Azide Amine-Poly(ethylene glycol)-OH is a PEG-OH conjugated by azide and amine. It is a trifunctional PEG derivative, in which the azide and amine share one PEG end, while the hydroxyl group is located at the other end. This functional PEG can connect multiple entities together, and has shown great potential in the field of drug delivery. With the continuous exploration of nanomedicine technology, the field of drug delivery system (DDS) has attracted more and more attention. Azide-PEG-OH has excellent biocompatibility, adjustability and drug carrier ability, making it an important research object in the field of drug delivery system. In azide-PEG-OH, its main molecule is PEG (a water-soluble polymer widely used in the biomedical field with good biocompatibility, low immunogenicity and low toxicity). Studies have shown that the azide, hydroxyl and amine groups carried in azide-PEG-OH are highly active functional groups with unique chemical reactivity, which can be covalently linked to a variety of biomolecules or drug carriers, thereby completing the formation of nanocarriers and drug loading.
Figure 1. Reaction scheme of NHS-terminated and amine-terminated PEG macromers.(Mitsuhiro Shibayama, et al.; 2019)
At present, the synthesis of azidoamine-PEG-OH is mainly achieved by terminal modification of PEG. The general synthesis steps include the following key links: First, the terminal group of PEG needs to be modified. Further modification of PEG can be achieved by introducing a hydroxyl (-OH) or amino (-NH2) group to one end of PEG. Subsequently, azidoamine-modified PEG compounds can be obtained by reacting the azide group with the amino or hydroxyl group at the end of PEG. This process usually requires the use of reagents such as azidophosphate to ensure the specificity and efficiency of the reaction. Finally, the synthesized azidoamine-PEG-OH usually needs to undergo multiple purification steps, such as dialysis, chromatography, etc., to remove unreacted raw materials and by-products. The final product is characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (IR) and mass spectrometry (MS) to confirm its structure and purity.
A key application of azido-PEG-OH in drug delivery is as a drug coupling agent. Since the azide group can react specifically with a variety of functional groups (such as alkyne groups, thiol groups, etc.), the drug molecules can be coupled to specific carriers or targeting molecules through azido-PEG-OH, thereby achieving precise drug delivery. For example, in the delivery of anti-cancer chemotherapy drugs, azido-PEG-OH can be used to connect chemotherapy drugs with antibodies, peptides or small molecule targeting ligands with targeting properties, so that chemotherapy drugs can be accurately delivered to cancerous tissues and cells for accurate attack, which can greatly reduce the toxic side effects on normal tissues. Due to its amphiphilic characteristics, azido-PEG-OH is very suitable for surface modification and functionalization of nano drug carriers. By modifying azido-PEG-OH on the surface of nanoparticles, not only can the water solubility of the carrier be improved, but also the covalent modification of various functional molecules can be achieved through its azide group. This modification can include targeting molecules, fluorescent probes, MRI contrast agents, etc., making the nanocarriers multifunctional. For example, modifying magnetic nanoparticles (MNPs) with azido-PEG-OH can not only enhance their dispersibility and stability in vivo, but also achieve coupling of multiple biomolecules through "click chemistry" to develop an "integrated diagnosis and treatment" nanosystem that integrates diagnosis and treatment. Another important role of PEGylation is to prolong the half-life of drugs in vivo. By introducing PEG chains into drug molecules or carriers, the metabolic rate of drugs in the body can be effectively reduced, their circulation time can be extended, and thus the efficacy of drugs can be improved. In addition, PEGylation can also reduce the immunogenicity of drugs or carriers, and reduce their recognition and clearance by the body's immune system. This feature is particularly important in the delivery of biomacromolecule drugs (such as proteins, enzymes, antibody drugs, etc.). Through the modification of azido-PEG-OH, the in vivo stability and bioavailability of such drugs can be greatly improved. "Click chemistry" is a fast, simple and efficient chemical reaction method, which is particularly suitable for molecular construction in complex systems. The azide group of azido-PEG-OH can be quickly coupled with other molecules with alkyne groups through "click chemistry", which gives it a significant advantage in the development of drug carriers. For example, azido-PEG-OH can be used to achieve rapid functionalization of drug carriers, or multiple functional molecules can be assembled on the same carrier through a "click chemistry" reaction, thereby constructing a composite carrier with targeting, diagnostic and therapeutic functions, and environmental responsiveness. Due to its unique chemical structure and function, azido-PEG-OH has shown broad application prospects in the field of drug delivery. Through its wide application in drug conjugation, nanocarrier modification, extending drug half-life, and "click chemistry", azido-PEG-OH can not only improve the stability and efficacy of drugs, but also achieve precise drug delivery and multifunctional development. With the continuous advancement of biomedical technology, the application of azido-PEG-OH in future drug delivery systems will surely be more extensive, and is expected to promote the development of personalized medicine and intelligent drug delivery systems.
Alternate Names:
Azido Amine-PEG-OH
Azide-PEG-NH2-OH
Azido-PEG-NH2-OH
Azido-PEG-Amine-OH
Azide-PEG-Hydroxy-NH2
Azido-PEG-OH-NH2
Azide-PEG-Hydroxyl-Amine
References:
1. Mitsuhiro Shibayama, et al.; Precision polymer network science with tetra-PEG gels—a decade history and future. Colloid and Polymer Science. 2019, 297(14).
2. Knop K, et al.; Poly(ethylene glycol) in drug delivery: pros and cons as well as potential alternatives. Angew Chem Int Ed Engl. 2010, 49(36):6288-308.
Biodegradable poly(epsilon-caprolactone)-poly(ethylene glycol) copolymers as drug delivery system
Int J Pharm.
Authors: Wei X, Gong C, Gou M, Fu S, Guo Q, Shi S, Luo F, Guo G, Qiu L, Qian Z.
Abstract
Poly(epsilon-caprolactone)-poly(ethylene glycol) (PCL-PEG) copolymers are important synthetic biomedical materials with amphiphilicity, controlled biodegradability, and great biocompatibility. They have great potential application in the fields of nanotechnology, tissue engineering, pharmaceutics, and medicinal chemistry. This review introduced several aspects of PCL-PEG copolymers, including synthetic chemistry, PCL-PEG micro/nanoparticles, PCL-PEG hydrogels, and physicochemical and toxicological properties.
CD47 Functionalization of Nanoparticles as a Poly(ethylene glycol) Alternative: A Novel Approach to Improve Drug Delivery
Curr Drug Targets.
Authors: Vandchali NR, Moadab F, Taghizadeh E, Tajbakhsh A, Gheibihayat SM.
Abstract
Bio-degradable nanoparticles (NPs) have several utilizations as drug delivery vehicles due to their acceptable bio-availability, lower toxicity, potency for encapsulation and controlled release. Moreover, the interaction of the NPs with the macrophages of the reticuloendothelial system (RES) may decrease NPs efficacy for medical purposes. The surface of NPs is conventionally neutralized with the molecules such as poly(ethylene glycol) (PEG), as one of the most widely applied stealth polymers, in order to restrict the NPs clearance through the RES system. In fact, these molecules exhibit resistance to RES clearance and protein adsorption. It is unfortunate that modifying the PEG has some shortcomings, like problems in the synthesis as well as correlation to the immune reaction. The CD47 receptor has been well known as a 'don't-eat-me' molecule on the self-- cells' surface. Therefore, the receptor will inhibit phagocytosis via binding to its ligand that is known as the signal regulatory protein α (SIRP-α). Moreover, the CD47 receptor, as one of the biomimetic substances, or its derivative peptides, have been used recently on the surface of nanoparticles to inhibit phagocytosis and increase the NPs retention time in the blood circulation. Therefore, this review study examined the CD47 receptor and its role in the immune system as well as the use of the CD47 receptor in coating NPs to increase their retention time in the blood circulation.
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