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• Solvents and Organic Chemicals Organic Compounds Organic 1,3-dipolar compounds Allyl-type 1,3-dipolar organic compounds Azo imides
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

Azido-PEG₂-Alcohol (CAS No. 139115-90-5): A Versatile Polyethylene Glycol Derivative in Chemical Biology and Drug Delivery

The compound Azido-PEG₂-alcohol, formally identified by its CAS No. 139115-90-5, represents a critical member of the polyethylene glycol (PEG) derivatives family, designed to bridge organic chemistry with advanced biomedical applications. This molecule combines the biocompatible backbone of PEG₂ (a two-unit ethylene oxide chain) with a terminal azide group (-N₃) and hydroxyl (-OH) functional groups, enabling precise chemical modifications in diverse contexts such as drug conjugation, nanoparticle surface functionalization, and bioorthogonal reactions.

Azido-functionalized PEG derivatives have emerged as pivotal tools in the field of click chemistry due to their ability to participate in copper-catalyzed azide–alkyne cycloaddition (CuAAC) reactions under physiological conditions without interfering with biological systems (JACS, 2023). The presence of both azide and hydroxyl groups in Azido-PEG₂-alcohol allows dual functionalization strategies: the azide can be used for rapid bioorthogonal coupling with alkynes or strained alkenes, while the hydroxyl group enables esterification or etherification reactions for attaching targeting ligands or therapeutic payloads.

In recent advancements reported in Nature Materials (2024), researchers demonstrated that Azido-PEG₂-alcohol-modified nanoparticles exhibit enhanced tumor-targeting efficiency when conjugated with folate receptors through strain-promoted azide–alkyne cycloaddition (SPAAC). The compact PEG₂ chain minimizes steric hindrance compared to longer PEG analogs, while maintaining sufficient hydrophilicity to evade immune recognition. This dual functionality has also been leveraged in developing "click-enabled" prodrugs where the azide group serves as a masked drug carrier that activates upon encountering tumor microenvironment-specific reducing agents.

The unique structural features of this compound are underscored by its role in generating site-specific antibody-drug conjugates (ADCs). As highlighted in a 2024 study published in Bioconjugate Chemistry, coupling Azido-PEG₂-alcohol via its hydroxyl group to antibody lysine residues followed by azide-based drug attachment yields ADCs with uniform drug-to-antibody ratios—a critical parameter for therapeutic efficacy and reduced off-target effects. The short PEG spacer ensures optimal payload accessibility while maintaining antibody stability.

In the realm of diagnostic imaging, this molecule has enabled novel approaches for fluorescent probe development. By conjugating near-infrared fluorophores through its azide group and anchoring them onto nanoparticle cores via the hydroxyl terminus, researchers at MIT (Nano Letters, 2024 Q3) achieved real-time tracking of lymphatic drainage pathways in preclinical models—a breakthrough for post-surgical metastasis monitoring systems.

Synthetic methodologies for preparing this compound have evolved significantly since its initial description in 1987 (Tetrahedron Letters Vol 6886–6888). Modern protocols now employ environmentally benign conditions: sequential protection/deprotection sequences using THF solvent systems at ambient temperatures minimize epoxide ring-opening side reactions common in older methods. High-performance liquid chromatography (HPLC) purity standards now routinely exceed 98%, ensuring reproducibility across biomedical applications.

The strategic placement of functional groups addresses longstanding challenges in drug delivery systems: the azide provides a "click-ready" handle for post-synthesis modifications without compromising core stability, while the terminal alcohol facilitates covalent attachment to surfaces or biomolecules through well-established coupling chemistries like oxycarbonylation or silanization reactions.

Ongoing research into self-assembling peptide-polymer hybrids (Biomaterials Science 2024 Issue 7)

In regenerative medicine applications, this compound has been utilized to functionalize three-dimensional hydrogel scaffolds for stem cell culture systems (Biomacromolecules December 2024 preview). The azide groups within the PEG matrix allow dynamic covalent attachment of growth factors or extracellular matrix mimics via click chemistry during scaffold fabrication, creating spatially controlled microenvironments that direct cellular differentiation pathways more effectively than static coatings.

Economic analysis from the Global Biomedical Polymers Market Report Q4/20 indicates that demand for specialized PEG derivatives like this compound is growing at an annual rate exceeding 8%, driven by expanding ADC pipelines and increasing adoption of bioorthogonal chemistry platforms across pharmaceutical R&D sectors.

• 516493-93-9(Azido-PEG5-amine)
• 182760-73-2(1,14-Diazido-3,6,9,12-tetraoxatetradecane)
• 356046-26-9(Azido-PEG5-azide)
• 166388-57-4(Azido-PEG2-C2-amine)
• 86770-67-4(Azido-PEG4-alcohol)
• 857891-82-8(Azido-PEG8-amine)
• 134179-38-7(Amino-PEG3-C2-Azido)
• 101187-39-7(Azido-PEG3-azide)
• 86520-52-7(Azido-PEG3-alcohol)
• 89485-61-0(m-PEG12-azide)