Overview
OO-PEG-OPSS is a specialized polyethylene glycol derivative functionalized with orthopyridyl disulfide (OPSS) groups at both termini. As a heterobifunctional crosslinker, it serves as a bridge between thiol-containing biomolecules (e.g., cysteine residues in proteins) and other functional groups. The PEG spacer provides hydrophilicity and reduces immunogenicity, while the OPSS groups enable reversible disulfide bond formation under mild conditions. This compound is particularly valuable in bioconjugation chemistry, where controlled and reversible coupling is required. Its applications span pharmaceutical development, nanotechnology, and diagnostic reagent preparation. The molecular weight can be customized by selecting different PEG chain lengths, typically ranging from 1,000 to 20,000 Daltons.
Physical and Chemical Properties
The physical state of OO-PEG-OPSS depends on its molecular weight: lower MW variants (1k-5k Da) are viscous liquids, while higher MW forms (10k-20k Da) appear as waxy solids. It exhibits excellent water solubility due to the PEG backbone's hydrophilic nature, with solubility decreasing in organic solvents as chain length increases. Chemically, the OPSS groups are highly reactive toward free thiols at neutral pH (6.5-8.0), forming stable disulfide bonds. This reaction is reversible under reducing conditions. The PEG spacer is chemically inert and provides steric stabilization, making it ideal for biomedical applications where protein aggregation must be minimized.
Main Applications
In biopharmaceuticals, OO-PEG-OPSS is used to create antibody-drug conjugates (ADCs) with controlled drug release profiles. The disulfide linkage allows intracellular drug release in the reducing environment of target cells. It's also employed in nanoparticle surface functionalization for targeted drug delivery systems. Diagnostic applications include the preparation of enzyme-linked immunosorbent assay (ELISA) reagents, where it conjugates detection enzymes to antibodies without affecting their activity. In research settings, it serves as a tool for studying protein-protein interactions through reversible crosslinking strategies.
Safety and Storage
As a reactive chemical, OO-PEG-OPSS requires careful handling. Use nitrile gloves, safety goggles, and work in a fume hood to prevent inhalation of dust. The OPSS group may cause skin and eye irritation upon contact. For long-term storage, keep sealed containers under argon or nitrogen at -20°C, with desiccant to prevent moisture absorption. Avoid repeated freeze-thaw cycles, which may degrade the OPSS functionality. Solutions should be prepared fresh and used immediately, as hydrolysis occurs over time in aqueous buffers.
B2B Procurement Guide
When sourcing OO-PEG-OPSS, specify: 1) PEG molecular weight (narrow distribution preferred), 2) degree of functionalization (typically >90%), 3) residual moisture content (<1% for stable storage), and 4) endotoxin levels (<1 EU/mg for biomedical use). Bulk quantities (100g+) may require custom synthesis with lead times of 4-8 weeks. Request certificates of analysis including NMR and HPLC purity data. For pharmaceutical applications, ensure vendors provide GMP-grade material with full documentation of synthesis and purification processes.
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