,20-21,23-24H,3-15,19,22,25H2,1-2H3;1H/q+1;/p-1

InChI key

RVWOHCBHAGBLLT-UHFFFAOYSA-M

General description

A cell-permeable imidazolium compound that inhibits the activity of bacterial histidine kinases (EnvZ, PhoQ, BvgS, and EvgS) and eukaryotic eEF-2 (elongation factor 2) kinase/CaMKIII (IC50 = 60 nM), while exhibiting much lower potency against PKC, PKA, and CaMKII (IC50 = 7.5, 80, and >100 µM, respectively). NIH125 is a known P-gp substrate, which limits its in vivo efficacy as an anticancer and antimicrobial agent.

Biochem/physiol Actions

Primary Target
Bacterial histidine kinases (EnvZ, PhoQ, BvgS, and EvgS) and eukaryotic eEF-2 (elongation factor 2) kinase/CaMKIII
Target IC50: 60 nM against the activity of bacterial histidine kinases (EnvZ, PhoQ, BvgS, and EvgS) and eukaryotic eEF-2 (elongation factor 2) kinase/CaMKIII

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Arora, S., et al. 2004. Mol. Pharmacol.66, 460.
Arora, S., et al. 2003. Cancer Res.63, 6894.
Yamamoto, K., et al. 2000. Biosci. Biotechnol. Biochem.64, 919.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Irritant (B)

Storage Class Code

11 - Combustible Solids

WGK

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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