128-53-0

Usage

Uses

Used in Biochemical Research:
N-Ethylmaleimide is used as a reagent for the covalent modification of cysteine residues in proteins, which is crucial for understanding protein structure and function.
Used in Cancer Research:
N-Ethylmaleimide is used in cancer research due to its possible antimitotic activity. It is a protein thiol modifier that inhibits apoptotic DNA fragmentation, making it a valuable tool for studying the mechanisms of cell division and cell death.
Used in Enzymology:
N-Ethylmaleimide is used as a sulfhydryl reagent in enzymology, where it helps in the modification of cysteine residues in proteins and peptides. This modification can provide insights into enzyme function and regulation.
Used in Inhibition of DNA Fragmentation:
N-Ethylmaleimide is used to inhibit Mg2+ dependent internucleosomal DNA fragmentation, which is an important process in the study of apoptosis and other cellular processes involving DNA damage and repair.
Used in Pharmaceutical Industry:
N-Ethylmaleimide is used as a reagent in the development of drugs targeting cysteine residues in proteins, which can have therapeutic applications in various diseases, including cancer and other conditions involving protein misfolding or dysfunction.

Hazard

Lachrymator when liquid, a strong irritant.

Biochem/physiol Actions

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

Safety Profile

Poison by intraperitoneal route. Human mutation data reported. Vapors are hlghly irritating. When heated to decomposition it emits toxic fumes of NOx.

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

Upstream product

• 4166-67-0 N-ethyl maleamic acid 
• 128438-93-7 N-ethyl maleamic acid 
• 1370477-99-8 diethyl 4,4′-((3aR,4R,7S,7aS)-2-ethyl-1,3-dioxo-2,3,3a,4,7,7ahexahydro-1H-4,7-epoxyisoindole-5,6-diyl)bis(5-methylthiophene-2-carboxylate) 
• 108-31-6 maleic anhydride 
• 75-04-7 ethylamine 
• 109-96-6 3-Pyrroline 
• 74-96-4 ethyl bromide 
• 81-88-9 rhodamine B 
• 557-66-4 ethanamine hydrochloride 
• 92147-32-5 2-ethyl-4-methyl-hexahydro-4,7-epioxido-isoindole-1,3-dione 

Downstream Products

• 14992-72-4 3-(4-chloro-phenyl)-1-ethyl-pyrrole-2,5-dione 
• 350030-47-6 2-(1-ethyl-2,5-dioxo-pyrrolidin-3-ylmercapto)-benzoic acid 
• 28915-98-2 2-ethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione 
• 67048-39-9 3-(4-chloro-phenyl)-5-ethyl-(3ar,6ac)-3a,6a-dihydro-pyrrolo[3,4-d]isothiazole-4,6-dione 
• 55240-60-3 2-ethyl-6-phenyl-(3at,7at)-3a,4,7,7a-tetrahydro-4r,7c-epioxido-pyrrolo[3,4-c]pyridine-1,3-dione 
• 66085-27-6 2-ethyl-4-phenyl-(3ac,11bc)-3a,11b-dihydro-4H-4r,11ac-episulfano-benzo[4,5]thiazolo[3,2-a]pyrrolo[3,4-c]pyridine-1,3,5-trione 
• 71371-13-6 8-ethyl-3-methyl-6-phenyl-pyrrolo[3,4-c]thiazolo[3,2-a]pyridine-5,7,9-trione 
• 71371-21-6 8-ethyl-2-methyl-6-phenyl-pyrrolo[3,4-c][1,3,4]thiadiazolo[3,2-a]pyridine-5,7,9-trione 
• 81910-91-0 5-Ethyl-3-(2-furoyl)-4,6-dioxo-4,6,7,8-tetrahydropyrrolo<3,4-d>-Δ²-pyrazoline 
• 21394-68-3 S-(N-ethyl-2,5-dioxopyrrolidin-3-yl)-L-glutathione 
• 79703-01-8 2-ethyl-5α,6-dimethyl-8α-<(benzyloxy)methyl>-2,4β,5β,8β,9β-pentahydro-1H-isoindole-1,3-dione 
• 838-85-7 diphenyl hydrogen phosphate 
• 79762-31-5 5-ethyl-2-phenylazo-5H-pyrrolo<3,4-d>thiazole-4,6-dione 
• 95616-55-0 C₂₂H₁₇N₃O₃S 

Related news

The Escherichia coli F 1 -ATPase mutant βTyr-297 → Cys: functional studies and asymmetry of the enzyme under various nucleotide conditions based on reaction of the introduced Cys with N-Ethylmaleimide (cas 128-53-0) and 7-chloro-4-nitrobenzofurazan09/30/2019

Conversion of residue βTyr-297 of the Escherichia coli F 1 -ATPase (ECF 1 ) to a Cys in the mutant βY297C led to impaired oxidative phosphorylation based on growth curves. The ATPase activity of ECF 1 isolated from the mutant βY297C was only 1% of wild-type activity, ...detailed

Quantitative proteome analysis using D-labeled N-Ethylmaleimide (cas 128-53-0) and 13C-labeled iodoacetanilide by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry09/29/2019

A new methodology for quantitative analysis of proteins is described, applying stable-isotope labeling by small organic molecules combined with one- or two-dimensional electrophoresis and MALDI-TOF-MS, also allowing concurrent protein identification by peptide mass fingerprinting. Our method eli...detailed

In vivo effect of N-Ethylmaleimide (cas 128-53-0) (NEM) on the measurement of nitrate in plasma10/01/2019

Bioavailability of nitric oxide in the body may be estimated by measuring the concentration of nitrate in plasma. However, it has not been reported whether sequestering of aminothiols in plasma affects the concentration of nitrate in the samples.N-ethylmaleimide (NEM) sequesters aminothiols in p...detailed

Relevant academic research and scientific papers

Photoreversible prodrugs and protags: Switching the release of maleimides by using light under physiological conditions

A water-soluble furyl-substituted diarylethene derivative has been prepared that can undergo reversible Diels-Alder reactions with maleimides to yield photoswitchable Diels-Alder adducts. Employing bioorthogonal visible light, the release of therapeutically effective concentrations of maleimide-based reactive inhibitors or labels from these "prodrugs" or "protags" could be photoreversibly triggered in buffered, aqueous solution at body temperature. It is shown how the release properties can be fine-tuned and a thorough investigation of the release dynamics is presented. Our system should allow for spatiotemporal control over the inhibition and labeling of specific protein targets and is ready to be surveyed in living organisms.

Iron(II) phenanthroline-resin hybrid as a visible light-driven heterogeneous catalyst for green oxidative degradation of organic dye

A novel resin immobilized iron(II) phenanthroline [FePR] is prepared, characterized and exploited to understand C-C/C-O cleavage in Rhodamine B dye under visible light.

9,10-Dibromo-N-aryl-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-diones: Synthesis and Investigation of Their Effects on Carbonic Anhydrase Isozymes I, II, IX, and XII

N-substituted maleimides were synthesized from maleic anhydride and primary amines. 1,4-Dibromo-dibenzo[e,h]bicyclo-[2,2,2]octane-2,3-dicarboximide derivatives (4a-f) were prepared by the [4+2] cycloaddition reaction of dibromoanthracenes with the N-substituted maleimide derivatives. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the new derivatives were assayed against the human (h) isozymes hCA I, II, IX, and XII. All tested bicyclo dicarboximide derivatives exhibited excellent inhibitory effects in the nanomolar range, with Ki values in the range of 117.73-232.87 nM against hCA I and of 69.74-111.51 nM against hCA II, whereas they were low micromolar inhibitors against hCA IX and XII. A series of 9,10-dibromo-N-aryl-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-diones (4a-f) were synthesized from N-substituted maleimide derivatives and 9,10-dibromoanthracene. Compounds 4a-f were assayed against human carbonic anhydrases (hCA) IX and XII, which are the two tumor-associated isozymes, and hCA I and II, which represent the most common off-targets for the development of selective anticancer CA inhibitors.

Cp?Co(III)-Catalyzed C-H Alkylation with Maleimides Using Weakly Coordinating Carbonyl Directing Groups

A novel protocol for ortho-C-H alkylation of aromatic and heteroaromatic ketones and esters under Cp?Co(III) catalysis has been developed for the first time. The reaction proceeds through initial cyclometalation via weak chelation-assisted C-H bond activation, followed by coordination of activated alkene, insertion between Co-C, and protodemetalation.

Visible-Light-Mediated Efficient Metal-Free Catalyst for α-Oxygenation of Tertiary Amines to Amides

A metal-free system has been discovered for the efficient α-oxygenation of tertiary amines to the corresponding amides using oxygen as an oxidant. This visible-light-mediated oxygenation reaction exhibited excellent substrates scope under mild reaction conditions and generated water as the only byproduct. The synthetic utility of this approach has been demonstrated by applying onto drug molecules. At the end, detailed mechanistic reactions clearly showed the role of oxygen and the photocatalyst.

Catalyst and Additive-Free Diastereoselective 1,3-Dipolar Cycloaddition of Quinolinium Imides with Olefins, Maleimides, and Benzynes: Direct Access to Fused N,N′-Heterocycles with Promising Activity against a Drug-Resistant Malaria Parasite

A convenient and eco-friendly synthesis of various fused N-heterocyclic compounds through catalyst and additive-free 1,3 dipolar cycloadditions of quinolinium imides with olefins, maleimides, and benzynes in excellent yields and diastereoselectivities is reported. The thermally controlled diastereoselective [3 + 2] cycloaddition reaction between quinolinium imides and olefins provided cis-isomers at low temperature and trans-isomers at high temperature. A reaction between quinolinium imides with substituted maleimides gave four-ring-fused N-heterocyclic compounds in high yields as a single diastereomer. The aryne precursors also provided four-ring-fused N,N′-heterocyclic compounds in high yields. The in vitro antiplasmodial activity of selected molecules revealed that this class of molecules possesses potential for ongoing studies against malaria.

Graphene Oxide as a Carbocatalyst for a Diels–Alder Reaction in an Aqueous Medium

The Diels–Alder (DA) reaction, a [4+2] cycloaddition reaction, is highly important in synthetic organic chemistry and is frequently used in the synthesis of natural products containing six-membered rings. Herein, we report an efficient protocol for the DA reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two-dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy features of this protocol. The heterogeneous GO catalyst can be easily recovered and used multiple times without any significant loss in catalytic activity.

An approach to "escape from flatland": Chemo-enzymatic synthesis and biological profiling of a library of bridged bicyclic compounds

A major reason for the low success rate in current drug development through chemical synthesis has been ascribed to the large fraction of quasi planar candidate molecules. Therefore, an "escape from flatland" strategy has been recommended for the generation of bioactive chemical entities. In a first attempt to test this recommendation, we synthesized a small collection of bridged bicyclic compounds possessing a rigid spherical core structure by combining a group of cyclic dienes with a collection of dienophiles. We started from planar biphenyl analogues and, by enzymatic dioxygenation, transformed them into hydroxylated diene structures. Using a small library of newly synthesized dienophiles, the dienes were converted into bridged bicycles via the Diels-Alder reaction. The resulting collection of 78 structures was first tested for bioactivity in a generic assay based on interference with the proliferation of mammalian cells. A more mechanism-targeted bioactivity profiling method, exploiting cellular impedance monitoring, was subsequently used to obtain suggestions for the mode of action exerted by those compounds that were the most active in the proliferation assay. Proteasome inhibition could be confirmed for 8 of a series of 9 respective candidates. Whilst 7 of these molecules showed relatively weak interference with proteasome activity, one candidate exerted a moderate but distinct inhibition. This result appears remarkable in view of the small size of the compound library, which was synthesized following a few basic considerations. It encourages the application of diverse synthetic approaches to further investigate the role of spherical shape for the success of compound libraries.

Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

Using light and a molecular switch to 'lock' and 'unlock' the Diels-Alder reaction

Light is used to 'gate' the Diels-Alder reaction using a photoresponsive dithienylfuran backbone and turn the reversibility of the Diels-Alder reaction 'off' and 'on' at 100 °C. These features make the reported system an excellent candidate for developing the next generation of self-healing polymers and photothermal drug delivery vehicles.