DOPE‑N3 (1,2‑Dioleoyl‑sn‑glycero‑3‑phosphoethanolamine‑N‑azide)

Basic Information

• Full Name: 1,2‑Dioleoyl‑sn‑glycero‑3‑phosphoethanolamine‑N‑azide
• Abbreviation: DOPE‑N3
• Molecular Formula: C44H81N4O9P
• Molecular Weight: 840.57
• Structure: A functionalized phospholipid consisting of a DOPE lipid core covalently linked to an azide (‑N₃) reactive head group.

Key Properties

• Amphiphilic Structure: Retains the hydrophobic dioleoyl tails and fusogenic properties of native DOPE, with a reactive azide moiety on the hydrophilic head group.
• Click Chemistry Reactivity: The azide group undergoes highly selective, bioorthogonal copper‑catalyzed azide‑alkyne cycloaddition (CuAAC) or strain‑promoted azide‑alkyne cycloaddition (SPAAC) with alkynes/DBCO‑modified molecules under mild conditions.
• Fusogenicity: Maintains DOPE’s ability to form non‑bilayer hexagonal (HII) phases, promoting membrane fusion and endosomal escape in delivery systems.
• Self‑Assembly: Spontaneously forms liposomes, micelles, or lipid bilayers in aqueous media.
• Solubility: Soluble in chloroform, methanol, DMSO, and other organic solvents; dispersible in aqueous buffers to form nanoparticles.
• Physical Form: Typically a white to off‑white solid or waxy material.
• Stability: Stable under standard biological conditions; stored at ‑20°C, desiccated and protected from light.

Applications

• Targeted Liposome & LNP Functionalization: Covalently conjugates targeting ligands (peptides, antibodies, aptamers) via click chemistry for cell‑specific delivery.
• Gene & Nucleic Acid Delivery: Enhances intracellular delivery of DNA, mRNA, siRNA by promoting endosomal escape.
• Fluorescent/Imaging Probe Labeling: Conjugates with DBCO‑fluorophores (Cy5, Cy7, FITC) for in vitro/in vivo tracking.
• Biomembrane & Exosome Engineering: Inserts into lipid bilayers for surface modification of cells, exosomes, and artificial membranes.
• Theranostic Nanoparticles: Enables modular assembly of multifunctional delivery systems combining targeting, imaging, and therapeutic payloads.
• Surface Modification of Biomaterials: Anchors functional molecules to hydrogels, microspheres, and implant surfaces.