Indication

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride[1], also known as EDC·HCl, is a popular carbodiimide coupling reagent used in bioconjugation chemistry. It is commonly used to activate carboxylic acids for peptide synthesis or to conjugate proteins, nucleic acids, and small molecules. EDC·HCl works by forming an amide bond between the carboxylic acid and the amine group of a second molecule, such as a protein or peptide. EDC·HCl has many advantages over other coupling reagents, including its water solubility, low price, and mild reaction conditions. It has become a widely used tool in many areas of chemical biology and biochemistry.

Figure 1 Chemical formula of 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Application

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is primarily used as a cross-linking agent to couple carboxylic acids to primary amines, forming amide bonds. Its main application is as a coupling agent for the formation of peptide bonds between amino acids or to link carboxylic acids to primary amines. It functions by activating carboxyl groups on one molecule and then reacting with an amine group on another molecule to form an amide bond. EDC HCl is also used for crosslinking proteins, modifying enzymes and antibodies, and for immobilizing biomolecules onto solid surfaces such as beads or plates[2-5].  It is commonly used in peptide synthesis to couple amino acids with carboxylic acids to form amide bonds, which are the backbone of a peptide chain. In protein synthesis, EDC·HCl can be used for site-specific labeling of proteins or to create cross-linked protein complexes. It can conjugate antibodies to other molecules of interest, such as fluorescent dyes or enzymes. This technique can be used in biomedical research and diagnostics to detect specific targets, such as cancer biomarkers.

EDC·HCl immobilize enzymes onto surfaces or other substrates for various applications, such as biosensors, biocatalysis, and biofuel cells. This immobilization can increase stability and activity of the enzyme, and also facilitate separation and reuse of the enzyme. It is a cross-linking agent to create hydrogels and other materials used in tissue engineering. These materials can serve as scaffolds to support cell growth and differentiation and to promote tissue regeneration. It can synthesize nanoparticles such as gold and silver nanoparticles for biomedical applications. EDC·HCl is used to cross-link the molecules that make up the nanoparticle, creating stable and uniform particles that can be functionalized with targeting ligands or drugs.

Overall, EDC·HCl is a valuable reagent that has numerous applications in the fields of biochemistry, materials science, and biomedical research. Its ability to form covalent amide bonds between carboxylic acids and primary amines makes it a versatile tool for chemical modification and conjugation.

Storage

The optimal storage conditions for 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) involve keeping it in a dry and cool location, away from any sources of heat and oxidizing agents. It is important to minimize exposure to air or moisture as EDC.HCl is hygroscopic and can decompose under damp conditions. To store it properly, one should consider placing it in a sealed glass container with desiccant to absorb any moisture. Alternatively, vacuum-sealed containers can be used to prevent any moisture uptake. Under appropriate storage conditions, EDC.HCl can remain effective for several years.

Safety

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) is a commonly used chemical reagent, but like all chemicals, it needs to be handled safely.

EDC.HCl can be irritating and corrosive to humans. Contact with the skin, eyes, or respiratory system can cause discomfort, pain, and swelling, and ingestion can lead to serious internal damage. Therefore, appropriate protective measures must be taken when using EDC.HCl, such as wearing gloves and safety goggles and ensuring that operations are conducted in well-ventilated laboratory environments. In addition, EDC.HCl is also flammable and should be kept away from sources of ignition. If a spill occurs, it should be cleaned up immediately, and care should be taken not to discharge it into the sewer or other water sources. In conclusion, proper storage and handling procedures, as well as appropriate safety measures, are key to ensuring the safety of 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride.

References

[1] Jones MB, Brennan JD. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide and related derivatives in peptide synthesis. [J] International Journal of Peptide and Protein Research, 1994, 43(6): 567-574.

[2] Empting MTM, Kelly CB, Soll R, et al. Recent Advances in Coupling Reactions Using Carbodiimides. [J] Angewandte Chemie International Edition, 2018, 57(51): 16736-16748.

[3] De La Fuente EJ, Barroso-Gonzalez R, Rojas-Torres MA, et al. Bioconjugation of Gold Nanoparticles with Antibodies Using a One-Step, Covalent Crosslinking Protocol: Synthesis and Characterization of Biofunctional Nanoparticles.[J] Nanoscale, 2016, 8(29): 15389-15408.

[4] Kim JS, Kwon OH, Park SH, et al. Covalently immobilized basic fibroblast growth factor on plasma-deposited hydrogel thin films for enhanced endothelialization of synthetic vascular grafts.[J] Biomaterials, 2008, 29(24-25): 3370-3378.

[5] Cetinkaya PR, Yanilmaz M, Duman SZ, Kabasakal L, Yagci Y. Graft Copolymers Based on Poly(ethylene glycol) Methacrylate Prepared by EDC/NHS-Mediated Polymerization.[J] Polymers, 2021, 13(12): 2034.