Review on production and medical applications of e{open}-polylysine

Biochemical Engineering Journal

Volumn 65, Issue , 2012, Pages 70-81

  Shukla, Swet Chand ^a   Singh, Amit ^b   Pandey, Anand Kumar ^a   Mishra, Abha ^a  

^a BANARAS HINDU UNIVERSITY   (India)

^b BANARAS HINDU UNIVERSITY   (India)

Author keywords

Conjugate; Drug carrier; E open Polylysine; Homopolyamide; S. albulus Lysinopolymerus; Targeting

Indexed keywords

CONJUGATE; DRUG CARRIER; HOMOPOLYAMIDE; POLYLYSINE; S. ALBULUS LYSINOPOLYMERUS; TARGETING;

AMINO ACIDS; DIAGNOSIS; DRUG DELIVERY; PH;

MEDICAL APPLICATIONS;

DRUG CARRIER; EPSILON POLYLYSINE; INTERFERON; LIPOSOME; NANOPARTICLE; POLYLYSINE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

BIOMEDICINE; BIOSYNTHESIS; DRUG COATING; DRUG DELIVERY SYSTEM; HYDROGEL; MOLECULAR GENETICS; MOLECULAR MECHANICS; NONHUMAN; PRIORITY JOURNAL; REVIEW; SCREENING; SYNTHESIS;

EID: 84860919545     PISSN: 1369703X     EISSN: 1873295X     Source Type: Journal    
DOI: 10.1016/j.bej.2012.04.001     Document Type: Review

References (159)

1. Oppermann-Sano F.B., Stenbuchel A. Occurrence, functions and biosynthess of polyamides in microorganisms and biotechnological productions. Naturwissenschaften 2002, 89:11-22.
2. Gad A.E., Slver B.L., Eytan G.D. Polycation-induced fusion of negatively charged vesicles. Biochem. Biophys. Acta 1982, 690:124-132.
3. Sela M., Katchalski E. Biological properties of poly-α-amino acids. Adv. Protein Chem. 1959, 14:392-479.
4. Hiraki J. e{open}-polylysine, its development and utilization. Fine Chem. 2000, 29:18-25.
5. Shima S., Sakai H. Polylysine produced by Streptomyces. Agric. Biol. Chem. 1977, 41:1807-1809.
6. Shima S., Sakai H. Poly-l-lysine produced by Streptomyces, Part II. Taxonomy and fermentation studies. Agric. Biol. Chem. 1981, 45:2497-2502.
7. Shima S., Sakai H. Poly-l-lysine produced by Streptomyces. Part III. Chemical studies. Agric. Biol. Chem. 1981, 45:2503-2508.
8. Hiraki J., Masakazu H., Hiroshi M., Yoshikazu I. Improved poly-l-lysine production of an S-(2-aminoethyl)-l-cystine resistant mutant of Streptomyces albulus. Seibutsukogaku 1998, 76:487-493.
9. Shima S., Matsuoka H., Iwamoto T., Sakai H. Antimicrobial action of e{open}-poly-l-lysine. J. Antibiot. 1984, 37:1449-1455.
10. Hiraki J., Ichikawa T., Ninomiya S.I., Seki H., Uohama K., Seki H., Kimura S., Yanagimoto Y., Barnett J.W. Use of ADME studies to confirm the safety of e{open}-polylysine as a preservative in food. Regul. Toxicol. Pharm. 2003, 37:328-340.
11. Shih I.L., Shen M.H., Van Y.T. Microbial synthesis of poly(e-lysine) and its various applications. Bioresource Technol. 2006, 97:1148-1159.
12. Ho Y.T., Ishizaki S., Tanaka M. Improving emulsifying activity of e{open}-polylysine by conjugation with dextran through the Maillard reaction. Food Chem. 2000, 68:449-455.
13. Kito Y., Hiramot S., Murao M., Horio Y., Miyazaki T., Kodama T., Hakabou Y. e{open}-Polylysine inhibits pancreatic lipase activity and suppresses postprandial hypertriacylglyceridemia in rats. J. Nutr. 2003, 133:1887-1891.
14. Kunioka M. Hydrolytic degradation and biodegradation of hydrogel prepared from microbial poly(e{open}-Lysine). Seni Gakkaishi 1995, 51:137-142.
15. Shih I.L., Van Y.T., Shen M.H. Biomedical applications of chemically and microbiologically synthesized poly(glutamic acid) and poly(lysine). Mini-Rev. Med. Chem. 2004, 4:179-188.
16. Nishikawa M., Ogawa K. Distribution of microbes producing antimicrobial e{open}-poly-l-lysine polymers in soil microflora determined by a novel method. Appl. Environ. Microbiol. 2002, 68:3575-3581.
17. Hirohara H., Takehara M., Saimura M., Masayuki A., Miyamoto M. Biosynthesis of poly(e{open}-l-lysine)s in two newly isolated strains of Streptomyces sp. Appl. Microbiol. Biotechnol. 2006, 73:321-331.
18. Kawai T., Kubota T., Hiraki J., Izumi Y. Biosynthesis of e{open}-poly-l-lysine in a cell-free system of Streptomyces albulus. Biochem. Biophys. Res. Commun. 2003, 311:635-640.
19. Dohren H.V., Keller U., Vater J., Zoher R. Multifunctional peptide synthetases. Chem. Rev. 1997, 97:2675-2705.
20. Lipmann F. Attempts to map a process evolution of peptide biosynthesis. Synthesis of peptide antibiotics from thiol-linked amino acids parallels fatty acid synthesis. Science 1971, 173:875-884.
21. Meister A. Glutathione synthesis. The Enzymes 1974, vol. 10:671-697. Academic Press, New York. third ed.
22. Finking R., Marahiel M.A. Biosynthesis of nonribosomal peptides. Annu. Rev. Microbiol. 2004, 58:453-488.
23. Walsh C.T. Polyketide and nonribosomal peptide antibiotics: modularity and versatility. Science 2004, 303:1805-1810.
24. Saimura M., Takehara M., Mizukami S., Kataoka K., Hirohara H. Biosynthesis of nearly monodispersed poly(epsilon-l-lysine) in Streptomyces species. Biotechnol. Lett. 2008, 30:377-385.
25. Yamanaka K., Maruyama C., Takagi H., Hamano Y. e{open}-Poly-l-lysine dispersity is controlled by a highly unusual nonribosomal peptide synthetases. Nat. Chem. Biol. 2008, 4(12):7667-7672.
26. Yamanaka K., Kito N., Imokawa Y., Maruyama C., Utagawa T., Hamano Y. Mechanism of e{open}-Poly-l-lysine production and accumulation revealed by identification and analysis of an e{open}-poly-l-lysine-degrading enzyme. Appl. Environ. Microbiol. 2010, 76:5669-5675.
27. Hamano Y., Nicchu I., Hoshino Y., Kawai T., Nakamori S., Takagi H. Development of gene delivery systems for the e{open}-poly-l-lysine producer, Streptomyces albulus. J. Biosci. Bioeng. 2005, 99:636-641.
28. Hamano Y. Biochemistry and enzymology of poly-epsilon-l-lysine biosynthesis. Amino-Acid Homopolymers Occurring in Nature 2010, Springer-Verlag, Berlin, Heidelberg.
29. Nishikawa M., Ogawa K. Inhibition of epsilon-poly-l-lysine biosynthesis in Streptomycetaceae bacteria by short-chain polyols. Appl. Environ. Microbiol. 2006, 72:2306-2312.
30. Nishikawa M. Molecular mass control using polyanionic cyclodextrin derivatives for the epsilon-poly-l-lysine biosynthesis by Streptomyces. Enzyme Microb. Technol. 2009, 45:295-298.
31. Takehara M., Hidohara H. Occurrence and production of poly-epsilon-l-lysine in microorganisms. Amino-Acid Homopolymers Occurring in Nature, Microbiology Monographs 15 2010, Springer-Verlag, Berlin, Heidelberg. Y. Hamano (Ed.).
32. Hamano Y., Yoshida T., Kito M., Nakamori S., Nagasawa T., Takagi Biological function of the pld gene product that degrades e{open}-poly-l-lysine in Streptomyces albulus. Appl. Microbiol. Biotechnol. 2006, 72:173-181.
33. Kito M., Takimoto R., Yoshida T., Nagasawa T. Purification and characterization of an e{open}-poly-l-lysine-degrading enzyme from an e{open}-poly-l-lysine-producing strain of Streptomyces albulus. Arch. Microbiol. 2002, 178:325-330.
34. Kito M., Onji Y., Yoshida T., Nagasawa T. Occurrence of e{open}-poly-l-lysine-degrading enzyme in e{open}-poly-l-lysine-tolerant Sphingobacterium multivorum OJ10: purification and characterization. FEMS Microbiol. Lett. 2002, 207:147-151.
35. Kito M., Takimoto R., Onji Y., Yoshda T., Nagasawa T. Purification and characterization of an e{open}-poly-l-lysine-degrading enzyme from the e{open}-poly-l-lysine-tolerant Chryseobacterium sp. OJ7. J. Biosci. Bioeng. Biochem. 2003, 96:92-94.
36. Ho C.H., Odermatt E., Berndt I., Tiller J.C. Ways of selective polycondensation of l-lysine towards linear α- and e{open}-poly-l-lysine. J. Polym. Sci.: Part A: Polym. Chem. 2008, 46:5053-5063.
37. Eom K.D., Kim J.S., Park S.M., Kim M.S., Yu R., Jung H.M., Kim S.G., Yoo H. A facile synthesis and physical properties of nano-sized dendritic α,e{open}-poly(l-lysine)s for the delivery of nucleic acids. J. Nanosci. Nanotechnol. 2006, 6:3532-3538.
38. Eom K.D., Park S.M., Tran H.D., Kim M.S., Yu R.N., Yoo1 H. Dendritic α,e{open}-poly(l-lysine)s as delivery agents for antisense oligonucleotides. Pharm. Res. 2007, 24:1581-1589.
39. Moccia M., Roviello G.N., Bucci E.M., Pedone C., Saviano M. Synthesis of a l-lysine-based alternate alpha,epsilon-peptide: a novel linear polycation with nucleic acids-binding ability. Int. J. Pharm. 2010, 397:179-183.
40. Guo J., Wei Y., Zhou D., Cai P., Jing X., Chen X.S., Huang Y. Chemosynthesis of poly(e{open}-lysine)-analogous polymers by microwave-assisted click polymerization. Biomacromolecules 2011, 12:737-746.
41. Roviello G.N., Gaetano S.D., Capasso D., Franco S., Crescenzo C., Bucci E.M., Pedone C. RNA-binding and viral reverse transcriptase inhibitory activity of a novel cationic diamino acid-based peptide. J. Med. Chem. 2011, 54:2095-2101.
42. Shima S., Oshima S., Sakai H. Biosynthesis of e{open}-poly-l-lysine by washed mycelium of Streptomyces albulus No-346. Nippon Nogeikagaku Kaishi 1983, 57:221-226.
43. Kahar P., Iwata T., Hiraki J., Park Y.E., Okabe M. Enhancement of e{open}-polylysine production by Streptomyces albulus strain 410 using pH control. J. Biosci. Bioeng. 2001, 91:190-194.
44. Kahar P., Kobayashi K., Iwata T., Hiraki J., Kojima M., Okabe M. Production of e{open}-polylysine in an airlift bioreactor (ABR). J. Biosci. Bioeng. 2002, 93:274-280.
45. Pinheiro I.R., Facciotti M.C.R. Retamycin production by immobilized cells of Streptomyces olindensis ICB20 in repeated-batch cultures. Process Biochem. 2008, 43:661-666.
46. Bankar S.B., Singhal R.S. Improved poly-e{open}-lysine biosynthesis using Streptomyces noursei NRRL 5126 by controlling dissolved oxygen during fermentation. J. Microbiol. Biotechnol. 2011, 21:652-658.
47. Shih I.L., Shen M.H. Application of response surface methodology to optimize production of poly(e{open}-lysine) by Streptomyces albulus IFO 14147. Enzyme Microb. Technol. 2006, 39:15-21.
48. Kobayashi K., Nishikawa M. Promotion of e{open}-poly-l-lysine production by iron in Kitasatospora kifunense. World J. Microbiol. Biotechnol. 2007, 3:1033-1036.
49. Bankar S.B., Singhal R.S. Metabolic precursors enhance the production of poly-e{open}-lysine by Streptomyces noursei NRRL 5126. Eng. Life Sci. 2011, 11:253-258.
50. Zhang Y., Feng X., Xu H., Yao Z., Ouyang P. e{open}-Poly-l-lysine production by immobilized cells of Kitasatospora sp. MY 5-36 in repeated fed-batch cultures. Bioresource Technol. 2010, 101:5523-5527.
51. Itzhaki R.F. Colorimetric method for estimating polylysine and polyarginine. Anal. Biochem. 1972, 50:569-574.
52. Lee H., Oyama K., Hiraki J., Hatakeyama M., Kurokawa Y., Morita H. Microbial production and conformation of poly(e{open}-l-lysine). Chem. Express 1991, 6:683-686.
53. Saimura M., Ikezaki A., Takahara M., Hirohara H. Structures of e{open}-polylysine produced by several actinomycetes and their classification on the basis of productivity of e{open}-polylysine. Annu. Meet. Soc. Biosci. Biotechnol. Biochem. Japan 2002, 54.
54. Jia S., Fan B., Wang G., Peng P., Jia Y. Fractionation and characterization of e{open}-poly-l-lysine from Strepomyces albulus CGMCC 1986. Food Sci. Biotechnol. 2010, 19(2):361-366.
55. Kushwaha D.R.S., Mathur K.E. Poly(e{open}-l-lysine) synthesis and conformation. Biopolymers 1980, 19:219-229.
56. 1H NMR characteristics. Chem. Express 1993, 8:745-748.
57. 13C NMR spectroscopies. J. Mol. Struct. 2003, 655:149-155.
58. 15N NMR. Polym. Bull. 2005, 53:259-267.
59. Rozenberg M., Shoham G. FTIR spectra of solid poly-l-lysine in the stretching NH mode range. Biophys. Chem. 2007, 125:166-171.
60. Shen W.C., Ryser H.J.P. Poly(l-lysine) has different membrane transport and drug carrier properties when complexed with heparin. Proc. Natl. Acad. Sci. U.S.A. 1981, 78:7589-7593.
61. Laemmli U.K. Characterization of DNA condensates induced by poly(ethylene oxide) and polylysine. Proc. Natl. Acad. Sci. U.S.A. 1975, 72:4288-4292.
62. Reich Z., Ittah Y., Weinberger S., Minsky A. Chiral and structural discrimination in binding of polypeptides with condensed nucleic acid structures. J. Biol. Chem. 1990, 265:5590-5594.
63. Shapiro J.T., Leng M., Felsenfeld G. Deoxyribonucleic acid-polylysine complexes. Structure and nucleotide specificity. Biochemistry 1969, 8:3219-3232.
64. Granados E.N., Bello J. Interactions of poly(N, N, N-tri-methyllysine) and polylysine with polynucleotides: circular dichroism and A-T sequence selectivity. Biochemistry 1981, 20:4761-4765.
65. Chang C., Weiskopf M., Li H.J. Conformational studies of nucleoprotein. Circular dichroism of deoxyribonucleic acid base pairs bound by polylysine. Biochemistry 1973, 12:3028-3032.
66. Baeza I., Gariglio P., Rangel L.M., Chavez P., Cenantes L., Arguello C., Wong C., Montanez C. Electron microscopy and biochemical properties of polyamine compacted DNA. Biochemistry 1987, 26:6387-6392.
67. Brinkley M. A brief survey of methods for preparing protein conjugates with dyes, haptens and cross-linking agents. Bioconjug. Chem. 1992, 3:2-13.
68. Baeumert H.G., Fasold H. Cross-linking techniques. Methods Enzymol. 1989, 172:584-609.
69. Hermanson G.T. Bioconjugate Techniques 1996, Academic Press, San Diego, CA.
70. Means G.E., Feeney R.E. Chemical modifications of proteins: history and applications. Bioconjug. Chem. 1990, 1:2-12.
71. Cotten M., Wagner E., Birnstiel M.L. Receptor mediated transport of DNA into eukaryotic cells. Methods Enzymol. 1993, 217:6l8-644l.
72. Trubetskoy V.S., Torchilin V.P., Kennel S.J., Huang L. Use of N-terminal modified poly(l-lysine)-antibody conjugate as a carrier for targeted gene delivery in mouse lung endothelial cells. Bioconjug. Chem. 1992, 3:323-327.
73. McKee T.D., DeRome M.E., Wu G.Y., Findeis M.A. Preparation of asialoorosomucoid-polylysine conjugates. Bioconjug. Chem. 1994, 5:306-331.
74. Gonsho A., Irie K., Susaki H., Iwaasawa H. Tissue-targeting ability of saccharide poly(l-lysine) conjugates. Biol. Pharm. Bull. 2009, 17(2):275-282.
75. AI-Jamala K.T., AI-Jamala W.T., Akermanb S., Podestaa J.E., Yilmazera A., Turtone J.A., Biancod A., Vargessone N., Kanthoub C., Florencea A.T., Tozerb G.M., Kostarelosa K. Systemic antiangiogenic activity of cationic poly-l-lysine dendrimer delays tumor growth. PNAS 2010, 107(9):3966-3971.
76. Sugao Y., Watanabe K., Higuchi Y., Kurihara R., Kawakami S., Hasida M., Katayama Y., Niidome T. NFκB decoy delivery using dendritic poly(l-lysine) for treatment of endotoxin-induced hepatitis in mice. Bioorg. Med. Chem. 2009, 17:4990-4995.
77. Han S., Yoshida D., Kanamoto T., Nakashima H., Uryu T., Yoshida T. Sulfated oligosaccharide cluster with polylysine core scaffold as a new anti-HIV dendrimer. Carbohydr. Polym. 2010, 80:1111-1115.
78. Ryser H.J.P., Shen W.C. Conjugation of methotrexate to poly(l-lysine) increase drug transport and overcome drug resistance in cultured cells. Proc. Natl. Acad. Sci. U.S.A. 1978, 75:3867-3870.
79. Shen W.C., Ryser H.J.P. Poly(l-lysine) and poly(d-lysine) conjugates of methotrexate: different inhibitory effect on drug resistant cells. Mol. Pharmacol. 1979, 16:614-622.
80. Shen W.C., Ryser H.J.P. Conjugation of poly-l-lysine to albumin and horseradish peroxidase: a novel method of enhancing the cellular uptake of proteins. Proc. Natl Acad. Sci. U.S.A. 1978, 75:1872-1876.
81. Brillanti S., Garson J., Foli M., Whitby K., Deaville R., Masci C., Miglioli M., Barbara L. A pilot study of combination therapy with ribavirin plus interferon alfa for interferon alfa-resistant chronic hepatitis C. Gastroenterology 1994, 107:812-817.
82. Stefano Di.G., Colonna P.F., Bongini A., Busi C., Mattioli A., Fiume L. Ribavirin conjugated with lactosaminated poly-l-lysine. Biochem. Pharmacol. 1997, 54:357-363.
83. Gac-breton S., Coudane J., Boustta M., Vert M.J. Norfloxacin-poly(l-lysine citramide imide) conjugates and structure-dependence of the drug release. Drug Target. 2004, 12(5):297-307.
84. Couffin-Hoarau A.C., Aubertin A.M., Boustta M., Schmidt S., Fehrentz J.A., Martinez J., Vert M. Peptide-poly(l-lysine citramide) conjugates and their in vitro anti-HIV behavior. Biomacromolecules 2009, 10(4):865-876.
85. Tian Z., Zhang A.Y., Ye L., Wang M., Feng Z.G. Preparation and evaluation of a linoleic-acid-modified amphiphilic polypeptide copolymer as a carrier for controlled drug release. Biomed. Mater. 2008, 3. 044116 (7pp).
86. Toncheva Y., Wolfert M.A., Dash P.R., Oupicky D., Ulbrich K., Seymour L.W., Schacht E.H. Novel vectors for gene delivery formed by self-assembly of DNA with poly-l-lysine/grafted with hydrophilic polymers. Biochim. Biophys. Acta 1998, 1380:354-368.
87. Choi J.S., Lee E.J., Choi Y.H., Jeong Y.J., Park J.S. Poly(ethylene glycol)-block-poly(l-lysine) dendrimer: novel linear polymer/dendrimer block copolymer forming a spherical water-soluble polyionic complex with DNA. Bioconjug. Chem. 1999, 10:62-65.
88. Asayama S., Nogawa M., Takei Y., Akaike T., Maruyama A. Synthesis of novel polyampholyte comb-type copolymers consisting of a poly(l-lysine) backbone and hyaluronic acid side chains for a DNA carrier. Bioconjug. Chem. 1998, 9:476-481.
89. Zhou X.H., Klibanov A.L., Huang L. Lipophilic polylysines mediate efficient DNA transfection in mammalian cells. Biochim. Biophys. Acta 1991, 1065:8-14.
90. Wang W., Tetle L., Uchegbu I.F. A new class of amphiphilic poly-l-lysine based polymers forms nanoparticles on probe sonication in aqueous media. Langmuir 2000, 16:7859-7866.
91. Locher C.P., Putnam D., Langer R., Witt S.A., Ashlock B.M., Levy J.A. Enhancement of a human immunodeficiency virus env DNA vaccine using a novel polycationic nanoparticle formulation. Immunol. Lett. 2003, 90(2-3):67-70.
92. Zheng L., Shiguo Z., Kai G., Qiuhong Z., Zhaoyang Z., Yanhong Z., Huaying L., Xiong W., Xiaoling L., Guiyuan L. Poly-l-lysine modified silica nanoparticles: a potential oral gene delivery system. J. Nanosci. Nanotechnol. 2005, 5(8):1199-1203.
93. Minigo G., Scholzen A., Tang C.K., Hanley J.C., Kalkanidis M., Pietersz G.A., Apostolopoulos V., Plebanski M. Poly-l-lysine-coated nanoparticles: a potent delivery system to enhance DNA vaccine efficacy. Vaccine 2007, 25:1316-1327.
94. Kar M., Vijayakumar P.S., Prasad B.L.V., Gupta S.S Synthesis and characterization of poly-l-lysine-grafted silica nanoparticles synthesized via NCA polymerization and click chemistry. Langmuir 2010, 26(8):5772-5781.
95. Babic M., Horák D., Trchova M., Jendelova P., Glogarova K., Lesny P., Herynek V., Hajek M., Sykova E. Poly(l-lysine)-modified iron oxide nanoparticles for stem cell labeling. Bioconjug. Chem. 2008, 19:740-750.
96. Y. Zhang, Method of preparing of Nanoparticles of Alginate-Galactosyl-Polysine, US Patent, US2008/0170988 A1.
97. Groman E.V., Yang M., Reinhardt C.P., Weinberg J.S., Vaccaro D.E. Polycationic nanoparticles: synthesis of a polylysine-MION conjugate and its application in labeling fibroblasts. J. Cardiovasc. Trans. Res. 2009, 2:30-38.
98. Zhou J., Qi X. Multi-walled carbon nanotubes/epilson-polylysine nanocomposite with enhanced antibacterial activity. Lett. Microbiol. 2010, 52:76-83.
99. Yu H., Li J., Shi K., Huang Q. Structure of modified 3-polylysine micelles and their application in improving cellular antioxidant activity of curcuminoids. Food Funct. 2011, 2:373-380.
100. Dorudi S., Northover J.M., Vile R.G. Gene transfer therapy in cancer. Br. J. Surg. 1993, 80:566-572.
101. Chiou H.C., Tangco M.V., Levine S.M., Robertson D., Kormis K., Wu C.H., Wu G.Y. Enhanced resistance to nuclease degradation of nucleic acids complexed to asialo glycoprotein polylysine carriers. Nucleic Acids Res. 1994, 22:5439-5446.
102. Crooke R.M. Cellular uptake, distribution and metabolism of phosphorothioate, phosphodiester, and methylphosphonate oligonucleotides. Antisense Research and Applications 1993, 427-449. CRC Press, Florida. S.T. Crooke, B. Lebleu (Eds.).
103. Cook P.D. Antisense medicinal chemistry. Antisense Research and Application: Handbook of Experimental Pharmacology 1998, 51-101. Springer-Verlag, Berlin. S.T. Crooke (Ed.).
104. Perales J.C., Ferkol T., Molas M., Hanson R.W. An evaluation of receptor mediated gene transfer using synthetic DNA-ligand complexes. Eur. J. Biochem. 1994, 226:255-266.
105. Junginger H.E. Mucoadhesive hydrogels. Pharm. Ind. 1991, 53:1056-1065.
106. Thu B., Bruheim P., Espevik T., Smidsrod O., Soon-Shiong P., Skjak-Braek G. Alginate polycation microcapsules: I. Interaction between alginate and polycation. Biomaterials 1996, 17:1031-1040.
107. Gombotz W.R., Wee S.F. Protein release from alginate matrices. Adv. Drug Deliv. Rev. 1998, 31:267-285.
108. Kabanov A.V. Taking polycation gene delivery systems from in vitro to in vivo. PSTT 1999, 2:365-372.
109. De Smedt S.C., Demeester J., Hennink W.E. Cationic polymer based gene delivery systems. Pharm. Res. 2000, 17:113-126.
110. Choi Y.H., Liu F., Park J.S., Kim S.W. Lactose-poly(ethylene glycol)-grafted poly-l-lysine as hepatoma cell-targeted gene carrier. Bioconjug. Chem. 1998, 9:708-718.
111. Klink D.T., Yu Q.C., Glick M.C., Scanlin T.F. Lactosylated poly-l-lysine targets a potential lactose receptor in cystic fibrosis and non-cystic fibrosis airway epithelial cells. Mol. Ther. 2003, 7:73-80.
112. Di Stefano G., Busi C., Mattioli A., Derenzini M., Trere D., Fiume L. Inhibition of [3H]thymidine incorporation into DNA of rat regenerating liver by 2',2'-difluorodeoxycytidine coupled to lactosaminated poly-l-lysine. Biochem. Pharmacol. 1999, 57:793-799.
113. Liu Y., Li J., Shao K., Huang R., Ye L., Lou J., Jiang C. A leptin derived 30-amino-acid peptide modified pegylated poly-l-lysine dendrigraft for brain targeted gene delivery. Biomaterials 2010, 31:5246-5257.
114. Midoux P., Mendes C., Legrand A., Raimond J., Mayer R., Monsigny M., Roche A.C. Specific gene transfer mediated by lactosylated poly-l-lysine into hepatoma cells. Nucleic Acids Res. 1993, 21:871-878.
115. Reinis M., Damkova M., Korec E. Receptor mediated transport of oligodeoxynucleotides into hepatic cells. J. Virol. Methods 1993, 42:99-105.
116. Kwoh D.Y., Coffin C.C., Lollo C.P., Jovenal J., Banaszczyk M.G., Mullen P., Phillips A., Amini A., Fabrycki J., Bartholomew R.M., Brostoff S.W., Carlo D.J. Stabilization of poly-l-lysine/DNA polyplexes for in vivo gene delivery to the liver. Biochim. Biophys. Acta 1999, 1444:171-190.
117. Choi Y.H., Liu F., Choi J.S., Kim S.W., Park J.S. Characterization of a targeted gene carrier lactose-polyethylene glycol-grafted poly-l-lysine and its complex with plasmid DNA. Hum. Gene Ther. 1999, 10(16):2657-2665.
118. Ferreiro M.G., Tillman L.G., Hardee G., Bodmeier R. Alginate/poly-l-lysine microparticles for the intestinal delivery of antisense oligonucleotides. Pharm. Res. 2002, 19(6):755-764.
119. Davis P.B., Kowalczyk T.H. Preparation and Analysis of PEGylated Poly-l-lysine DNA Nanoparticles for Gene Delivery 2007, CSHL Press: Cold Spring Harbor, New York, USA.
120. Ma D.D., Wei A.Q. Enhanced delivery of synthetic oligonucleotides to human leukaemic cells by liposomes and immunoliposomes. Leuk. Res. 1996, 20:925-930.
121. Oliveira M.C., Fattal E., Ropert C., Malvy C., Couvreur P. Delivery of antisense oligonucleotides by means of pH-sensitive liposomes. J. Control. Release 1997, 48:179-184.
122. Waelti E.R., Gluck R. Delivery to cancer cells of antisense l-myc oligonucleotides incorporated in fusogenic, cationic-lipid-reconstituted influenza-virus envelopes (cationic virosomes). Int. J. Cancer 1998, 77:728-733.
123. Harashima H., Kiwada H. The pharmacokinetics of liposomes in tumor targeting. Adv. Drug Deliv. Rev. 1999, 40:1-2.
124. Thierry A.R., Rahman A., Dritschilo A. Overcoming multidrug resistance in human tumor cells using free and liposomally encapsulated antisense oligodeoxynucleotides. Biochem. Biophys. Res. Commun. 1993, 190:952-960.
125. Zelphati O., Szoka F.C. Liposomes as a carrier for intracellular delivery of antisense oligonucleotides: a real or magic bullet?. J. Control. Release 1996, 41:99-119.
126. Michel M., Vautier D., Voegel J.C., Schaaf P., Ball V. Layer-by-layer self assembled polyelectrolyte multilayers with embedded phospholipid vesicles. Langmuir 2004, 20:4835-4839.
127. Michel M., Izquierdo A., Decher G., Voegel J.C., Schaaf P., Ball V. Layer-by-layer self-assembled polyelectrolyte multilayers with embedded phospholipid vesicles obtained by spraying: integrity of the vesicles. Langmuir 2005, 21:7854-7859.
128. Wang S., Cheng L., Yu F., Pan W., Zhang J. Delivery of different length poly(l-lysine)-conjugated ODN to HepG2 cells using N-stearylactobionamide-modified liposomes and their enhanced cellular biological effects. Int. J. Pharm. 2006, 311:82-88.
129. Noguchi S., Hirasshima N., Nakanishi M. Asialoganglioside enhances the efficiency of gene transfection mediated by cationic liposomes with a cationic cholesterol derivative. Biol. Pharm. Bull. 2003, 26:1306-1310.
130. Kawakami S., Munakata C., Fumoto S., Yamashita F., Hashida M. Novel galactosylated liposomes for hepatocyte-selective targeting of lipophilic drugs. J. Pharm. Sci. 2001, 90:105-113.
131. Kallinteri P., Papadimitriou E., Antimisiaris S.G. Uptake of liposomes which incorporate a glycopeptide fraction of asialofetuin by HepG2 cells. J. Liposome Res. 2001, 11:175-193.
132. Volodkin D., Mohwald H., Voegel J.C., Ball V. Coating of negatively charged liposomes by polylysine: drug release study. J. Control. Release 2007, 117:111-120.
133. Volodkin D., Ball Y., Schaaf P., Yoegel J.C., Mohwald H. Complexation of phosphocholine liposomes with polylysine. Stabilization by surface coverage versus aggregation. Biochim. Biophys. Acta 2007, 1768:280-290.
134. Fields A.K., Tytell A.A., Lampson G.P., Hilleman M.R. Inducers of interferon and host resistance. Multistranded synthetic polynucleotide complexes. Proc. Natl. Acad. Sci. U.S.A. 1967, 58:1004-1009.
135. Levy H.B., Baer G., Baron S., Buckler C.E., Gibbs C.J., Ladarola M.J., London W.T., Rice J. A modified polyriboinosinic-polyribocytidylic acid complex that induces interferon in primates. J. Infect. Dis. 1975, 132:434-439.
136. Levine A.S., Sivulich M., Wiernik P.H., Levy H.B. Initial clinical trials in cancer patients of polyriboinosinic-polyribocytidylic acid stabilized with poly-l-lysine, in carboxymethylcellulose [poly(lCLC)], a highly effective interferon inducer. Cancer Res. 1979, 39:1645-1650.
137. Ewel C.H., Urba W.J., Kopp W.C., Smith J.W., Steiss R.G., Rodario J.L., Longo D.L., Jones M.J., Alvord W.G., Pinsky C.M. Polyinosinic-polycytidylic acid complexed with poly-l-1ysine and carboxymethylcellulose in combination with interleukin 2 in patients with cancer: clinical and immunological effects. Cancer Res. 1992, 52:3005-3010.
138. Yamamoto M.M., Mori Y., Osada K., Murakami H. Enhancement of production of IgM and Interferon-β in human cell lines by poly-lysine. Biosci. Biotechnol. Biochem. 1995, 59(10):1842-1845.
139. Wakamoto H., Matsuda H., Kawamoto K., Makino S. Epsilon-Polylysine microparticle adjuvant drives cytokine production to Th1 profile. J. Vet. Med. Sci. 2007, 69(7):717-723.
140. Kido Y., Hiramoto S., Murao M., Horio Y., Miyazaki T., Kodama T., Nakabou Y. e{open}-Polylysine inhibits pancreatic lipase activity and suppresses postprandial hypertriacylglyceridemia in rats. J. Nutr. 2003, 133:1887-1891.
141. Tsujita T., Sumiyoshi M., Takaku T., Momsen W.E., Lowe M.E., Brockman H.L. Inhibition of lipases by e{open}-polylysine. J. Lipid Res. 2003, 44:2278-2286.
142. Tsujita T., Takaichi H., Takaku T., Aoyama S., Hiraki J. Antiobesity action of e{open}-polylysine, a potent inhibitor of pancreatic lipase. J. Lipid Res. 2006, 47:1852-1858.
143. Dubroyskii S.A., Afanaseva M.V., Lagutina M.A., Kazanskii K.S. Comprehensive characterization of superabsorbent polymer hydrogels. Polym. Bull. 1990, 24:107-110.
144. Park T.G., Hoffman A.S. Synthesis and characterization of pH-and/or temperature sensitive hydrogels. J. Appl. Polym. Sci. 1992, 46:659-664.
145. Kunioka M., Choi H.J. Properties of biodegradable hydrogels prepared by γ irradiation of microbial poly(e{open}-lysine) aqueous solutions. J. Appl. Polym. Sci. 1995, 58:801-806.
146. Choi H.L., Yang R., Kunioka M. Synthesis and characterization of pH-sensitive and biodegradable hydrogels prepared by γ-irradiation using microbial poly(e{open}-glutamic acid) and poly(e{open}-lysine). J. Appl. Polym. Sci. 1995, 58:807-814.
147. Kuraray Co. Water swelling polymer gel and its production method. JP patent (2001) 278984.
148. Hynes S.R., Rauc M.F., Bertram J.P., Lavik E.B. A library of tunable poly(ethylene glycol)/poly(l-lysine) hydrogels to investigate the materials cues that influence neural cell differentiation. J. Biomed. Mater. Res. 2008, 89A:499-509.
149. Wei Y.T., Sun X.D., Xia X., Cui F.Z., He Y., Liu B.F., Xu Q.Y. Hyaluronic acid hydrogel modified with Nogo-66 receptor antibody and poly(l-lysine) enhancement of adherence and survival of primary hippocampal neurons. J. Bioact. Compat. Pol. 2009, 24(3):205-219.
150. Azze R.O., Olivares M.N., Rodriguez J.C.M. Use of poly-l-lysine precoating in an ELISA for the detection of antibodies against serogroup C Neisseria meningitidis capsular polysaccharide. Biotecnologia Aplicada 1999, 16:173-175.
151. Ahn J., Choi J., Joo C.H., Seo I., Kim D.H., Yoon S.Y., Kim Y.K., Lee H. Susceptibility of mouse primary cortical neuronal cells to coxsackievirus B. J. Gen. Biol. 2004, 85:1555-1564.
152. Hirayama C., Sakata M., Nakamura M., Ihara H., Kunitake M., Todokoro M. Preparation of poly(e{open}-lysine) adsorbents and application to selective removal of lipopolysaccharides. Chromatogr. B 1999, 721:187-195.
153. Okada N., Miyamoto H., Yoshioka T., Sakamoto K., Katsume A., Saito H., Nakagawa S., Ohsugi Y., Mayumi T. Immunological studies of SK2 hybridoma cells micro-encapsulated with alginate-poly(l)lysine-alginate (APA) membrane following allogenic transplantation. Biochem. Biophys. Res. Commun. 1997, 230:524-527.
154. Machuluf M., Orsola A., Atala A. Controlled release of therapeutic agents: slow delivery and cell encapsulation. World J. Urol. 2000, 18:80-83.
155. Suye S.I., Kumon Y., Ishigaki A. Immobilization of glucose oxidase on poly(l-lysine)-modified polycarbonate membrane. Biotechonol. Appl. Biochem. 1998, 27:245-248.
156. Yamaguchi H., Miyazaki M., Asanomi Y., Maeda H. Poly-lysine supported cross-linked enzyme aggregates with efficient enzymatic activity and high operational stability. Catal. Sci. Technol. 2011, 1:1256-1261.
157. Limei H., Zheng W., Jiancheng Q., Shuang W., Lili H., Jinhui W., Jingquan Y. Preparation of immobilized e{open}-polylysine PET nonwoven fabrics and antibacterial activity evaluation. J. Wuhan Univ. Technol.-Mater. Sci. Ed. Aug. 2011, 675-680.
158. Choi H.S., Yui N. Design of rapidly assembling supramolecular systems responsive to synchronized stimuli. Prog. Polym. Sci. 2006, 31:121-144.
159. Zivanovia M., Aleksic M., Ostatna V., Doneux T., Palecek E. Polylysine-catalyzed hydrogen evolution at mercury electrodes. Electroanalysis 2010, 22:2064-2070.