Name: Azido-PEG6-NHS ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Azido-PEG6-NHS;Azido-PEG6-CH2CO2-NHS; N3-PEG6-C2-NHS ester; N3-PEG6-CH2CH2COONHS Ester; 1-[(1-Azido-21-oxo-3,6,9,12,15,18-hexaoxahenicosan-21-yl)oxy]-2,5-pyrrolidinedione; 2,5-Pyrrolidinedione, 1-[(21-azido-1-oxo-4,7,10,13,16,19-hexaoxaheneicos-1-yl)oxy]-; 2,5-Dioxopyrrolidin-1-yl 1-azido-3,6,9,12,15,18-hexaoxahenicosan-21-oate

IUPAC Name

(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate

Canonical SMILES

C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]

InChI

InChI=1S/C19H32N4O10/c20-22-21-4-6-28-8-10-30-12-14-32-16-15-31-13-11-29-9-7-27-5-3-19(26)33-23-17(24)1-2-18(23)25/h1-16H2

InChIKey

WXKOAPGNZNSYPW-UHFFFAOYSA-N

Solubility

Soluble in DCM, DMF, DMSO, Water

Appearance

Pale Yellow or Colorless Oily Liquid

Shelf Life

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

Shipping

-20°C (International: -20°C)

Storage

Store at -20°C, keep in dry and avoid sunlight

Form

Solid

Azido-PEG6-NHS ester is widely used in biomedical research for site-specific bioconjugation. One of its key applications is in protein labeling. The NHS ester portion of the molecule reacts with primary amines found on lysine residues in proteins, forming stable amide bonds. The azide group at the other end allows for subsequent click chemistry reactions, usually with alkynes, to attach various probes or tags. This dual functionality enables precise modification of proteins for a variety of studies, including tracking protein interactions, understanding protein functions, and developing targeted drug delivery systems.

Another significant application of Azido-PEG6-NHS ester is in the creation of bioorthogonal crosslinkers. These crosslinkers are crucial in studying complex molecular systems within living organisms without interfering with native biochemical processes. Through the azide group, the compound can participate in click chemistry reactions with alkyne-functionalized molecules, facilitating the formation of covalent bonds between different biomolecules. This ability makes Azido-PEG6-NHS ester an invaluable tool for researchers looking to map out interactions within cells, understand molecular pathways, and construct complex biomolecular assemblies in a controlled manner.

Azido-PEG6-NHS ester also plays a vital role in drug delivery research. By conjugating therapeutic agents to Azido-PEG6-NHS ester, researchers can improve the solubility, stability, and targeted delivery of these agents. The polyethylene glycol (PEG) spacer enhances the solubility of hydrophobic drugs, allowing them to be delivered more efficiently in aqueous environments. The azide group enables the attachment of targeting moieties, such as antibodies or peptides, through click chemistry, ensuring that the drug is delivered specifically to desired cells or tissues. This targeted approach helps in reducing side effects and enhancing the efficacy of therapeutic treatments.

In the field of diagnostic imaging, Azido-PEG6-NHS ester is utilized for the synthesis of imaging probes. The molecule can be conjugated to fluorescent dyes or radiolabels via the NHS ester and azide groups, allowing for precise imaging of specific biological processes or structures. For instance, PET and MRI contrast agents can be engineered using Azido-PEG6-NHS ester to improve their targeting capabilities and overall imaging performance. This application is critical in medical diagnostics, where early and accurate detection of diseases can lead to better outcomes and informed treatment decisions.