Name: 3-Maleimidopropionic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

1H-Pyrrole-1-propanoic acid, 2,5-dihydro-2,5-dioxo-; 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-propanoic acid; 3-Pyrroline-1-propionic acid, 2,5-dioxo-; 2,5-Dioxopyrrole-1-propanoic acid; 3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-propionic acid; 3-(2,5-Dioxo-2H-pyrrol-1(5H)-yl)propanoic acid; 3-(Maleimido)propanoic acid; BMPA; BMPA (imide); N-(2-Carboxyethyl)maleimide; N-Maleoyl-β-alanine; β-Maleimidopropionic acid

IUPAC Name

3-(2,5-dioxopyrrol-1-yl)propanoic acid

Canonical SMILES

C1=CC(=O)N(C1=O)CCC(=O)O

InChI

InChI=1S/C7H7NO4/c9-5-1-2-6(10)8(5)4-3-7(11)12/h1-2H,3-4H2,(H,11,12)

InChIKey

IUTPJBLLJJNPAJ-UHFFFAOYSA-N

Density

1.473±0.06 g/cm3

Solubility

Soluble in Alcohol, Dimethyl Formamide, Dimethyl Sulfoxide, DMSO (Slightly), Methanol, Water (Slightly)

Melting Point

103-106°C

Appearance

White powder

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Store at -20°C

Signal Word

Warning

Boiling Point

382.5±25.0°C at 760 mmHg

3-Maleimidopropionic acid, a versatile chemical widely utilized in the bioscience industry, serves various indispensable purposes. Here are four key applications presented with a high degree of perplexity and burstiness:

Bioconjugation Chemistry: At the heart of biomolecular interactions, 3-Maleimidopropionic acid plays a pivotal role in forging steadfast covalent bonds between biomolecules like proteins and peptides. Its usage extends to conjugating antibodies with other vital molecules like enzymes or drugs, crafting targeted therapies and diagnostic aids that propel the boundaries of medicine.

Protein Engineering: Delving into the intricacies of protein modification, 3-Maleimidopropionic acid emerges as a critical agent for introducing functional entities into proteins or peptides. By engaging thiol groups on cysteine residues, it enables precise labeling or cross-linking of proteins, a fundamental process that unveils the secrets of protein structure and function, revolutionizing the realms of biotechnology.

Drug Delivery Systems: The symphony of advanced drug delivery systems owes a debt to 3-Maleimidopropionic acid for its role in enhancing precision and efficacy. Through its maleimide group, it facilitates the attachment of therapeutic cargos to carriers such as nanoparticles or liposomes, ushering in a new era of targeted drug delivery that promises heightened therapeutic impact and efficiency.

Biomaterials Science: In the realm of materials science, 3-Maleimidopropionic acid emerges as a transformative force, empowering the modification of surfaces to birth biomaterials with bespoke traits. By affixing bioactive molecules onto surfaces, it amplifies cell adhesion and growth, a boon particularly cherished in the domains of tissue engineering and regenerative medicine, where the promise of healing and restoration beckons.

1. Small-molecule albumin ligand modification to enhance the anti-diabetic ability of GLP-1 derivatives

Xiaoliang Sun, Ziyuan Zhang, Meiyan Liu, Peng Zhang, Liqin Nie, Yuqing Liu, Ye Chen, Fengjiao Xu, Zhonghua Liu, Youlin Zeng Biomed Pharmacother. 2022 Apr;148:112722. doi: 10.1016/j.biopha.2022.112722. Epub 2022 Feb 21.

Glucagon-like peptide-1 (GLP-1) receptor agonists modified with albumin ligands which can specificity bind to the human serum albumin (HSA) was an efficient strategy to prolong the half-time of GLP-1. Herein, we investigated the effect of small-molecule albumin ligand modification on the hypoglycemic activities of GLP-1 derivatives. Two GLP-1 derivatives MPA-C12-GLP-1 and Rhein-C12-GLP-1 were achieved by modification of the side chain amino of lysine in position 26 of the Arg34-GLP-1(7-37)-OH with Rhein and 3-Maleimidopropionic acid respectively using 12-aminolauric acid as a linker, and its specific albumin-conjugating characteristics, pharmaceutical characterization, and the antidiabetic effects were investigated. In vitro level, two GLP-1 derivatives demonstrated a higher binding capacity to GLP-1 receptor than that of Arg34-GLP-1(7-37)-OH. Interestingly, although the binding ability of MPA-C12-GLP-1 was equal to liraglutide, the binding ability of Rhein-C12-GLP-1 was 10-fold higher than liraglutide. In vivo level, the two GLP-1 derivatives can significantly increase their glucose tolerance and prolong their half-life in ICR mice, and they were also superior to GLP-1 in controlling glucose homeostasis and suppression of food intake and water consumption in db/db mice. Importantly, the two GLP-1 derivatives showed comparable efficacy to liraglutide for the therapy of type 2 diabetes mellitus. The in vitro INS-1 cells toxicity and the in vivo hepatotoxicity indicated that the Rhein-C12-GLP-1 was a safe candidate for the therapy of type 2 diabetes, and the serum biomarkers determination results showed that the Rhein-modified GLP-1 could significantly improve the HbA1c and blood lipids, and the H&E stain exhibited that the Rhein-C12-GLP-1 can effectively promote β-cell proliferation and differentiation. In conclusion, the 3-Maleimidopropionic acid or Rhein-modified GLP-1derivatives have great potential for development as a Type 2 diabetes mellitus therapeutic drug.

2. Generation of Rat Monoclonal Antibody to Detect Hydrogen Sulfide and Polysulfides in Biological Samples

Shingo Kasamatsu, Yuki Kakihana, Taisei Koga, Hisashi Yoshioka, Hideshi Ihara Antioxidants (Basel). 2020 Nov 21;9(11):1160. doi: 10.3390/antiox9111160.

Hydrogen sulfide (H2S) is endogenously produced by enzymes and via reactive persulfide/polysulfide degradation; it participates in a variety of biological processes under physiological and pathological conditions. H2S levels in biological fluids, such as plasma and serum, are correlated with the severity of various diseases. Therefore, development of a simple and selective H2S measurement method would be advantageous. This study aimed to generate antibodies specifically recognizing H2S derivatives and develop a colorimetric immunoassay for measuring H2S in biological samples. We used N-ethylmaleimide (NEM) as an H2S detection agent that forms a stable bis-S-adduct (NEM-S-NEM). We also prepared bis-S-heteroadduct with 3-maleimidopropionic acid, which, in conjugation with bovine serum albumin, was to immunize Japanese white rabbits and Wistar rats to enable generation of polyclonal and monoclonal antibodies, respectively. The generated antibodies were evaluated by competitive enzyme-linked immunosorbent assay. We could obtain two stable hybridoma cell lines producing monoclonal antibodies specific for NEM-S-NEM. By immunoassay with the monoclonal antibody, the H2S level in mouse plasma was determined as 0.2 μM, which was identical to the level detected by mass spectrometry. Taken together, these monoclonal antibodies can be a useful tool for a simple and highly selective immunoassay to detect H2S in biological samples.

3. Polymeric mercaptosilane-modified platinum electrodes for elimination of interferants in glucose biosensors

S K Jung, G S Wilson Anal Chem. 1996 Feb 15;68(4):591-6. doi: 10.1021/ac950424p.

An oxidase-based glucose sensor has been developed that uses a mercaptosilane-modified platinum electrode to achieve selectivity of electrochemical interferants. A platinum-iridium (9:1) wire (0.178 mm o.d., sensing area of 1.12 mm2) is modified with (3-mercaptopropyl)trimethoxysilane. The modified sensors show excellent operational stability for more than 5 days. Glucose oxidase is immobilized on the modified surface (i) by using 3-maleimidopropionic acid as a linker or (ii) by cross-liking with bovine serum albumin using glutaraldehyde. Sensitivities in the range of 9.97 nA/mM glucose are observed when the enzyme is immobilized by method ii. Lower sensitivities (1.13 x 10(-1) nA/mM glucose) are observed when immobilization method i is employed. In terms of linear response range, the sensor enzyme-immobilized by method i is superior to that immobilized by method ii. The linearity is improved upon coating the enzyme layer with polyurethane. The sensor immobilized by method ii and coated with polyurethane exhibits a linear range to 15 mM glucose and excellent selectivity to glucose (0.47 nA/mM) against interferants such as ascorbic acid, uric acid, and acetaminophen.