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Maleimide

Maleimide is a reactive chemical group commonly used in bioconjugation and chemical modification processes.
It forms stable thioether bonds with sulfhydryl (thiol) groups, allowing for the selective labeling of biomolecules such as proteins, peptides, and nucleic acids.
Maleimide-based reactions are widely employed in drug delivery, biosensing, and proteomics applications.
Researchers can optimize their maleimide protocols using PubCompare.ai, an AI-driven tool that helps identify the most effective products and practices from published literature, preprints, and patents.
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Most cited protocols related to «Maleimide»

Fn isolated from human plasma (see Text S1) was doubly labeled with Alexa 488 and Alexa 546 (Molecular Probes, http://probes.invitrogen.com/) as FRET donors and acceptors, respectively, using two different labeling schemes based on established protocols [24 (link),25 (link)]. To produce cys/cys Fn-DA, Fn was site-specifically labeled exclusively on buried cysteines within modules III7 and III15 of each dimer arm. Isolated plasma Fn at ∼1 g/l in PBS was denatured in an equal volume of 8 M GdnHCl and incubated for 2 h with a 15-fold molar excess each of Alexa 546 maleimide and Alexa 488 maleimide. Fn-DA was separated from free dye by size exclusion chromatography (PD-10 Sephadex, Amersham, http://www.amersham.com/). Western blot analysis was used to determine the point at which Fn fragments contaminated the eluent (data not shown). Fn was also labeled to produce amine/cys Fn-DA with donors and acceptors located on random amines and cysteines, respectively. Fn at ∼1 g/l in PBS was denatured in an equal volume of 8 M GdnHCl and incubated for 1 h with a 30-fold excess of Alexa 546 maleimide. Acceptor-labeled Fn was separated from free dye by overnight dialysis (Slide-a-lyzer dialysis cassette, 10,000 MW cutoff; Pierce, http://www.piercenet.com/) with three changes of amine labeling buffer (PBS with 0.1 M NaHCO3 [pH 8.5]). Subsequently acceptor-labeled Fn was incubated with a 70-fold excess of Alexa 488 succinimidyl ester for 1 h. Fn-DA was separated from free dye using a PD-10 column equilibrated with PBS. The labeling ratio of donors to acceptors per Fn dimer was determined by measuring the absorbances of Fn-DA at 280, 496, and 556 nm and using published extinction coefficients for dyes and Fn. Fn-DA was stored with 10% glycerol at −20 °C until needed and used within 5 d of thawing and storage at 4 °C.
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Publication 2007
Amines Bicarbonate, Sodium Buffers Cysteine cysteinylcysteine Dialysis Donors Dyes Esters Extinction, Psychological Fluorescence Resonance Energy Transfer Glycerin Homo sapiens maleimide Molar Molecular Probes Molecular Sieve Chromatography Plasma sephadex Western Blot
The 40 aa flagelliform peptide (GPGGA)8 was crosslinked to maleimide-functionalized DNA. The peptide/DNA conjugate was labelled with organic fluorophores for fluorescence-force spectroscopy to determine the force per end-to-end distance of the peptide. For more detailed information see Online Methods and Supplementary Note III.
Publication 2010
Fluorescence Spectroscopy maleimide Peptides
Previously described methods were used to synthesize MeHA30 (~92% methacrylation) from sodium hyaluronate (Lifecore), MeAlg (~70% modification) from sodium alginate (Sigma), and MeDex (~50% modification) from dextran (Sigma). MeMaHA with ~14% and ~10.5% methacrylate and maleimide modification, respectively, was synthesized via the coupling of the tetrabutylammonium salt of NaHA (HA-TBA) with 2-amino methacrylate hydrochloride (Sigma) and 2-amino maleimide trifluoroacetate salt (Sigma) (Supplementary Fig. S20). The chemical structures and 1H NMR spectra of MeHA, MeAlg, MeDex and MeMaHA are provided in Supplementary Fig. S21, Supplementary Fig. S22, Supplementary Fig. S23, and Supplementary Fig. S24, respectively. The integrin binding peptide GCGYRGDSPG (Genscript; italics indicates cell adhesive domain) was conjugated to MeHA, MeAlg, and MeDex (754 µM, matching that used in the described physically crosslinked alginate studies), and to MeMaHA (1 mM) via 30 min reaction in pH 8.0 PBS at 25 °C prior to crosslinking. Passage 3 hMSCs (Lonza) were encapsulated either into MeMaHA (1 million hMSCs ml−1) hydrogels using Michael addition reactions between MeMaHA maleimides and the MMP degradable peptide GCRDVPMS↓MRGGDRCG (Genscript; down arrow indicates cleavage site by MMP-2), or into MeHA, MeAlg, or MeDex (15 million hMSCs ml−1) using photo-initiated free radical polymerization (Exfo Omnicure S1000 lamp with a 320–390 nm filter, exposure of 10 mW cm−2 for 5 min) in the presence of 0.05 wt% Irgacure 2959 (I2959; Ciba), a photoinitiator chosen for its aqueous solubility and good cytocompatibility38 (link). For CD44 blocking studies, hMSCs were incubated with anti-CD44 (3/1000, mouse mAb CD44, Abcam) in a buffer (2 mM EDTA and 2% FBS in PBS) for 45 min on ice, washed twice in buffer, and resuspended in growth media prior to encapsulation. All gels were transferred to FBS-supplemented MEM-α (Invitrogen). MeMaHA hydrogels were secondarily photopolymerized at day 0 (“D0 UV”) or day 7 (“D7 UV”) by incubating with I2959 and exposing to UV light as described above. The elastic modulus of the hydrogels was measured via parallel plate compression testing at 10% ramped strain min−1 as previously reported27 (link). For differentiation studies, following 7 days of incubation in growth media, hydrogels were transferred to a 1:1 mixture of adipogenic:osteogenic media (R&D Systems), with media changes every 3 days. For ROCK inhibition studies, selected −UV gels were treated with 10 µM Y-27632 (Sigma) daily during either the growth media (day 1–7) or mixed media (day 7–21) incubation periods.
Publication 2013
CpG/ODN amphiphiles were synthesized using an ABI 394 synthesizer on a 1.0 micromole scale. All lipophilic phosphoramidites were conjugated as a final ‘base’ on the 5′ end of oligos19 . Antigen amphiphiles were synthesized by reacting N-terminal cysteine-modified peptides with maleimide-PEG2000-DSPE in DMF.
Publication 2014
1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-methoxy-poly(ethylene glycol 2000) ABI1 protein, human Antigens CPG-ODN Cysteine maleimide Peptides phosphoramidite

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Publication 2017
Antibodies B-Lymphocytes Buffers Cell Culture Techniques Cell Lines Cells Combined Antibody Therapeutics Genes, vpr HIV-2 Homo sapiens Infection Intercalating Agents Isotopes maleimide Metals Microspheres Palatine Tonsil Physiology, Cell tetraxetan Tissue Donors Virion Virus Virus Diseases

Most recents protocols related to «Maleimide»

First, 50 μM
of purified LUCOS-base proteins were diluted in 1 mL 100 mM sodium
phosphate buffer (pH 7) and reduced with 5 mM tris(2-carboxyethyl)phosphine
(TCEP) for 1 h at room temperature (shaking incubator 500 rpm). Next,
to remove the excess of TCEP, the sample was loaded onto a PD-10 desalting
column (Cytvia) that was first equilibrated with 100 mM sodium phosphate
buffer (pH 7) with 25 μM TCEP. For the maleimide coupling reaction,
the reduced LUCOS-base protein was mixed with the cortisol-3-CMO-maleimide
in a 1:10 molar ratio (7.5 μM sensor protein with 75 μM
cortisol-3-CMO-maleimide) in 100 mM sodium phosphate buffer (pH 7,
with 5% DMSO). The reaction mixture was subsequently incubated for
2 h at room temperature (500 rpm). Next, a PD-10 desalting column
was used to remove excess, unreacted cortisol-3-CMO-maleimide and
exchange the reaction buffer with PBS (pH 7.2). Successful incorporation
of the analog was confirmed with Q-ToF LC-MS (Waters MassLynx v4.1),
using MagTran v1.03 for MS deconvolution (Figures 2b,c and S5). Proteins
were stored at −70 °C until use.
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Publication 2024
A Gly-Gly-Gly-Cys peptide with C-terminal amidation (Genscript) was dissolved at 173 mM in degassed coupling buffer (50 mM HEPES (pH 7.4), 20 mM TCEP (pH adjusted to 7.5)). Sulfo-Cyanine5 maleimide (Lumiprobe) dissolved in degassed DMSO was mixed in a 2:1 molar ratio (dye:peptide) and incubated overnight at 4 °C. The following morning, the reaction was quenched with 10 mM DTT. The labeling reaction mixture was separated using on a C-18 reverse phase HPLC Column (Beckman Ultrasphere C-18, 4.6 25 cm) that was pre-equilibrated with Buffer 1(filtered MilliQ with 0.1% Trifluoroacetic acid (Sigma-Aldrich)). The protein was eluted at 1.5 ml/min using the following gradient- 0–1 min: 10% buffer 2 (filtered Acetonitrile (Sigma-Aldrich) with 0.1% TFA); 1–16 min: 70% buffer 2; 16–17 min: 90% buffer 2; 17–22 min: 90% buffer 2. The column eluent was monitored at 200 nm and 650 nm. Under these conditions, unlabelled GGGC peptide eluted at ~11 min and GGGCCy5 peptide eluted at ~15 min, respectively, under these conditions. The free Cy5 dye was eluted from the column only after washing with 100% buffer 2. The GGGCCy5 peptide was lyophilized and stored at −80 °C.
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Publication 2024
Ten mg hydrocortisone
3-(O-carboxymethyl)oxime (Toronto Research Chemicals) and 10.4 mg
2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate
(HATU, Fluorochem) were dissolved in 2 mL DMF. Subsequently, 44 μL
diisopropylethylamine (DIPEA, Sigma) was added together with 16.5
mg 1-(2 aminoethyl)maleimide hydrochloride (Sigma) before the mixture
was stirred for 4 h at room temperature. DMF was removed using a Buchi
rotary evaporator and a diaphragm pump. The remaining compound was
dissolved in Milli-Q water with 25% HPLC-grade acetonitrile and 0.1%
formic acid. Cortisol-3-CMO-maleimide was purified with a preparative
LC-MS system comprising of an LCQ Deca XP Max (Thermo Finnigan) ion-trap
mass spectrometer equipped with a Surveyor photodiode detector array
(PDA) detector (Thermo Finnigan). The mixture was purified with a
Phenomex kinetex 2.6 μm EVO C18 50 × 2.1 mm column and
an isocratic acetonitrile gradient of 34%. Fractions with the correct
mass (E/Z isomers were not separated) were collected using a PrepFC
fraction collector (Gilson Inc.) and subsequently freeze-dried before
being dissolved in DMSO and stored at −30 °C (Figure S4).
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Publication 2024
AF488 maleimide or AF647 maleimide (Jena Bioscience) was added in a tenfold molar excess to Archease-S147C (50 µM) or RTCB (50 µM), respectively. RTCB was labeled in the presence of Mn2+ (500 µM) and GMPCPP (500 µM). After 2 h incubation at room temperature, the reaction was stopped with an excess of β-mercaptoethanol. The sample was applied onto a desalting column (HiTrap Desalting, Cytiva) and eluted with desalting buffer (25 mM HEPES, pH 7.3, 250 mM NaCl2, 5% Glycerol, 1 mM TCEP) to remove excess dye. Labeled Archease-S147C or RTCB was flash-frozen in liquid nitrogen and stored at 80 °C, protected from light.
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Publication 2024
To incorporate the negatively charged chondroitin sulfate to the cell surface, maleimide-conjugated chondroitin sulfate (MCS) was synthesized using the modified version of a previously reported method [28 (link)]. Briefly, 2 g of chondroitin sulfate sodium salt (CS, cat# C0335, Tokyo Chemical Industry, Tokyo, Japan) was dissolved in 40 ml of PBS with vigorous magnetic stirring. Next, 286 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDC, cat# 39391, Sigma-Aldrich, St. Louis, MO, USA) and 328 mg of N-hydroxysulfosuccinimide sodium salt (NHS, cat# 56485, Sigma-Aldrich, St. Louis, MO, USA) were dissolved in 10 ml of PBS. After the CS was completely dissolved, the mixture containing EDC and NHS was added to the CS solution and stirred for 20 min at room temperature. Then, 250 mg of N-(2-aminoethyl)maleimide trifluoroacetate salt (maleimide, cat# 56951-1G-F, Sigma-Aldrich, St. Louis, MO, USA) was dissolved in 10 ml of PBS, added to the mixture, and incubated for 5 h with gentle stirring at room temperature. Afterward, the solution was dialyzed with a dialysis membrane (cat#132676, Spectrum Laboratories, CA, USA) against distilled water for 4 days (distilled water was renewed every 12 h) at room temperature and freeze-dried until future use.
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Publication 2024

Top products related to «Maleimide»

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Alexa Fluor 488 C5 maleimide is a fluorescent dye used for labeling proteins and other biomolecules. It is a reactive dye that forms a covalent bond with thiol groups, allowing for the specific labeling of cysteine residues within proteins.
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Zeba Spin Desalting Columns are a size-exclusion chromatography product designed to quickly remove salts, buffers, and other small molecules from protein samples. The columns are pre-packed with a proprietary resin that efficiently separates proteins from small molecules based on their size difference. This allows for the effective desalting and buffer exchange of protein samples in a simple, rapid, and reproducible manner.
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Fetal Bovine Serum (FBS) is a cell culture supplement derived from the blood of bovine fetuses. FBS provides a source of proteins, growth factors, and other components that support the growth and maintenance of various cell types in in vitro cell culture applications.
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Alexa Fluor 647 C2 maleimide is a fluorescent dye molecule designed for labeling proteins and other biomolecules. It contains a maleimide reactive group that can form a covalent bond with sulfhydryl groups, allowing it to be conjugated to cysteine residues in proteins. The dye has an absorption maximum of 650 nm and an emission maximum of 665 nm, making it suitable for detection in the red region of the visible spectrum.
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N-ethylmaleimide is a chemical compound used in various laboratory applications. It functions as a reagent for the selective modification of sulfhydryl groups in proteins and peptides.
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DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.
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Fluorescein-5-maleimide is a fluorescent labeling agent. It is used to covalently attach fluorescein to sulfhydryl groups on proteins and other molecules.
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IRDye800CW maleimide is a near-infrared fluorescent dye that can be used for various labeling applications. It contains a maleimide functional group, which allows for covalent attachment to thiol-containing biomolecules. The dye has an excitation maximum at 778 nm and an emission maximum at 794 nm, making it suitable for near-infrared imaging.
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The PD-10 desalting column is a laboratory equipment used for the separation and purification of biomolecules. It functions by removing salts, buffer components, or other small molecular weight substances from protein or nucleic acid samples, allowing for the recovery of the desired macromolecules in a purified form.
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The PD-10 column is a size-exclusion chromatography column designed for desalting and buffer exchange of protein samples. It is commonly used to separate low molecular weight substances from high molecular weight compounds, such as proteins, in a rapid and efficient manner.

More about "Maleimide"

Maleimide, bioconjugation, chemical modification, thioether bonds, sulfhydryl groups, proteins, peptides, nucleic acids, drug delivery, biosensing, proteomics, PubCompare.ai, Alexa Fluor 488 C5 maleimide, Alexa Fluor 647 C2 maleimide, IRDye800CW maleimide, Zeba Spin Desalting Columns, PD-10 desalting columns, DMSO, FBS, N-ethylmaleimide, Fluorescein-5-maleimide