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Propargyl-PEG4-NHS ester | CAS 1428629-70-2
| Catalog Number | R01-0228 |
| Category | Alkynes |
| Molecular Formula | C16H23NO8 |
| Molecular Weight | 357.35 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
Chemical Information
Product Specification
Application
Computed Properties
Patents
| Synonyms | Alkyne-PEG4-NHS;2,5-dioxopyrrolidin-1-yl 4,7,10,13-tetraoxahexadec-15-yn-1-oate; |
| Purity | ≥98% |
| IUPAC Name | |
| Canonical SMILES | C#CCOCCOCCOCCOCCC(=O)ON1C(=O)CCC1=O |
| InChI | InChI=1S/C16H23NO8/c1-2-6-21-8-10-23-12-13-24-11-9-22-7-5-16(20)25-17-14(18)3-4-15(17)19/h1H,3-13H2 |
| InChIKey | GRIZGOGILWMGRU-UHFFFAOYSA-N |
| Solubility | DMSO, DCM, DMF |
| Density | 1.2±0.1 g/cm3 |
| Appearance | Soild powder |
| Boiling Point | 463.1±55.0 °C at 760 mmHg |
| Vapor Pressure | 0.0±1.1 mmHg at 25°C |
| LogP | -2.32 |
| Excitation | 678 |
| Emission | 694 |
| Storage | -20 °C |
Propargyl-PEG4-NHS ester, a functional reagent in the field of bioconjugation, has gained prominence due to its versatile properties. As a member of the PEGylation reagents family, it contains a propargyl (alkyne) group, a polyethylene glycol (PEG4) spacer, and an N-hydroxysuccinimide (NHS) ester. The PEG4 spacer increases solubility in aqueous environments, enhancing the reagent’s accessibility to various biological molecules. The NHS ester is reactive towards primary amines, making it a go-to choice for amine modification in proteins, peptides, or any biomolecules possessing a primary amino group. The propargyl group, on the other hand, allows for further modifications via copper-catalyzed azide-alkyne cycloaddition (CuAAC), frequently termed “click chemistry,” enabling researchers to append other functional groups or molecules.
One key application of Propargyl-PEG4-NHS ester is in the field of protein labeling. The NHS ester reacts with lysine residues on proteins, attaching the propargyl-PEG4 moiety onto the biomolecule. This modification is particularly useful for adding labels or probes to proteins, which can then undergo click chemistry for further labeling with azides, such as fluorescent markers or biotin. This allows for efficient protein tracking and isolation, essential in various biological studies and diagnostic applications.
Another significant application lies in drug delivery systems. Propargyl-PEG4-NHS ester can be used to modify drug molecules, rendering them more soluble and stable. By attaching PEG chains through NHS ester coupling, drugs benefit from improved pharmacokinetics and reduced immunogenicity. This method is particularly beneficial in the development of antibody-drug conjugates, where precise and controlled drug attachment is crucial for therapeutic efficacy and safety.
The third application involves the synthesis of hydrogels for tissue engineering. The propargyl group in Propargyl-PEG4-NHS ester enables crosslinking via click chemistry, facilitating the formation of stable hydrogels. These hydrogels can be used as scaffolds that mimic the extracellular matrix, supporting cell growth and differentiation for tissue regeneration. The biocompatibility and tunable properties of PEG-based hydrogels make them ideal for creating customized environments for various tissues.
Lastly, Propargyl-PEG4-NHS ester is employed in the development of biosensors. By immobilizing enzymes or antibodies on sensor surfaces through NHS ester linkages, these modified surfaces can detect specific analytes in complex samples. The propargyl group allows for further functionalization via click chemistry, adding various biorecognition elements that enhance the sensitivity and specificity of the biosensor, proving invaluable for medical diagnostics and environmental monitoring.
| XLogP3 | -1.3 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 15 |
| Exact Mass | 357.14236669 g/mol |
| Monoisotopic Mass | 357.14236669 g/mol |
| Topological Polar Surface Area | 101Ų |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Complexity | 468 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
| Publication Number | Title | Priority Date |
|---|---|---|
| WO-2022263944-A1 | Azido-containing monomers, polymers, and articles | 2021-06-16 |
| WO-2022133281-A1 | Compositions and methods for the treatment of human immunodeficiency virus | 2020-12-17 |
| US-10689430-B2 | Insulin receptor partial agonists | 2016-05-25 |
| US-2019177393-A1 | Insulin receptor partial agonists | 2016-05-25 |
| WO-2017205309-A1 | Insulin receptor partial agonists | 2016-05-25 |
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