25987-06-8 Usage
Uses
Used in Detergents:
PEI is used as a water treatment agent for its ability to flocculate cellular contaminants, nucleic acids, lipids, and debris from cellular homogenates to facilitate purification of soluble proteins.
Used in Adhesives:
PEI is used as an adhesion promoter and lamination primer due to its ability to form strong bonds with various surfaces.
Used in Water Treatment:
PEI is used as a flocculant and cationic dispersant in water treatment processes to remove impurities and improve water quality.
Used in Printing Inks:
PEI is used as a stability enhancer and surface activator in printing inks to improve ink performance and print quality.
Used in Dyes:
PEI is used as a chelating agent in dyes to bind and stabilize dye molecules.
Used in Cosmetics:
PEI is used as a fixative agent in cosmetics to help maintain the stability and effectiveness of cosmetic products.
Used in Paper Industry:
PEI is used in the paper industry for various applications, including paper manufacturing and as a component in paper products.
Used in Gene Delivery and Therapy:
PEI is used as a vehicle for nonviral gene delivery and therapy due to its excellent transfection efficiencies in both in vitro and in vivo models.
Used in Drug Delivery Systems:
PEI is used for the delivery of small drugs and in photodynamic therapy (PDT) as a carrier for drugs and as a component in drug delivery systems.
Used in Antimicrobial Coating:
PEI is used in antimicrobial coatings to improve the stability and effectiveness of coatings against bacterial growth.
Used in Preparation of Nano-sized Delivery Vectors:
PEI is used in the preparation of nanoparticles for drug delivery, allowing for efficient drug accumulation at target sites in the body.
Used in Non-invasive Optical Imaging Devices:
PEI is used in non-invasive optical imaging devices, such as Near Infrared (NIR) imaging, to assess cellular functions like caspases' activity in vitro.
Features
Polyethylenimine(PEI) is one of the most widely used synthetic polycations in various applications because of its chemical functionality arising from the presence of cationic primary (25%), secondary (50%), and tertiary amines (25%)[12,13]. PEI is formed by the linking of iminoethylene units and can have linear, branched, comb, network, and dendrimer architectures depending upon its synthesis and modification methods, which greatly influences its properties, both physical and chemical[14]. Furthermore, these synthetic approaches enable PEI to be available in a wide range of molecular weights. At room temperature, branched PEI (BPEI) is a highly viscous liquid while linear PEI (LPEI) is a solid. PEI has several attractive features for its use in widespread applications, such as low toxicity, ease of separation and recycling, and (last but not least) it being odorless. In addition to these attractive features, there is a distinct feature of PEI which places it ahead of other polyions (e.g. polyallylamine or chitosan) when it comes to loading, and which justifies its widespread use in fields as varied as detergents, adhesives, water treatment, cosmetics, carbon dioxide capture,[15-18] as a DNA transfection agent, and in drug delivery[19,20] despite being a weak polymeric base with pKa values between 7.9 and 9.6, it possesses a high ionic charge density, which in practical terms translates into being a more cost-effective material. This derives from the possibility of either reaching the same loadings with reduced amounts of the polymer (which would colloquially mean "getting a bigger bang for the buck") or reaching loadings that are beyond the reach of the aforementioned examples while avoiding enzyme agglomeration thanks to its multi-branched network.
For gene delivery
The potential of PEI as a gene delivery vector was first discussed in 1995[35] following which there have been numerous studies reporting its application in gene delivery both in vitro and in vivo. PEIs of molecular weights ranging from 800 to 25 kDa have been investigated in gene delivery[36-38]. The results showed that PEIs having molecular weight 25 kDa were the most suitable for transfection. Higher molecular weight increases cytotoxicity due to cell surface aggregation of the polymer[39]. Though low molecular weight PEIs is less toxic, they do not display effective transfection property. Due to the low positive charge, low molecular weights PEIs are incapable of condensing DNA effectively. Also, the low surface charge of the PEI/DNA complexes does not induce effective cellular uptake through charge-mediated interactions[38].
PEI polymers can be broadly classified into branched and linear PEI. Compared to linear PEI, highly branched PEI forms stronger and smaller complexes with DNA[40,41]. The complexation of branched PEI with DNA is less dependent on the buffer conditions than the high molecular weight linear PEI, which is dependent on the buffer condition. Linear PEI (22 kDa) on complexation with DNA in a high ionic strength solution has been observed to form larger-sized complexes (1 μm), whereas in 5% glucose, the complex size was found to be 30 60 nm. The in vivo studies showed that linear PEI/DNA complexes prepared in high salt conditions were less efficient in transfection than those formed in low salt condition[42].
The transfection efficiency/cytotoxicity profile of PEIs is largely influenced by their molecular weight, degree of branching, zeta potential and particle size. With increase in molecular weight, branched PEIs exhibit high transfection efficiency; however, cytotoxicity has also been found to increase concurrently[38]. To overcome the cytotoxicity associated with PEIs, different strategies have been studied. These include using linear high molecular weight PEI, substituting or linking high molecular weight branched PEIs with polysaccharides, hydrophilic polymers such as PEG, disulfide linkers, lipid moieties, etc. PEI and its derivatives have been used to deliver nucleic acids in vivo and the results are promising and have been used in cancer and RNA interference (RNAi) therapy. There are several reports suggesting delivery of nucleic acids by PEI derivatives in vivo that showcase the potential of PEI in delivery of therapeutics. These derivatives are either polysaccharide-decked PEIs or cross-linked PEI nanoparticles. The use of polysaccharides such as chondroitin sulphate, hyaluronic acid, gellan gum or dextran to modify branched PEI (Mw 25 kDa) has made the resulting polymers less toxic thereby improving their transfection efficiency in vivo[43, 44]. Also, the linkers such as polyglutamic acid, polyethyleneglycol-bis (aminoethylphosphate), piperazine-N, N¢-dibutyric acid, butane-1, 4-diol bis glycidyl ether (BDG) when used to crosslink PEI (25 kDa) resulted in the formation of vectors with significantly enhanced transfection efficacy in vivo[45,46]. Subsequent sections will elaborate on low and high molecular weight branched and linear PEI-mediated delivery of therapeutic genes to various tissues in a specific manner.
Reference
Polyethylemine and ethylenimine, Chemical Safety Information from Intergovernmental Organizations Document, 12-13-05, (http://www.inchem.org/documents/jecfa/jecmono/v20je08.htm)
Cordes, R.M.; Sims, W.B.; Glatz, C.E. Precipitation of nucleic acids with poly(ethyleneimine). Biotechnol. Prog., 1990, 6(4), 283.
Kirk, N.; Cowan, D. Optimising the recovery of recombinant thermostable proteins expressed in mesophilic hosts. J. Biotechnol., 1995 , 42(2), 177.
Milburn, P.; Bonnerjea, J.; Hoare, M.; Dunnill, P. Selective flocculation of nucleic acids, lipids, and colloidal particles from a yeast cell homogenate by polyethyleneimine, and its scale-up. Enzyme Microb. Technol., 1990, 12(7), 527.
Bahulekar, R.; Ayyangar, N.R.; Ponrathnam, S. Polyethyleneimine in immobilization of biocatalysts. Enzyme Microb. Technol., 1991, 13(11), 858.
Cong, L.; Kaul, R.; Dissing, U.; Mattiasson, B. A model study on Eudragit and polyethyleneimine as soluble carriers of aamylase for repeated hydrolysis of starch. J. Biotechnol., 1995, 42, 75.
Suh, J.; Cho, Y.; Lee, K. J. Macrocyclic metal complexes built on polyethyleneimine. J. Am. Chem. Soc., 1991, 113, 4198.
Boussif, O.; Lezoualc’h, F.; Zanta, M. A.; Mergny, M. D.; Scherman, D.; Demeneix. B.; Behr, J. P. A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: polyethylenimine. Proc. Nat. Acad. Sci. USA, 1995, 92, 7297.
Godbey, W.T.; Mikos, A.G. Recent progress in gene delivery using non-viral transfer complexes. J. Control Release, 2001, 72, 115.
Godbey, W.T.; Wu K.K.; Mikos, A.G. Poly(ethylenimine) and its role in gene delivery. J. Control Release, 1999, 60, 149.
Kichler, A.; Leborgne, C.; Coeytaux, E.; Danos, O. Polyethylenimine-mediated gene delivery: a mechanistic study. J. Gene Med., 2001, 3, 135.
B. Brissault, A. Kichler, C. Guis, C. Leborgne, O. Danos and H. Cheradame, Bioconjugate Chem., 2003, 14, 581–587.
S. K. Samal, M. Dash, S. Van Vlierberghe, D. L. Kaplan, E. Chiellini, C. van Blitterswijk, L. Moroni and P. Dubruel, Chem. Soc. Rev., 2012, 41, 7147–7194.
Q. Yang and T. Runge, ACS Sustainable Chem. Eng., 2016, 4, 6951–6961.
S. Hammache, J. S. Hoffman, M. L. Gray, D. J. Fauth, B. H. Howard and H. W. Pennline, Energy Fuels, 2013, 27, 6899–6905.
L. Y. Yurlova, A. P. Kryvoruchko and B. P. Yatsik, J. Water Chem. Technol., 2014, 36, 115–119.
W. Zhang, H. Liu, C. Sun, T. C. Drage and C. E. Snape, Chem. Eng. Sci., 2014, 116, 306–316.
E. P. Dillon, C. A. Crouse and A. R. Barron, ACS Nano, 2008, 2, 156–164.
W. Y. Seow, K. Liang, M. Kurisawa and C. A. E. Hauser, Biomacromolecules, 2013, 14, 2340–2346.
S. Sajeesh, T. Y. Lee, S. W. Hong, P. Dua, J. Y. Choe, A. Kang, W. S. Yun, C. Song, S. H. Park, S. Kim, C. Li and D. Lee, Mol. Pharmaceutics, 2014, 11, 872–884.
C. R. Dick and G. E. Ham, J. Macromol. Sci., Part A: Pure Appl. Chem., 1970, 4, 1301–1314.
S. Kobayashi, Prog. Polym. Sci., 1990, 15, 751–823.
Chu, A. J; Beydoun, S.; Mathews, S.; Hoang, T. Novel anticoagulant polyethylenimine: inhibition of thrombin-catalyzed fibrin formation. Arch. Biochem. Biophys., 2003, 415, 101.
Helander, I. M.; Alakomi, H.-L.; Latva-Kala, K.; Koski, P. Polyethyleneimine is an effective permeabilizer of gram-negative bacteria. Microbiology, 1997, 143, 3193.
Setty, C. M.; Sahoo, S. S.; Sa, B. Alginate-coated alginatepolyethyleneimine beads for prolonged release of furosemide in simulated intestinal fluid. Drug Dev. Ind. Pharm., 2005, 31, 435.
Tegos, G. P.; Anbe, M.; Yang, C.; Demidova, T. N.; Satti, M.; Mroz, P.; Janjua, S.; Gad, F.; Hamblin, M. R. Protease-stable polycationic photosensitizer conjugates between polyethyleneimine and chlorin(e6) for broad-spectrum antimicrobial photoinactivation. Antimicrob. Agents Chemother., 2006, 50(4), 1402.
Soukos, N. S.; Ximenez-Fyvie, L. A.; Hamblin, M. R.; Socransky, S. S.; Hasan, T. Targeted antimicrobial photochemotherapy. Antimicrob. Agents Chemother., 1998, 42, 2595.
Bourgeois, S.; Laham, A.; Besnard, M.; Andremont, A.; Fattal, E. In vitro and in vivo evaluation of pectin beads for the colon delivery of beta-lactamases. J. Drug Target, 2005, 13, 277.
Bourgeois, S.; Fattal, E.; Andremont, A.; Couvreur, P. 2003 PCT/FR03/02474.
Kra?mer, M.; Stumby?, J.-F.; Turk, H.; Krause, S.; Komp, A.; Delineau, L.; Prokhorova, S.; Kautz, H.; Haag, R. pH-responsive molecular nanocarriers based on dendritic core-shell architectures. Angew. Chem. Int. Ed., 2002, 41, 4252.
Xu, S.; Kra?mer, M.; Haag, R. pH-Responsive dendritic core-shell architectures as amphiphilic nanocarriers for polar drugs. J. Drug Target, 2006, 14, 367.
Kra?mer, M.; Kopaczynska, M.; Krause, S.; Haag, R. Dendritic polyamine architectures with lipophilic shells as nanocompartments for polar guest molecules: A comparative study of their transport behavior. J. Polym. Sci.[A1], 2007, 45, 2287.
Thunemann, A. F.; General, S. Nanoparticles of a polyelectrolytefatty acid complex: carriers for Q10 and triiodothyronine. J. Control Release, 2001, 75, 237.
Kim, K.; Lee, M.; Park, H.; Kim, J.-H.; Kim, S.; Chung, H.; Choi, K.; Kim, I.-S.; Seong, B. L.; Kwon, I. C. Cell-permeable and biocompatible polymeric nanoparticles for apoptosis imaging. J. Am. Chem. Soc., 2006, 128(11), 3490.
Boussif O, Lezoualc’h F, Zanta MA, et al. A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: polyethylenimine. Proc Natl Acad Sci USA 1995;92:7297-301
Baker A, Saltik M, Lehrmann H, et al. Polyethylenimine (PEI) is a simple, inexpensive and effective reagent for condensing and linking plasmid DNA to adenovirus for gene delivery. Gene Ther 1997;4:773-82
Meunier-Durmort C, Grimal H, Sachs LM, et al. Adenovirus enhancement of polyethylenimine-mediated transfer of regulated genes in differentiated cells. Gene Ther 1997;4:808-14
Godbey WT, Wu KK, Mikos AG. Size matters: molecular weight affects the efficiency of poly(ethylenimine) as a gene delivery vehicle. J Biomed Mater Res 1999;45:268-75
Morimoto K, Nishikawa M, Kawakami S, et al. Molecular weight-dependent gene transfection activity of unmodified and galactosylated polyethyleneimine on hepatoma cells and mouse liver. Mol Ther 2003;7:254-61
Wightman L, Kircheis R, Rossler V, et al. Different behavior of branched and linear polyethylenimine for gene delivery in vitro and in vivo. J Gene Med 2001;3:362-72
Goula D, Remy JS, Erbacher P, et al. Size, diffusibility and transfection performance of linear PEI/ DNA complexes in the mouse central nervous system. Gene Ther 1998;5:712-17
Merkel OM, Zheng M, Debus H, Kissel T. Pulmonary gene delivery using polymeric nonviral vectors. Bioconjug Chem 2012;23:3-20
Goyal R, Tripathi SK, Tyagi S, et al. Gellan gum blended PEI nanocomposites as gene delivery agents: evidences from in vitro and in vivo studies. Eur J Pharm Biopharm 2011;79:3-14
Tripathi SK, Goyal R, Gupta KC. Surface modification of crosslinked dextran nanoparticles influences transfection efficiency of dextran-polyethylenimine nanocomposites. Soft Matter 2011;7:11360-71
Tripathi SK, Goyal R, Ansari KM, et al. Polyglutamic acid-based nanocomposites as efficient non-viral gene carriers in vitro and in vivo. Eur J Pharm Biopharm 2011;79:473-84
Patnaik S, Tripathi SK, Goyal R, et al. Polyethylenimine-polyethyleneglycol-bis (aminoethylphosphate) nanoparticles mediated efficient DNA and siRNA transfection in mammalian cells. Soft Matter 2011;7:6103-12
Check Digit Verification of cas no
The CAS Registry Mumber 25987-06-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,9,8 and 7 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 25987-06:
(7*2)+(6*5)+(5*9)+(4*8)+(3*7)+(2*0)+(1*6)=148
148 % 10 = 8
So 25987-06-8 is a valid CAS Registry Number.
InChI:InChI=1/C2H8N2.C2H5N/c3-1-2-4;1-2-3-1/h1-4H2;3H,1-2H2