Dendritic Molecular Capsules for Hydrophobic Compounds

Journal of the American Chemical Society

Volumn 125, Issue 50, 2003, Pages 15485-15489

  Morgan, Meredith T ^a,b   Carnahan, Michael A ^a,b   Immoos, Chad E ^a,b   Ribeiro, Anthony A ^a,b,c   Finkelstein, Stella ^a,b   Lee, Stephen J ^a,b,d   Grinstaff, Mark W ^a,b  

^a BOSTON UNIVERSITY   (United States)

^b DUKE UNIVERSITY   (United States)

^c DUKE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d U S ARMY RESEARCH OFFICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTICANCER DRUGS;

CELLS; DATA REDUCTION; DENDRIMERS; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TUMORS;

MOLECULAR DYNAMICS;

10 HYDROXYCAMPTOTHECIN; ANTINEOPLASTIC AGENT; CARBOXYLIC ACID; DENDRIMER; DYE; POLY(GLYCEROL SUCCINIC ACID); PROTON; REICHARDT DYE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CELL STRAIN MCF 7; CELL VIABILITY; CONTROLLED STUDY; DIELECTRIC CONSTANT; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; ENCAPSULATION; HUMAN; HUMAN CELL; HYDROPHOBICITY; MACROMOLECULE; MOTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE;

BENZENE DERIVATIVES; COLORING AGENTS; GLYCEROL; HYDROPHOBICITY; POLYMERS; SPECTROPHOTOMETRY, ULTRAVIOLET; SUCCINIC ACIDS;

EID: 0346850023     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0347383     Document Type: Article

References (50)

1. Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688.
2. Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712.
3. Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1999, 38, 884-905.
4. Majoral, J. P.; Caminade, A. M. Chem. Rev. 1999, 99, 845-880.
5. Mathews, O. A.; Shipway, A. N.; Stoddart, J. F. Prog. Polym. Sci. 1998, 23, 1-56.
6. Newkome, G. R.; Moorefield, C. N.; Keith, J. N.; Baker, G. R.; Escamilla, G. H. Angew. Chem., Int. Ed. Engl. 1994, 106, 701-703.
7. Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413-2420.
8. Vögtle, F. Dendrimers I; Springer: Berlin; Vol. 197.
9. Vögtle, F. Dendrimers II: Architecture, Nanostructure, and Supramolecular Chemistry; Springer: Berlin; Vol. 210.
10. Vögtle, F. Dendrimers III: Design, Dimension, Function; Springer: Berlin, 2001; Vol. 212.
11. Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendritic Molecules: Concepts, Synthesis, Perspectives; VCH: New York, 1996.
12. Fréchet, J. M. J.; Tomalia, D. A. Dendrimers and Other Dendritic Polymers Chichester, UK, 2001.
13. Fréchet, J. M. J. Proc. Natl. Acad. Sci. 2002, 99, 4782-4787.
14. Buhleier, W.; Wehner, F. V.; Vögtle, F. Synthesis 1987, 155-158.
15. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 2, 7638-7647.
16. Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117-132.
17. Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466-2468.
18. Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003-2004.
19. Harth, E.; Hecht, S.; Helms, B.; Malmstrom, E.; Fréchet, J. M. J. ; Hawker, C. J. Am. Chem. Soc. 2002, 124, 3926-3938.
20. Carnahan, M. A.; Grinstaff, M. W. J. Am. Chem. Soc. 2001, 123, 2905-2906.
21. Camahan, M. A.; Grinstaff, M. W. Macromolecules 2001, 34, 7648-7655.
22. Carnahan, M. A.; Middleton, C.; Kim, J.; Kim, T.; Grinstaff, M. W. J. Am. Chem. Soc. 2002. 124, 5291-5293.
23. Grinstaff, M. W. Chem. Eur. J. 2002, 8, 2838-2846.
24. Kopecek, J. Polym. Med. 1977, 7, 191-221.
25. Langer, R. Nature 1998, S392, 5-10.
26. Uhrich, K. E.; Cannizzaro, S. M.; Langer, R.; Shakesheff, K. M. Chem. Rev. 1999, 99, 3181-3198.
27. Schultz, L. G.; Zimmerman, S. C. Pharm. News 1999, 6, 25-29.
28. Liu, H.; Farrell, S.; Uhrich, K. E. J. Controlled Release 2000, 68, 167-174.
29. Liu, M.; Kono, K.; Fréchet, J. M. J. J. Controlled Release 2000, 65, 121-131.
30. Malik, N.; Wimattanapatapee, R.; Klopsch, R.; Lorenz, K.; Frey, H.; Weener, J. W.; Meijer, E. W.; Paulus, W.; Duncan, R. J. Controlled Release 2000, 65, 133-148.
31. Esfand, R.; Tomalia, D. A. Drug Discovery Today 2001, 6, 427-436.
32. Kim, Y. H.; Webster, O. W. J. Am. Chem. Soc. 1990, 112, 4592-4593.
33. Newkome, G. R.; Moorefield, C. N. Angew. Chem., Int. Ed. Engl. 1991, 30, 1178-1180.
34. Jansen, J. G. F. A.; Drabander-van den Berg, E. M. M.; Meijer, E. W. Science 1994, 266, 1226-1229.
35. Naylor, A.; Goddard, W.; Kiefer, G.; Tomalia, D. J. Am. Chem. Soc. 1989, 111, 2339-2341.
36. Pistolis, G.; Malliaris, A. Langmuir 2002, 18, 246-251.
37. Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1993, 1287-1297.
38. Richter-Egger, D.; Tesfai, A.; Tucker, S. Anal. Chem. 2001, 73, 5743-5751.
39. Yokoyama, S.; Otomo, A.; Mashiko, S. Appl. Phys. Lett. 2002, 80, 7-9.
40. Zimmerman, S.; Wednland, M.; Rakow, N.; Zharov, I.; Suslick, K. Nature 2002, 418, 399-403.
41. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358.
42. UV-vis spectra for various ratios of encapsulated Reichardt's dye in [G4]-PGLSA-OH are available in the SI (SI Figure 4).
43. See figure in the SI.
44. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed. ; VCH: Weinheim, Germany, 1988.
45. Zachariasse, K.; Phuc, N.; Kozankiewicz, B. J. Phys. Chem. 1981, 85, 2676-2683.
46. 1H COSY for both the encapsulated and free Reichardt's dye are shown in the SI (SI Figures I and 2).
47. Dwek, R. Nuclear Magnetic Resonance (NMR) Applications to Enzymatic Systems; Oxford University Press: London, 1973.
48. Wuthrich, K. NMR of Proteins and Nucleic Acids: John Wiley & Sons: New York, 1986.
49. 1H NOESY spectra of free Reichardt's dye is available in the SI (SI Figure 3).
50. Wani, M. C.; Wall, M. E. J. Org. Chem. 1968, 34, 1364-1367.