Saccharide-functionalized alkanethiols for fouling-resistant self-assembled monolayers: Synthesis, monolayer properties, and antifouling behavior

Langmuir

Volumn 27, Issue 24, 2011, Pages 15034-15047

  Fyrner, Timmy ^a   Lee, Hung Hsun ^a   Mangone, Alberto ^a   Ekblad, Tobias ^a   Pettitt, Michala E ^b   Callow, Maureen E ^b   Callow, James A ^b   Conlan, Sheelagh L ^c   Mutton, Robert ^c   Clare, Anthony S ^c   Konradsson, Peter ^a   Liedberg, Bo ^a   Ederth, Thomas ^a  

^a LINKÖPING UNIVERSITY   (Sweden)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^c NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE CHAINS; ALKANETHIOLS; ANTIFOULING; ANTIFOULING PROPERTY; BALANUS AMPHITRITE; BUFFER SOLUTIONS; HEAD GROUPS; INFRARED REFLECTION ABSORPTION SPECTROSCOPY; MACRO ALGAE; MARINE ORGANISMS; MIXED SAM; NONSPECIFIC ADSORPTION; PACKING DENSITY; PROTEIN ADSORPTION; SAMS; SPECIFIC INTERACTION; STRUCTURAL QUALITIES; SUGAR MOIETY; SURFACE DILUTIONS; ULVA LINZA; WETTING MEASUREMENTS;

ADSORPTION; FOULING; MARINE BIOLOGY; PARAFFINS; SUGARS;

SELF ASSEMBLED MONOLAYERS;

ALKANE; DISINFECTANT AGENT; MONOSACCHARIDE; OLIGOSACCHARIDE; PROTEIN; THIOL DERIVATIVE;

ADSORPTION; ANIMAL; ARTICLE; BACTERIAL SPORE; BINDING SITE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; INFRARED SPECTROPHOTOMETRY; METABOLISM; PHYSIOLOGY; PROTEIN BINDING; REFRACTOMETRY; SPECTROSCOPY; SYNTHESIS; THORACICA; ULVA; WETTABILITY;

ADSORPTION; ALKANES; ANIMALS; BINDING SITES; DISINFECTANTS; MONOSACCHARIDES; OLIGOSACCHARIDES; PROTEIN BINDING; PROTEINS; REFRACTOMETRY; SPECTROPHOTOMETRY, INFRARED; SPECTRUM ANALYSIS; SPORES; SULFHYDRYL COMPOUNDS; THORACICA; ULVA; WETTABILITY;

EID: 83455264398     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la202774e     Document Type: Article

References (49)

1. Varki, A.; Cummings, R.; Esko, J.; Freeze, H.; Hart, G.; Marth, J. Essentials of Glycobiology; Cold Spring Harbor Laboratory Press: New York, 1999.
2. Varma, A. J.; Kennedy, J. F.; Galgali, P. Carbohydr. Polym. 2004, 56, 429-445
3. Finkenstadt, V. L. Appl. Microbiol. Biotechnol. 2005, 67, 735-745
4. Dai, L.; StJohn, H. A. W.; Bi, J.; Zientek, P.; Chatelier, R. C.; Griesser, H. J. Surf. Interface Anal. 2000, 29, 46-55
5. Liu, Y.; Chan-Park, M. B. Biomaterials 2009, 30, 196-207
6. Löfs, S.; Johnsson, B. J. Chem. Soc., Chem. Commun. 1990, 1526-1528
7. Fukui, S.; Feizi, T.; Galustian, C.; Lawson, A. M.; Chai, W. Nat. Biotechnol. 2002, 20, 1011-1017
8. Morra, M.; Cassineli, C. J. Biomater. Sci., Polym. Ed. 1999, 10, 1107-1124
9. Martwiset, S.; Koh, A. E.; Chen, W. Langmuir 2006, 22, 8192-8196
10. Cao, X.; Pettit, M. E.; Conlan, S. L.; Wagner, W.; Ho, A. D.; Clare, A. S.; Callow, J. A.; Callow, M. E.; Grunze, M.; Rosenhahn, A. Biomacromolecules 2009, 10, 907-915
11. Prime, K. L.; Whitesides, G. M. Science 1991, 252, 1164-1167
12. Hederos, M.; Konradsson, P.; Liedberg, B. Langmuir 2005, 21, 2971-2980
13. Ederth, T.; Ekblad, T.; Pettitt, M. E.; Conlan, S. L.; Du, C.-X.; Callow, M. E.; Callow, J. A.; Mutton, R.; Clare, A. S.; D'Souza, F.; Donnelly, G.; Bruin, A.; Willemsen, P.; Su, X. J.; Wang, S.; Zhao, Q.; Hederos, M.; Konradsson, P.; Liedberg, B. ACS Appl. Mater. Interfaces 2011, 3, 3890-3901
14. Luk, Y.-Y.; Kato, M.; Mrksich, M. Langmuir 2000, 16, 9604-9608
15. Metzke, M.; Guan, Z. Biomacromolecules 2007, 9, 208-215
16. Bandyopadhyay, D.; Prashar, D.; Luk, Y.-Y. Langmuir 2011, 27, 6124-6131
17. Pale-Grosdemange, C.; Simon, E. S.; Prime, K. L.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 12-20
18. Wang, R. L. C.; Kreuzer, H. J.; Grunze, M. J. Phys. Chem. B 1997, 101, 9767-9773
19. Harder, P.; Grunze, M.; Dahint, R.; Whitesides, G. M.; Laibinis, P. E. J. Phys. Chem. B 1998, 102, 426-436
20. Chapman, R. G.; Ostuni, E.; Takayama, S.; Holmlin, R. E.; Yan, L.; Whitesides, G. M. J. Am. Chem. Soc. 2000, 122, 8303-8304
21. Railkin, A. I. Marine Biofouling: Colonization Processes and Defenses. CRC Press: Boca Raton, FL, 2003.
22. Borgh, A.; Ekeroth, J.; Petoral, R. M., Jr.; Uvdal, K.; Konradsson, P.; Liedberg, B. J. Colloid Interface Sci. 2006, 295, 41-49
23. Svedhem, S.; Öhberg, L.; Borrelli, S.; Valiokas, R.; Andersson, M.; Oscarson, S.; Svensson, S. C. T.; Liedberg, B.; Konradsson, P. Langmuir 2002, 18, 2848-2858
24. Grant, C. F.; Kanda, V.; Yu, H.; Bundle, D. R.; McDermott, M. T. Langmuir 2008, 24, 14125-14132
25. Chernyak, A. Y.; Sharma, G. V. M.; Kononov, L. O.; Krishna, P. R.; Levinsky, A. B.; Kochetkov, N. K.; Rama Rao, A. V. Carbohydr. Res. 1992, 223, 303-309
26. Hadfield, A. F.; Lazo, J. S.; Sartorelli, A. C. Carbohydr. Res. 1979, 77, 51-59
27. Mikata, Y.; Kakuchi, K.; Yano, S. Fullerene derivative and composition comprising the same. Jap. pat. JP2002-212197A, July 31, 2002.
28. Ohlsson, J.; Magnusson, G. Tetrahedron 2000, 56, 9975-9984
29. Porter, M. D.; Bright, T. B.; Allara, D. L.; Chidsey, C. E. D. J. Am. Chem. Soc. 1987, 109, 3559-3568
30. Nuzzo, R. G.; Dubois, L. H.; Allara, D. L. J. Am. Chem. Soc. 1990, 112, 558-569
31. Malysheva, L.; Onipko, A.; Valiokas, R.; Liedberg, B. J. Phys. Chem. B 2005, 109, 13221-13227
32. Valiokas, R.; Svedhem, S.; Östblom, M.; Svensson, S. C. T.; Liedberg, B. J. Phys. Chem. B 2001, 105, 5459-5469
33. Clegg, R. S.; Hutchison, J. E. Langmuir 1996, 12, 5239-5243
34. Tam-Chang, S.-W.; Biebuyck, H. A.; Whitesides, G. M.; Jeon, N.; Nuzzo, R. G. Langmuir 1995, 11, 4371-4382
35. Jenny, N. S.; Mann, K. G. In Thrombosis and Hemorrhage; Loscalzo, J.; Schafer, A. I., Eds.; Lippincott Williams & Wilkins: Philadelphia, 2003; pp 1-21.
36. Lee, R. G.; Adamson, C.; Kim, S. W. Thromb. Res. 1974, 4, 485-490
37. Kidoaki, S.; Matsuda, T. Langmuir 1999, 15, 7639-7646
38. Benesch, J.; Svedhem, S.; Svensson, S. C. T.; Valiokas, R.; Liedberg, B.; Tengvall, P. J. Biomater. Sci., Polym. Ed. 2001, 12, 581-597
39. Schilp, S.; Rosenhahn, A.; Pettitt, M. E.; Bowen, J.; Callow, M. E.; Callow, J. A.; Grunze, M. Langmuir 2009, 25, 10077-10082
40. Prime, K. L.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 10714-10721
41. Sokal, R. R.; Rohlf, F. J. Biometry, 4 th ed.; W. H. Freeman: New York, 2005.
42. Callow, M. E.; Callow, J. A.; Ista, L. K.; Coleman, S. E.; Nolasco, A. C.; Lopez, G. P. Appl. Environ. Microbiol. 2000, 66, 3249-3254
43. Bennett, S. M.; Finlay, J. A.; Gunari, N.; Wells, D. D.; Meyer, A. E.; Walker, G. C.; Callow, M. E.; Callow, J. A.; Bright, F. V.; Detty, M. R. Biofouling 2010, 26, 235-246
44. Schilp, S.; Kueller, A.; Rosenhahn, A.; Grunze, M.; Pettitt, M. E.; Callow, M. E.; Callow, J. A. Biointerphases 2007, 2, 143-150
45. Aldred, N.; Li, G.; Gao, Y.; Clare, A. S.; Jiang, S. Biofouling 2010, 26, 673-683
46. Callow, M. E.; Callow, J. A.; Pickett-Heaps, J. D.; Wetherbee, R. J. Phycol. 1997, 33, 938-947
47. Finlay, J. A.; Callow, M. E.; Schultz, M. P.; Swain, G. W.; Callow, J. A. Biofouling 2002, 18, 251-256
48. Callow, M. E.; Jennings, A. R.; Brennan, A. B.; Seegert, C. E.; Gibson, A.; Wilson, L.; Feinberg, A.; Baney, R.; Callow, J. A. Biofouling 2002, 18, 237-245
49. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512-7515