Name: Maleimido-tri(ethylene glycol)-propionic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

Mal-PEG3-acid; Mal-PEG3-CH2CH2COOH; Mal-PEG3-COOH; Maleimide-PEG3-CH2CH2COOH; Mal-PEG3-propionic acid; 3-(2-(2-(2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy)ethoxy)ethoxy)propanoic acid; 3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-5-hydroxy-2,2-bis(2-hydroxyethyl)pentanoic acid; Propanoic acid, 3-[2-[2-[2-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethoxy]ethoxy]ethoxy]-

IUPAC Name

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

Canonical SMILES

C1=CC(=O)N(C1=O)C(CCO)C(CCO)(CCO)C(=O)O

InChI

InChI=1S/C13H19NO7/c15-6-3-9(14-10(18)1-2-11(14)19)13(4-7-16,5-8-17)12(20)21/h1-2,9,15-17H,3-8H2,(H,20,21)

InChIKey

AMOPUHDFPSFVHL-UHFFFAOYSA-N

Density

1.293±0.06 g/cm3 (Predicted)

Solubility

Soluble in DMSO (10 mm)

Flash Point

337.3±31.5 °C

Index Of Refraction

1.597

PSA

135.37000

Vapor Pressure

0.0±4.2 mmHg at 25°C

Appearance

Pale Yellow Oily Matter

Quantity

Data not available, please inquire.

Shelf Life

0-4°C for short term (days to weeks), or -20°C for long term (months).

Shipping

Room temperature, or blue ice upon request.

Storage

Store at 2-8°C

Boiling Point

491.4±40.0°C (Predicted)

Form

Solid

Maleimido-tri(ethylene glycol)-propionic acid, a versatile chemical compound with a multitude of scientific and industrial uses, finds itself at the forefront of innovation in various fields.

Bioconjugation: Maleimido-tri(ethylene glycol)-propionic acid plays a pivotal role in bioconjugation techniques, serving as a bridge to connect proteins, peptides, and other biomolecules. With its maleimide group readily engaging thiol groups present in cysteine residues, stable thioether bonds are formed, allowing for the attachment of functional groups or labels. This fusion enables the customization of biomolecules for diverse applications in diagnostics, imaging, and therapeutics, showcasing the compound’s versatility in molecular assembly.

Drug Delivery Systems: Embracing cutting-edge advancements in drug delivery, this compound contributes to the development of sophisticated drug transportation systems. The tri(ethylene glycol) spacer provides enhanced solubility and flexibility, empowering the creation of drug carriers with extended circulation times and improved biodistribution. By conjugating therapeutic agents like antibodies or small molecules, targeted drug delivery is optimized, elevating treatment efficacy while minimizing adverse effects.

Surface Modification: Delving into the realm of material science, Maleimido-tri(ethylene glycol)-propionic acid emerges as a valuable asset for surface modification. By augmenting the surfaces of nanoparticles and medical devices, biocompatibility and functionalization are enhanced. The ethylene glycol units mitigate nonspecific protein binding, while the maleimide group facilitates specific biomolecule attachment, enabling tailored surface properties suitable for applications such as biosensors and implants. Unlock the potential of tailored surfaces with this compound’s distinct properties.

Protein Cross-Linking: In protein chemistry, maleimido-tri(ethylene glycol)-propionic acid takes center stage in protein cross-linking endeavors. This compound serves as a catalyst for bridging proteins, unraveling protein-protein interactions, and fortifying protein structures. Through the establishment of covalent bonds between proteins or subunit interfaces, deeper understanding of structural configurations and functional dynamics is attained.

1. Charge-reversal nanoparticles: novel targeted drug delivery carriers

Xinli Chen, Lisha Liu, Chen Jiang Acta Pharm Sin B. 2016 Jul;6(4):261-7.doi: 10.1016/j.apsb.2016.05.011.Epub 2016 Jun 8.

Spurred by significant progress in materials chemistry and drug delivery, charge-reversal nanocarriers are being developed to deliver anticancer formulations in spatial-, temporal- and dosage-controlled approaches. Charge-reversal nanoparticles can release their drug payload in response to specific stimuli that alter the charge on their surface. They can elude clearance from the circulation and be activated by protonation, enzymatic cleavage, or a molecular conformational change. In this review, we discuss the physiological basis for, and recent advances in the design of charge-reversal nanoparticles that are able to control drug biodistribution in response to specific stimuli, endogenous factors (changes in pH, redox gradients, or enzyme concentration) or exogenous factors (light or thermos-stimulation).

2. Fast determination of ethylene glycol, 1,2-propylene glycol and glycolic acid in blood serum and urine for emergency and clinical toxicology by GC-FID

Tomáš Hložek, Miroslava Bursová, Radomír Čabalaa Comparative StudyTalanta. 2014 Dec;130:470-4.doi: 10.1016/j.talanta.2014.07.020.Epub 2014 Jul 15.

A simple, cost effective, and fast gas chromatography method with flame ionization detection (GC-FID) for simultaneous measurement of ethylene glycol, 1,2-propylene glycol and glycolic acid was developed and validated for clinical toxicology purposes. This new method employs a relatively less used class of derivatization agents - alkyl chloroformates, allowing the efficient and rapid derivatization of carboxylic acids within seconds while glycols are simultaneously derivatized by phenylboronic acid. The entire sample preparation procedure is completed within 10 min. To avoid possible interference from naturally occurring endogenous acids and quantitation errors 3-(4-chlorophenyl) propionic acid was chosen as an internal standard. The significant parameters of the derivatization have been found using chemometric procedures and these parameters were optimized using the face-centered central composite design. The calibration dependence of the method was proved to be quadratic in the range of 50-5000 mg mL(-1), with adequate accuracy (92.4-108.7%) and precision (9.4%). The method was successfully applied to quantify the selected compounds in serum of patients from emergency units.

3. Colorimetric and gas chromatographic procedures for glycolic acid in serum: the major toxic metabolite of ethylene glycol

A D Fraser, W MacNeil J Toxicol Clin Toxicol. 1993;31(3):397-405.doi: 10.3109/15563659309000408.

Monitoring of individuals poisoned with ethylene glycol involves analysis of ethylene glycol in serum. The objective of this procedure was to validate a colorimetric and gas chromatographic procedure for glycolic acid in serum. The colorimetric procedure requires no sophisticated instrumentation and has been shown to be specific for glycolic acid. A gas chromatographic procedure has also been developed involving methyl derivatization of glycolic acid and the internal standard (propionic acid). These methods have been used for the analysis of serum specimens from ethylene glycol poisoned patients. Glycolic acid has been recognized as the major toxic agent in ethylene glycol poisoning but current methods available do not allow analysis in a clinically relevant turnaround time. These two procedures allow glycolic acid quantitation by procedures readily set up in most clinical toxicology laboratories.