Azido-PEG2-NHS ester

• CAT Number: I022915
• CAS Number: 1312309-64-0
• Molecular Formula: C11H16N4O6
• Molecular Weight: 300.27
• Purity: 98%
• Synonyms: Azido-PEG2-NHS ester
• Target: ADC Linker
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 2,5-dioxopyrrolidin-1-yl 3-(2-(2-azidoethoxy)ethoxy)propanoate
• InChI: InChI=1S/C11H16N4O6/c12-14-13-4-6-20-8-7-19-5-3-11(18)21-15-9(16)1-2-10(15)17/h1-8H2
• InChIKey: XDXWXTIRKQZRNN-UHFFFAOYSA-N
• SMILES: O=C(ON1C(CCC1=O)=O)CCOCCOCCN=[N+]=[N-]

Azido-PEG2-NHS ester (Cat.No:I022915) is a PEG derivative containing an azide group and an NHS ester. The hydrophilic PEG spacer increases solubility in aqueous media. The azide group can react with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules.

Reference

1: Sano K, Nakajima T, Miyazaki K, Ohuchi Y, Ikegami T, Choyke PL, Kobayashi H. Short PEG-linkers improve the performance of targeted, activatable monoclonal antibody-indocyanine green optical imaging probes. Bioconjug Chem. 2013 May 15;24(5):811-6. doi: 10.1021/bc400050k. Epub 2013 May 3. PubMed PMID: 23600922; PubMed Central PMCID: PMC3674550.
2: Harrison E, Coulter JA, Dixon D. Gold nanoparticle surface functionalization: mixed monolayer versus hetero bifunctional peg linker. Nanomedicine (Lond). 2016 Apr;11(7):851-65. Review. PubMed PMID: 27021417.
3: Augusto MT, Hollmann A, Porotto M, Moscona A, Santos NC. Antiviral Lipopeptide-Cell Membrane Interaction Is Influenced by PEG Linker Length. Molecules. 2017 Jul 15;22(7). pii: E1190. doi: 10.3390/molecules22071190. PubMed PMID: 28714870; PubMed Central PMCID: PMC5776016.
4: Tuma R, Russell M, Rosendahl M, Thomas GJ Jr. Solution conformation of the extracellular domain of the human tumor necrosis factor receptor probed by Raman and UV-resonance Raman spectroscopy: structural effects of an engineered PEG linker. Biochemistry. 1995 Nov 21;34(46):15150-6. PubMed PMID: 7578129.
5: Kanazaki K, Sano K, Makino A, Yamauchi F, Takahashi A, Homma T, Ono M, Saji H. Feasibility of poly(ethylene glycol) derivatives as diagnostic drug carriers for tumor imaging. J Control Release. 2016 Mar 28;226:115-23. doi:10.1016/j.jconrel.2016.02.017. Epub 2016 Feb 8. PubMed PMID: 26869546.