55750-53-3

Basic information

• Product Name: 6-Maleimidocaproic acid
• Synonyms: N-MALEOYL-6-AMINO-CAPROIC ACID;N-EPSILON-MALEIMIDOCAPROIC ACID;N-(5-CARBOXYPENTYL)MALEIMIDE;EMCA;EPSILON-MALEIMIDOCAPROIC ACID;6-MALEIMIDOCAPROIC ACID;6-MALEIMIDOHEXANOIC ACID;6-MALEIMIDOCAPROIC ACID, 98+%
• CAS NO: 55750-53-3
• Molecular Formula: C₁₀H₁₃NO₄
• Molecular Weight: 211.21
• EINECS: 1533716-785-6
• Product Categories: Maleimide Derivatives;Cross Linking Reagents;MTS & Sulfhydryl Active Reagents
• Mol File: 55750-53-3.mol
• Article Data: 53

Chemical Properties

• Melting Point: 86-91 °C
• Boiling Point: 407.3°C at 760 mmHg
• Flash Point: 200.1°C
• Appearance: White to pale yellow/Powder
• Density: 1.285g/cm³
• Vapor Pressure: 8.97E-08mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 4.74±0.10(Predicted)
• Water Solubility: Soluble in water, methanol, ethanol, dimethyl sulfoxide. Insoluble in ether.
• Sensitive: Moisture Sensitive
• BRN: 1532405
• CAS DataBase Reference: 6-Maleimidocaproic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Maleimidocaproic acid(55750-53-3)
• EPA Substance Registry System: 6-Maleimidocaproic acid(55750-53-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-36-39
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 55750-53-3(Hazardous Substances Data)

Usage

Description

6-Maleimidocaproic acid contains a maleimide group and a terminal carboxylic acid. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.

Chemical Properties

White to yellow solid, powder, crystals or crystaline powder.

Uses

6-Maleimidohexanoic acid is used as a probe for introducing maleimides groups into biomolecules and active pharmaceutical ingredients. Further, it is used with N-hydroxysuccinimide ester as a bifunctional cross-linking reagent. In addition to this, it acts as a probe for thiol groups in membrane proteins.

Definition

ChEBI: 6-Maleimidocaproic acid is a medium-chain fatty acid. It contains a maleimide group and a terminal carboxylic acid. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.

Application

6-Maleimidocaproic acid is a sulfhydryl reactive heterobifunctional crosslinking reagent. It can be widely used probe for introducing maleimides groups into biomolecules. A probe for thiol groups in proteins. Spacer Arm: 9.4 Angstroms. Probe for thiol groups (SH-groups) in membrane proteins.

InChI:InChI=1/C10H13NO4/c12-8-5-6-9(13)11(8)7-3-1-2-4-10(14)15/h5-6H,1-4,7H2,(H,14,15)

Upstream product

• 108-30-5 succinic acid anhydride 
• 60-32-2 6-aminohexanoic acid 
• 108-31-6 maleic anhydride 
• 660-88-8 5-aminopentanoic acid 
• 7440-44-0 pyrographite 
• 108-20-3 di-isopropyl ether 
• 57079-14-8 6-(3-carboxyacryloylamino)caproic acid 
• 57079-14-8 C₁₀H₁₅NO₅ 

Downstream Products

• 82333-93-5 benzyl N-(4-aminophenethyl)-N-methyl-L-valinate dihydrochioride 
• 558483-53-7 C₂₀H₃₁NO₆ 
• 558483-51-5 C₃₁H₄₄N₂O₁₀ 
• 1610922-24-1 C₂₃H₂₉NO₆S 
• 55750-63-5 6-maleimidohexanoic acid N-hydroxylsuccinimide ester 

Relevant articles and documents

Photopolymerization of maleimide perfluoropolyalkylethers without a photoinitiator

Perfluoropolyalkylethers derived from hexafluoropropylene oxide were functionalized with maleimide groups. Irradiated by UV-light, the new maleimide macromonomers demonstrated very fast polymerization kinetics with a curing time as fast as 8 s. The effect on photopolymerization of different features such as the molecular weight of the fluorinated chain and the chain length of the hydrogenated spacer were studied, as well as the influence of the type of photoinitiator and the presence of air. Thermal and surface properties of the UV-cured polymers were examined and were typical to fluoropolymers in view of water–oil repellent coatings.

Multifunctional Tumor-Targeting Cathepsin B-Sensitive Gemcitabine Prodrug Covalently Targets Albumin in Situ and Improves Cancer Therapy

We report a new type of amide bond-bearing cathepsin B-sensitive gemcitabine (GEM) prodrugs, capable of in situ covalently targeting circulating albumin and then making a hitchhike to the tumor. Specially, less plasma-enzyme deactivation, long plasma half-life, independence on nucleoside transporters, outstanding tumor targeting, and site-specific drug release are achieved, and as such these multifunctional advantages contribute to the dramatically increased in vivo antitumor efficacy.

Cytosine arabinoside prodrug designed to bind plasma serum albumin for drug delivery

Rational design of anticancer prodrugs for efficient albumin binding can show distinct advantages in drug delivery in terms of high drug availability, long systemic circulation, potential targeting effect, and enhanced chemotherapy effect. In the present study, we reported a cytosine arabinoside (Ara-C) prodrug which could well formulate in solution and instantly transform into long-circulating nanocomplexes by hitchhiking blood-circulating albumin after i.v. administration. Specifically, Ara-C was conjugated with an albumin-binding maleimide derivative, the resulting Ara-C maleimide caproic acid conjugate (AM) was well formulated in aqueous solution, conferring high albumin-binding ability in vitro albumin-binding studies. Moreover, in vivo fluorescence images of sulfo-cyanine5 maleimide indirectly demonstrated that AM showed better accumulation in tumors, exhibiting superior tumor targeting ability and antitumor activity compared to Ara-C. Such a uniquely developed strategy, integrating high albumin-binding capability, has great potential to be applied in clinical cancer therapy.

Linker, Antibody-Drug Conjugate Including Same and Use Thereof

Provided are a linker represented by Formula I or I′, an antibody-drug conjugate containing the same, and use of thereof, a pharmaceutical composition comprising the antibody-drug conjugate, and use of the antibody-drug conjugate for treating and/or preventing a disease.

A designed cyclic peptide based on Trastuzumab used to construct peptide-drug conjugates for its HER2-targeting ability

Human epidermal growth factor receptor 2 (HER2) has been recognized as an important therapeutic target for its overexpression in many cancers. Trastuzumab is a monoclonal antibody targeting HER2, which has been approved by FDA to treat HER2-positive cancer. In this research, cyclic peptide Cyclo-GCGPep1 was designed based on the binding mode between antibody and HER2 protein in silico, which has been confirmed possessing good affinity with HER2. Cyclo-GCGPep1 was also used to construct peptide-drug conjugates with Camptothecin. Biological evaluations demonstrated that Conjugate 1 has a good antiproliferative activity on SK-BR-3 and NCI-N87 cells. Conjugate 1 retained the pro-apoptotic and Topo I inhibitory ability of Camptothecin. Meanwhile, it has good targeting ability towards HER2-positive cells with the help of Cyclo-GCGPep1. It also has better permeability in the tumor spheroid model than Camptothecin. In summary, the design of cyclic peptide derived from antibody is of significance for the discovery of targeting peptides and Conjugate 1 is expected as a good therapeutic agent for HER2-positive cancers.