Maleimido-tri(ethylene glycol)-propionic acid - CAS 518044-40-1

Maleimido-tri(ethylene glycol)-propionic acid - CAS 518044-40-1 Catalog number: BADC-01131

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Maleimido-tri(ethylene glycol)-propionic acid is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). Maleimido-tri(ethylene glycol)-propionic acid is used for the preparation of neolymphostin-based ADC precursors for site-specific cysteine mutant trastuzumab-A114C conjugation.

Category
ADCs Linker
Product Name
Maleimido-tri(ethylene glycol)-propionic acid
CAS
518044-40-1
Catalog Number
BADC-01131
Molecular Formula
C13H19NO7
Molecular Weight
301.29
Maleimido-tri(ethylene glycol)-propionic acid

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Description
Maleimido-tri(ethylene glycol)-propionic acid is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). Maleimido-tri(ethylene glycol)-propionic acid is used for the preparation of neolymphostin-based ADC precursors for site-specific cysteine mutant trastuzumab-A114C conjugation.
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
LogP
-1.29
PSA
135.37000
Vapor Pressure
0.0±4.2 mmHg at 25°C
Appearance
Pale Yellow Oily Matter
Purity
≥95%
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
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.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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