Azido-PEG3-maleimide - CAS 1858264-36-4

Azido-PEG3-maleimide - CAS 1858264-36-4 Catalog number: BADC-01013

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Azido-PEG3-maleimide is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs. Azido-PEG3-maleimide is also a cleavable 3 unit PEG ADC linker used in the synthesis of antibody-drug conjugates (ADCs).

Category
ADCs Linker
Product Name
Azido-PEG3-maleimide
CAS
1858264-36-4
Catalog Number
BADC-01013
Molecular Formula
C15H23N5O6
Molecular Weight
369.37
Purity
>98.0%
Azido-PEG3-maleimide

Ordering Information

Catalog Number Size Price Quantity
BADC-01013 -- $-- Inquiry
Description
Azido-PEG3-maleimide is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs. Azido-PEG3-maleimide is also a cleavable 3 unit PEG ADC linker used in the synthesis of antibody-drug conjugates (ADCs).
Synonyms
Azido-PEG3-Maleimide Kit;N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamide
IUPAC Name
N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]-3-(2,5-dioxopyrrol-1-yl)propanamide
Canonical SMILES
C1=CC(=O)N(C1=O)CCC(=O)NCCOCCOCCOCCN=[N+]=[N-]
InChI
InChI=1S/C15H23N5O6/c16-19-18-5-8-25-10-12-26-11-9-24-7-4-17-13(21)3-6-20-14(22)1-2-15(20)23/h1-2H,3-12H2,(H,17,21)
InChIKey
OGSSEPXEBBNVGN-UHFFFAOYSA-N
Solubility
10 mm in DMSO
LogP
-0.60
Appearance
Solid
Shelf Life
0-4°C for short term (days to weeks), or -20°C for long term (months).
Shipping
Room temperature
Storage
Store at -20 °C, keep in dry and avoid sunlight.
Form
Solid

Azido-PEG3-maleimide, a versatile heterobifunctional crosslinker with widespread use in biochemical and biotechnological research, serves as the cornerstone for a myriad of applications. Here are four key applications of Azido-PEG3-maleimide, presented with high perplexity and burstiness:

Bioconjugation: Positioned at the forefront of bioconjugation techniques, Azido-PEG3-maleimide plays a crucial role in connecting proteins, peptides, or other biomolecules through their thiol groups. The azido group’s remarkable versatility enables seamless integration into click chemistry reactions, providing a reliable pathway for site-specific conjugation. This remarkable capability facilitates the intricate assembly of bioconjugates tailored for a diverse array of applications, spanning from cutting-edge drug delivery to state-of-the-art diagnostic imaging.

Drug Delivery Systems: Harnessing the transformative potential of Azido-PEG3-maleimide, researchers can engineer sophisticated drug delivery systems by modifying therapeutic agents or carrier molecules. This compound empowers precise attachment of drugs to carriers, like nanoparticles or liposomes, via thiol groups, enabling targeted delivery. The resulting constructs exhibit augmented pharmacokinetics and biodistribution, significantly enhancing the therapeutic efficacy of a wide array of drugs.

Surface Modification: Azido-PEG3-maleimide emerges as an indispensable asset for enhancing the biocompatibility and functionality of biomaterials or nanoparticles through surface modification. By anchoring this crosslinker to surfaces, researchers can introduce azide groups capable of engaging in click chemistry reactions for further functionalization. This application serves as a linchpin in the advancement of cutting-edge biosensors, medical implants, and other biomedical devices, pushing the boundaries of biotechnological innovation.

Protein Labeling: Within the intricate realm of protein biology, Azido-PEG3-maleimide finds profound utility in specific protein labeling endeavors aimed at unraveling protein-protein interactions or intracellular localization. The maleimide group’s interaction with cysteine residues on proteins, coupled with the azido group’s ability to facilitate subsequent tagging with fluorescent probes via click chemistry, forms the foundation for a myriad of analytical and imaging applications in cell biology and biochemistry. This technique enables precise visualization and exploration of complex molecular processes, opening new avenues for research and discovery.

1. Detection of proteolytic activity by covalent tethering of fluorogenic substrates in zymogram gels
Ameya A Deshmukh, Jessica L Weist, Jennifer L Leight Biotechniques. 2018 May;64(5):203-210. doi: 10.2144/btn-2018-0005.
Current zymographic techniques detect only a subset of known proteases due to the limited number of native proteins that have been optimized for incorporation into polyacrylamide gels. To address this limitation, we have developed a technique to covalently incorporate fluorescently labeled, protease-sensitive peptides using an azido-PEG3-maleimide crosslinker. Peptides incorporated into gels enabled measurement of MMP-2, -9, -14, and bacterial collagenase. Sensitivity analysis demonstrated that use of peptide functionalized gels could surpass detection limits of current techniques. Finally, electrophoresis of conditioned media from cultured cells resulted in the appearance of several proteolytic bands, some of which were undetectable by gelatin zymography. Taken together, these results demonstrate that covalent incorporation of fluorescent substrates can greatly expand the library of detectable proteases using zymographic techniques.
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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