imide, the -C(O)NHC(O)- functional group. Maleimides are also a class of derivatives of the parent maleimide where the NH group is replaced with alkyl...

In enzymology, a maleimide hydrolase (EC 3.5.2.16) is an enzyme that catalyzes the chemical reaction maleimide + H2O ⇌ {\displaystyle \rightleftharpoons...

thermosetting polymers used in structural composites are benzoxazine resins, bis-maleimide resins (BMI), cyanate ester resins, epoxy (epoxide) resins, phenolic (PF)...

colorless solid. Maleamic acid is the product of the action of the enzyme maleimide hydrolase. A variety of maleamic acids are known. Commonly they are prepared...

chromatography. TCEP is particularly useful when labeling cysteine residues with maleimides. TCEP can keep the cysteines from forming di-sulfide bonds and, unlike...

two reactive groups at opposite ends: N-hydroxysuccinimide-ester and maleimide, reactive with amines and thiols respectively. SMCC is often used in bioconjugation...

Ramachandra S.; Liebman, Joel F. (1997). "The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide...

Ramachandra S.; Liebman, Joel F. (May 1997). "The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide...

hydrogen bonding. The N-H group is weakly acidic as indicated in the case of maleimide, with a pKa estimated at 10. Many high strength or electrically conductive...

Pencolide is a maleimide isolate of Penicillium and seaweed endophytic fungi. Birkinshaw, JH; Kalyanpur, MG; Stickings, CE (1963). "Studies in the biochemistry...

reversible cross-linking of polymers bearing pendent anthracene group with maleimides. However, the reversible reaction occurred only partially upon heating...

than typical thiols such as glutathione towards alkylating agents like maleimides. It also resists oxidation by air. However, ergothioneine can be slowly...

labeling experiments to investigate biomolecular structure and dynamics. Maleimides selectively attach to cysteine using a covalent Michael addition. Site-directed...

T in the name. In presence of a bismaleimide, the double bond of the maleimide group can copolymerize with the cyano groups to heterocyclic 6-membered...

reactions are often reversible at high temperatures. In the case of furan–maleimide adducts, the retro-cycloaddition is accessible at temperatures as low...

topoisomerase I inhibitor payload Deruxtecan linked via a highly stable maleimide linker, allowing for improved plasma stability and a broader therapeutic...

carboxylate, isothiocyanate, hydrazine), carboxyl groups (carbodiimide), thiol (maleimide, acetyl bromide), and organic azide (via click chemistry or non-specifically...

brentuximab (cAC10, which targets the cell-membrane protein CD30) linked with maleimide attachment groups, cathepsin-cleavable linkers (valine-citrulline), and...

Eosin-5-maleimide binding test: Positive (reduced mean fluorescence), as the test will demonstrate a reduced ability of the eosin-5-maleimide dye to bind...

which ends in a highly reactive moiety such as N-hydroxysuccinimide or maleimide. Many analogs of standard Cy 2 / 3 / 3.5 / 5 / 5.5 / 7 / 7.5 dyes were...

Farinomalein is a natural maleimide with formula C10H13NO4 - was first isolated from the entomopathogenic fungus Isaria farinosa (Paecilomyces farinosus)...

Tetramethrin is a potent synthetic insecticide in the pyrethroid family. It is a white crystalline solid with a melting point of 65–80 °C. The commercial...

Leiske, Chris I.; Li, Fu; Senter, Peter D. (2014). "Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug...

compound gained attention for its unusual structure, which includes a maleimide ring fused to a ribose sugar, distinguishing it from other nucleoside...

Deruxtecan is a chemical compound and a derivative of exatecan that acts as topoisomerase I inhibitor. It is available linked to specific monoclonal antibody...

fumaric acid succinic acid crotonic acid Related compounds maleic anhydride maleimide Except where otherwise noted, data are given for materials in their standard...

time-controlled sequential addition of highly-reactive N-substituted maleimides in the atom transfer radical polymerization of styrene, which led to programmed...

acid forms esters, an imide, and an anhydride, i.e. diethyl maleate, maleimide, and maleic anhydride. Fumaric acid, as fumarate, is an intermediate in...

Catalysts for Stereoselective 1,4‐Additions of 2‐Oxindoles to Maleimides". Angewandte Chemie International Edition. 58 (16): 5447–5451. doi:10...

Tripamide (INN) is a diuretic. Diels-Alder reaction between maleimide and cyclopentadiene gives a compound that is called noreximide [6319-06-8]. This...

biologically active compounds. This core structure includes a central maleimide group with two indole groups attached. Examples of bisindolylmaleimide...

Dienophile N2 > CO2 > naphthalene > benzene, nitriles > methacrylate > maleimides > cyclopentadiene, imines, alkenes > alkynes Because the Diels–Alder reaction...

Orange was replaced by N-[4-(7-diethylamino-4-methyl-3-coumarinyl)phenyl]maleimide (CPM), a compound that only fluoresces after reacting with a nucleophile...

that contains two reactive functional groups, a succinimide ester and a maleimide. The succinimide group of SMCC reacts with the free amino group of a lysine...

quenching by a stereospecific Diels-Alder reaction with the substituted maleimide. In particular, the syn-substituted product gave the anti-WH product,...

anti-cancer agent from the antibody, a polyethylene glycol spacer, and a maleimide linker which is attached to a cysteine in the antibody's (rovalpituzumab's)...

SO, Hunter JH, Anderson ME, et al. (October 2014). "Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody–drug...

functionalized with an anti-folate-receptor antibody (αFR-Ab) via a PEG-maleimide-succinimide and using the infrared dye IR780 as the Raman reporter, henceforth...

cathepsin-cleavable linker is blue, and the attachment group (consisting of maleimide and caproic acid) is brown. The whole radical inside the four boxes is...

3-Dipolar Cycloaddition Reaction of Carbonyl Ylide with N-Substituted Maleimides and Dimethyl Fumarate B Chem Soc Jpn 2001, 74, 1115. Geng, Zhe; Chen,...

with carbodiimide and subsequent coupling with amine); thiol (e.g. via maleimide or iodoacetamides); azide (e.g. via click chemistry with terminal alkyne);...

(ATP-hydrolysing) EC 3.5.2.15: cyanuric acid amidohydrolase EC 3.5.2.16: maleimide hydrolase EC 3.5.2.17: hydroxyisourate hydrolase EC 3.5.2.18: enamidase...

transferrin-antibody were connected using a SMCC bifunctional linker (NHS ester and maleimide moiety) to radiolabelled and cys-bearing ASOs targeting HIV mRNA. Marcin...

Bian, Fengling (2012-12-14). "The Reaction of Tertiary Anilines with Maleimides under Visible Light Redox Catalysis". Advanced Synthesis & Catalysis....

could then be used to asymmetrically catalyze a [2+2] photoaddition of maleimide and inert aromatic compound fluoranthene, which previously have not been...

spacer is needed. Preferred end groups for heterobifunctional PEGs are maleimide, vinyl sulfones, pyridyl disulfide, amine, carboxylic acids and NHS esters...

N-methylaniline 100–61–8 C7H9NO2 ammonium benzoate 1863–63–4 C7H9NO2 ethylmethyl maleimide 29720–92–1 C7H9NO2S methanesulfanilide 1197–22–4 C7H9NO4S dimethyl...

carboxyhemoglobin which is currently in late clinical development. Similarly, maleimide PEG conjugated human carboxyhemoglobin had previously been the subject...

MMAF with a monoclonal antibody (MAB). The attachment group consists of maleimide and caproic acid. About eight such structures are bound to a single antibody...

used as an initiator to initiate polymerizations, such as with N-phenyl maleimide. Using the parylene C/SiO2 nanocomposites, parylene C could be used as...

Aldoxorubicin (INNO-206) is a tumor-targeted doxorubicin conjugate in development by CytRx. Specifically, it is the (6-maleimidocaproyl) hydrazone of doxorubicin...

susceptibility (χ) −78.4×10−6 cm3/mol Related compounds Related Amides Maleimide Related compounds Phthalic anhydride Except where otherwise noted, data...

Safety data sheet (SDS) External MSDS Related compounds Related Imides Maleimide, N-Chlorosuccinimide, N-Bromosuccinimide Except where otherwise noted...

these labeled cells in small samples using flow cytometry. Biotin-PEG2-maleimide Biotin-PEG3-amine Biotin-PEG4-NHS "EZ-Link™ Amine-PEG2-Biotin". Bronfman...

Functional groups like alkyne, norbornene, maleimide, nitrite, and cyanate have been used for this purpose. Maleimide and norbornene end-capped oligomers can...

level of biotinylation is required. Sulfhydryl-reactive groups such as maleimides, haloacetyls and pyridyl disulfides, require free sulfhydryl groups for...

RI-1 is a selective inhibitor of RAD51, which is a central gene molecule of homologous recombination, with IC50 ranging from 5 to 30 μM. RAD51 is a eukaryote...

R. J. (September 1971). "Nucleoside antibiotics. Biosynthesis of the maleimide nucleoside antibiotic, showdomycin, by Streptomyces showdoensis". Biochemistry...

thiolate nucleophile, which will react with soft electrophiles, such as maleimides and iodoacetamides (shown in the first two reactions in Figure 2 below)...

forms in use include Pacific Blue succinimidyl ester and Pacific Blue C5-Maleimide. Lee, Wei-Chuan (1998). "Synthesis of Novel Fluorinated Coumarins: Excellent...

(April 2011). "Detection of hereditary pyropoikilocytosis by the eosin-5-maleimide (EMA)-binding test is attributable to a marked reduction in EMA-reactive...

succinimidyl-esters for labeling proteins through lysine residues, and as maleimide derivatives for labeling proteins through cysteine residues. Antibodies...

toluene, or PhNCS, THF, RT 71–90% c O2, S8, or Se, toluene, reflux 54–68% g Maleimide, THF, RT 47–84% d R1CH=CHR2, THF, RT 25–68% h Dimethylacetylene dicarboxylate...

crosslinker Sulfo-SMCC, which converts lysine residues to sulfhydryl-reactive maleimide groups. A sulfhydryl-containing hapten can then be reacted with the KLH...

oligonucleotide, could be subjected to a Diels-Alder reaction with a variety of maleimide derivatives. After completion of the desired reaction step, the identity...

and the deployment of both membrane-permeant and membrane-impermeant maleimides (Zhen et al. 1994); (8) Identification of acidic residues required for...

contrast for breast carcinoma imaging in mice. Biotin-Peg2-Amine Biotin-Peg2-Maleimide Biotin-Peg3-Amine Biotin-Peg4-NHS Mono BOC Cystamine[permanent dead link]...

Aaron D.; Kiick, Kristi L. (October 19, 2011). "Tunable Degradation of Maleimide–Thiol Adducts in Reducing Environments". Bioconjugate Chemistry. 22 (10):...

nucleotides react with the fluorophore linked to a reactive leaving group like maleimide. Biotin-linked nucleotides rely on the same indirect labelling principle...

Aalten DM (February 2004). "Interactions of LY333531 and other bisindolyl maleimide inhibitors with PDK1". Structure. 12 (2): 215–26. doi:10.1016/j.str.2004...

receptors. These ligands are attached to the microbubbles using carbodiimide, maleimide, or biotin-streptavidin coupling. Biotin-streptavidin is the most popular...

approach is based on the well-known Michael nucleophilic addition to maleimides (Fig. 7). Synthetic "Gylcolipids" – one family of the FSL constructs are...

weaker bonds. Furyl-telechelic poly(ethylene adipate) (PEAF2) and tris-maleimide (M3) can be combined through a DA reaction in order to bring about self-healing...

chelator to bind ions together. The polymer terminates with a thiol or a maleimide that links it to reduced disulfides in the Fc region of the antibody....

stibinidene and other substrates, such as methyl propiolate and N-alkyl/aryl-maleimides, RN(C(O)CH)2 (R = Me, tBu, Ph).  These findings highlight the reactivity...

derivative of meleagrin Pencolide seaweed-derived endophytic fungi bio-active maleimide Penicitrinol J marine-derived Penicillium bio-active citrinin dimer Penicitrinol...

N-Ethylmaleimide (NEM) is an organic compound that is derived from maleic acid. It is a unstable substance that reacts rapidly with thiols and is commonly...

Kinoshita, Fumio Ihara, Yasuhiro Igarashi and Takuya Nihira. Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus Paecilomyces farinosus...

research measured and interpreted the stable carbon isotopic compositions of maleimides (small, polar, nitrogen-containing molecules) in sedimentary organic matter...

carboxyfluorescein 3.2 488 Alexa 488 1.96, 4.35 22.5±0.5 488 Atto 655-maleimide 4.07 ± 0.1 25 663 Atto 655-carboxylicacid 4.26 ± 0.08 25 663 2′, 7′-difluorofluorescein...

[4]dendralene shows a tandem Diels-Alder reaction with the dienophile N-methyl-maleimide (NMM). Complete site selectivity is possible with the addition of the...

are based on polyethylene glycol PEGylated bovine carboxyhemoglobin and maleimide PEG conjugated human carboxyhemoglobin. Porphyrin structures such as heme...

the18F-labeled thio-reactive reagent N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide". Nuclear Medicine and Biology. 34 (1): 5–15. doi:10.1016/j.nucmedbio...

JJ, Fuior E, Knutson JR (March 2002). "Fluorescence studies of pyrene maleimide-labeled translin: excimer fluorescence indicates subunits associate in...

peptide and nucleic acid synthesis, while reactive ones (with succinimidyl, maleimide and hydrazide) suit conjugation by conventional chemistry, while FluoProbes...

dithiols and thiols which yields disulfide bonds, and a reaction between maleimide derivatives and thiols, which yields thioether bonds." Amine groups are...

E. Pearson; C. R. Park; J. H. Park (1981). "15N- and 2H-substituted Maleimide Spin Labels: Improved Sensitivity and Resolution for Biological EPR Studies"...

particular was used as a precursor for thermoplastics based on epoxy resin or maleimide and was identified as a potential substitute for bisphenol A (BPA). The...

Inman, and A. Lees. Reaction of tris(2-carboxyethyl)phosphine (TCEP) with maleimide and -haloacyl groups: Anomalous elution of TCEP by gel filtration. Anal...

indolocarbazole and bis-indole protein kinase C inhibitors. II. Substitution on maleimide nitrogen with functional groups bearing a labile hydrogen". J. Antibiot...

Grigorieff N (Sep 2003). "Electron cryomicroscopy structure of N-ethyl maleimide sensitive factor at 11 A resolution". The EMBO Journal. 22 (17): 4365–74...

surfaces similarly to thiomers. These polymers have acryloyl, methacryloyl, maleimide, boronate and N‐hydroxy (sulfo) succinimide ester groups in their structure...

alkanethiolates on gold. The monolayers contain capture ligands (e.g. biotin or maleimide) that can selectively immobilize a peptide of interest. Subsequently,...

"Photo-crosslinking of poly[ethene-stat-(methacrylic acid)] functionalised with maleimide side groups". Polym. Int. 58 (7): 720. doi:10.1002/pi.2583. Corey, E....

antibody is stochastically conjugated via a valine-alanine cleavable, maleimide linker to a cytotoxic (anticancer) pyrrolobenzodiazepine (PBD) dimer.[medical...

Wiley-VCH, 1999). Jerome A. Berson and Ronald Swidler, "A Synthesis of Maleimide," Journal of the American Chemical Society 76 (1954): 2835. Jerome A....

Wattanadilok; et al. (1 August 2005). "Dibromotyrosine Derivatives, a Maleimide, Aplysamine-2 and Other Constituents of the Marine Sponge Pseudoceratina...

Ruairí P.; Opanasopit, Praneet; Khutoryanskiy, Vitaliy V. (2016-10-12). "Maleimide-bearing nanogels as novel mucoadhesive materials for drug delivery". Journal...

PMID 21592136. S2CID 20297050. Henry, Stephen; Rodionov, Igor (2012). FSL-RFG(Maleimide) FSL Construction Kit Technical Bulletin. Scholarly Commons. hdl:10292/2241...

thiomalate MeSH D02.241.081.337.502 – maleates MeSH D02.241.081.337.502.524 – maleimides MeSH D02.241.081.337.502.524.418 – ethylmaleimide MeSH D02.241.081.337...

amino acids, with cysteine number 93 carrying a doubly methoxy-PEGylated maleimide derivative with a molecular mass of 40 kDa. Tolcher AW, Sweeney CJ, Papadopoulos...

Rob van; Herz, Werner (2005-08-01). "Dibromotyrosine Derivatives, a Maleimide, Aplysamine-2 and Other Constituents of the Marine Sponge Pseudoceratina...

groups specifically react with the functional groups methanethiosulfonate, maleimide, and iodoacetamide, creating a covalent bond with the amino acid Cys....

pyrroles MeSH D03.383.129.578.150 – cromakalim MeSH D03.383.129.578.399 – maleimides MeSH D03.383.129.578.399.418 – ethylmaleimide MeSH D03.383.129.578.617...