NH-125 | CAS#278603-08-0 | eEF-2 kinase inhibitor

MedKoo Cat#: 562979 | Name: NH-125

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

NH-125 is a eukaryotic elongation factor 2 (eEF-2) kinase (CaMK III) inhibitor.

Chemical Structure

NH-125

CAS#278603-08-0

Theoretical Analysis

MedKoo Cat#: 562979

Name: NH-125

CAS#: 278603-08-0

Chemical Formula: C27H45IN2

Exact Mass:

Molecular Weight: 524.57

Elemental Analysis: C, 61.82; H, 8.65; I, 24.19; N, 5.34

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 300.00
10mg	USD 500.00
50mg	USD 1,400.00

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Related CAS #

No Data

Synonym

NH-125; NH 125; NH125;

IUPAC/Chemical Name

1-Hexadecyl-2-methyl-3-(phenylmethyl)-1H-imidazolium iodide

InChi Key

RVWOHCBHAGBLLT-UHFFFAOYSA-M

InChi Code

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

SMILES Code

CC1=[N+](CC2=CC=CC=C2)C=CN1CCCCCCCCCCCCCCCC.[I-]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 524.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Basak A, Abouelhassan Y, Zuo R, Yousaf H, Ding Y, Huigens RW. Antimicrobial peptide-inspired NH125 analogues: bacterial and fungal biofilm-eradicating agents and rapid killers of MRSA persisters. Org Biomol Chem. 2017 Jul 5;15(26):5503-5512. doi: 10.1039/c7ob01028a. PubMed PMID: 28534905. 2: Abouelhassan Y, Basak A, Yousaf H, Huigens RW 3rd. Identification of N-Arylated NH125 Analogues as Rapid Eradicating Agents against MRSA Persister Cells and Potent Biofilm Killers of Gram-Positive Pathogens. Chembiochem. 2017 Feb 16;18(4):352-357. doi: 10.1002/cbic.201600622. Epub 2017 Jan 16. PubMed PMID: 27925693. 3: Kim W, Fricke N, Conery AL, Fuchs BB, Rajamuthiah R, Jayamani E, Vlahovska PM, Ausubel FM, Mylonakis E. NH125 kills methicillin-resistant Staphylococcus aureus persisters by lipid bilayer disruption. Future Med Chem. 2016;8(3):257-69. doi: 10.4155/fmc.15.189. Epub 2016 Feb 24. PubMed PMID: 26910612; PubMed Central PMCID: PMC4976882. 4: Bender CL, Yang Q, Sun L, Liu SJ. NH125 reduces the level of CPEB3, an RNA binding protein, to promote synaptic GluA2 expression. Neuropharmacology. 2016 Feb;101:531-7. doi: 10.1016/j.neuropharm.2015.03.017. Epub 2015 Apr 2. PubMed PMID: 25842244; PubMed Central PMCID: PMC4592363. 5: McCamphill PK, Farah CA, Anadolu MN, Hoque S, Sossin WS. Bidirectional regulation of eEF2 phosphorylation controls synaptic plasticity by decoding neuronal activity patterns. J Neurosci. 2015 Mar 11;35(10):4403-17. doi: 10.1523/JNEUROSCI.2376-14.2015. PubMed PMID: 25762683. 6: Usui T, Okada M, Hara Y, Yamawaki H. Eukaryotic elongation factor 2 kinase regulates the development of hypertension through oxidative stress-dependent vascular inflammation. Am J Physiol Heart Circ Physiol. 2013 Sep 1;305(5):H756-68. doi: 10.1152/ajpheart.00373.2013. Epub 2013 Jun 28. PubMed PMID: 23812389; PubMed Central PMCID: PMC4073962. 7: Devkota AK, Tavares CD, Warthaka M, Abramczyk O, Marshall KD, Kaoud TS, Gorgulu K, Ozpolat B, Dalby KN. Investigating the kinetic mechanism of inhibition of elongation factor 2 kinase by NH125: evidence of a common in vitro artifact. Biochemistry. 2012 Mar 13;51(10):2100-12. doi: 10.1021/bi201787p. Epub 2012 Mar 5. PubMed PMID: 22352903; PubMed Central PMCID: PMC3673019. 8: Chen Z, Gopalakrishnan SM, Bui MH, Soni NB, Warrior U, Johnson EF, Donnelly JB, Glaser KB. 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. doi: 10.1074/jbc.M111.301291. Epub 2011 Oct 21. PubMed PMID: 22020937; PubMed Central PMCID: PMC3243513. 9: Arora S, Yang JM, Utsumi R, Okamoto T, Kitayama T, Hait WN. P-glycoprotein mediates resistance to histidine kinase inhibitors. Mol Pharmacol. 2004 Sep;66(3):460-7. PubMed PMID: 15322237. 10: Yamamoto K, Kitayama T, Ishida N, Watanabe T, Tanabe H, Takatani M, Okamoto T, Utsumi R. Identification and characterization of a potent antibacterial agent, NH125 against drug-resistant bacteria. Biosci Biotechnol Biochem. 2000 Apr;64(4):919-23. PubMed PMID: 10830522.