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Polyethylene glycol modifier (PEG modifier) ​​and other derivatives
First, polyethylene glycol modifier
In recent years, biomacromolecules and natural product drug molecules such as protein peptides have been increasingly used in the field of disease treatment, which has greatly promoted the development of the pharmaceutical industry. However, the role of biomacromolecules in the medicinal process is greatly limited by problems such as short half-life, easy to produce immunogenic antigenicity, easy to be enzymatically hydrolyzed, and certain pharmacological toxicity. In order to effectively solve this problem, the National Biochemical Engineering Technology Research Center (Beijing) has developed a series of polyethylene glycol modifiers to achieve the purpose of prolonging the efficacy by chemically modifying the drug molecules with polyethylene glycol. Because of the steric hindrance of the polyethylene glycol chain, the resistance of the modified protein to the enzymatic hydrolysis of the protease is greatly enhanced, and the molecular exclusion volume of the modified molecule is significantly increased, so that the renal filtration clearance rate is significantly reduced. At the same time, the structural specificity of the polyethylene glycol molecule reduces the ability of the liver reticuloendothelial system to recognize the uptake and clearance of the modified protein, and can reduce or eliminate the ability to induce neutralizing antibodies and bind to antibodies. It is difficult to be recognized and cleared by the immune system. These effects make the polyethylene glycol modified drug molecule have better pharmacological pharmacokinetic properties than the unmodified drug.
Multi-site modification protein
Site-directed modified protein
Microcapsule modification
The types of polyethylene glycol modifiers provided by the National Biochemical Engineering Technology Center include:
1. A general-purpose modifier mPEG-SC, mPEG-SCM capable of modifying almost all free amino groups of the protein (N-terminal and lysine ω-amino in the sequence):
product name
structure
Terminal group
Modified group
Molecular weight
The molecular weight distribution
mPEG-SC
Succinimide carbonate
NH2
5k
≤1.06
20k
≤1.1
mPEG-SCM
Succinimide acetate
NH2
5k
≤1.06
20k
≤1.1
2. Specific modifiers mPEG-PTS, mPEG-hydrazide and mPEG-ALD that allow for site-specific quantitative modification of specific sites of the protein:
product name
structure
Terminal group
Modified group
Molecular weight
The molecular weight distribution
mPEG-PTS
Thiobenzenesulfonate
SH
5k
≤1.06
20k
≤1.1
mPEG-ALD
Propionaldehyde
N end
5k
≤1.06
20k
≤1.1
mPEG -hydrazide
Acylhydrazine
Carbonyl
5k
≤1.06
20k
≤1.1
3. In the modification chemistry, in some cases, the branched polyethylene glycol has a larger apparent molecular weight after binding to the protein on the same molecular weight linear polyethylene glycol, and can be at a single attachment site. Combining two polyethylene glycol chains reduces the chance of protein inactivation, so it is more effective in protecting proteins from protein digestion, reducing antigenicity and immunogenicity. The center can provide branched polyethylene. The alcohol is:
product name
structure
Terminal group
Modified group
Molecular weight
The molecular weight distribution
Branch type
Lysine
NH2
4k
≤1.06
10k
≤1.1
40k
≤1.1
Lysine
Succinate
NH2
4k
≤1.06
10k
≤1.1
40k
≤1.1
The chemical modification experiments were carried out on various proteins and anticancer drugs by using various modifiers prepared by the engineering center, and all of them obtained good modification effects:
Branched PEG modified G-CSF, linear PEG modified G-CSF
And pharmacokinetic comparison of unmodified G-CSF, branched PEG
The half-life of the modified product can be increased by more than 5 times.
HPSEC detection of PEG-PTS modified G-CSF, proving its
Has high modification selectivity and maintains activity above 60%
mPEG-hydrazide modified doxorubicin and not
Comparison of pharmacokinetics of modified doxorubicin, half-life
Increased nearly 10 times
Different molecular weight PEG-ALD modified rh-ngEpo and unmodified
Comparison of pharmacokinetics of rh-ngEpo (PEG modification can
The AUC of rh-ngEpo is increased by 9-13 times, half-life
Increase 14-32 times)
Second, polyethylene glycol crosslinker
At the same time, polyethylene glycol has good dissociation ability and biocompatibility. Therefore, heterocyclic difunctional polyethylene glycol with two different functional groups has been widely used as a macromolecular coupling agent. Molecular cross-linking and surface modification of the material and good results. The heterocyclic difunctional polyethylene glycols currently developed by the National Biochemical Engineering Technology Center include:
product name
Terminal group
Coupling group
Molecular weight
The molecular weight distribution
PTS-PEG -hydrazide
Thiobenzenesulfonate
Acylhydrazine
Base
Carbonyl
2k
≤1.05
3.5k
≤1.05
5k
≤1.05
7.5k
≤1.1
PTS-PEG -COOH
Thiobenzenesulfonate
carboxyl
Base
Amino
2k
≤1.05
3.5k
≤1.05
5k
≤1.05
7.5k
≤1.1
NH2-PEG -COOH
Aminocarboxyl
Carbonyl
Amino
2k
≤1.05
3.5k
≤1.05
5k
≤1.05
7.5k
≤1.1
PTS-PEG -SCM
Thiobenzenesulfonate
Succinimide acetate
Base
Amino
2k
≤1.05
3.5k
≤1.05
5k
≤1.05
7.5k
≤1.1
Third, polyethylene glycol intermediates
Polyethylene glycol with reactive functional groups can be used as a key derivative of various modifiers and coupling agents for the preparation of more novel polyethylene glycol compounds. The polyethylene glycol intermediates we currently offer include mPEG-COOH, mPEG-NH2 and mPEG-Br:
product name
Terminal group
Molecular weight
The molecular weight distribution
mPEG-CH 2 -COOH
carboxyl
2k
≤1.05
4k
≤1.06
5k
≤1.06
20k
≤1.1
mPEG-CH 2 -CH 2 -NH 2
Amino
2k
≤1.05
4k
≤1.06
5k
≤1.06
20k
≤1.1
mPEG-CH 2 -CH 2 -Br
bromine
2k
≤1.05
4k
≤1.06
5k
≤1.06
20k
≤1.1
4. Separation and analysis of polyethylene glycol compounds
The purity and activation of polyethylene glycol compounds have always been a concern of users. Since the raw materials, products and by-products before and after the reaction are not much different in molecular weight, solubility, polarity and other physicochemical properties, the removal of by-products and the accurate detection of the content of the derivatized groups have been difficult, and A challenging problem in polymer chemistry. Through years of experimental work, the National Biochemical Engineering Technology Research Center (Beijing) has established system separation and purification methods and analytical detection methods, including nuclear magnetic resonance (NMR), time-of-flight mass spectrometry (MALDI-ToF MS), and gel permeation. Chromatography (GPC), liquid chromatography (HPLC), infrared spectroscopy (IR), ultraviolet spectroscopy (UV), chemical titration/chromogenic and ion exchange chromatography, reverse phase preparative chromatography, and gel preparation chromatography. Through these means, the center can guarantee that the purity of the products provided is consistent with the COA, and can provide specific test data for each customer's requirements.
The PEG products provided by the Center can be used in many other fields besides drug molecular modification or cross-linking, for example, preparation of ligands with biologically active compounds, peptide synthesis carriers, polymer graft compounds, and polymerization of new materials. Ethylene glycol coating and modification functionalization. The center's products have been widely used by Tsinghua University, National Key Laboratory of Biochemical Engineering, South China University of Technology, South China Normal University, Sichuan University and many corporate users.