Water-soluble dendritic core-shell-type architectures based on polyglycerol for solubilization of hydrophobic drugs

Chemistry - A European Journal

Volumn 13, Issue 15, 2007, Pages 4187-4196

  Türk, Holger ^a,c   Shukla, Anuj ^a   Rodrigues, Paula Cristina Alves ^b   Rehage, Heinz ^a   Haag, Rainer ^a,c  

^a TU DORTMUND UNIVERSITY   (Germany)

^b Formerly Baver Material Science AG   (Germany)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Core shell architectures; Dendrimers; Drug carrier systems; Hydrophobic interactions; Supramolecular chemistry

Indexed keywords

CORE-SHELL ARCHITECTURES; DRUG-CARRIER SYSTEMS; HYDROPHOBIC INTERACTIONS; POLYGLYCEROL;

DENDRIMERS; DERIVATIVES; DRUG PRODUCTS; PYRENE; SYNTHESIS (CHEMICAL); TRANSMISSION ELECTRON MICROSCOPY;

MOLECULAR STRUCTURE;

DENDRIMER; GLYCEROL; NIMODIPINE; POLYGLYCEROL; POLYMER; PYRENE; PYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DRUG DELIVERY SYSTEM; HYDROPHOBICITY; SOLUBILITY; SYNTHESIS;

DENDRIMERS; DRUG DELIVERY SYSTEMS; GLYCEROL; HYDROPHOBICITY; NIMODIPINE; POLYMERS; PYRENES; SOLUBILITY;

EID: 34250344885     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601337     Document Type: Article

References (73)

1. a) H. Ringsdorf, B. Schlarb, J. Venzmer, Angew. Chem. 1988, 100, 117-162;
2. Angew. Chem. Int. Ed. Engl. 1988, 27, 113-158;
3. b) R. Langer, Nature 1998, 392, 5-10;
4. c) K. E. Uhrich, S. M. Cannizzaro, R. S. Langer, K. M. Shakesheff, Chem. Rev. 1999, 99, 3181-3198;
5. d) R. Duncan, Nat. Rev. Drug Discovery 2003, 2, 347-360;
6. e) R. Haag, Angew. Chem. 2004, 116, 280-284;
7. Angew. Chem. Int. Ed. 2004, 43, 278-282;
8. f) C. C. Lee, J. A. MacKay, J. M. J. Fréchet, F. C. Szoka, Nat. Biotechnol. 2005, 23, 1517-1526;
9. g) R. Satchi-Fainaro, R. Duncan, C. M. Barnes. Adv. Polym. Sci. 2006, 193, 1-65;
10. h) R. Haag, F. Kratz, Angew. Chem. 2006, 118, 1218-1237;
11. Angew. Chem. Int. Ed. 2006, 45, 1198-1215.
12. U. Gupta, H. B. Agashe, A. Asthana, N. K. Jain, Biomacromolecules 2006, 7, 649-658.
13. a) K. Kataoka, A. Harada, Y. Nagasaki, Adv. Drug Delivery Rev. 2001, 47, 113-131;
14. b) N. Nishiyama, K. Kataoka, Adv. Polym. Sci. 2006, 193, 67-101.
15. G. S. Kwon, M. Naito, K. Kataoka, M. Yokoyama, Y. Sakurai, T. Okano, Colloids Surf B 1994, 2, 429-434.
16. M.-C. Jones, M. Ranger, J.-C. Leroux, Bioconjugate Chem. 2003, 14, 774-781.
17. G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders, S. H. Grossman, Angew. Chem. 1991, 103, 1207-1209;
18. Angew. Chem. Int. Ed. Engl. 1991, 30, 1178-1180.
19. M. Liu, K. Kono, J. M. J. Fréchet, J. Controlled Release 2000, 65, 121-131.
20. C. Kojima, K. Kono, K. Maruyama, T. Takagishi, Bioconjugate Chem. 2000, 11, 910-917.
21. a) H. Liu, S. Farrell, K. E. Uhrich, J. Controlled Release 2000, 65, 167-174;
22. h) H. Liu, A. Jiang, J. Guo, K. E. Uhrich, J. Polym. Sci. A: Polym. Chem. 1999, 37, 703-711;
23. c) J. Djordjevic, M. Barch, K. E. Uhrich, Pharm. Res. 2005, 22, 24-32.
24. a) A. W. Bosman, H. M. Janssen, E. W. Meijer, Chem. Rev. 1999, 99, 1665-1688;
25. b) M. Fischer, F. Vögtle, Angew. Chem. 1999, 111, 934-955;
26. Angew. Chem. Int. Ed. 1999, 38, 884-905;
27. c) F. Zeng, S. C. Zimmerman, Chem. Rev. 1997, 97, 1681-1712;
28. d) C. Gao, D. Yan, Prog. Polym. Sci. 2004, 29, 183-275.
29. a) M. W. P. L. Baars, R. Kleppinger, M. H. J. Koch, S.-L. Yeu, E. W. Meyer, Angew. Chem. 2000, 112, 1341-1344;
30. Angew. Chem. Int. Ed. 2000, 39, 1285-1288;
31. b) A. V. Ambade, E. N. Savariar, S. Thayumanavan, Mol. Pharm. 2005, 2, 264-272.
32. R. Haag, A. Sunder, J.-F. Stumbé, J. Am. Chem. Soc. 2000, 122, 2954-2955.
33. T. Ooya, J. Lee, K. Park, J. Controlled Release 2003, 93, 121-127.
34. T. Ooya, J. Lee, K. Park, Bioconjugate Chem. 2004, 15, 1221-1229.
35. G. Pistolis, A. Malliaris, Langmuir 2002, 18, 246-251.
36. C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Parkin Trans. 1 1993, 1287-1297.
37. H. Yang, J. J. Morris, S. T. Lopina, J. Colloid Interface Sci. 2004, 273, 148-154.
38. L. J. Twyman, A. E. Beezer, R. Esfand, M. J. Hardy, J. C. Mitchell, Tetrahedron Lett. 1999, 40, 1743-1746.
39. M. T. Morgan, M. A. Carnahan, C. E. Immoos, A. A. Ribeiro, S. Finkelstein, S. J. Lee, M. W. Grinstaff, J. Am. Chem. Soc. 2003, 125, 15485-15489.
40. E. R. Gillies, J. M. J. Fréchet, J. Am. Chem. Soc. 2002, 124, 14137-14146.
41. E. R. Gillies, J. M. J. Fréchet. Bioconjugate Chem. 2005, 16, 361-368.
42. G. Chen, X. S. Ma, Z. Guan, J. Am. Chem. Soc. 2003, 125, 6697-6704.
43. G. Chen, Z. Guan, J. Am. Chem. Soc. 2004, 126, 2662-2663.
44. a) A. Sunder, R. Mülhaupt, DE-19947631 A1, 1998;
45. b) R. Haag, H. Turk, S. Mecking, DE-10211664 A1, 2002.
46. A. Sunder, R. Hanselmann, H. Frey, R. Mülhaupt, Macromolecules 1999, 32, 4240-4246.
47. A. Sunder, R. Mülhaupt, R. Haag, H. Frey. Adv. Mater. 2000, 12, 235-239.
48. H. Frey, R. Haag, Rev. Mol. Biotechnol. 2002, 90, 257-267.
49. R. K. Kainthan, J. Janzen, E. Levin, D. V. Devine, D. E. Brooks, Biomacromolecules 2006, 7, 703-709.
50. a) D. Howes, R. Wilson, C. T. James, Food Chem. Toxicol. 1998, 36, 719-738;
51. b) R. Wilson, B. J. Van Schie, D. Howes, Food Chem. Toxicol. 1998, 36, 711-718.
52. R. Haag, J.-F. Stumbé, A. Sunder, H. Frey, A. Hebel, Macromolecules 2000, 33, 8158-8166.
53. M. Krämer, J.-F. Stumbé, H. Türk, S. Krause, A. Komp, L. Delineau, S. Prokhorova, H. Kautz, R. Haag, Angew. Chem. 2002, 114, 4426-4431;
54. Angew. Chem. Int. Ed. 2002, 41, 4252-4256.
55. H. Turk, PhD Thesis, University of Dortmund (Germany), 2006.
56. J. Uenishi, M. Motoyama, K. Takahashi, Tetrahedron: Asymmetry 1994, 5, 101-110.
57. a) A. Hebel, R. Haag, J. Org. Chem. 2002, 67, 9452-9455;
58. b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
59. R. Haag, A. Sunder, A. Hebel, S. Roller, J. Comb. Chem. 2002, 4, 112-119.
60. H. Meyer, F. Bossert, W. Vater, K. Stoepel, US-3799934, 1983.
61. A. Grunenberg, B. Keil, J.-O. Henck, Int. J. Pharm. 1995, 118, 11-21; in our own measurements we observed a solubility of 1.1 mg L-1.
62. D. Hoff, DE-3316510 A1, 1983.
63. P. Kurka, P. Serno, R. Rupp, B. Klinksiek, K.-H. Dee, H.-D. Friedel, EP-560138 A1, 1993.
64. a) D. Yan, Y. Zhou, J. Hou, Science 2004, 303, 65-67;
65. b) Y. Zhou, D. Yan. Angew. Chem. 2004, 116, 5004-5007;
66. Angew. Chem. Int. Ed. 2004, 43, 4896-4899.
67. M. Kellermann, W. Bauer, A. Hirsch, B. Schade, K. Ludwig, C. Böttcher, Angew. Chem. 2004, 116, 3019-3022;
68. Angew. Chem. Int. Ed. 2004, 43, 2959-2962.
69. D. R. Vutukuri, S. Basu, S. Thayumanavan, J. Am. Chem. Soc. 2004, 126, 15636-15637.
70. V. M. Garamus, T. V. Maksimova, H. Kautz, E. Barriau, H. Frey, U. Schlotterbeck, S. Mecking, W. Richtering, Macromolecules 2004, 37, 8394-8399.
71. a) J.-P. Xu, J. Ji, W.-D. Chen, J.-C. Shen, Macromol. Biosci. 2005, 5, 164-171;
72. b) M. Ogawa, A. Momotake, T. Arai, Tetrahedron Lett. 2004, 45, 8515-8518.
73. C.-J. Jang, J.-H. Ryu, J.-D. Lee, D. Sohn, M. Lee, Chem. Mater. 2004, 76, 4226-4231.