Surfaces of fluorinated pyridinium block copolymers with enhanced antibacterial activity

Langmuir

Volumn 22, Issue 26, 2006, Pages 11255-11266

  Krishnan, Sitaraman ^a   Ward, Rebekah J ^b   Hexemer, Alexander ^c   Sohn, Karen E ^c   Lee, Kristen L ^b,e   Angert, Esther R ^b   Fischer, Daniel A ^d   Kramer, Edward J ^c   Ober, Christopher K ^a  

^a Cornell University   (United States)

^b Department of Obstetrics Gynecology   (United States)

^c University of California   (United States)

^d NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

^e UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBACTERIAL ACTIVITY; CONTACT ANGLE MEASUREMENTS; FLUORINATED PYRIDINIUM SURFACES; NEAR EDGE X RAY ABSORPTION FINE STRUCTURE SPECTROSCOPY;

ABSORPTION; CONTACT ANGLE; MOLECULAR WEIGHT; POLYSTYRENES; SURFACE TREATMENT; X RAY PHOTOELECTRON SPECTROSCOPY;

BLOCK COPOLYMERS;

1 BROMOHEXANE; 1-BROMOHEXANE; ANTIINFECTIVE AGENT; FLUOROCARBON; HALOGENATED HYDROCARBON; POLYSTYRENE BLOCK POLY(4 VINYLPYRIDINE); POLYSTYRENE DERIVATIVE; POLYSTYRENE-BLOCK-POLY(4-VINYLPYRIDINE); POLYVINYL DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; ESCHERICHIA COLI; GROWTH, DEVELOPMENT AND AGING; METHODOLOGY; SPECTROMETRY; STAPHYLOCOCCUS AUREUS; SURFACE PROPERTY;

ANTI-BACTERIAL AGENTS; ESCHERICHIA COLI; FLUOROCARBONS; HYDROCARBONS, HALOGENATED; POLYSTYRENES; POLYVINYLS; PYRIDINES; SPECTROMETRY, X-RAY EMISSION; STAPHYLOCOCCUS AUREUS; SURFACE PROPERTIES;

EID: 33846382692     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la061384v     Document Type: Article

References (65)

1. Ikeda, T.; Lee, B.; Yamaguchi, H.; Tazuke, S. Biochim. Biophys. Acta, Biomembranes 1990, 1021, 56-62.
2. Ivanov, I.; Vemparala, S.; Pophristic, V.; Kuroda, K.; DeGrado, W. F.; McCammon, J. A.; Klein, M. L. J. Am. Chem. Soc. 2006, 125, 1778-1779.
3. Ikeda, T.; Hirayama, H.; Yamaguchi, H.; Tazuke, S.; Watanabe, M. Antimicrob. Agents Chemother. 1986, 30, 132-136.
4. Ikeda, T.; Tazuke, S.; Suzuki, Y. Makromol. Chem. 1984, 185, 869-876.
5. Ikeda, T.; Yamaguchi, H.; Tazuke, S. Biochim. Biophys. Acta, Biomembranes 1990, 1026, 105-112.
6. Ikeda, T.; Yamaguchi, H.; Tazuke, S. J. Bioactive Compatible Polym. 1990, 5, 31-41.
7. Chen, C. Z.; Beck-Tan, N. C.; Dhurjati, P.; van Dyk, T. K.; LaRossa, R. A.; Cooper, S. L. Biomacromolecules 2000, 1, 473-480.
8. Sauvet, G.; Fortuniak, W.; Kazmierski, K.; Chojnowski, J. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2939-2948.
9. Thome, J.; Holländer, A.; Jaeger, W.; Trick, I.; Oehr, C. Surf. Coat. Technol. 2003, 174-175, 584-587.
10. Gelman, M. A.; Weisblum, B.; Lynn, D. M.; Gellman, S. H. Org. Lett. 2004, 6, 557-560.
11. Ilker, M. F.; Nüsslein, K.; Tew, G. N.; Coughlin, E. B. J. Am. Chem. Soc. 2004, 126, 15870-15875.
12. Lee, S. B.; Koepsel, R. R.; Morley, S. W.; Matyjaszewski, K.; Sun, Y.; Russell, A. J. Biomacromolecules 2004, 5, 877-882.
13. Waschinski, C. J.; Tiller, J. C. Biomacromolecules 2005, 6, 235-243.
14. Kawabata, N.; Nishiguchi, M. Appl. Environ. Microbiol. 1988, 54, 2532-2535.
15. Li, G.; Shen, J.; Zhu, Y. J. Appl. Polym. Sci. 1998, 67, 1761-1768.
16. Li, G.; Shen, J. J. Appl. Polym. Sci. 2000, 78, 676-684.
17. Tiller, J. C.; Liao, C.-J.; Lewis, K.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5981-5985.
18. Grapski, J. A.; Cooper, S. L. Biomaterials 2001, 22, 2239-2246.
19. Cen, L.; Neoh, K. G.; Kang, E. T. Langmuir 2003, 19, 10295-10303.
20. Park, E. S.; Kim, H. S.; Kim, M. N.; Yoon, J. S. Eur. Polym. J. 2004, 40, 2819-2822.
21. Kanazawa, A.; Ikeda, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 335-343.
22. Kanazawa, A.; Ikeda, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 1467-1472.
23. Kanazawa, A.; Ikeda, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 3031-3038.
24. Kanazawa, A.; Ikeda, T.; Endo, T. J. Appl. Polym. Sci. 1994, 53, 1237-1244 and the references therein.
25. Kanazawa, A.; Ikeda, T.; Endo, T. J. Appl. Polym. Sci. 1994, 53, 1245-1249 and the references therein.
26. Kenawy, E.-R.; Abdel-Hay, F. I.; El-Shanshoury, A. E.-R. R.; El-Newehy, M. H. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2384-2393.
27. Popa, A.; Davidescu, C. M.; Trif, R.; Ilia, Gh.; Iliescu, S.; Dehelean, Gh. React. Funct. Polym 2003, 55, 151-158.
28. Kanazawa, A.; Ikeda, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 2873-2876.
29. Dathe, M.; Schuemann, M.; Wieprecht, T.; Winkler, A.; Beyermann, M.; Krause, E.; Matsuzaki, K.; Murase, O.; Bienert, M. Biochemistry 1996, 35, 12612-12622.
30. Friedrich, C. L.; Moyles, D.; Beveridge, T. J.; Hancock, R. E. W. Amimicrob. Agents Chemother. 2000, 44, 2086-2092.
31. Lockwood, N. A.; Mayo, K. H. Drugs Future 2003, 25, 911-923.
32. Bradshaw, J. P. BioDrugs 2003, 17, 233-240.
33. Lohner, K.; Blondelle, S. E. Comb. Chem. High Throughput Screen. 2005, 8, 241-236.
34. Lin, J.; Qiu, S.; Lewis, K.; Klibanov, A. M. Biotechnol. Bioeng. 2003, 83, 168-172.
35. Milović, N. M.; Wang, J.; Lewis, K.; Klibanov, A. M. Biotechnol. Bioeng. 2005, 90, 715-722.
36. Kügler, R.; Bouloussa, O.; Rondelez, F. Microbiology 2005, 151, 1341-1348.
37. Tew, G. N.; Liu, D.; Chen, B.; Doerksen, R. J.; Kaplan, J.; Carroll, P. J.; Klein, M. L.; DeGrado, W. F. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5110-5114.
38. Rennie, J.; Arnt, L.; Tang, H.; Nüsslein, K.; Tew, G. N. J. Ind. Microbiol. Biotechnol. 2005, 32, 296-300.
39. Sawada, H.; Wake, A.; Maekawa, T.; Kawase, T.; Hayakawa, Y.; Tomita, T.; Baba, M. J. Fluorine Chem. 1997, 83, 125-131.
40. Sawada, H.; Katayama, S.; Ariyoshi, Y.; Kawase, T.; Hayakawa, Y.; Tomita, T.; Baba, M. J. Mater. Chem. 1998, 8, 1517-1524.
41. Isquith, A. J.; Abbott, E. A.; Walters, P. A. Appl. Microbiol. 1972, 24, 859-863.
42. Tiller, J. C.; Lee, S. B.; Lewis, K.; Klibanov, A. M. Biotechnol. Bioeng. 2002, 79, 465-471.
43. Förster, S.; Zisenis, M.; Wenz, E.; Antonietti, M. J. Chem. Phys. 1996, 104, 9956-9970.
44. Höpken, J.; Möller, M.; Boileau, S. New Polym. Mater. 1991, 2, 339-356.
45. Wang, J.; Ober, C. K. Liq. Cryst. 1999, 26, 637-648.
46. Wang, J.; Ober, C. K. Macromolecules 1997, 30, 7560-7567.
47. Stöhr J. NEXAFS Spectroscopy; Springer-Verlag: New York, 1996; Chapter 5, p 114.
48. Rosenberg, R. A.; Love, P. J.; Rehn, V. Phys. Rev. B 1986, 33, 4034-4037.
49. Panov, V. P ; Vorontsov, E. D.; Evdakov, V. P. J. Appl. Spectrosc. 1975, 23, 958-962.
50. Masson, P.; Gramain, P.; Guillon, D. Macromol. Chem. Phys. 1999, 200, 616-620.
51. 2 (ref 52).
52. Jiang, X.; Tanaka, K.; Takahara, A.; Kajiyama, T. Polymer 1998, 39, 2615-2620.
53. Pittman, A. G. In Fluropolymers; High Polymers Series XXV; Wall, L. A., Ed.; Wiley-Interscience: New York, 1972; p 419-449.
54. The edge jump is given by the difference of the electron yield about 30 eV above the ionization threshold (320 eV in C 1s NEXAFS spectra and 430 eV in N 1s spectra) and the electron yield just below the first resonance (cf. ref 55). As discussed in Section 2.5, the latter is ∼0 for both C 1s and N 1s spectra. and the C 1s edge jump has been set to unity.
55. Stöhr J. NEXAFS Spectroscopy; Springer-Verlag: New York, 1996; Chapter 7, p 211.
56. Kolczewski, C.; Püttner, R.; Plashkevych, O.; Ågren, H.; Staemmler, V.; Martins, M.; Snell, G.; Schlachter, A. S.; Sant'Anna, M.; Kaindl, G.; Pettersson, L. G. M. J. Chem. Phys. 2001, 115, 6426-6437.
57. Ito, E.; Oji, H.; Araki, T.; Oichi, K.; Ishii, H.; Ouchi, Y.; Ohta, T.; Kosugi, N.; Maruyama, Y.; Naito, T.; Inabe, T.; Seki, K. J. Am. Chem. Soc. 1997, 119, 6336-6344.
58. Fujii, S.; Armes, S. P.; Araki, T.; Ade, H. J. Am. Chem. Soc. 2005, 127, 16808-16809.
59. The degree of quaternization estimated using this procedure will differ from that obtained by more conventional methods (such as IR or elemental analysis) if the low-surface-energy alkyl groups in the quaternized polymer form a thin layer at the surface covering the higher-surface-energy pyridinium rings. The maximum thickness of this layer can be estimated to be ∼7.7 Å, corresponding to a fully stretched n-hexyl chain attached to the pyridinium nitrogen. In such a case, the degree of quaternization obtained from the NEXAFS spectra will be a slight overestimate.
60. To displace the PS block from the surface, the decrease in P4VP block surface energy contributed by the perfluorooctyl groups must compensate for the increased energy of the exposed P4VP surface. This compensation will require a high areal density of perfluorooctyl groups, resulting in the necessity of the P4VP chains to stretch away from the surface. The free energy penalty for the required P4VP stretching increases as the P4VP block length increases and, thus, above some block length, the perfluorooctyl end group will be ineffective in bringing the P4VP block to the surface.
61. Cotton, J. P.; Decker, D.; Benoit, H.; Farnoux, B.; Higgins, J.; Jannink, G.; Ober, R.; Picot, C.; des Cloizeaux, J. Macromolecules 1974, 7, 863-872.
62. 66kH6Br surfaces prepared by the spin-coating (Figure 6) and the spray-coating (Figure 7) techniques are attributed to the different processing conditions used for the two surfaces. The spin-coated samples were annealed at 150°C, which is above the glass transition temperature of the PS block, while the spray-coated samples were dried at 60°C.
63. Biggerstaff, J. P.; Le Puil, M.; Weidow, B. L.; Prater, J.; Glass, K.; Radosevich, M.; White, D. C. Mol. Cell. Probes 2006, 20, 141-146.
64. Boulos, L.; Prévost, M.; Barbeau, B.; Coallier, J.; Desjardins, R. J. Microbiol. Methods 1999, 37, 77-86.
65. Krishnan, S.; Finlay, J. A.; Hexemer, A.; Wang, N.; Ober, C. K.; Kramer, E. J.; Callow, M. E.; Callow, J. A.; Fischer, D. A. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2005, 46, 1248-1249.