N-EthylmaleimideA protein thiol modifier which inhibits apoptotic DNA fragmentation

N-Ethylmaleimide (CAS 128-53-0)

N-Ethylmaleimide | CAS 128-53-0 is rated 5.0 out of 5 by 1.
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Synonym: 1-Ethyl-1H-pyrrole-2,5-dione; NEM
Application: A protein thiol modifier which inhibits apoptotic DNA fragmentation
CAS Number: 128-53-0
Purity: ≥98%
Molecular Weight: 125.13
Molecular Formula: C6H7NO2
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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N-Ethylmaleimide (NEM) is an electrophilic small molecule, used in biological research to alkylate and covalently modify nucleophilic thiol residues on proteins. Covalent modification of the active-site thiol residue of cysteine proteases ablates enzyme function. N-Ethylmaleimide also demonstrates inhibition of Mg2+-dependent internucleosomal DNA fragmentation, a defining occurrence of the apoptotic pathway. Other thiophilic species such as Hg2+ and Cd2+ inhibit fragmentation as well, indicating that a thiol moiety is crucial for this degradation to occur. NADP-dependent isocitrate dehydrogenase in yeast is disabled by N-Ethylmaleimide, showing alkylation of a cysteine residue followed by a slower alkylation of a lysine residue on the enzyme. N-Ethylmaleimide is an activator of PLA2.


References

1. Banger, K.K., et al. 1993. Biochem. J. 290: 199-204. PMID: 8439289
2. Mattingly, J.R., et al. 1993. J. Biol. Chem. 268: 26320-26327. PMID: 8253754
3. Cain, K., et al. 1994. Biochem. Cell Biol. 72: 631-638. PMID: 7654337
4. Huang, Y.C., et al. 1995. Arch. Biochem. Biophys. 316: 485-492. PMID: 7840654
5. Neve, E.P., et al. 1995. Biochem. Pharmacol. 49: 57-63. PMID: 7840783
6. Cain, K., et al. 1995. FEBS Lett. 358: 255-261. PMID: 7843412

Appearance :
Crystalline
Physical State :
Solid
Solubility :
Soluble in ethanol (50 mg/ml), water (1 g/l) at 20° C, chloroform, methanol, and toluene (1115 g/l) at 20° C.
Storage :
Store at room temperature
Melting Point :
43-46° C
Boiling Point :
209-211° C
Density :
1.21 g/cm3 (Predicted)
Refractive Index :
n20D 1.51 (Predicted)
IC50 :
Monoglyceride Lipase: IC50 = 16.6 µM (human); Short circuit current : IC50 = 22 µM (pancreatic duct cells); HIV YU2 gp120 to CD4 binding: IC50 = 3.22 µM
Ki Data :
N8-Acetylspermidine deacetylase : Ki= 860 µM (rat liver cytosol)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
UX9625000
PubChem CID :
4362
Merck Index :
14: 3822
MDL Number :
MFCD00005509
EC Number :
204-892-4
Beilstein Registry :
112448
SMILES :
CCN1C(=O)C=CC1=O

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N-Ethylmaleimide  Product Citations

See how others have used N-Ethylmaleimide. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 15 total

PMID: # 30770245  Arora, H. et al. 2019. Immunity.

PMID: # 29467492  Di Costanzo, A. et al. 2018. Oncogene. 37: 2559-2572.

PMID: # 26782056  Harraz, MM. et al. 2016. Molecular psychiatry. 21: 313-9.

PMID: # 23935042  Butler, EK. et al. 2013. J. Bacteriol. 195: 4639-49.

PMID: # 20308550  Vivanco, I. et al. 2010. Proc. Natl. Acad. Sci. U.S.A. 107: 6459-6464.

PMID: # 19387865  van Diggelen, OP. et al. 2009. J. Inherit. Metab. Dis. 32: 416-423.

PMID: # 19694490  Babavali, M. et al. 2009. Biochemistry. 48: 9022-9030.

PMID: # 18081316  Applegate, MA. et al. 2008. Biochemistry. 47: 473-478.

PMID: # 18192653  Nagle, CA. et al. 2008. J. Lipid Res. 49: 823-831.

PMID: # 17286327  Sagan, SM. et al. 2007. Angew. Chem. Int. Ed. Engl. 46: 2005-2009.

Citations 1 to 10 of 15 total
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Rated 5 out of 5 by from Various publications cite the use of N Various publications cite the use of N-Ethylmaleimide (NEM) to alkylate and covalently modify nucleophilic thiol residues on proteins. N-Ethylmaleimide also demonstrates inhibition of Mg2+-dependent internucleosomal DNA fragmentation, a defining occurrence of the apoptotic pathway. -SCBT Publication Review
Date published: 2015-04-21
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