Poly(1-vinylimidazole) Prospects in Gene Delivery

Elena N. Danilovtseva; Stanislav N. Zelinskiy; Viktor A. Pal'shin; Gayathri Kandasamy; Uma Maheswari Krishnan; Vadim V. Annenkov

doi:10.1007/s10118-019-2240-1

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Poly(1-vinylimidazole) Prospects in Gene Delivery

ARTICLE | Updated：2021-02-18

- Poly(1-vinylimidazole) Prospects in Gene Delivery
- Poly(1-vinylimidazole) Prospects in Gene Delivery
- Chinese Journal of Polymer Science 2019年37卷第7期页码：637-645
- Affiliations：
  
  a.Limnological Institute of the Siberian Branch of the Russian Academy of Sciences, 3, Ulan-Batorskaya St., P.O. Box 278, Irkutsk 664033, Russia
  b.Centre for Nanotechnology & Advanced Biomaterials (CeNTAB), School of Chemical and Biotechnology, SASTRA University, Thanjavur 613401, Tamil Nadu, India
- Author bio：
  
  annenkov@lin.irk.ru
- Funds：
  
  We acknowledge the financial support from a joint grant of the Russian Science Foundation (16-45-02001) and the Department of Science Technology of the Ministry of Science and Technology of the Republic of India (INT/RUS/RSF/10).
- DOI：10.1007/s10118-019-2240-1
  中图分类号：
- 收稿：2018-12-11，
  
  修回：2019-2-11，
  
  录用：2019-2-16，
  
  网络首发：2019-03-26，
  
  纸质出版：2019-07
- Accepted：
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Citation: Danilovtseva, E. N.; Zelinskiy, S. N.; Pal'shin, V. A.; Kandasamy, G.; Krishnan, U. M.; Annenkov, V. V. Poly(1-vinylimidazole) prospects in gene delivery. Chinese J. Polym. Sci. 2019, 37, 637–645

Elena N. Danilovtseva, Stanislav N. Zelinskiy, Viktor A. Pal'shin, et al. Poly(1-vinylimidazole) Prospects in Gene Delivery[J]. Chinese Journal of Polymer Science, 2019, 37(7): 637-645.
Citation: Danilovtseva, E. N.; Zelinskiy, S. N.; Pal'shin, V. A.; Kandasamy, G.; Krishnan, U. M.; Annenkov, V. V. Poly(1-vinylimidazole) prospects in gene delivery. Chinese J. Polym. Sci. 2019, 37, 637–645 DOI： 10.1007/s10118-019-2240-1.

Elena N. Danilovtseva, Stanislav N. Zelinskiy, Viktor A. Pal'shin, et al. Poly(1-vinylimidazole) Prospects in Gene Delivery[J]. Chinese Journal of Polymer Science, 2019, 37(7): 637-645. DOI： 10.1007/s10118-019-2240-1.

摘要

Abstract

Polymeric amines are being studied intensively as components of systems for gene delivery in genetic engineering and gene therapy of genetic disorders

including cancer. Despite remarkable achievements in the field

polymeric amines

such as polyethyleneimine

show some disadvantages. Strong interaction between the amine-containing polymer and nucleic acid hampers the release of nucleic acid in the cell cytoplasm. Amine groups can interact with the cell membrane which results in cell death. These limitations of polymeric amines stimulated an investigation of new structures for gene delivery. Imidazole-containing polymers have attracted attention as lesser basic substances

while they are able to interact with polymeric acids. Further development of imidazole-based gene delivery agents requires knowledge about some fundamental aspects of interaction between nucleic acids

and polymeric imidazoles. In this work

we studied the complexation of poly(1-vinylimidazole) and oligomeric DNA. We found that the number of active sites capable of binding with negatively charged phosphate groups is comparable with the number of protonated imidazole units in the case of high molecular weight polymer. The increase in polymer charge by 1-bromopropane quaternizating 1%−5% imidazole units or by decreasing the pH to 6.5−7 considerably increased the ability of poly(1-vinylimidazole) to interact with oligonucleotides. The pH sensitivity of this interaction is interesting for cancer gene therapy because the tumours have a lowered intercellular pH (stable oligonucleotide complex) and a higher extracellular pH which can lead to complex dissociation. Minimal critical length for complexation of quaternized poly(1-vinylimidazole) and DNA is below eight units which corresponds to polymers with amine groups. Fluorescence-tagged poly(1-vinylimidazole) samples were obtained and their potential for monitoring the polymer and polymer-oligonucleotide complex internalization into living cells was demonstrated.

关键词

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references

Boussif, O.; Lezoualc’h, F.; Zanta, M. A.; Mergny, M. D.; Scherman, D. A.; Demeneix, B.; Behr, J. P . A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo : Polyethylenimine . Proc. Natl. Acad. Sci. , 1995 . 92 7297 - 7301 . DOI: 10.1073/pnas.92.16.7297 http://doi.org/10.1073/pnas.92.16.7297 .

Fischera, D.; Lib, Y.; Ahlemeyerc, B.; Krieglsteinc, J.; Kissel, T . In vitro cytotoxicity testing of polycations: Influence of polymer structure on cell viability and hemolysis . Biomaterials , 2003 . 24 1121 - 1131 . DOI: 10.1016/S0142-9612(02)00445-3 http://doi.org/10.1016/S0142-9612(02)00445-3 .

Miao, H.; Wang, Y. F.; Dong, H. Y.; Chen, D. Y . Complexation induced by weak interaction between DNA and PEO- b -P4VP below the CMC of the polymer . Chinese J. Polym. Sci. , 2017 . 35 ( 1 ): 46 - 53 . DOI: 10.1007/s10118-016-1857-6 http://doi.org/10.1007/s10118-016-1857-6 .

Annenkov, V. V.; Danilovtseva, E. N.; Saraev, V. V.; Mikhaleva, A. I . Complexation of copper(II) ions with imidazole-carboxylic polymeric systems . J. Polym. Sci., Part A: Polym. Chem. , 2003 . 41 2256 - 2263 . DOI: 10.1002/(ISSN)1099-0518 http://doi.org/10.1002/(ISSN)1099-0518 .

Asayama, S.; Sekine, T.; Kawakami, H.; Nagaoka, S . Design of aminated poly(1-vinylimidazole) for a new pH-sensitive polycation to enhance cell-specific gene delivery . Bioconjugate Chem. , 2007 . 18 1662 - 1667 . DOI: 10.1021/bc700205t http://doi.org/10.1021/bc700205t .

Dulea, M.; Biswasa, M.; Biswasa, Y.; Mandal, K.; Jana, N. R.; Mandal, T. K . Cysteine-based amphiphilic peptide-polymer conjugates via thiol-mediated radical polymerization: Synthesis, self-assembly, RNA polyplexation and N -terminus fluorescent labeling for cell imaging . Polymer , 2017 . 112 125 - 135 . DOI: 10.1016/j.polymer.2017.01.083 http://doi.org/10.1016/j.polymer.2017.01.083 .

Ihm, J. E.; Han, K. O.; Han, I. K.; Ahn, K. D.; Han, D. K.; Cho, C. S . High transfection efficiency of poly(4-vinylimidazole) as a new gene carrier . Bioconjugate Chem. , 2003 . 14 707 - 708 . DOI: 10.1021/bc025611q http://doi.org/10.1021/bc025611q .

Ihm, J. E.; Han, K. O.; Hwang, C. S.; Kang, J. H.; Ahn, K. D.; Han, I. K.; Han, D. K.; Hubbell, J. A.; Cho, C. S . Poly(4- vinylimidazole) as nonviral gene carrier: In vitro and in vivo transfection . Acta Biomater. , 2005 . 1 165 - 172 . DOI: 10.1016/j.actbio.2004.12.002 http://doi.org/10.1016/j.actbio.2004.12.002 .

Asayama, S.; Nishinohara, S.; Kawakami, H . Zinc-chelated imidazole groups for DNA polyion complex formation . Metallomics , 2011 . 680 - 682 . .

Asayama, S.; Matsuda, K.; Negishiband, Y.; Kawakami, H . Intracellular co-delivery of zinc ions and plasmid DNA for enhancing gene transfection activity . Metallomics , 2014 . 6 82 - 87 . DOI: 10.1039/C3MT00226H http://doi.org/10.1039/C3MT00226H .

Asayama, S.; Hakamatani, T.; Kawakami, H . Synthesis and characterization of alkylated poly(1-vinylimidazole) to control the stability of its DNA polyion complexes for gene delivery . Bioconjugate Chem. , 2010 . 21 646 - 652 . DOI: 10.1021/bc900411m http://doi.org/10.1021/bc900411m .

Shuai, X.; Merdan, T.; Unger, F.; Kissel, T . Supramolecular gene delivery vectors showing enhanced transgene expression and good biocompatibility . Bioconjugate Chem. , 2005 . 16 322 - 329 . DOI: 10.1021/bc0498471 http://doi.org/10.1021/bc0498471 .

Pouton, C. W.; Lucas, P.; Thomas, B. J.; Uduehi, A. N.; Milroy, D. A.; Moss, S. H . Polycation-DNA complexes for gene delivery: A comparison of the biopharmaceutical properties of cationic polypeptides and cationic lipids . J. Control. Release , 1998 . 53 289 - 299 . DOI: 10.1016/S0168-3659(98)00015-7 http://doi.org/10.1016/S0168-3659(98)00015-7 .

Asayama, S.; Seno, K.; Kawakami, H . Synthesis of carboxymethyl poly(1-vinylimidazole) as a polyampholyte for biocompatibility . Chem. Lett. , 2013 . 42 358 - 360 . DOI: 10.1246/cl.121263 http://doi.org/10.1246/cl.121263 .

Allen, M. H.; Day, K. N.; Hemp, S. T.; Long, T. E . Synthesis of folic acid-containing imidazolium copolymers for potential gene delivery applications . Macromol. Chem. Phys. , 2013 . 214 797 - 805 . DOI: 10.1002/macp.v214.7 http://doi.org/10.1002/macp.v214.7 .

Asayama, S.; Nishinohara, S.; Kawakami, H . Zinc-chelated poly(1-vinylimidazole) and a carbohydrate ligand polycation form DNA ternary complexes for gene delivery . Bioconjugate Chem. , 2011 . 22 1864 - 1868 . DOI: 10.1021/bc2003378 http://doi.org/10.1021/bc2003378 .

Dréan, M.; Debuigne, A.; Jérôme, C.; Goncalves, C.; Midoux, P.; Rieger, J.; Guégan, P . Poly( N -methylvinylamine)-based copolymers for improved gene transfection . Macromol. Biosci. , 2018 . 1700353 .

Pack, D. W.; Putnam, D.; Langer, R . Design of imidazole-containing endosomolytic biopolymers for gene delivery . Biotechnol. Bioeng. , 2000 . 67 ( 2 ): 217 - 23 . DOI: 10.1002/(ISSN)1097-0290 http://doi.org/10.1002/(ISSN)1097-0290 .

Sakurai, M.; Imai, T.; Yamashita, F . Temperature dependence of viscosities and potentiometric titration behavior of poly( n -vinylimidazole) in aqueous salt solutions . Polym. J. , 1994 . 26 658 - 664 . DOI: 10.1295/polymj.26.658 http://doi.org/10.1295/polymj.26.658 .

Annenkov, V. V.; Danilovtseva, E. N.; Likhoshway, Y. V.; Patwardhanand, S. V.; Perry, C. C . Controlled stabilisation of silicic acid below pH 9 using poly(1-vinylimidazole) . J. Mater. Chem. , 2008 . 18 553 - 559 . DOI: 10.1039/B716367N http://doi.org/10.1039/B716367N .

Eskin, V. E.; Magarik, S. Y.; Zhuraev, U. B.; Rudkovskaya, G. D . Light-scattering, viscosity and dynamic birefringence of poly-normal-vinylimidazole solutions . Vysokomol. Soedin., Ser. A , 1978 . 20 2219 - 2223 . .

Du, X. L.; Zhang, H. S.; Deng, Y. H.; Wang, H . Design and synthesis of a novel fluorescent reagent, 6-oxy-(ethylpiperazine)-9-(2-methoxycarbonyl) fluorescein, for carboxylic acids and its application in food samples using high-performance liquid chromatography . J. Chromatogr. A , 2008 . 1178 92 - 100 . .

Zelinskiy, S. N.; Danilovtseva, E. N.; Pal'shin, V. A.; Krishnan, U. M.; Annenkov, V. V . Reagents for labeling with pH-independent fluorescein-based tags . Arkivoc , 2018 . vii .

Mazyar, N. L.; Annenkov, V. V.; Kruglova, V. A.; Ananiev, S. M.; Danilotseva, E. N.; Rokhin, A. V.; Zinchenko, S. V . Acid-base properties of poly(1-vinylazoles) in aqueous solution . Russ. Chem. Bull. , 2000 . 4912 2013 - 2017 . .

Sandeli, E. B.; West, T. S . Recommended nomenclature for titrimetric analysis . Pure Appl. Chem. , 1969 . 18 427 - 436 . .

Henrichs, P. M.; Whitlock, L. R.; Sochor, A. R.; Tan, J. S . Conformational behavior of poly( n -vinylimidazole)-potentiometric titration, viscosity, and proton nuclear magnetic resonance studies . Macromolecules , 1980 . 13 1375 - 1381 . DOI: 10.1021/ma60078a009 http://doi.org/10.1021/ma60078a009 .

Annenkov, V. V.; Danilovtseva, E. N.; Tenhu, H.; Aseyev, V.; Hirvonen, S. P.; Mikhaleva, A. I . Copolymers of 1-vinylimidazole and (meth)acrylic acid: Synthesis and polyelectrolyte properties . Eur. Polym. J. , 2004 . 40 1027 - 1032 . DOI: 10.1016/j.eurpolymj.2003.12.014 http://doi.org/10.1016/j.eurpolymj.2003.12.014 .

Annenkov, V. V.; Krishnan, U. M.; Pal'shin, V. A.; Zelinskiy, S. N.; Kandasamy, G.; Danilovtseva, E. N . Design of the oligonucleotide carriers: Importance of polyamine chain length . Polymers , 2018 . 10 ( 12 ): 1297 DOI: 10.3390/polym10121297 http://doi.org/10.3390/polym10121297 .

Basché, T.; Müllen, K.; Schmidt, M . From single molecules to nanoscopically structured materials . Adv. Polym. Sci. , 2014 . 260 1 - 288 . .

Yoshikawa, K . Controlling the higher-order structure of giant DNA molecules . Adv. Drug Deliv. Rev. , 2001 . 52 235 - 244 . DOI: 10.1016/S0169-409X(01)00210-1 http://doi.org/10.1016/S0169-409X(01)00210-1 .

Tsuchida, E.; Abe, K . Interactions between macromolecules in solution and intermacromolecular complexes . Adv. Polym. Sci. , 1982 . 45 15 - 130 . DOI: 10.1007/BFb0017549 http://doi.org/10.1007/BFb0017549 .

Shirmanova, M. V.; Druzhkova, I. N.; Lukina, M. M.; Matlashov, M. E.; Belousov, V. V.; Snopova, L. B.; Prodanetz, N.; Dudenkova, V. V.; Lukyanov, S. A.; Zagaynova, E. V . Intracellular pH imaging in cancer cells in vitro and tumors in vivo using the new genetically encoded sensor SypHer2 . Biochim. Biophys. Acta , 2015 . 1850 1905 - 1911 . DOI: 10.1016/j.bbagen.2015.05.001 http://doi.org/10.1016/j.bbagen.2015.05.001 .

Heiden, M. G. V.; Cantley, L. C.; Thompson, C. B . Understanding the Warburg effect: The metabolic requirements of cell proliferation . Science , 2009 . 324 ( 5930 ): 1029 - 1033 . DOI: 10.1126/science.1160809 http://doi.org/10.1126/science.1160809 .

Lu, Z. N.; Tian, B.; Guo, X. L . Repositioning of proton pump inhibitors in cancer therapy . Cancer Chemother. Pharmacol. , 2017 . 80 925 - 937 . DOI: 10.1007/s00280-017-3426-2 http://doi.org/10.1007/s00280-017-3426-2 .

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