Propargyl-PEG4-NHS ester

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Propargyl-PEG4-NHS ester

Propargyl-PEG4-NHS ester | 1428629-70-2

Catalog Number R01-0228
Category Alkynes
Molecular Formula C16H23NO8
Molecular Weight 357.35
Catalog Number Size Price Quantity

Chemical Information

Synonyms Alkyne-PEG4-NHS;2,5-dioxopyrrolidin-1-yl 4,7,10,13-tetraoxahexadec-15-yn-1-oate;
Purity ≥98%
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
InChI Key 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
  • Product Specification
  • Application
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.

Computed Properties

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

Patents

Publication NumberTitlePriority 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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