| AC-PEG-SCM (Acrylate PEG Succinimidyl NHS ester) |
|
| PHB-960 | AC-PEG-SCM, MW 2k |
| PHB-961 | AC-PEG-SCM, MW 3.4k |
| PHB-962 | AC-PEG-SCM, MW 5k |
| PHB-963 | AC-PEG-SCM, MW 10k |
| PHB-964 | AC-PEG-SCM, MW 1k |
Description:
Acrylate-PEG-SCM is a linear heterobifunctional PEG reagent with an Acrylate and an activated NHS ester.
It is a useful crosslinking reagent with a PEG spacer.
Acrylate can polymerize with UV light or radical initiator, and SCM is one type of NHS esters, often called succinimidyl carboxyl methyl (SCM) ester.
SCM is very reactive with primary amine to form a stable amide bond.
Acrylate-PEG-SCM may be used to introduce an amine reactive functional group in crosslinked PEG hydrogel.
References:
1. Protein Conjugation (Amine PEGylation) to PEG Hydrogel - Bioartificial matrices for therapeutic vascularization, Proc Natl Acad Sci USA. 2010; 107(8): 3323–3328, Text.
2. Crosslinking Proteins to PEG Hydrogels - Injectable laminin-functionalized hydrogel for nucleus pulposus regeneration, Biomaterials, 2013 (34): 7381-7388, Text.
3. Crosslinking Proteins to PEG Hydrogels - Photocrosslinkable laminin-functionalized polyethylene glycol hydrogel for intervertebral disc regeneration, Acta Biomaterialia 10 (2014) 1102–1111, Text.
4. Bioartificial matrices for therapeutic vascularization. Proceedings of the National Academy of Sciences 107.8 (2010): 3323-3328. Text.
5. PEG-PCL Hydrogel and Conjugation of Proteins - Shape Memory RGD-Containing Networks: Synthesis, Characterization, and Application in Cell Culture, Macromol. Symp. 2011, 309/310, 162–172,Text.
6. N-cadherin is Key to Expression of the Nucleus Pulposus Cell Phenotype under Selective Substrate Culture Conditions,Scientific Reports, Article number: 28038 (2016), Text.
7. Design of Hydrogel Particle Morphology for Rapid Bioassays. Analytical Chemistry. 2018 Oct 19. Text.
Q: What are the differences among your PEG NHS ester & PEG Acid products?
A: We offer a variety of PEG Acid and PEG NHS ester. These NHS esters react with primary and secondary amine to form a stable amide linkage. This reaction may be carried out in an organic solution with an organic base or may be carried out in an aqueous solution at or around neutral pH or slightly acidic or basic. To PEGylate proteins or nanoparticles, it often requires a large excess of PEG NHS esters due to the competitive hydrolysis reaction in an aqueous solution. Stability of NHS esters is compared by their hydrolysis half-life (T1/2). To mitigate the competitive hydrolysis reaction, organic solvents such as amine-free, anhydrous DMF and DMSO may be used in combination with an aqueous buffer solution.
PEG NHS esters | Structural characteristics | Amine reactivity | Stability |
|---|
| Type A: SCM | Methylene (CH2) linkage between PEG and NHS ester | Highly reactive | Hydrolysis half-life: less than five minutes. It often requires the use of a large excess of PEG reagents. |
| Type B: SG | C4 aliphatic ester linkage between PEG and NHS ester | Very reactive | Hydrolysis half-life: around 20 minutes. |
| Type C: SS | C3 aliphatic ester linkage between PEG and NHS ester | Very reactive | Hydrolysis half-life: around 10 minutes. |
| Type D: GAS | C4 aliphatic amide linkage between PEG and NHS ester | Very reactive | Hydrolysis half-life: around 20 minutes. |
| Type E: SAS | C3 aliphatic amide linkage between PEG and NHS ester | Very reactive | Hydrolysis half-life: around 10 minutes. |
SCM: Succinimidyl Carboxyl Methyl ester; SG: Succinimidyl Glutarate ester; SS: Succinimidyl Succinate ester; GAS: GlutarAmide Succinimidyl ester; SAS: SuccinAmide Succinimidyl ester. Note: hydrolysis half-life depends on pH, temperature and other factors of the testing conditions.
| PEG acids | Structural characteristics |
|---|
| Type A: AA | Methylene (CH2) linkage between PEG and acid (COOH) |
| Type B: GA | C4 aliphatic ester linkage between PEG and acid (COOH) |
| Type C: SA | C3 aliphatic ester linkage between PEG and acid (COOH) |
| Type D: GAA | C4 aliphatic amide linkage between PEG and acid (COOH) |
| Type E: SAA | C3 aliphatic amide linkage between PEG and acid (COOH) |
AA: Acetic Acid, also called CM - Carboxyl Methyl; GA: Glutaric Acid; SA: Succinic Acid; GAA: GlutarAmide Acid; SAS: SuccinAmide Acid.
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