Effect of the diacetylene position on the chromatic properties of polydiacetylenes from self-assembled peptide amphiphiles

Biomacromolecules

Volumn 11, Issue 6, 2010, Pages 1676-1683

  Van Den Heuvel, Maaike ^a   Löwik, Dennis W P M ^a   Van Hest, Jan C M ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALKYLATION; HYDROGEN BONDS; HYDROPHOBICITY; LANGMUIR BLODGETT FILMS; PEPTIDES; POLYMERIZATION; POLYMERS;

ALKYL CHAIN; CONJUGATION LENGTH; DIACETYLENE MOIETY; DIACETYLENES; HYDROPHOBIC TAILS; PEPTIDE AMPHIPHILES; POLYDIACETYLENES; SELF-ASSEMBLED PEPTIDES; STABLE STRUCTURES; TRIPLE BONDS;

AMPHIPHILES;

ACETYLENE DERIVATIVE; AMPHOPHILE; DIACETYLENE; POLYMER; UNCLASSIFIED DRUG; ACETYLENE; OLIGOPEPTIDE; POLYACETYLENE DERIVATIVE; POLYDIACETYLENE; SURFACTANT;

ARTICLE; CHEMICAL STRUCTURE; COLOR; CONJUGATION; HYDROGEN BOND; HYDROPHOBICITY; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN ASSEMBLY; AMINO ACID SEQUENCE; CHEMISTRY; CIRCULAR DICHROISM; MOLECULAR GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SURFACE PROPERTY; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROPHOTOMETRY;

ACETYLENE; AMINO ACID SEQUENCE; CIRCULAR DICHROISM; COLOR; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR SEQUENCE DATA; OLIGOPEPTIDES; POLYACETYLENES; POLYMERS; SPECTROPHOTOMETRY, ULTRAVIOLET; SURFACE PROPERTIES; SURFACE-ACTIVE AGENTS;

EID: 77954616783     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm100376q     Document Type: Article

References (60)

1. Wegner, G. Makromol. Chem. 1972, 154, 35-48.
2. Tieke, B.; Graf, H. J.; Wegner, G.; Naegele, B.; Ringsdorf, H.; Banerjie, A.; Day, D.; Lando, J. B. Colloid Polym. Sci. 1977, 255, 521-531.
3. Biesalski, M. A.; Knaebel, A.; Tu, R.; Tirrell, M. Biomaterials 2006, 27, 1259-1269.
4. Hupfer, B.; Ringsdorf, H.; Schupp, H. Chem. Phys. Lipids 1983, 33, 355-374.
5. Okada, S.; Peng, S.; Spevak, W.; Charych, D. Acc. Chem. Res. 1998, 31, 229-239.
6. Biesalski, M.; Tu, R.; Tirrell, M. V. Langmuir 2005, 21, 5663-5666.
7. Jahnke, E.; Millerioux, A. S.; Severin, N.; Rabe, J. P.; Frauenrath, H. Macromol. Biosci. 2007, 7, 136-143.
8. Jahnke, E.; Lieberwirth, I.; Severin, N.; Rabe, J. P.; Frauenrath, H. Angew. Chem., Int. Ed. 2006, 45, 5383-5386.
9. Löwik, D. W. P. M.; ShklyaRevskiy, I. O.; Ruizendaal, L.; Christianen, P. C. M.; Maan, J. C.; van Hest, J. C. M. Adv. Mater. 2007, 19, 1191-1195.
10. Hsu, L.; Cvetanovich, G. L.; Stupp, S. I. J. Am. Chem. Soc. 2008, 130, 3892-3899.
11. van den Heuvel, M.; Löwik, D. W. P. M.; van Hest, J. C. M. Biomacromolecules 2008, 9, 2727-2734.
12. Wenz, G.; Muller, M. A.; Schmidt, M.; Wegner, G. Macromolecules 1984, 17, 837-850.
13. Schott, M. J. Phys. Chem. B 2006, 110, 15864-15868.
14. Lim, K. C.; Kapitulnik, A.; Zacher, R.; Heeger, A. J. J. Chem. Phys. 1985, 82, 516-521.
15. Adler-Abramovich, L.; Gazit, E. J. Pept. Sci. 2008, 14, 217-223.
16. Tieke, B.; Lieser, G.; Wegner, G. J. Polym. Sci., Part A 1979, 17, 1631-1644.
17. Cheng, Q.; Yamamoto, M.; Stevens, R. C. Langmuir 2000, 16, 5333-5342.
18. Yuan, Z. Z.; Lee, C. W.; Lee, S. H. Angew. Chem., Int. Ed. 2004, 43, 4197-4200.
19. Potisatityuenyong, A.; Rojanathanes, R.; Turncharern, G.; Sukwattanasinitt, M. Langmuir 2008, 24, 4461-4463.
20. Wu, S.; Niu, L. F.; Shen, J.; Zhang, Q. J.; Bubeck, C. Macromolecules 2009, 42, 362-367.
21. Mino, N.; Tamura, H.; Ogawa, K. Langmuir 1992, 8, 594-598.
22. Zhou, W. D.; Li, Y. L.; Zhu, D. B. Chem. Asian J. 2007, 2, 222-229.
23. Jonas, U.; Shah, K.; Norvez, S.; Charych, D. H. J. Am. Chem. Soc. 1999, 121, 4580-4588.
24. Song, J.; Cisar, J. S.; Bertozzi, C. R. J. Am. Chem. Soc. 2004, 126, 8459-8465.
25. Song, J.; Cheng, Q.; Kopta, S.; Stevens, R. C. J. Am. Chem. Soc. 2001, 123, 3205-3213.
26. Charych, D. H.; Nagy, J. O.; Spevak, W.; Bednarski, M. D. Science 1993, 261, 585-588.
27. Lio, A.; Reichert, A.; Ahn, D. J.; Nagy, J. O.; Salmeron, M.; Charych, D. H. Langmuir 1997, 13, 6524-6532.
28. Jung, Y. K.; Kim, T. W.; Kim, J.; Kim, J. M.; Park, H. G. Adv. Funct. Mater. 2008, 18, 701-708.
29. Lee, J.; Kim, H. J.; Kim, J. J. Am. Chem. Soc. 2008, 130, 5010-5011.
30. Lee, S. W.; Kang, C. D.; Yang, D. H.; Lee, J. S.; Kim, J. M.; Ahn, D. J.; Sim, S. J. Adv. Funct. Mater. 2007, 17, 2038-2044.
31. Pindzola, B. A.; Nguyen, A. T.; Reppy, M. A. Chem. Commun. 2006, 906-908.
32. Huo, Q.; Wang, S. P.; Pisseloup, A.; Verma, D.; Leblanc, R. M. Chem. Commun. 1999, 1601-1602.
33. Huo, Q.; Russell, K. C.; Leblanc, R. M. Langmuir 1999, 15, 3972-3980.
34. Filhol, J. S.; Deschamps, J.; Dutremez, S. G.; Boury, B.; Barisien, T.; Legrand, L.; Schott, M. J. Am. Chem. Soc. 2009, 131, 6976-6988.
35. Cheng, Q.; Stevens, R. C. Langmuir 1998, 14, 1974-1976.
36. Hupfer, B.; Ringsdorf, H. Chem. Phys. Lipids 1983, 33, 263-282.
37. Tachibana, H.; Yamanaka, Y.; Sakai, H.; Abe, M.; Matsumoto, M. Macromolecules 1999, 32, 8306-8309.
38. van den Heuvel, M.; Prenen, A. M.; Gielen, J. C.; Christianen, P. C. M.; Broer, D. J.; Lowik, D.; van Hest, J. C. M. J. Am. Chem. Soc. 2009, 131, 15014-15017.
39. Miyawaki, K.; Goto, R.; Takagi, T.; Shibakami, M. Synlett 2002, 1467-1470.
40. Mowery, M. D.; Evans, C. E. Tetrahedron Lett. 1997, 38, 11-14.
41. Lin, D.; Zhang, J. Y.; Sayre, L. M. J. Org. Chem. 2007, 72, 9471-9480.
42. Gung, B. W.; Dickson, H. Org. Lett. 2002, 4, 2517-2519.
43. Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161-214.
44. Van Nispen, J. W.; Polderdijk, J. P.; GReven, H. M. Recl. TraV. Chim. Pays-Bas 1985, 104, 99-100.
45. Kaiser, E.; Colescot, Rl; Bossinge, Cd; Cook, P. I. Anal. Biochem. 1970, 34, 595-598.
46. Arx, E. V.; Faupel, M.; Brugger, M. J. Chromatogr. 1976, 120, 224-228.
47. Cerami, C.; FRevert, U.; Sinnis, P.; Takacs, B.; Clavijo, P.; Santos, M. J.; Nussenzweig, V. Cell 1992, 70, 1021-1033.
48. Löwik, D. W. P. M.; Garcia-Hartjes, J.; Meijer, J. T.; van Hest, J. C. M. Langmuir 2005, 21, 524-526.
49. Schmittel, M.; Vavilala, C. J. Org. Chem. 2005, 70, 4865-4868.
50. Otsuki, T.; Brooker, R. F.; Funk, M. O. Lipids 1986, 21, 178-181.
51. Singh, A.; Schnur, J. M. Synth. Commun. 1986, 16, 847-852.
52. Pattison, F. L. M.; Stothers, J. B.; Woolford, R. G. J. Am. Chem. Soc. 1956, 78, 2255-2259.
53. Wolffs, M.; George, S. J.; Tomovic, Z.; Meskers, S. C. J.; Schenning, A.; Meijer, E. W. Angew. Chem., Int. Ed. 2007, 46, 8203-8205.
54. Tieke, B.; Lieser, G. J. Colloid Interface Sci. 1982, 88, 471-486.
55. Tieke, B.; Lieser, G. J. Colloid Interface Sci. 1981, 83, 230-239.
56. Hupfer, B.; Ringsdorf, H.; Schupp, H. Macromol. Chem. Phys. 1981, 182, 247-253.
57. Hirst, A. R.; Huang, B. Q.; Castelletto, V.; Hamley, I. W.; Smith, D. K. Chem.-Eur. J. 2007, 13, 2180-2188.
58. Lauher, J. W.; Fowler, F. W.; Goroff, N. S. Acc. Chem. Res. 2008, 41, 1215-1229.
59. Baughman, R. H. J. Appl. Phys. 1972, 43, 4362-4370.
60. Britt, D. W.; Hofmann, U. G.; Mobius, D.; Hell, S. W. Langmuir 2001, 17, 3757-3765.