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Chemical Compound Review

Polyaziridine     aziridine

Synonyms: Azirane, Aziridine, Everamine, Polymin, Aziran, ...
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Disease relevance of Polyethyleneimine

  • To gain insight into the potential clinical relevance of this polymorphism in terms of breast cancer hormone dependence, we compared the 265 cytosols for their [3H]tamoxifen aziridine- and [3H]estradiol-binding capacities using the above-mentioned method and the conventional dextran-coated charcoal assay [1].
  • Additionally, polyethyleneimine induced significant local toxicity after i.m. injection, whereas C32 demonstrated no toxicity [2].
  • Significantly, highly efficient rescue can be achieved by polyethyleneimine-induced endosome rupture or by coinfection with adenovirus as long as uptake of the two viruses is simultaneous and the adenovirus is capable of deploying pVI, a capsid protein with endosomolytic activity [3].
  • Unexpected parallels between several of nature's most efficient DNA viruses and nonviral polyethylenimine/DNA nanocomplexes were revealed to include motor protein-driven transport through the cytoplasm toward the nucleus on microtubules [4].
  • PEI does not induce proteinuria in rats, nor does it produce glomerular morphologic alterations when ten times the tracer dosage is administered intravenously [5].

Psychiatry related information on Polyethyleneimine

  • However, many genes involved in other cellular responses such as apoptosis, stress responses and oncogenesis were activated in PEI+, supporting the theory of immunostimulation by danger genes, but also pointing toward possible adverse reactions such as Alzheimer's disease [6].
  • GI pharmacology of polyethyleneimine II: motor activity in anesthetized dogs [7].
  • The effect of reaction time on aziridine yield reveals an S-shaped profile that is accentuated by the position of the substituent and this effect is observed for both the homogeneously catalysed pathway and the heterogeneously catalysed reaction [8].

High impact information on Polyethyleneimine

  • In rats receiving PEI, deposits were localized within the glomerular basement membrane (GBM) of all peripheral capillary walls and in the mesangium [9].
  • Bovine serum albumin (BSA)-anti-BSA immune complexes made in 40 times antigen excess were administered following intravenous injection of PEI [9].
  • Glomerular localization of immune deposits was assessed by quantitative immunofluorescence and electron microscopy and compared to controls receiving diluent without PEI followed by the same dose in immune complexes [9].
  • The pharmacokinetics of E09 and its metabolite E05A with an open aziridine ring was determined using a new high-pressure liquid chromatographic method and noncompartmental calculation of kinetic parameters [10].
  • We failed to identify a specific [3H]tamoxifen aziridine electrophoretic pattern with respect to the tumor estrogen receptor content as measured by the dextran-coated charcoal assay [1].

Chemical compound and disease context of Polyethyleneimine


Biological context of Polyethyleneimine


Anatomical context of Polyethyleneimine

  • The chimeric oligonucleotide was either complexed with polyethylenimine or encapsulated in anionic liposomes, administered i.v., and targeted to the hepatocyte via the asialoglycoprotein receptor [20].
  • Branched polyethylenimine (PEI) chains with an average molecular mass of 2 kDa (PEI2) have been covalently attached to gold nanoparticles (GNPs), and the potency of the resulting PEI2-GNPs conjugates as vectors for the delivery of plasmid DNA into monkey kidney (COS-7) cells in the presence of serum in vitro has been systematically investigated [21].
  • The receptor was selectively precipitated with Polymin P from high-speed supernatants derived from 800 g of intestinal mucosa and then sequentially chromatographed on DNA-cellulose [22].
  • In a first series of experiments, plasma membranes were prepared with a technique based on the electrostatic attachment of isolated hepatocytes to polyethyleneimine-coated beads [23].
  • Styrene microspheres treated with polyethyleneimine were used to label the surface of neurites in order to determine the site and pattern of surface addition during the experimental "towed growth" regime [24].

Associations of Polyethyleneimine with other chemical compounds

  • It will be clinically important to see whether the tumors positive for [3H]tamoxifen aziridine only correspond to the small subset of tumors (10%) which respond to tamoxifen treatment despite very low estrogen receptor levels, as measured by the dextran-coated charcoal technique [1].
  • Using tryptic digestion followed by mass spectrometry and amino acid sequencing, the aziridine-containing ligand is shown to alkylate specifically cysteine 67 of HLA-B27 [25].
  • The techniques employed for the purification include selective precipitation of the receptor by Polymin P (polyethyleneimine) and (NH4)2SO4 and batch adsorption to and selective elution from hydroxylapatite, followed by gel exclusion and DEAE-cellulose chromatography [26].
  • The nuclear estrogen receptors from the parental MCF-7 and the two variant cells, when covalently labeled with [3H]-tamoxifen aziridine in intact cells and then salt extracted have identical molecular weights of approximately 62,000, as determined by sodium dodecyl sulfate-polyacrylamide gel electrophoresis [27].
  • Inhibition of DNA replicon initiation by 4-nitroquinoline 1-oxide, adriamycin, and ethyleneimine [28].

Gene context of Polyethyleneimine

  • Aerosol delivery of glucosylated polyethylenimine/phosphatase and tensin homologue deleted on chromosome 10 complex suppresses Akt downstream pathways in the lung of K-ras null mice [29].
  • When the cells were prelabelled with [3H]tamoxifen aziridine ([3H]TAZ) before their exposure to E2, ER cleavage could not be detected due to the lack of activation potency of the antiestrogenic ligand [30].
  • Furthermore, in the PEI group, chaperone genes and members of the p38 mitogen-activated protein kinase pathway were also upregulated, suggesting a possible explanation for the better performance of PEI in gene delivery systems [31].
  • In gene delivery studies, GE11-conjugated polyethylenimine (PEI) vectors were less mitogenic, but still quite efficient at transfecting genes into EGFR highly expressing cells and tumor xenografts [32].
  • Enhanced cell growth inhibition following PTEN nonviral gene transfer using polyethylenimine and photochemical internalization in endometrial cancer cells [33].

Analytical, diagnostic and therapeutic context of Polyethyleneimine


  1. Comparison of tritiated estradiol and tamoxifen aziridine for measurement of estrogen receptors in human breast cancer cytosols. Piccart, M.J., Muquardt, C., Bosman, C., Pirotte, P., Veenstra, S., Grillo, F., Leclercq, G. J. Natl. Cancer Inst. (1991) [Pubmed]
  2. A polymer library approach to suicide gene therapy for cancer. Anderson, D.G., Peng, W., Akinc, A., Hossain, N., Kohn, A., Padera, R., Langer, R., Sawicki, J.A. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  3. Parvoviral virions deploy a capsid-tethered lipolytic enzyme to breach the endosomal membrane during cell entry. Farr, G.A., Zhang, L.G., Tattersall, P. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  4. Efficient active transport of gene nanocarriers to the cell nucleus. Suh, J., Wirtz, D., Hanes, J. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  5. Glomerular anionic site distribution in nonproteinuric rats. A computer-assisted morphometric analysis. Pilia, P.A., Swain, R.P., Williams, A.V., Loadholt, C.B., Ainsworth, S.K. Am. J. Pathol. (1985) [Pubmed]
  6. PEI - a potent, but not harmless, mucosal immuno-stimulator of mixed T-helper cell response and FasL-mediated cell death in mice. Regnström, K., Ragnarsson, E.G., Köping-Höggård, M., Torstensson, E., Nyblom, H., Artursson, P. Gene Ther. (2003) [Pubmed]
  7. GI pharmacology of polyethyleneimine II: motor activity in anesthetized dogs. Tansy, M.F., Martin, J.S., Innes, D.L., Kendall, F.M., Melamed, S., Moss, J.N. Journal of pharmaceutical sciences. (1977) [Pubmed]
  8. Catalytic asymmetric heterogeneous aziridination of styrene derivatives using bis(oxazoline)-modified Cu2+-exchanged zeolite Y. Ryan, D., McMorn, P., Bethell, D., Hutchings, G. Org. Biomol. Chem. (2004) [Pubmed]
  9. Enhancement of glomerular immune complex deposition by a circulating polycation. Barnes, J.L., Venkatachalam, M.A. J. Exp. Med. (1984) [Pubmed]
  10. Phase I and pharmacologic study of the novel indoloquinone bioreductive alkylating cytotoxic drug E09. Schellens, J.H., Planting, A.S., van Acker, B.A., Loos, W.J., de Boer-Dennert, M., van der Burg, M.E., Koier, I., Krediet, R.T., Stoter, G., Verweij, J. J. Natl. Cancer Inst. (1994) [Pubmed]
  11. An RGD-oligolysine peptide: a prototype construct for integrin-mediated gene delivery. Harbottle, R.P., Cooper, R.G., Hart, S.L., Ladhoff, A., McKay, T., Knight, A.M., Wagner, E., Miller, A.D., Coutelle, C. Hum. Gene Ther. (1998) [Pubmed]
  12. Successful in vivo tumor targeting of prostate-specific membrane antigen with a highly efficient J591/PEI/DNA molecular conjugate. Moffatt, S., Papasakelariou, C., Wiehle, S., Cristiano, R. Gene Ther. (2006) [Pubmed]
  13. Efficient gene delivery into human dendritic cells by adenovirus polyethylenimine and mannose polyethylenimine transfection. Diebold, S.S., Lehrmann, H., Kursa, M., Wagner, E., Cotten, M., Zenke, M. Hum. Gene Ther. (1999) [Pubmed]
  14. Gene transfer with synthetic virus-like particles via the integrin-mediated endocytosis pathway. Erbacher, P., Remy, J.S., Behr, J.P. Gene Ther. (1999) [Pubmed]
  15. Systemic co-administration of depsipeptide selectively targets transfection enhancement to specific tissues and cell types. Liu, Y., Liggitt, D., Fong, S., Debs, R.J. Gene Ther. (2006) [Pubmed]
  16. A peptide nucleic acid-nuclear localization signal fusion that mediates nuclear transport of DNA. Brandén, L.J., Mohamed, A.J., Smith, C.I. Nat. Biotechnol. (1999) [Pubmed]
  17. Brain clathrin light chain 2 can be phosphorylated by a coated vesicle kinase. Schook, W.J., Puszkin, S. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  18. Antitumor effect of in vivo somatostatin receptor subtype 2 gene transfer in primary and metastatic pancreatic cancer models. Vernejoul, F., Faure, P., Benali, N., Calise, D., Tiraby, G., Pradayrol, L., Susini, C., Buscail, L. Cancer Res. (2002) [Pubmed]
  19. DNA strand scission and cross-linking by diaziridinylbenzoquinone (diaziquone) in human cells and relation to cell killing. Szmigiero, L., Erickson, L.C., Ewig, R.A., Kohn, K.W. Cancer Res. (1984) [Pubmed]
  20. Correction of the UDP-glucuronosyltransferase gene defect in the gunn rat model of crigler-najjar syndrome type I with a chimeric oligonucleotide. Kren, B.T., Parashar, B., Bandyopadhyay, P., Chowdhury, N.R., Chowdhury, J.R., Steer, C.J. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  21. Conjugation to gold nanoparticles enhances polyethylenimine's transfer of plasmid DNA into mammalian cells. Thomas, M., Klibanov, A.M. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  22. Purification of chicken intestinal receptor for 1,25-dihydroxyvitamin D. Pike, J.W., Haussler, M.R. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  23. Presence of functional cytochrome P-450 on isolated rat hepatocyte plasma membrane. Loeper, J., Descatoire, V., Maurice, M., Beaune, P., Feldmann, G., Larrey, D., Pessayre, D. Hepatology (1990) [Pubmed]
  24. Tensile regulation of axonal elongation and initiation. Zheng, J., Lamoureux, P., Santiago, V., Dennerll, T., Buxbaum, R.E., Heidemann, S.R. J. Neurosci. (1991) [Pubmed]
  25. Covalent HLA-B27/peptide complex induced by specific recognition of an aziridine mimic of arginine. Weiss, G.A., Valentekovich, R.J., Collins, E.J., Garboczi, D.N., Lane, W.S., Schreiber, S.L., Wiley, D.C. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  26. Purification of chicken intestinal receptor for 1 alpha, 25-dihydroxyvitamin D3 to apparent homogeneity. Simpson, R.U., DeLuca, H.F. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  27. Antiestrogen binding in antiestrogen growth-resistant estrogen-responsive clonal variants of MCF-7 human breast cancer cells. Miller, M.A., Lippman, M.E., Katzenellenbogen, B.S. Cancer Res. (1984) [Pubmed]
  28. Inhibition of DNA replicon initiation by 4-nitroquinoline 1-oxide, adriamycin, and ethyleneimine. Painter, R.B. Cancer Res. (1978) [Pubmed]
  29. Aerosol delivery of glucosylated polyethylenimine/phosphatase and tensin homologue deleted on chromosome 10 complex suppresses Akt downstream pathways in the lung of K-ras null mice. Kim, H.W., Park, I.K., Cho, C.S., Lee, K.H., Beck, G.R., Colburn, N.H., Cho, M.H. Cancer Res. (2004) [Pubmed]
  30. Protein synthesis is not implicated in the ligand-dependent activation of the estrogen receptor in MCF-7 cells. El Khissiin, A., Cleeren, A., Borràs, M., Leclercq, G. J. Steroid Biochem. Mol. Biol. (1997) [Pubmed]
  31. Gene expression profiles in mouse lung tissue after administration of two cationic polymers used for nonviral gene delivery. Regnström, K., Ragnarsson, E.G., Fryknäs, M., Köping-Höggård, M., Artursson, P. Pharm. Res. (2006) [Pubmed]
  32. Identification and characterization of a novel peptide ligand of epidermal growth factor receptor for targeted delivery of therapeutics. Li, Z., Zhao, R., Wu, X., Sun, Y., Yao, M., Li, J., Xu, Y., Gu, J. FASEB J. (2005) [Pubmed]
  33. Enhanced cell growth inhibition following PTEN nonviral gene transfer using polyethylenimine and photochemical internalization in endometrial cancer cells. Maurice-Duelli, A., Ndoye, A., Bouali, S., Leroux, A., Merlin, J.L. Technol. Cancer Res. Treat. (2004) [Pubmed]
  34. Functional estrogen receptors in a human preosteoclastic cell line. Fiorelli, G., Gori, F., Petilli, M., Tanini, A., Benvenuti, S., Serio, M., Bernabei, P., Brandi, M.L. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  35. Detection of 1,N6-propanodeoxyadenosine in acrolein-modified polydeoxyadenylic acid and DNA by 32P postlabeling. Smith, R.A., Williamson, D.S., Cerny, R.L., Cohen, S.M. Cancer Res. (1990) [Pubmed]
  36. alpha-Hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes. Phillips, D.H., Carmichael, P.L., Hewer, A., Cole, K.J., Poon, G.K. Cancer Res. (1994) [Pubmed]
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