Name: N-[4-(-Carboxycyclohexylmethyl)]maleimide
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Synonyms

Cyclohexanecarboxylic acid, 4-[(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl]-; 4-[(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl]cyclohexanecarboxylic acid; 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carboxylic acid; 4-(N-Maleimidomethyl)cyclohexanecarboxylic acid; 4-(Maleimidomethyl)cyclohexanecarboxylic acid

IUPAC Name

4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexane-1-carboxylic acid

Canonical SMILES

C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)O

InChI

InChI=1S/C12H15NO4/c14-10-5-6-11(15)13(10)7-8-1-3-9(4-2-8)12(16)17/h5-6,8-9H,1-4,7H2,(H,16,17)

InChIKey

LQILVUYCDHSGEU-UHFFFAOYSA-N

Density

1.329±0.06 g/cm3

Solubility

Soluble in Chloroform (Slightly), Methanol (Slightly)

Melting Point

89-91°C

Appearance

White to Light Orange Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Store at -20°C

Boiling Point

433.6±18.0°C at 760 mmHg

N-[4-(Carboxycyclohexylmethyl)]maleimide is a versatile compound extensively utilized in bioconjugation, particularly in the development of antibody-drug conjugates (ADCs). Its maleimide functional group reacts selectively with thiol groups, enabling the formation of stable thioether linkages. This specificity is critical in creating ADCs with precise drug-to-antibody ratios, improving therapeutic efficacy and minimizing off-target effects. In addition, the compound's stability under physiological conditions ensures that the conjugate remains intact until it reaches the target site, further enhancing its value in pharmaceutical applications.

Another significant application of N-[4-(Carboxycyclohexylmethyl)]maleimide is in protein labeling and modification. The carboxylic acid group allows for the introduction of hydrophilic characteristics, making the compound suitable for aqueous environments. This property is particularly beneficial in designing protein-based diagnostics and therapeutics, as it minimizes aggregation and ensures solubility. The selective reactivity of the maleimide group also enables the precise modification of proteins, facilitating the study of their structure and function in various biological systems.

The compound also finds utility in polymer chemistry, where it serves as a crosslinking agent. Its dual functional groups, carboxyl and maleimide, enable the formation of complex polymer networks with tailored properties. Such polymers are employed in drug delivery systems, where they offer controlled release capabilities and enhanced biocompatibility. Additionally, these polymers are integral in tissue engineering, providing scaffolds that mimic natural extracellular matrices for cell growth and differentiation.

In addition to its roles in pharmaceuticals and polymer science, N-[4-(Carboxycyclohexylmethyl)]maleimide is widely used in the development of biosensors. Its ability to conjugate with biomolecules makes it ideal for immobilizing enzymes, antibodies, or other biological entities on sensor surfaces. This application enhances the sensitivity and specificity of biosensors, making them valuable tools in medical diagnostics, environmental monitoring, and food safety analysis.

1.In vitro characterization of ligand-induced oligomerization of the S. cerevisiae G-protein coupled receptor, Ste2p.

Shi C1, Paige MF, Maley J, Loewen MC. Biochim Biophys Acta. 2009 Jan 1;1790(1):1-7. doi: 10.1016/j.bbagen.2008.10.003. Epub 2008 Oct 21.

BACKGROUND: The S. cerevisiae alpha-factor receptor, Ste2p, is a G-protein coupled receptor that plays key roles in yeast signaling and mating. Oligomerization of Ste2p has previously been shown to be important for intracellular trafficking, receptor processing and endocytosis. However the role of ligand in receptor oligomerization remains enigmatic.

2.A novel pathway for maytansinoid release from thioether linked antibody-drug conjugates (ADCs) under oxidative conditions.

Fishkin N1, Maloney EK, Chari RV, Singh R. Chem Commun (Camb). 2011 Oct 14;47(38):10752-4. doi: 10.1039/c1cc14164c. Epub 2011 Aug 26.

A novel pathway for ex vivo maytansinoid release from thioether linked antibody maytansinoid conjugates (AMCs) upon incubation in human plasma has been identified. A thioether succinimide-linked AMC can undergo chemical oxidation followed by sulfoxide elimination under mild aqueous conditions (pH 5.5-7.5, 37 °C). Oxidized thioether-linked AMCs exhibit high, target-specific cytotoxicity toward cancer cells.

3.The design and evaluation of a novel targeted drug delivery system using cationic emulsion-antibody conjugates.

Goldstein D1, Nassar T, Lambert G, Kadouche J, Benita S. J Control Release. 2005 Nov 28;108(2-3):418-32. Epub 2005 Oct 13.

In an attempt to design a targeted drug delivery system to tumors' over-expressing H-ferritin specifically recognized by a monoclonal antibody, AMB8LK, a cationic emulsion - AMB8LK conjugate was prepared. A novel cross-linker molecule bearing maleimide group was synthesized and added to cationic emulsion formulation for AMB8LK Fab' fragment covalent coupling. NMR spectroscopy confirmed the cross-linker synthesis and the preservation of the active maleimide function. SDS gel-electrophoresis results corroborated the formation of the Fab' fragment. Different densities of Fab' fragments (10-200 Fab'/oil droplet) were conjugated to emulsion droplet interface and no changes in the physico-chemical properties were observed ( approximately 120 nm size and zeta potential of approximately +30 mV). The coupling efficiency ranged from 55% to 70% and was visualized by TEM showing gold particles attached to the droplet interface. Cell culture studies demonstrated specific binding to cells as confirmed by the occurrence of the marked reduction in binding when free AMB8LK Mab was incubated before adding the AMB8LK-emulsion conjugate to the cells.

4.[Determination of drug antibody ratio in an antibody-drug conjugate].

Yu CF, Li M, Guo W, Wang L, Zhang F, Liu CY, Wang WB, Wang JZ, Gao K. Yao Xue Xue Bao. 2014 Mar;49(3):363-7.

This paper reports the determination of the drug antibody ratio in an antibody-drug conjugate with two methods, i.e. LC-MS and UV/VIS, and to provide a reliable method to scientifically evaluate and effectively control the drug antibody ratio. Deglycosylated sample was analyzed with C4 column followed by MS, and the number of conjugated drugs in the antibody was determined by the molecular weight increase due to the addition of different number of drugs to the antibody, and then drug antibody ratio was calculated by weighted average of different number of drugs conjugated to the antibody. Optical density at 252 and 280 nm was measured with UV/VIS, and due to the difference of extinction coefficients between the antibody and the drug, the drug antibody ratio was calculated from linear equation with two unknowns. The drug antibody ratio was 3.21 and 3.25 respectively measured by the two methods, and the results were similar with the two methods.