E3876

N-Ethylmaleimide

Name: <I>N</I>-Ethylmaleimide
Brand: SIAL

crystalline, ≥98% (HPLC)

Sinónimos:

NEM

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About This Item

Fórmula empírica (notación de Hill):

C₆H₇NO₂

Número CAS:

128-53-0

Peso molecular:

125.13

UNSPSC Code:

12352106

NACRES:

NA.21

PubChem Substance ID:

24278420

EC Number:

204-892-4

Beilstein/REAXYS Number:

112448

MDL number:

MFCD00005509

Nombre del producto

N-Ethylmaleimide, crystalline, ≥98% (HPLC)

InChI key

HDFGOPSGAURCEO-UHFFFAOYSA-N

InChI

1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3

SMILES string

CCN1C(=O)C=CC1=O

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

crystalline

storage condition

(Tightly closed. Dry. Keep in a well-ventilated place. )

technique(s)

activity assay: suitable
co-immunoprecipitation (co-IP): suitable
immunoblotting: suitable

color

white to faint yellow

bp

210 °C (lit.)

mp

43-46 °C (lit.)

solubility

ethanol: 50 mg/mL, clear to slightly hazy, colorless to faint yellow or tan

suitability

suitable for Western blot

application(s)

life science and biopharma

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... KCNQ2(3785), KCNQ4(9132), KCNQ5(56479), SLC6A3(6531), SLC6A4(6532)

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Application

Reagent for the covalent modification of cysteine residues in proteins.

Biochem/physiol Actions

Augments currents from native M-channels in sympathetic neurons and acts as an opener for KCNQ2, KCNQ4 and KCNQ5 channels.

Sulfhydryl alkylating agent that inactivates NADP-dependent isocitrate dehydrogenase and many endonucleases.

Other Notes

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Preparation Note

NEM gives a clear solution in ethanol at 50 mg/ml. NEM dissolves in water (>50 mg in 4 ml); however, aqueous solutions are unstable. The rate of hydrolysis is pseudo-first order and significantly dependent on pH.

pictograms

GHS06,GHS05

signalword

Danger

hcodes

H300,H311,H314,H317

pcodes

P260 - P272 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Clase de almacenamiento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

163.2 °F - closed cup

flash_point_c

72.9 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Mapping of sites facing aqueous environment of voltage-gated proton channel at resting state: a study with PEGylation protection.

Tatsuki Kurokawa et al.

Biochimica et biophysica acta, 1838(1 Pt B), 382-387 (2013-10-22)

Hv1 (also named, voltage-sensor only protein, VSOP) lacks an authentic pore domain, and its voltage sensor domain plays both roles in voltage sensing and proton permeation. The activities of a proton channel are intrinsic to protomers of Hv1, while Hv1

Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors.

Nicolas Matuszak et al.

Journal of medicinal chemistry, 52(23), 7410-7420 (2009-07-09)

The endocannabinoid 2-arachidonoylglycerol (2-AG) plays a major role in many physiological processes, and its action is quickly terminated via enzymatic hydrolysis catalyzed by monoglyceride lipase (MGL). Regulating its endogenous level could offer therapeutic opportunities; however, few selective MGL inhibitors have

Shear stress triggers insertion of voltage-gated potassium channels from intracellular compartments in atrial myocytes.

Hannah E Boycott et al.

Proceedings of the National Academy of Sciences of the United States of America, 110(41), E3955-E3964 (2013-09-26)

Atrial myocytes are continuously exposed to mechanical forces including shear stress. However, in atrial myocytes, the effects of shear stress are poorly understood, particularly with respect to its effect on ion channel function. Here, we report that shear stress activated

Selective accumulation of aggregation-prone proteasome substrates in response to proteotoxic stress.

Florian A Salomons et al.

Molecular and cellular biology, 29(7), 1774-1785 (2009-01-23)

Conditions causing an increase in misfolded or aberrant proteins can impair the activity of the ubiquitin/proteasome system (UPS). This observation is of particular interest, given the fact that proteotoxic stress is closely associated with a large variety of disorders. Although

Targeting of Gamma-Glutamyl-Cysteine Ligase by miR-433 Reduces Glutathione Biosynthesis and Promotes TGF-β-Dependent Fibrogenesis.

Cristina Espinosa-Diez et al.

Antioxidants & redox signaling, 23(14), 1092-1105 (2014-10-30)

Glutathione (GSH) is the main antioxidant against cell damage. Several pathological states course with reduced nucleophilic tone and perturbation of redox homeostasis due to changes in the 2GSH/GSSG ratio. Here, we investigated the regulation of the rate-limiting GSH biosynthetic heterodimeric

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