Synthesis of fluorogenic polymers for visualizing cellular internalization

Organic Letters

Volumn 10, Issue 14, 2008, Pages 2997-3000

  Mangold, Shane L ^a   Carpenter, Rachael T ^a   Kiessling, Laura L ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLESTERASE; CELL SURFACE RECEPTOR; FLUORESCENT DYE; POLYMER;

ANIMAL; ARTICLE; B LYMPHOCYTE; CHEMICAL STRUCTURE; DRUG EFFECT; ENZYMOLOGY; FLUORESCENCE MICROSCOPY; HUMAN; IMMUNOLOGY; LIVER; METABOLISM; PHYSIOLOGY; SWINE; SYNTHESIS;

ANIMALS; B-LYMPHOCYTES; CARBOXYLESTERASE; FLUORESCENT DYES; HUMANS; LIVER; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; POLYMERS; RECEPTORS, CELL SURFACE; SWINE;

EID: 52049111425     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800932w     Document Type: Article

References (60)

1. Hawker, C. J.; Wooley, K. I. Science 2005, 309, 1200-1205.
2. (a) Lutolf, M. P.; Hubbell, J. A. Nat. Biotechnol. 2005, 23, 47-55.
3. (b) Langer, R.; Tirrell, D. A. Nature 2004, 428, 487-492.
4. (c) Ratner, B. D.; Bryant, S. J. Annu. Rev. Biomed. Eng. 2004, 6, 41-75.
5. (d) Drury, J. L.; Mooney, D. J. Biomaterials 2003, 24, 4337-4351.
6. (a) Kataoka, K.; Harada, A.; Nagasaki, Y. Adv. Drug Del. Rev. 2001, 47, 113-131.
7. (b) Peppas, N. A.; Bures, P.; Leobandung, W.; Ichikawa, H. Eur. J. Pharm. Biopharm. 2000, 50, 27-46.
8. (c) Christie, R. J.; Grainger, D. W. Adv. Drug. Del. Rev. 2003, 55, 421-437.
9. (d) Murthy, N.; Xu, M.; Schuck, S.; Kunisawa, J.; Shastri, N.; Frechet, J. M. J. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 4995-5000.
10. (a) Kiick, K. L. Science 2007, 317, 1182-1183.
11. (b) Duncan, R. Nat. Rev. Drug. Discovery 2003, 2, 347-360.
12. (c) Lee, C. C.; MacKay, J. A.; Frechet, J. M. Nat. Biotechnol. 2005, 23, 1517-1526.
13. (d) Boas, U.; Heegard, P. M. H. Chem. Soc. Rev. 2004, 33, 43-63.
14. (e) Haag, R.; Kratz, F. Angew. Chem., Int. Ed. 2006, 45, 1198-1215.
15. (a) Kiessling, L. L.; Gestwicki, J. E.; Strong, L. E. Angew. Chem., Int. Ed. 2006, 45, 2342-2368.
16. (b) Borrok, M. J.; Kolonko, E. M. ACS Chem. Biol. 2008, 3, 101-109.
17. (c) Mammen, M.; Choi, S-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794.
18. Mortell, K. H.; Gringas, M.; Kiessling, L. L. J. Am. Chem. Soc. 1994, 116, 12053-12054.
19. (a) Smith, D.; Pentzer, E. B.; Nguyen, S. T. Polymer Rev. 2007, 47, 419-459.
20. (b) Gestwicki, J. E.; Kiessling, L. L. Nature 2002, 415, 81-84.
21. (c) Lee, Y.; Sampson, N. S. Curr. Opin. Struct. Biol. 2006, 16, 544-550.
22. (d) Geng, J.; Mantovani, G.; Tao, L.; Nicolas, J.; Chen, G.; Wallis, R.; Mitchell, D. A.; Johnson, B. R. G.; Evans, S. D.; Haddleton, D. M. J. Am. Chem. Soc. 2007, 129, 15156-15163.
23. (e) Ladmiral, V.; Mantovani, G.; Clarkson, G. J.; Cauet, S.; Irwin, J. L.; Haddleton, D. M. J. J. Am. Chem. Soc. 2006, 128, 4823-4830.
24. (f) Kiessling, L. L.; Owen, R. M. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 3, pp 180-225.
25. (g) Maynard, H. D.; Okada, S. Y.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 1275-1279.
26. (h) Rawal, M.; Gama, C. I.; Matson, J. B.; Hsieh-Wilson, L. C. J. Am. Chem. Soc. 2008, 130, 2959-2961.
27. (a) Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 3760-3765.
28. (b) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
29. Puffer, E. B.; Pontrello, J. K.; Hollenbeck, J. J.; Kink, J. A.; Kiessling, L. L. ACS Chem. Biol. 2007, 2, 252-262.
30. (a) Chandran, S. S.; Dickson, K. A.; Raines, R. T. J. Am. Chem. Soc. 2005, 127, 1652-1653.
31. (b) Lavis, L. D.; Chao, T.-Y.; Raines, R. T. ChemBioChem 2006, 7, 1151-1154.
32. (c) Lavis, L. D.; Chao, T.-Y.; Raines, R. T. ACS Chem. Biol. 2006, 1, 252-260.
33. Amsberry, K. L.; Gerstenberger, A. E.; Borchardt, R. T. Pharm. Res. 1991, 8, 455-461.
34. (a) Rostovtsev, V. V.; Green, L. G.; Folkin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
35. (b) Tornoe, C. W.; Christensen, C.; Meldal, M. J. J. Org. Chem. 2002, 67, 3057-3064.
36. (a) Lutz, J.-F. Angew. Chem., Int. Ed. 2007, 46, 1018-1025.
37. (b) Fournier, D.; Hoogenboom, R.; Schubert, U. S. Chem. Soc. Rev. 2007, 36, 1369-1380.
38. Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687.
39. (a) Yang, S. K.; Weck, M. Macromolecules 2008, 41, 346-351.
40. (b) Binder, W. H.; Kluger, C. Macromolecules 2004, 37, 9329-9330.
41. (a) Zhang, W.; Moore, J. S. Adv. Synth. Catal. 2007, 349, 93-120.
42. (b) van de Weghe, P.; Bisseret, P.; Blanchard, N. J. Organomet. Chem. 2006, 691, 5078-5108.
43. (c) Furstner, A.; Davis, P. W. Chem. Commun. 2005, 18, 2307-2320.
44. (d) Lloyd-Jones, G. C.; Margue, R. G.; de Vries, J. G. Angew. Chem., Int. Ed. 2005, 44, 7442-7447.
45. (a) Gordon, E. J.; Gestwicki, J. E.; Strong, L. E.; Kiessling, L. L. Chem. Biol. 2000, 7, 9-16.
46. (b) Owen, R. M.; Gestwicki, J. E.; Young, T.; Kiessling, L. L. Org. Lett. 2002, 4, 2293-2296.
47. (c) Hilf, S.; Berger-Nicoletti, E.; Grubbs, R. H.; Kilbinger, A. F. M. Angew. Chem., Int. Ed. 2006, 45, 8045-8048.
48. (d) Gibson, V. C.; Okada, T. Macromolecules 2000, 33, 655-656.
49. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554.
50. Lal, B.; Pramanik, B. M.I.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1977, 18, 1977-1980.
51. Stork, G.; Niu, D.; Fujimoto, A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239-3242.
52. (a) Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2003, 42, 1743-1746.
53. (b) Choi, T-L.; Grubbs, R. H. Angew. Chem., Int. Ed. 2003, 42, 1743-1746.
54. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Folkin, V. V. Org. Lett. 2004, 6, 2853-2855.
55. (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Folkin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193.
56. (b) Link, J. A.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165.
57. (c) Link, J. A.; Mock, M. L.; Tirrell, D. A. Curr. Opin. Biotech. 2003, 14, 603-609.
58. (d) Speers, A. E.; Cravatt, B. F. Chem. Biol. 2004, 11, 535-546.
59. (e) Sawa, M.; Hsu, T-L.; Itoh, T.; Sugiyama, M.; Hanson, S. R.; Vogt, P. K.; Wong, C-H. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 12371-12376.
60. (f) Agard, N. J.; Baskin, J. M.; Prescher, J. A.; Lo, A.; Bertozzi, C. R. ACS Chem. Biol. 2006, 1, 644-648.