Nanostructure formation in aqueous solution of amphiphilic copolymers of 2-(N,N-dimethylaminoethyl)methacrylate and alkylacrylate: Characterization, antimicrobial activity, DNA binding, and cytotoxicity studies

International Journal of Pharmaceutics

Volumn 414, Issue 1-2, 2011, Pages 298-311

  Dutta, Pranabesh ^a   Dey, Joykrishna ^a   Shome, Anshupriya ^b   Das, Prasanta Kumar ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Antimicrobial activity; Biocompatibility; DNA binding; Hydrophobically modified polymer; Transmission electron microscopy

Indexed keywords

2 (DIMETHYLAMINOETHYL)METHACRYLATE DODECYLACRYLATE COPOLYMER; 2 (DIMETHYLAMINOETHYL)METHACRYLATE HEXYLACRYLATE COPOLYMER; 2 (DIMETHYLAMINOETHYL)METHACRYLATE OCTYLACRYLATE COPOLYMER; ACRYLIC ACID DERIVATIVE; COPOLYMER; METHACRYLIC ACID DERIVATIVE; NANOMATERIAL; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTIMICROBIAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; BACILLUS SUBTILIS; BIOCOMPATIBILITY; CALF (BOVINE); CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; ESCHERICHIA COLI; FLUORESCENCE; GRAM NEGATIVE BACTERIUM; HYDRODYNAMICS; HYDROPHOBICITY; LIGHT SCATTERING; MEASUREMENT; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR INTERACTION; NANOTECHNOLOGY; NONHUMAN; PRIORITY JOURNAL; STATIC ELECTRICITY; SURFACE TENSION; THYMUS; TRANSMISSION ELECTRON MICROSCOPY; VISCOSITY;

3T3 CELLS; ACRYLATES; ANIMALS; ANTI-INFECTIVE AGENTS; CELL SURVIVAL; CYTOTOXINS; DNA; DRUG CARRIERS; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; INDICATORS AND REAGENTS; MALE; METHACRYLATES; MICE; MICE, INBRED BALB C; MICROBIAL SENSITIVITY TESTS; NANOSTRUCTURES; POLYMERS; SURFACE PROPERTIES; VISCOSITY; WATER;

EID: 79959685842     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.05.006     Document Type: Article

References (53)

1. A. Asokan, and M.J. Cho Exploitation of intracellular pH gradients in the cellular delivery of macromolecules J. Pharm. Sci. 91 2002 903 913 (Pubitemid 34640914)
2. S. Bhattacharya, and A. Bajaj Advances in gene delivery through molecular design of cationic lipids Chem. Commun. 2009 4632 4656
3. G. Domagk A new class of disinfectants Dtsch. Med. Wochenschr. 61 1935 829 832
4. P. Dutta, J. Dey, G. Ghosh, and R.R. Nayak Self-association and microenvironment of random amphiphilic copolymers of sodium N-acryloyl-l- valinate and N-dodecylacrylamide in aqueous solution Polymer 50 2009 1516 1525
5. T.J. Franklin, and G.A. Snow Biochemistry of Antimicrobial Action 1981 London Chapman and Hall
6. T.K. Georgiou, M. Vamvakaki, L.A. Phylactou, and C.S. Patrickios Synthesis, characterization, and evaluation as transfection reagents of double-hydrophilic star copolymers: effect of star architecture Biomacromolecules 6 2005 2990 2997 (Pubitemid 41764053)
7. B. Goodson, A. Ehrhardt, S. Ng, J. Nuss, K. Johnson, M. Giedlin, R. Yamamoto, W.H. Moos, A. Krebber, M. Ladner, M.B. Giacona, C. Vitt, and J. Winter Characterization of novel antimicrobial peptoids Antimicrob. Agents Chemother. 43 1999 1429 1434 (Pubitemid 29259338)
8. Z. Gu, Y. Yuan, J. He, M. Zhang, and P. Ni Facile approach for DNA encapsulation in functional polyion complex for triggered intracellular gene delivery: design, synthesis, and mechanism Langmuir 25 2009 5199 5208
9. N.G. Hoogeveen, M.A. Cohen Stuart, and G. Fleer Can charged (block co)polymers act as stabilisers and flocculants of oxides? Colloids Surf. A: Physicochem. Eng. Aspects 117 1996 77 88 (Pubitemid 26293487)
10. J. Huang, R.R. Koepsel, H. Murata, W. Wu, S.B. Lee, T. Kowalewski, A.J. Russell, and K. Matyjaszewski Nonleaching antibacterial glass surfaces via "Grafting Onto": the effect of the number of quaternary ammonium groups on biocidal activity Langmuir 24 2008 6785 16785
11. J. Huang, H. Murata, R.R. Koepsel, A.J. Russell, and K. Matyjaszewski Antibacterial polypropylene via surface-initiated atom transfer radical polymerization Biomacromolecules 8 2007 1396 1399 (Pubitemid 46865108)
12. M. Ignatova, S. Voccia, B. Gilbert, N. Markova, P.S. Mercuri, M. Galleni, V. Sciannamea, S. Lenoir, D. Cossement, R. Gouttebaron, R. Jerome, and C. Jerome Synthesis of copolymer brushes endowed with adhesion to stainless steel surfaces and antibacterial properties by controlled nitroxide-mediated radical polymerization Langmuir 20 2004 10718 10726
13. T. Ikeda, H. Hirayama, K. Suzuki, H. Yamaguchi, and S. Tazuke Biologically active polycations, 6. Polymeric pyridinium salts with well-defined main chain structure Die Makromolekulare Chemie 187 1986 333 340
14. T. Ikeda, H. Yamaguchi, and S. Tazuke New polymeric biocides: synthesis and antibacterial activities of polycations with pendant biguanide groups Antimicrob. Agents Chemother. 26 1984 139 144 (Pubitemid 14050214)
15. K. Kalyanasundaram Photochemistry in Microheterogeneous Systems 1987 Academic Press New York p. 40
16. A. Kanazawa, T. Ikeda, and T. Endo Polymeric phosphonium salts as a novel class of cationic biocides. II. Effects of counter anion and molecular weight on antibacterial activity of polymeric phosphonium salts J. Polym. Sci.; Part A: Polym. Chem. 31 1993 1441 1447 (Pubitemid 23637958)
17. Y. Katanasaka, T. Ida, T. Asai, K. Shimizu, F. Koizumi, N. Maeda, K. Baba, and N. Oku Antiangiogenic cancer therapy using tumor vasculature-targeted liposomes encapsulating 3-(3,5-dimethyl-1H-pyrrol-2-ylmethylene)-1,3-dihydro- indol-2-one, SU5416 Cancer Lett. 270 2008 260 268
18. N. Kawabata Capture of micro-organisms and viruses by pyridinium-type polymers and application to biotechnology and water purification Prog. Polym. Sci. 17 1992 1 34 (Pubitemid 23602707)
19. S. Keely, S.M. Ryan, D.M. Haddleton, A. Limer, G. Mantovani, E.P. Murphy, S.P. Colgan, and D.J. Brayden Dexamethasone-pDMAEMA polymeric conjugates reduce inflammatory biomarkers in human intestinal epithelial monolayers J. Controlled Release 135 2009 35 43
20. E.R. Kenawy, S.D. Worley, and R. Broughton The chemistry and applications of antimicrobial polymers: a state-of-the-art review Biomacromolecules 8 2007 1359 1384 (Pubitemid 46865105)
21. T.H. Kim, H.L. Jiang, D. Jere, I.K. Park, M.H. Cho, J.W. Nah, Y.J. Choi, T. Akaike, and C.S. Cho Chemical modification of chitosan as a gene carrier in vitro and in vivo Prog. Polym. Sci. 32 2007 726 753 (Pubitemid 46977435)
22. M. Kurisawa, M. Yokoyama, and T. Okano Transfection efficiency increases by incorporating hydrophobic monomer units into polymeric gene carriers J. Controlled Release 68 2000 1 8 (Pubitemid 30407057)
23. J.R. Lakowicz Principles of Fluorescence Spectroscopy 3rd ed. 2006 Plenum Press New York
24. U. Lakowicz, M. Breunig, T. Blunk, and A. Göpferich Polyethylenimine-based non-viral gene delivery systems Eur. J. Pharm. Biopharm. 60 2005 247 266 (Pubitemid 40804565)
25. S.B. Lee, R.R. Koepsel, S.W. Morley, K. Matyjaszewski, Y. Sun, and A.J. Russell Permanent, nonleaching antibacterial surfaces. 1. Synthesis by atom transfer radical polymerization Biomacromolecules 5 2004 877 882 (Pubitemid 38702260)
26. S.B. Lee, A.J. Russell, and K. Matyjaszewski ATRP synthesis of amphiphilic random, gradient, and block copolymers of 2-(dimethylamino)ethyl methacrylate and n-butyl methacrylate in aqueous media Biomacromolecules 4 2003 1386 1393 (Pubitemid 37184656)
27. S. Lenoir, C. Pagnoulle, C. Detrembleur, M. Galleni, and R. Jerome Antimicrobial activity of polystyrene particles coated by photo-crosslinked block copolymers containing a biocidal polymethacrylate e-Polymers 074 2005 1 11
28. S Lenoir, C. Pagnoulle, C. Detrembleur, M. Galleni, and R. Jerome New antibacterial cationic surfactants prepared by atom transfer radical polymerization J. Polym. Sci.; Part A: Polym. Chem. 44 2006 1214 1224 (Pubitemid 43288552)
29. H. Lv, S. Zhang, B. Wang, S. Cui, and J. Yan Toxicity of cationic lipids and cationic polymers in gene delivery J. Controlled Release 114 2006 100 109 (Pubitemid 44128621)
30. P.B. Malafaya, G.A. Silva, and R.L. Reis Natural-origin polymers as carriers and scaffolds for biomolecules and cell delivery in tissue engineering applications Adv. Drug. Deliv. Rev. 59 2007 207 233 (Pubitemid 46879967)
31. Y. Merle Synthetic polyampholytes. 5. Influence of nearest-neighbor interactions on potentiometric curves J. Phys. Chem. 91 1987 3092 3098
32. Y. Morishima, T. Kobayashi, and S. Nozakura Amphiphilic polyelectrolytes with various hydrophobic groups: intramolecular hydrophobic aggregation in aqueous solution Polym. J. (Tokyo) 21 1989 267 274
33. R.N. Mitra, A. Shome, P. Paul, and P.K. Das Antimicrobial activity, biocompatibility and hydrogelation ability of dipeptide-based amphiphiles Org. Biomol. Chem. 7 2009 94 102
34. A. Mohanty, and J. Dey Effect of the headgroup structure on the aggregation behavior and stability of self-assemblies of sodium N-[4-(n-dodecyloxy)benzoyl]-l-aminoacidates in water Langmuir 23 2007 1033 1040
35. M. Niwa, M. Morikawa, K. Yagi, and N. Higashi Interaction between polylysine monolayer and DNA at the air-water interface Int. J. Biol. Macromol. 30 2002 47 54 (Pubitemid 34226566)
36. T. Nonaka, L. Hua, T. Ogata, and S. Kurihara Synthesis of water-soluble thermosensitive polymers having phosphonium groups from methacryloyloxyethyl trialkyl phosphonium chlorides-N-isopropylacrylamide copolymers and their functions J. Appl. Polym. Sci. 87 2003 386 393
37. E.F. Palermo, and K. Kuroda Chemical structure of cationic groups in amphiphilic polymethacrylates modulates the antimicrobial and hemolytic activities Biomacromolecules 10 2009 1416 1428
38. E.F. Palermo, I. Sovadinova, and K. Kuroda Structural determinants of antimicrobial activity and biocompatibility in membrane-disrupting methacrylamide random copolymers Biomacromolecules 10 2009 3098 3107
39. T.G. Park, J.H. Jeong, and S.H. Kim Current status of polymeric gene delivery systems Adv. Drug. Deliv. Rev. 58 2006 467 486 (Pubitemid 43949425)
40. W.G. Pitt, M.O. Mcbride, J.K. Lunceford, R.J. Roper, and R.D. Sagers Ultrasonic enhancement of antibiotic action on gram-negative bacteria Antimicrob. Agents Chemother. 38 1994 2577 2582 (Pubitemid 24332590)
41. M. Pradny, and S. Sevcik Precursors of hydrophilic polymers, 3. The potentiometric behaviour of isotactic and atactic poly(2-dimethylaminoethyl methacrylate) in water/ethanol solutions Makromol. Chem. 186 1985 111 121
42. L.B. Rawlinson, S.M. Ryan, G. Mantovani, J.A. Syrett, D.M. Haddleton, and D.J. Brayden Antibacterial effects of poly(2-(dimethylamino ethyl)methacrylate) against selected gram-positive and gram-negative bacteria Biomacromolecules 11 2010 443 453
43. D. Roy, J.S. Knapp, J.T. Guthrie, and S. Perrier Antibacterial cellulose fiber via RAFT surface graft polymerization Biomacromolecules 9 2008 91 99 (Pubitemid 351201586)
44. S. Roy, A. Mohanty, and J. Dey Microviscosity of bilayer membranes of some N-acylamino acid surfactants determined by fluorescence probe method Chem. Phys. Lett. 414 2005 23 27 (Pubitemid 41764912)
45. S. Roy, and P.K. Das Antibacterial hydrogels of amino acid-based cationic amphiphiles Biotechnol. Bioeng. 100 2008 756 764 (Pubitemid 351914002)
46. U. Rungsardthong, M. Deshpande, L. Bailey, M. Vamvakaki, S.P. Armes, M.C. Garnett, and S. Stolnik Copolymers of amine methacrylate with poly(ethylene glycol) as vectors for gene therapy J. Controlled Release 73 2001 359 380 (Pubitemid 32539263)
47. J.F. Tan, H.P. Too, T.A. Hatton, and K.C. Tam Aggregation behavior and thermodynamics of binding between poly(ethylene oxide)-block-poly(2- (diethylamino)ethyl methacrylate) and plasmid DNA Langmuir 22 2006 3744 3750 (Pubitemid 43672546)
48. T. Tashiro Antibacterial and bacterium adsorbing macromolecules Macromol. Mater. Eng. 286 2001 63 87
49. P. Van de Wetering, J.Y. Cherng, H. Talsma, and W.E. Hennink Relation between transfection efficiency and cytotoxicity of poly(2-(dimethylamino)ethyl methacrylate)/plasmid complexes J. Controlled Release 49 1997 59 69 (Pubitemid 27417901)
50. P.V.D. Wetering, J.Y. Cherng, H. Talsma, D.J.A. Crommelin, and W.E. Hennink 2-(dimethylamino)ethyl methacrylate based (co)polymers as gene transfer agents J. Controlled Release 53 1998 145 153 (Pubitemid 28219308)
51. P.V.D. Wetering, E.E. Moret, N.M.E. Nieuwenbroek, M.J.V. Steenbergen, and W.E. Hennink Structure-activity relationships of water-soluble cationic methacrylate/methacrylamide polymers for nonviral gene delivery Bioconjug. Chem. 10 1999 589 597 (Pubitemid 29355237)
52. F. Zhang, Q. Wu, Z. Chen, M. Zhang, and X. Lin Hepatic-targeting microcapsules construction by self-assembly of bioactive galactose-branched polyelectrolyte for controlled drug release system J. Colloid Interface Sci. 317 2008 477 484 (Pubitemid 350116099)
53. S. Zhu, N. Yang, and D. Zhang Poly(N,N-dimethylaminoethyl methacrylate) modification of activated carbon for copper ions removal Mater. Chem. Phys. 113 2009 784 789