57078-98-5

Basic information

• Product Name: 4-MALEIMIDOBUTYRIC ACID
• Synonyms: γ-Maleimidobutyric acid, 4-Maleimidobutanoic acid, N-(3-Carboxypropyl)maleimide, N-Maleoyl-4-aminobutyric acid, N-Maleoyl-GABA;4-Maleimidobutyric acid,γ-Maleimidobutyric acid, 4-Maleimidobutanoic acid, N-(3-Carboxypropyl)maleimide, N-Maleoyl-4-aminobutyric acid, N-Maleoyl-GABA;2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-butanoic Acid;2-Cyclopropyl-5,6,7,8-tetrahydropyrido[4,3-d]pyriMidine hydrochloride;MBA 4-Maleimidobutyric acid;omega-Maleimidobutyric acid;4-(2,5-dioxo-2H-pyrrol-1(5H)-yl)butanoic acid;RARECHEM AL CD 0913
• CAS NO: 57078-98-5
• Molecular Formula: C₈H₉NO₄
• Molecular Weight: 183.16
• EINECS: 1533716-785-6
• Product Categories: Maleimide Derivatives;MTS & Sulfhydryl Active Reagents;Nitric Oxide Reagents;Cross Linking Reagents
• Mol File: 57078-98-5.mol

Chemical Properties

• Melting Point: 95-98 °C
• Boiling Point: 400.1 °C at 760 mmHg
• Flash Point: 195.8 °C
• Appearance: White Solid
• Density: 1.395 g/cm³
• Vapor Pressure: 1.61E-07mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
• PKA: 4.59±0.10(Predicted)
• BRN: 1455876
• CAS DataBase Reference: 4-MALEIMIDOBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-MALEIMIDOBUTYRIC ACID(57078-98-5)
• EPA Substance Registry System: 4-MALEIMIDOBUTYRIC ACID(57078-98-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 57078-98-5(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry and Molecular Biology:
4-MALEIMIDOBUTYRIC ACID is used as a short crosslinking reagent for the modification of thiol groups in proteins. This allows for the connection of biomolecules with a thiol, which is crucial in various research and diagnostic applications.
Used in Pharmaceutical Industry:
4-MALEIMIDOBUTYRIC ACID is used as a modification reagent for thiol groups in proteins. Its ability to form stable amide bonds with primary amine groups in the presence of activators, such as EDC or HATU, makes it a valuable tool in drug development and the creation of novel therapeutic agents.
Used in Chemical Synthesis:
As a part of the maleimide derivatives family, 4-MALEIMIDOBUTYRIC ACID is used in the synthesis of various chemical compounds, contributing to the development of new materials and products in different industries.
Used in Research and Development:
4-MALEIMIDOBUTYRIC ACID is used as an MTS & Sulfhydryl active reagent, enabling researchers to study the interactions between biomolecules and their potential applications in various fields, including medicine, biotechnology, and materials science.

InChI:InChI=1/C8H9NO4/c10-6-3-4-7(11)9(6)5-1-2-8(12)13/h3-4H,1-2,5H2,(H,12,13)

Upstream product

• 15938-22-4 C₈H₁₁NO₅ 
• 108-31-6 maleic anhydride 
• 56-12-2 4-amino-n-butyric acid 

Downstream Products

• 80307-12-6 4-maleimidobutyric acid N-hydroxysuccinimide ester 
• 57-13-6 urea 
• 1207598-12-6 N-(2-(5-(3-(2,4-dihydroxy-5-isopropylphenyl)-5-hydroxy-4H-1,2,4-triazol-4-yl)-1H-indol-1-yl)ethyl)-4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-methylbutanamide 
• 658053-67-9 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butanoic acid 4-hydroxymethyl-2-nitro-phenyl ester 
• 658053-71-5 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butanoic acid 4-tert-butyldimethylsilanyloxymethyl-phenyl ester 
• 158504-51-9 N-benzyloxycarbonyl-3-(N-maleimidobutyryloxymethyl)-2,2,4,4-tetramethylpyrrolidine 

Relevant articles and documents

Skeletal Analogues of UCS1025A and B by Cyclization of Maleimides: Synthesis and Biological Activity

Application of a direct ring-closing approach which exploits an intramolecular aldol reaction with a ketene silyl acetal onto a remote imide function leading to the core skeleton of UCS1025A and B effectively provides access to small library of substituted analogues; of interest is their complete lack of antibacterial activity against MRSA (Gram+) and E. coli (Gram-) bacterial strains.

Synthesis of desmosine-BSA/KLH conjugates via Sonogashira/Negishi cross-coupling reactions

Desmosine is an elastin crosslinking amino acid that is expected to be a useful biomarker of diseases related to elastin degradation including chronic obstructive pulmonary disease (COPD). In this study, conjugates of desmosine and carrier proteins, such

CONJUGATES OF A CELL-BINDING MOLECULE WITH CAMPTOTHECIN ANALOGS

Provided are conjugates of camptothecin analogs with a cell-binding molecule of formula (I), wherein R1, R2, R3, R4, R5, X, L, n, m, T and ----- are defined herein. It also provides methods of making the conjugates of camptothecin analogs to a cell-binding agent, as well as methods of using the conjugates in targeted treatment of cancer, infection, and immunological disorders.

A CONJUGATE OF AN AMANITA TOXIN WITH BRANCHED LINKERS

Provided herein is the conjugation of an amanita toxin compound to a cell-binding molecule with branched linkers for having better targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of an amanita molecule to a cell-binding ligand, as well as methods of using the conjugate in targets treatment of cancer, infection and autoimmune disease.

A CONJUGATE OF A CYTOTOXIC AGENT TO A CELL BINDING MOLECULE WITH BRANCHED LINKERS

Provided is a conjugation of cytotoxic drug to a cell-binding molecule with a side-chain linker. It provides side-chain linkage methods of making a conjugate of a cytotoxic molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and immunological disorders.

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

Amide compounds for regulating WNT signal channel and application of compounds

The invention belongs to the technical field of medicine, and particularly relates to amide compounds for regulating a WNT signal channel and an application of the compounds. The compounds have a structure represented by a general formula I shown in the description.

Depletion of protein thiols and the accumulation of oxidized thioredoxin in Parkinsonism disclosed by a red-emitting and environment-sensitive probe

Protein sulfhydryl groups play a vital role in maintaining cellular redox homeostasis and protein functions and have attracted increasing interests for the selective detection of protein thiols over low-molecular-weight thiols (LMWTs). Herein, we reported a red-emitting and environment-sensitive probe (FM-red) for detecting and labeling protein thiols. The probe contains a maleimide unit as a thiol receptor and an environment-sensitive fluorophore as a sensor. The emission signal of the probe was exclusively switched on by binding to protein sulfhydryl groups through the twisted intramolecular charge transfer mechanism, while negligible fluorescence was observed when FM-red reacted with LMWTs. Various experiments verified that FM-red possessed fast responsivity (～10 min) and high selectivity to sense protein thiols over LMWTs with a red emission (～655 nm). These favorable properties enable the probe to image protein sulfhydryl groups in live cells and in vivo. In addition, as FM-red has a relatively high molecular weight (MW 688), it is able to separate the labeled proteins from the unlabeled ones after FM-red derivatization via routine protein electrophoresis, which may be applied to determine the redox states of thioredoxin, a small redox protein ubiquitous in all cells. With the aid of the probe, we demonstrated a significant decrease in the protein thiols and the accumulation of oxidized thioredoxin in a cellular model of Parkinson's disease.

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.