Host-[2]rotaxanes as cellular transport agents

Journal of the American Chemical Society

Volumn 125, Issue 27, 2003, Pages 8290-8301

  Dvornikovs, Vadims ^a   House, Brian E ^a   Kaetzel, Marcia ^a   Dedman, John R ^a   Smithrud, David B ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ASSOCIATION REACTIONS; CELLS;

CELLULAR TRANSPORT AGENTS;

CROWN ETHERS;

AMINO ACID; CYCLOPHANE; DIMETHYL SULFOXIDE; DIPEPTIDE; FLUORESCEIN; PHOSPHATE; PROTEIN KINASE C INHIBITOR; ROTAXANE;

ANIMAL CELL; ARTICLE; CELL MEMBRANE TRANSPORT; CELL NUCLEUS; CELL STRAIN COS7; CONTROLLED STUDY; FLUORESCENCE ANALYSIS; INTERMETHOD COMPARISON; NONHUMAN; PROTEIN BINDING; PROTEIN DOMAIN;

ANIMALS; ARGININE; BIOMIMETIC MATERIALS; CARRIER PROTEINS; CERCOPITHECUS AETHIOPS; COS CELLS; DRUG CARRIERS; ETHERS, CYCLIC; FLUORESCEIN; KINETICS; MODELS, MOLECULAR; ROTAXANES;

EID: 0037668140     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034918c     Document Type: Article

References (46)

1. Grawe, T.; Schrader, T.; Finocchiaro, P.; Consiglio, G.; Failla, S. Org. Lett. 2001, 3, 1597-1600.
2. Peczuh, M. W.; Hamilton, A. D. Chem. Rev. 2000, 100, 2479-2493.
3. Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perk. Trans 1 2000, 19, 3155-3184.
4. Peri, F.; Grell D.; Dumy, P.; Yokokawa, Y.; Welzenbach, K.; Weitz-Schmidt; Mutter, M. J. Pept. Sci. 1999, 5, 313-322.
5. Tuchscherer, G.; Mutter, M. J. Biotech. 1995, 41, 197-210.
6. Park, H. S.; Lin, Q.; Hamilton, A. D. Proc. Natl. Acad. Sci., USA 2002, 99, 5105-5109.
7. Park, H. S.; Lin, Q.; Hamilton A. D. J. Am. Chem. Soc. 1999, 121, 8-13.
8. Hamuro, Y.; Calama, M. C.; Park H. S.; Hamilton A. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2680-2683.
9. Kirchner, R.; Seidel, J.; Wolf, G.; Wulff, G. J. Incl. Phenom. Macro. 2002, 43, 279-283.
10. Piletsky, S. A.; Alcock, S.; Turner, A. P. F. Trends Biotechnol. 2001, 19, 9-12.
11. Whitcombe, M. J.; Vulfson, E. N. Adv. Mater. 2001, 13, 467-478.
12. Miyabe, K.; Guiochon, G. A. Biotechnol. Prog. 2000, 16, 617-629.
13. Wulff, G. Templated Synthesis of Polymers-Molecularly Imprinted Materials for Recognition and Catalysis in Template Organic Synthesis; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Verlag Weinheim, 2000.
14. Haupt, K.; Mosbach, K. Chem. Rev. 2000, 100, 2495-2504.
15. Yoshikawa, M.; Shimada, A.; Izumi, J. Analyst 2001, 126, 775-780.
16. Boon, J. M.; Smith, B. D. Curr. Opin. Chem. Biol. 2002, 6, 749-756.
17. Smukste, I.; House, B. E.; Smithrud, D. B. J. Org. Chem. 2003, 68, 2559-2571.
18. Smukste, I.; Smithrud, D. B. J. Org. Chem. 2003, 68, 2547-2558.
19. Chen, C. S.; Poenie, M. J. Biol. Chem. 1993, 268, 15812-15822.
20. Diederich, F. In Cyclophanes, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: London, 1991.
21. Cram, D. J. Angew. Chem., Int. Ed. 1986, 25, 1039-1134.
22. Diederich, F.; Smithrud, D. B.; Sanford, E. M.; Wyman, T. B.; Ferguson, S. B.; Carcanague, D. R.; Chao, I.; Houk, K. N. Acta Chem. Scand. 1992, 46, 205-215.
23. Smithrud, D. B.; Wyman, T. B.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5420-5426.
24. Smithrud, D. B.; Sanford, E. M.; Chao, I.; Ferguson, S. B.; Carcanague, D. R.; Evanseck, J. D.; Houk, K. N.; Diederich, F. Pure Appl. Chem. 1990, 62, 2227-2236.
25. Smithrud, D. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 339-343.
26. Goshe, A. J.; Steele, I. M.; Ceccarelli, C.; Rheingold, A. L.; Bosnich, B. Proc. Natl. Acad., U.S.A. 2002, 99, 4823-4829.
27. Tamaru, S.; Shinkai, S.; Khasanov, A. B.; Bell, T. W. Proc. Natl. Acad., U.S.A. 2002, 99, 4972-4976.
28. Shizuma, M.; Kadoya, Y.; Takai, Y.; Imamura, H.; Yamada, H.; Takeda, T.; Arakawa, R.; Takahashi, S.; Sawada, M. J. Org. Chem. 2002, 67, 4795-4807.
29. Jansen, R. J.; de Gelder, R.; Rowan, A. E.; Scheeren, H. W.; Nohe, R. S. M. J. Org. Chem. 2001, 66, 2643-2653.
30. Isaacs, L.; Witt, D.; Lagona, J. Org. Lett. 2001, 3, 3221-3224.
31. Sebo, L.; Schweizer, B.; Diederich, F. Helv. Chim. Acta 2000, 83, 80-92.
32. Potluri, V. K.; Maitra, U. J. Org. Chem. 2000, 65, 7764-7769.
33. Hernandez, J. V.; Almaraz, M.; Raposo, C.; Martin, M.; Lithgow, A.; Crego, M.; Caballero, C.; Moran, J. R. Tetrahedron Lett. 1998, 39, 7401-7404.
34. Murray, B. A.; Whelan, G. S. Pure Appl. Chem. 1996, 68, 1561-1567.
35. Zehnder, D.; Smithrud, D. B. Org. Lett. 2001, 16, 2485-2486.
36. Krieger, C.; Diederich, F. Chem. Ber. 1985, 118, 3620-3631.
37. For a representative titration plot, see ref 17, Figure 3 for cyclophane 2.
38. Hypercube, Inc., Gainesville, FL.
39. Hortala, M. A.; Fabbrizzi, L.; Marcotte, N.; Stomeo, F.; Taglietti, A. J. Am. Chem. Soc. 2003, 125, 20-21.
40. Tsubaki, K.; Kusumoto, T.; Hayashi, N.; Nuruzzaman, M.; Fuji, K. Org. Lett. 2002, 4, 2313-2316.
41. Rensing, S.; Schrader, T. Org. Lett. 2002, 4, 2161-2164.
42. Ait-Haddou, H.; Wiskur, S. L.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2001, 123, 11296-11297.
43. Mizutani, T.; Wada, K.; Kitagawa, S. J. Am. Chem. Soc. 1999, 121, 11425-11431.
44. Martell, A. E.; Motekaitis, R. J. The Determination and Use of Stability Constants; VCH: New York, 1988.
45. Conners, K. A. Binding Constants, The Measurement of Molecular Complex Stability; Wiley: New York, 1987.
46. Tadros, W. J. Chem. Soc. 1949, 442-444.