Synthesis of a regioregular zwitterionic conjugated oligoelectrolyte, usable as an optical probe for detection of amyloid fibril formation at acidic pH

Journal of the American Chemical Society

Volumn 127, Issue 7, 2005, Pages 2317-2323

  Herland, Anna ^a,b   Nilsson, K Peter R ^a,b   Olsson, Johan D M ^a,b   Hammarström, Per ^a,b   Konradsson, Peter ^a,b   Inganäs, Olle ^a,b  

^a LINKÖPING UNIVERSITY   (Sweden)

^b Dept of Biomolec/Organ Electron ^*  (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMYLOID FIBRILS; BIOMOLECULES; CONJUGATED OLIGOELECTROLYTES; OPTICAL PROBES;

ABSORPTION; ELECTRONIC STRUCTURE; EMISSION SPECTROSCOPY; OLIGOMERS; ORGANIC POLYMERS; PH EFFECTS; SENSORS; SYNTHESIS (CHEMICAL);

POLYELECTROLYTES;

AMPHOLYTE; AMYLOID; BOVINE INSULIN; ELECTROLYTE; LYSOZYME; OLIGOELECTROLYTE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ACIDITY; ARTICLE; CHEMICAL STRUCTURE; ELECTROCHEMICAL ANALYSIS; FLAME PHOTOMETRY; GEOMETRY; MOLECULAR INTERACTION; PH MEASUREMENT; POLARIMETRY; PROTEIN DETERMINATION; SENSOR; SYNTHESIS;

AMYLOID; ANIMALS; CATTLE; CHICKENS; CIRCULAR DICHROISM; ELECTROLYTES; HYDROGEN-ION CONCENTRATION; INSULIN; MURAMIDASE; POLYMERS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; THIOPHENES;

EID: 13944280204     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045835e     Document Type: Article

References (44)

1. Wang, J.; Wang, D.; Miller, E. K.; Moses, D.; Bazan, G. C.; Heeger, A. J. Macromolecules 2000, 33, 5153-5158.
2. Wang, D.; Gong, X.; Heeger, P. S.; Rininsland, F.; Bazan, G. C.; Heeger. A. J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 49-53.
3. Liu, B.; Gaylord, B. S.; Wang, S.; Bazan, G. C. J. Am. Chem. Soc. 2003, 125, 6705-6714.
4. Heeger, P. S.; Heeger, A. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12219-12221.
5. Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. J. Am. Chem. Soc. 2003, 125, 896-900.
6. Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 10954-10957.
7. Ho, H.-A.; Boissinot, M.; Bergeron, M. G.; Corbeil, G.; Dore, K.; Boudreau, D.; Leclerc, M. Angew Chem. Int. Ed. 2002, 41, 1548-1551.
8. Ho, H. A.; Leclerc, M. J. Am. Chem. Soc. 2004, 126, 1384-1387.
9. Nilsson, K. P.; Inganas, O. Nat. Mater. 2003, 2, 419-424.
10. Nilsson, K. P.; Rydberg, J.; Baltzer, L.; Inganas, O. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 10170-10174.
11. Nilsson, K. P.; Rydberg, J.; Baltzer, L.; Inganas, O. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11197-11202.
12. Nilsson, K. P.; Inganas, O. Macromolecules 2004, 37, 9109-9113.
13. Martin, R. E.; Diederich, F. Angew Chem. Int. Ed. 1999, 38.
14. Müllen, K.; Wegner, G. Electronic materials: the oligomer approach; Wiley-VCH; Weinhem, 1997.
15. Meier, H.; Stalmach, U.; Kolshorn, H. Acta Polym. 1997, 48, 379-384.
16. Frere, P.; Raimundo, J. M.; Blanchard, P.; Delaunay, J.; Richomme, P.; Sauvajol, J. L.; Orduna, J.; Garin, J.; Roncali, J. J. Org. Chem. 2003, 68, 7254-7265.
17. Dobson, C. M. Trends Biochem. Sci. 1999, 24, 329-332.
18. Sunde, M.; Serpell, L. C.; Bartlam, M.; Fraser, P. E.; Pepys, M. B.; Blake, C. C. J. Mol. Biol. 1997, 273, 729-739.
19. Lansbury, P. T.; Kelly, J. W. Amyloid 1994, 1, 186-205.
20. Sacchettini, J. C.; Kelly, J. W. Nat. Rev. Drug Discov. 2002, 1, 267-275.
21. Dobson, C. M. Nature 2003, 426, 884-890.
22. Carrell, R. W.; Lomas, D. A. Lancet 1997, 350, 134-138.
23. Pepys, M. B. In The Oxford Textbook of Medicine, 3rd ed.; Weatherall, D. J., Ledingham, J. G. G., Warell, D. A., Eds.; Oxford University Press: Oxford, 1996; Vol. 2, pp 1512-1524.
24. Cohen, A. S.; Shirahama, T.; Skinner, M. In Electron Microscopy of Protein; Harris, I., Ed.; Academic Press: London, 1981; Vol. 3, pp 165-205.
25. Blundell, T. L.; Cutfield, J. F.; Dodson, G. G.; Dodson, E.; Hodgkin, D. C.; Mercola, D. Biochem. J. 1971, 125, 50P-51P.
26. Brange, J.; Andersen, L.; Laursen, E. D.; Meyn, G.; Rasmussen, E. J. Pharm. Sci. 1997, 86, 517-525.
27. Waugh, D. F. J. Am. Chem. Soc. 1946, 68, 247-250.
28. Nielsen, L.; Frokjaer, S.; Carpenter, J. F.; Brange, J. J. Pharm. Sci. 2001, 90, 29-37.
29. Waugh, D. F.; Wilhelmson, D. F.; Commerford, S. L.; Sackler, M. L. J. Am. Chem. Soc. 1953, 75, 2592-2600.
30. Nielsen, L.; Khurana, R.; Coats, A.; Frokjaer, S.; Brange, J.; Vyas, S.; Uversky, V. N.; Fink, A. L. Biochemistry 2001, 40, 6036-6046.
31. Ahmad, A.; Millett, I. S.; Doniach, S.; Uversky, V. N.; Fink, A. L. Biochemistry 2003, 42, 11404-11416.
32. Nettleton, E. J.; Tito, P.; Sunde, M.; Bouchard, M.; Dobson, C. M.; Robinson, C. V. Biophys J. 2000, 79, 1053-1065.
33. Bouchard, M.; Zurdo, J.; Nettleton, E. J.; Dobson, C. M.; Robinson, C. V. Protein Sci. 2000, 9, 1960-1967.
34. Glenner, G. G. Prog. Histochem. Cytochem. 1981, 13, 1-37.
35. Parakka, J. P.; Jeevarajan, J. A.; Jeevarajan, A. S.; Kispert, L. D.; Cava, M. P. Adv. Mater. 1996, 8, 54-59.
36. Martina, S.; Enkelmann, V.; Schlueter, A. D.; Wegner, G. Synth. Metals 1991, 41, 403-406.
37. Sugimoto, R.; Takeda, S.; Gu, H. B.; Yoshino, K. Chem. Exp. 1986, 1, 635.
38. Yoshino, K.; Hayash, S.; Sugimoto, R.-I. Jpn. J. Appl. Phys. 1984, 23, L899.
39. Nilsson, K. P.; Herland, A.; Hammarström, P.; Inganäs, O. Biochemistry 2005, in press.
40. Kim, B.; Chen, L.; Gong, J.; Osada, Y. Macromolecules 1999, 32, 3964-3969.
41. Faïd, K.; Leclerc, M. J. Am. Chem. Soc. 1998, 120, 5274-5278.
42. McCullough, R. D.; Ewbank, P. C.: Loewe, R. S. J. Am. Chem. Soc. 1997, 119, 633-634.
43. Berggren, M.; Bergman, P.; Fagerstrom, J.; Inganas, O.; Andersson, M.; Weman, H.; Granstrom, M.; Stafstrom, S.; Wennerstrom, O.; Hjertberg, T. Chem. Phys. Lett. 1999, 304, 84-90.
44. Nilsson, K. P. R.; Andersson, M. R.; Inganäs, O. J. Phys.; Condens. Matter 2002, 14, 1-10.