Overview
Hydroxy-Polyethylene Glycol-Thiol (HO-PEG-SH) is a versatile heterobifunctional polyethylene glycol (PEG) derivative featuring both hydroxyl (-OH) and thiol (-SH) terminal groups. The PEG backbone provides hydrophilicity and biocompatibility, while the reactive termini enable selective conjugation chemistry. This compound is particularly valuable in biopharmaceutical applications where controlled modification of biomolecules or surfaces is required. As a synthetic polymer, HO-PEG-SH is typically produced through anionic polymerization of ethylene oxide, followed by selective end-group modification. Commercial grades are available with varying PEG chain lengths (commonly 1kDa to 20kDa), allowing customization of molecular spacing and hydrodynamic properties. The compound's dual functionality makes it a key building block in precision bioconjugation strategies.
Physical and Chemical Properties
HO-PEG-SH exhibits typical PEG polymer characteristics including high water solubility, low immunogenicity, and resistance to protein adsorption. The hydroxyl group provides a site for further modification through esterification or ether formation, while the thiol group readily reacts with maleimides, iodoacetamides, and gold surfaces via thiol-ene click chemistry or chemisorption. The physical state varies with molecular weight - lower MW versions (<1kDa) are viscous liquids, while higher MW forms are waxy solids. Solution viscosity depends strongly on concentration and temperature. Importantly, the thiol group is prone to oxidation, forming disulfide bonds, which necessitates careful handling under inert atmosphere and often requires addition of reducing agents (e.g., TCEP) during applications.
Main Applications
In drug delivery systems, HO-PEG-SH serves as a linker for attaching therapeutic payloads to targeting molecules or carrier nanoparticles. The hydroxyl group can be activated for coupling with carboxyl-containing drugs, while the thiol enables conjugation to maleimide-functionalized antibodies or proteins. This creates stable, cleavable, or stimuli-responsive drug conjugates with improved pharmacokinetics. Surface modification represents another major application area. The thiol group forms stable bonds with gold surfaces (Au-S), creating self-assembled monolayers used in biosensors and diagnostic devices. Meanwhile, the hydroxyl group provides a handle for subsequent functionalization. In materials science, HO-PEG-SH is used to create hydrogels through thiol-maleimide or thiol-acrylate crosslinking, producing biocompatible scaffolds for tissue engineering.
Safety and Storage
HO-PEG-SH requires careful handling due to its reactive thiol group. In solid form, it should be stored under nitrogen or argon at 2-8°C, protected from light and moisture. Solutions are best prepared fresh using degassed buffers, with consideration given to adding antioxidants (e.g., EDTA) to prevent thiol oxidation. Long-term storage of solutions is not recommended. From a safety perspective, while PEG itself is generally regarded as non-toxic, the thiol group may cause skin and eye irritation. Proper personal protective equipment (gloves, goggles) should be worn when handling. Spills should be contained and cleaned promptly with water. Material safety data sheets (MSDS) should always be consulted for specific handling protocols and emergency measures.
B2B Procurement Guide
When procuring HO-PEG-SH, buyers should clearly specify the required PEG molecular weight (typically 1kDa-20kDa), as this significantly impacts performance and price. Higher purity grades (>95%) are recommended for biomedical applications to minimize side reactions. Certificates of analysis should be requested, including NMR verification of end-group functionality and GPC data for molecular weight distribution. For research-scale purchases, small vials (1-5g) with pre-divided aliquots can prevent degradation from repeated freeze-thaw cycles. Bulk industrial buyers should negotiate nitrogen-flushed packaging and consider stabilization additives. Lead times may vary as some suppliers customize chain lengths. Always verify biocompatibility claims if the material will be used in medical applications.
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