Polyaziridine or Polyethylenimine (PEI) is a polymer with repeating units composed of the amine group and two carbon aliphatic CH2CH2 spacers.
Polyaziridine is produced on an industrial scale and finds many applications usually derived from its polycationic character.
Polyaziridine is also used as flocculating agent with silica sols and as a chelating agent with the ability to complex metal ions such as zinc and zirconium.
CAS Number: 9002-98-6
Chemical formula: (C2H5N)n
Molar mass: 43.04
Totally branched, dendrimeric forms of Polyaziridine were also reported.
Linear polyethyleneimines contain all secondary amines, in contrast to branched PEIs which contain primary, secondary and tertiary amino groups.
Properties of Polyaziridine:
The linear Polyaziridine is a semi-crystalline solid at room temperature while branched PEI is a fully amorphous polymer existing as a liquid at all molecular weights.
Linear polyethyleneimine is soluble in hot water, at low pH, in methanol, ethanol, or chloroform.
Polyaziridine is insoluble in cold water, benzene, ethyl ether, and acetone.
Polyaziridine has a melting point of around 67 °C.
Both linear and branched polyethyleneimine can be stored at room temperature.
Polyaziridine is able to form cryogels upon freezing and subsequent thawing of its aqueous solutions.
Polyethylenimines (PEI) are low to high molecular weight compounds with the general formula -[CH2-CH2-NH2]-, made by ring opening polymerization of aziridine.
These polymers are available as linear, partly branched or repetitively branched polymers (dendrimers).
The linear form contains only primary amines in the backbone whereas branched PEI also contains secondary and tertiary amines.
Thus, these polymers have different properties and reactivities.
Linear high MW Polyaziridine is usually solid at room temperature while branched PEIs are typically liquids at all molecular weights.
All three forms are soluble in water, methanol, ethanol, and chloroform but insoluble in solvents of low polarity such as benzene, ethyl ether, and acetone.
Synthesis of Polyaziridine:
Polyaziridine can be synthesized by the ring opening polymerization of aziridine.
Depending on the reaction conditions different degree of branching can be achieved.
Linear Polyaziridine is available by post-modification of other polymers like poly(2-oxazolines) or N-substituted polyaziridines.
Linear Polyaziridine was synthesised by the hydrolysis of poly(2-ethyl-2-oxazoline) and sold as jetPEI.
The current generation in-vivo-jetPEI uses bespoke poly(2-ethyl-2-oxazoline) polymers as precursors.
Applications of Polyaziridine:
Polyaziridine finds many applications in products like: detergents, adhesives, water treatment agents and cosmetics.
Owing to its ability to modify the surface of cellulose fibres, Polyaziridine is employed as a wet-strength agent in the paper-making process.
There are also other highly specialized Polyaziridine applications:
Biology:
Polyaziridine has a number of uses in laboratory biology, especially tissue culture, but is also toxic to cells if used in excess.
Toxicity is by two different mechanisms, the disruption of the cell membrane leading to necrotic cell death (immediate) and disruption of the mitochondrial membrane after internalisation leading to apoptosis (delayed).
Attachment promoter:
Polyethyleneimines are used in the cell culture of weakly anchoring cells to increase attachment.
Polyaziridine is a cationic polymer; the negatively charged outer surfaces of cells are attracted to dishes coated in Polyaziridine, facilitating stronger attachments between the cells and the plate.
Transfection reagent:
Poly(ethylenimine) was the second polymeric transfection agent discovered, after poly-L-lysine.
Polyaziridine condenses DNA into positively charged particles, which bind to anionic cell surface residues and are brought into the cell via endocytosis.
Once inside the cell, protonation of the amines results in an influx of counter-ions and a lowering of the osmotic potential.
Osmotic swelling results and bursts the vesicle releasing the polymer-DNA complex (polyplex) into the cytoplasm.
If the polyplex unpacks then the DNA is free to diffuse to the nucleus.
Permeabilization of gram negative bacteria:
Poly(ethylenimine) is also an effective permeabilizer of the outer membrane of Gram-negative bacteria.
CO2 capture:
Both linear and branched polyethylenimine have been used for CO2 capture, frequently impregnated over porous materials.
First use of PEI polymer in CO2 capture was devoted to improve the CO2 removal in space craft applications, impregnated over a polymeric matrix.
After that, the support was changed to MCM-41, an hexagonal mesostructured silica, and large amounts of Polyaziridine were retained in the so-called "molecular basket".
MCM-41-Polyaziridine adsorbent materials led to higher CO2 adsorption capacities than bulk Polyaziridine or MCM-41 material individually considered.
The authors claim that, in this case, a synergic effect takes place due to the high Polyaziridine dispersion inside the pore structure of the material.
As a result of this improvement, further works were developed to study more in depth the behaviour of these materials.
Exhaustive works have been focused on the CO2 adsorption capacity as well as the CO2/O2 and CO2/N2 adsorption selectivity of several MCM-41-Polyaziridine materials with PEI polymers.
Also, Polyaziridine impregnation has been tested over different supports such as a glass fiber matrix and monoliths.
However, for an appropriate performance under real conditions in post-combustion capture (mild temperatures between 45-75 °C and the presence of moisture) it is necessary to use thermally and hydrothermally stable silica materials, such as SBA-15, which also presents an hexagonal mesostructure.
Moisture and real world conditions have also been tested when using Polyaziridine-impregnated materials to adsorb CO2 from the air.
A detailed comparison among Polyaziridine and other amino-containing molecules showed an excellent performance of Polyaziridine-containing samples with cycles.
Also, only a slight decrease was registered in their CO2 uptake when increasing the temperature from 25 to 100 °C, demonstrating a high contribution of chemisorption to the adsorption capacity of these solids.
For the same reason, the adsorption capacity under diluted CO2 was up to 90% of the value under pure CO2 and also, a high unwanted selectivity towards SO2 was observed.
Lately, many efforts have been made in order to improve Polyaziridine diffusion within the porous structure of the support used.
A better dispersion of Polyaziridine and a higher CO2 efficiency (CO2/NH molar ratio) were achieved by impregnating a template-occluded PE-MCM-41 material rather than perfect cylindrical pores of a calcined material, following a previously described route.
The combined use of organosilanes such as aminopropyl-trimethoxysilane, AP, and Polyaziridine has also been studied.
The first approach used a combination of them to impregnate porous supports, achieving faster CO2-adsorption kinetics and higher stability during reutilization cycles, but no higher efficiencies.
A novel method is the so-called "double-functionalization".
It is based on the impregnation of materials previously functionalized by grafting (covalent bonding of organosilanes).
Amino groups incorporated by both paths have shown synergic effects, achieving high CO2 uptakes up to 235 mg CO2/g (5.34 mmol CO2/g).
CO2 adsorption kinetics were also studied for these materials, showing similar adsorption rates as impregnated solids.
This is an interesting finding, taking into account the smaller pore volume available in double-functionalized materials.
Thus, it can be also concluded that their higher CO2 uptake and efficiency compared to impregnated solids can be ascribed to a synergic effect of the amino groups incorporated by two methods (grafting and impregnation) rather than to a faster adsorption kinetics.
Low work function modifier for electronics:
Poly(ethylenimine) and poly(ethylenimine) ethoxylated (PEIE) have been shown as effective low-work function modifiers for organic electronics by Zhou and Kippelen et al.
Polyaziridine could universally reduce the work function of metals, metal oxides, conducting polymers and graphene, and so on.
It is very important that low-work function solution-processed conducting polymer could be produced by the Polyaziridine or PEIE modification.
Based on this discovery, the polymers have been widely used for organic solar cells, organic light-emitting diodes, organic field-effect transistors, perovskite solar cells, perovskite light-emitting diodes, quantum-dot solar cells and light-emitting diodes etc.
Use in delivery of HIV-gene therapies:
Polyaziridine, a cationic polymer, has been widely studied and shown great promise as an efficient gene delivery vehicle.
Likewise, the HIV-1 Tat peptide, a cell-permeable peptide, has been successfully used for intracellular gene delivery.
DESCRIPTION of Polyaziridine:
Polyaziridine or polyaziridine is a polymer with repeating unit composed of the amine group and two carbon aliphatic CH2CH2 spacer.
Linear polyethyleneimines contain all secondary amines, in contrast to branched PEIs which contain primary, secondary and tertiary amino groups.
Totally branched, dendrimeric forms were also reported.
Polyaziridine is produced on industrial scale and finds many applications usually derived from its polycationic character.
DESCRIPTION of Polyaziridine:
General description of Polyaziridine:
Polyaziridine is a hydrophilic cationic polymer widely used as a nonviral nucleotide delivery reagent.
Branched Polyaziridine can be synthesized by cationic ring-opening polymerization of aziridine.
Polyaziridine-based particles can also be used as adjuvants for vaccines.
Owing to its excellent physicochemical properties, Polyaziridine is applied in many fields like the separation and purification of proteins, carbon dioxide absorption, drug carriers, effluent treatment, and biological labels.
Applications of Polyaziridine:
Polyethyleneimine can be used as a non-viral synthetic polymer vector for in vivo delivery of therapeutic nucleic acids.
The interaction between negatively charged nucleic acids and positively charged polymer backbone results in the formation of nano-sized complexes.
This neutralized complex protects the enclosed nucleic acid from enzymes and maintains its stability till the cellular uptake takes place.
For example, human serum albumin conjugated Polyaziridine shows good pDNA transfection and low toxicity.
Polyaziridine can be used to functionalize single-walled nanotubes (SWNTs) to improve their solubility and biocompatibility while maintaining the structural integrity of the original SWNT.
Covalently functionalized SWNTs find application in CO2 absorption and gene delivery.
Branched Polyaziridine can also be used to modify the surface properties of adsorbents.
Polyaziridine-modified hydrous zirconium oxide/PAN nanofibers are used for the defluorination of groundwater as they show high fluoride adsorption capacity and a wide working pH range.
Features and Benefits of Polyaziridine:
Primary and secondary amine groups of Polyaziridine can efficiently bind to drugs, nucleic acids, and other functional moieties.
Branched Polyaziridine has better complexation andbuffering capacity.
Physical form of Polyaziridine:
Branched polymer
Synonym(s):
PEI
Linear Formula:
H(NHCH2CH2)nNH2
CAS Number:
9002-98-6
MDL number:
MFCD00084427
PubChem Substance ID:
24865591
NACRES:
NA.23
IUPAC name:
Poly(iminoethylene)
Other names:
Polyaziridine, Poly[imino(1,2-ethanediyl)]
Polyaziridine or Polyethylenimine (PEI) is a polymer with repeating units composed of the amine group and two carbon aliphatic CH2CH2 spacers.
KEYWORDS:
9002-98-6, Pei-1000, Pei-1400, Pei-14M, Pei-1500, Pei-1750, Pei-250, Pei-2500, Pei-275, Pei-35
Property Highlights of Polyaziridine:
Isoelectric Point: ~11
Displaceable: Not displaceable – strongly bound to the particle surface
Positively charged
Good salt stability: stable in highly saline solutions
Toxicity: BPEI has a higher in-vitro toxicity than many of the other surfaces offered at nanoComposix.
Solvent compatibility: Water, ethanol, chloroform, many other polar solvents
Applications of Polyaziridine:
Polyaziridine is stable in combination with other positively charged particles
Layer by layer construction of nanoparticle surfaces
Binding to negatively charged substrates or larger particles
Color engineering
Polyaziridine, a polycation with high ionic charge density, has recently been used as a gene therapy delivery agent.
We have defined the optimal conditions for Polyaziridine-based transfection of airway epithelial cells in vitro and in vivo and used these conditions to restore Cl− channel activity in a CF mouse model.
Three forms of Polyaziridine, a linear 22 kDa (ExGen 500) form and branched 25 or 50 kDa forms were evaluated.
All forms of Polyaziridine significantly increased luciferase reporter gene expression compared to the liposome DCChol/DOPE in a human bronchial epithelial cell line (16HBE) irrespective of the extent of cell confluency.
With subconfluent cells, gene expression was around 1000-, 200- and 25-fold higher than liposomes using linear 22, 25 and 50 kDa Polyaziridine, respectively.
The transfection efficiency was reduced in confluent and polarized epithelial cells but linear 22 kDa Polyaziridine showed the smallest decrease and gave 8000-fold better transfection in polarized cells compared to liposomes.
A comparison of linear 22 or 25 kDa Polyaziridine with DCChol/DOPE for airway delivery in vivo via intranasal instillation was also performed.
Linear 22 kDa PEI gave significantly better luciferase reporter gene expression of 350-fold in the lung, 180-fold in the nose and 85-fold in the trachea compared to liposome.
In contrast, the 25 kDa form of Polyaziridine was no better than DCChol/DOPE.
Repeat dosing with linear 22 kDa Polyaziridine failed to give reporter gene delivery comparable to the initial dose.
To establish that Polyaziridine can be used to deliver a physiologically relevent gene in vivo, we used it to restore Cl− secretion by CFTR gene delivery in the airways of a CF mouse model.
Identifiers of Polyaziridine:
CAS Number: 9002-98-6
ChemSpider: none
ECHA InfoCard: 100.123.818
CompTox Dashboard (EPA): DTXSID1051272
Polyaziridine, an organic branched or linear polyamine polymer, has been successfully used in the past for DNA complexation and transfection in vitro and in vivo into several cell lines and tissues.
Polyaziridine was also applied in different fields from gene therapy and several studies have emphasized the importance of this polymer in medicinal chemistry.
In this brief critical review the uses and applications of this versatile polymeric molecule will be discussed.
Linearized Polyaziridine (molecular weight 40,000) is a highly charged cationic polymer that readily binds to DNA or other negatively charged biomacromolecules, making it a common and effective cell transfection reagent.
In principle, Polyaziridine condenses DNA plasmid into positively charged complexes.
The complexes can adhere to negatively charged cell surface residues, and then enters the cell through endocytosis.
Properties of Polyaziridine:
Chemical formula: (C2H5N)n, linear form
Molar mass: 43.04 (repeat unit), mass of polymer variable
Introduction of Polyaziridine:
Polyaziridine, as a nonviral cationic polymer, has been widely used as gene delivery nanosystem.
Although a number of investigations have highlighted its toxic impacts on target cells through induction of apoptosis/necrosis, still it is essential to look at its structural impacts on target cells.
Methods of Polyaziridine:
In this current study, cytogenomic impacts of 25 kD linear and branched Polyaziridine (LPEI and BPEI, respectively) in A431 cells are reported to address possible mechanism for induction of apoptosis.
At 40-50% confluency, A431 cells were exposed to Polyaziridine at a recommended concentration for 4 hr.
After 24 hr, to detect apoptosis and DNA damage, the treated cells were subjected to MTT assay, FITC-labeled annexin V flow cytometry and comet assay.
Results:
Flow cytometry assessments revealed that the BPEI can result in greater internalization than the linear Polyaziridine, which also induced greater cytotoxicity.
Annexin V assay confirmed early and late apoptosis by BPEI, imposing somewhat DNA damage detected by comet assay.
Western blot analysis resulted in induction of Akt-kinase which is possibly one of biomolecules affected by PEI.
Conclusion:
These results highlight that, despite induction of Akt-kinase, the BPEI can elicit apoptosis in target cells.
Get highly sensitive rapid detection of Polyaziridine to prove your therapy meets recommended ICH Q6B guidelines.
Polyaziridine is routinely used as a transfection reagent to deliver genes into mammalian cells, including Cell and Gene Therapies (CGT).
Developers of Polyaziridine-employing therapies are required to demonstrate that levels of this impurity have been minimized in their drug substance by well controlled manufacturing processes.
With state-of-the-art instrumentation, experienced scientists, and fast turnaround times, we provide you reliable results to push your project forward.
High-molecular-mass polyethylenimines (PEIs) are widely used vectors for nucleic acid delivery.
We found that removal of the residual N-acyl moieties from commercial linear 25-kDa PEI enhanced its plasmid DNA delivery efficiency 21 times in vitro, as well as 10,000 times in mice with a concomitant 1,500-fold enhancement in lung specificity.
Several additional linear Polyethylenimines (PEI) were synthesized by acid-catalyzed hydrolysis of poly(2-ethyl-2-oxazoline), yielding the pure polycations.
PEI87 and PEI217 exhibited the highest efficiency in vitro: 115-fold and 6-fold above those of the commercial and deacylated PEI25s, respectively; moreover, PEI87 delivered DNA to mouse lung as efficiently as the pure PEI25 but at a lower concentration and with a 200-fold lung specificity.
These improvements stem from an increase in the number of protonatable nitrogens, which presumably results in a tighter condensation of plasmid DNA and a better endosomal escape of the PEI/DNA complexes.
As a validation of the potential of such linear, fully deacylated PEIs in gene therapy for lung diseases, systemic delivery in mice of the complexes of a short interfering RNA (siRNA) against a model gene, firefly luciferase, and PEI25 or PEI87 afforded a 77% and 93% suppression of the gene expression in the lungs, respectively.
Furthermore, a polyplex of a siRNA against the influenza viral nucleocapsid protein gene and PEI87 resulted in a 94% drop of virus titers in the lungs of influenza-infected animals.
Chemical Name: Polyethylenimine (Branched) (Technical Grade)
Synonyms: Ethylenediamine-ethylenimine copolymer; Aziridine-1,2-diaminoethane copolymer; Ethylenediamine, polymer with ethylenimine
CAS Number: 25987-06-8
Molecular Formula: N/A
Appearance: Colourless Oil
Molecular Weight: N/A
Storage: 4°C, Inert atmosphere
Solubility: Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly)
Category: Building Blocks; Monomers;
Applications: Polyethylenimine (cas# 25987-06-8) is a useful research chemical.
Polyethylenimine(PEI) magnetic particles are superparamagnetic beads covalently functionalized with PEI.
Polyaziridine is a kind of branched polymer with a high-density amine group.
The ratio of primary amine to secondary amine to tertiary amine is 1:2:1.
In each Polyaziridine molecule, one nitrogen atom in every two carbon atoms is protonated.
Due to the different pKa values of primary, secondary, and tertiary amino groups, Polyaziridine could capture protons under different pH conditions, which is called the "proton sponge" mechanism.
As a cationic polymer, Polyaziridine is also a widely used transfection reagent in molecular biology and a dispersant in nanotechnology.
Polyaziridine can form a positively charged complex with DNA, which binds to anionic cell surface residues and enters the cell via endocytosis.
Absolute Mag Polyaziridine Magnetic Particles are available with an organic matrix of a polystyrene polymer.
The Polyaziridine magnetic particles can capture negatively charged molecules, such as DNA and RNA, through charge-charge interaction.
Synonyms:
aziridine, homopolymer
ethylenimine, homopolymer
PEI-1000
poly(ethylenimine)
Polyethyleneimine
Polyethylene imine
poly(ethylene imine)
poly(ethyleneimine)
CHEBI:53231
DTXSID1051272
PEI compound
Polyaziridines
Polyethyleneimines
Polyethylenimines
poly-ethylene imine
Regulatory process names:
Aziridine, polymer with oxirane
IUPAC names:
Ethoxylated polyethyleneimine
Polyethyleneimine,80% ethoxylated
Other names:
Modified polyethyleneimine
Other identifiers:
26658-46-8
Regulatory process names:
AZIRIDINE, HOMOPOLYMER
Aziridine, homopolymer
IUPAC names:
aziridine
Aziridine Homopolymer
AZIRIDINE, HOMOPOLYMER
Aziridine, Homopolymer
Aziridine, homopolymer
Ethyleneimine, Polymer
PEI-2500
POLYETHYLENEIMINE
Polyethyleneimine
polyethyleneimine
Polyethyleneimine (ca. 30% in Water) [for Biochemical Research]
Polyethylenimin
Polyethylenimin
Polyethylenimine
Polyethylenimine linear
Trade names:
15T
210T
2MB
AC 871
Aziridin, homopolymer
Aziridine homopolymerisée
Aziridine homopolymérisée
Aziridine polymer
Aziridine, homopolymer
Aziridine, homopolymer 1300; MG=1300
Aziridine, homopolymer 17000-28000; V=17000-28000 mPas
Aziridine, homopolymer 2000000; MG=2000000
Aziridine, homopolymer 2000; MG=2000
Aziridine, homopolymer 25000; MG=25000
Aziridine, homopolymer 500-1000; V=500-1000 mPas
Aziridine, homopolymer 5000; MG=5000
Aziridine, homopolymer 750000; MG=750000
Aziridine, homopolymer 800; MG=800
Aziridine, homopolymer; n
BASOPHOB RSI; 50% Active Matter; active substance
CF 218
CF 218 (polymer)
Corcat P 100
Corcat P 12
Corcat P 145
Corcat P 150
Corcat P 18
Corcat P 200
Corcat P 600
EL 402
EL 420
Epomin 1000
Epomin 150T
Epomin D 3000
Epomin P 003
Epomin P 1000
Epomin P 1500
Epomin P 500
Epomin SP 003
Epomin SP 006
Epomin SP 012
Epomin SP 018
Epomin SP 103
Epomin SP 110
Epomin SP 200
Epomin SP 300
Ethyleneimine, homopolymer
Ethylenimine, polymers
Everamine
Everamine 150T
Everamine 210T
Everamine 500T
Everamine 50T
K 203C
Lugalvan G 15
Lugalvan G 20
Lugalvan G 35
LUPASOL G 20 WASSERFREI; MG=1300; 98% Active Matter; active substance
LUPASOL G 20; MG=1300; 50% Active Matter; active substance
LUPASOL G 35; MG=2000; 50% Active Matter; active substance
LUPASOL HF; MG=25000; 55% Active Matter; active substance
LUPASOL P; MG=750000; 50% Active Matter; active substance
LUPASOL PS; MG=750000; 33% Active Matter; active substance
LUPASOL SK; MG=2000000; 24% Active Matter; active substance
LUPASOL WF; MG=25000; 99% Active Matter; active substance
Luprasol P; in Water; 50% Active Matter; active substance
Montrek 1000
Montrek 12
Montrek 18
Montrek 6
Montrek 600
P 100 (polyamine)
P 1000
Pei-10
Pei-10 (INCI)
Pei-1000
Pei-1000 (INCI)
Pei-1400
Pei-1400 (INCI)
Pei-14M
Pei-14M (INCI)
Pei-15
Pei-15 (INCI)
Pei-1500
Pei-1500 (INCI)
Pei-1750
Pei-1750 (INCI)
Pei-250
Pei-250 (INCI)
Pei-2500
Pei-2500 (INCI)
Pei-275
Pei-275 (INCI)
Pei-35
Pei-35 (INCI)
Pei-45
Pei-45 (INCI)
Pei-7
Pei-7 (INCI)
Pei-700
Pei-700 (INCI)
POLYETHLENEIMINE (MELT)
Polyethylenimin
Polymin FG; unbekannt 1
Polymin HS; V=500-1000 mPas; 20% Active Matter; active substance
Polymin P; V=17000-28000 mPas
Polymin-P
SEDIPUR CL 930; 30% Active Matter; active substance