Porphyrin and tetrabenzoporphyrin dendrimers: Tunable membrane-impermeable fluorescent pH nanosensors

Journal of the American Chemical Society

Volumn 125, Issue 16, 2003, Pages 4882-4893

  Finikova, Olga ^a   Galkin, Alexander ^b   Rozhkov, Vladimir ^a   Cordero, Maria ^a   Hägerhäll, Cecilia ^b   Vinogradov, Sergei ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CHARACTERIZATION; FLUORESCENCE; MEMBRANES; PH EFFECTS; PHOSPHOLIPIDS; PORPHYRINS; PROTONS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

PROTON GRADIENTS;

DENDRIMERS;

CARBOXYLIC ACID; DENDRIMER; PORPHYRIN DERIVATIVE; TETRABENZOPORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; ENCAPSULATION; FLUORESCENCE; HYDROPHILICITY; MEMBRANE PERMEABILITY; MOLECULAR SIZE; NANOTECHNOLOGY; PH; PHOSPHOLIPID MEMBRANE; PREDICTION; SENSOR; SOLUBILITY; STATISTICAL SIGNIFICANCE; TITRIMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

BENZENE DERIVATIVES; ELECTROSTATICS; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; KINETICS; MODELS, MOLECULAR; NANOTECHNOLOGY; POLYMERS; PORPHYRINS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; TITRIMETRY;

EID: 0242515825     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0341687     Document Type: Article

References (104)

1. For selected reviews, see: (a) Fréchet, J. M. J. Science 1994, 263, 1710.
2. (b) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1999, 38, 885.
3. (c) Grayson, S. K.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819.
4. (d) Tomalia, D. A.; Fréchet, J. M. J. J. Polym. Sci., A 2002, 40, 2719.
5. For selected reviews, see: (a) Smith, D. K.; Diederich, F. Chem. - Eur. J. 1998, 4, 1353.
6. (b) Gorman, C. B.; Smith, J. C. Acc. Chem. Res. 2001, 34. 60.
7. (c) Vögtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987.
8. (d) Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74.
9. (e) Dykes, G. M. J. Chem. Technol. Biotechnol. 2001, 76, 903.
10. (f) Stiriba, S. E.; Frey, H.; Haag, R. Angew. Chem., Int. Ed. 2002, 41, 1329.
11. (g) Cameron, C. S.; Gorman, C. B. Adv. Funct. Mater. 2002, 12, 17.
12. (a) Stewart, G. M.; Fox, M. A. J. Am. Chem. Soc. 1996, 118, 4354.
13. (b) Devadoss, C.; Bharathi, P.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 9635.
14. (c) Plevoets, M.: Vögtle, F.; De Cola, L.; Balzani, V. New J. Chem. 1999, 23, 63.
15. (d) Gilat, S. L.; Adronov, A.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 1999, 38, 1422.
16. (f) Schultze, X.; Serin, J.; Adronov, A.; Fréchet, J. M. J. Chem. Commun. 2001, 1160.
17. (g) Choi, M. S.; Aida, T.; Yamazaki, T.; Yamazaki, I. Angew. Chem., Int. Ed. 2001, 40, 3194.
18. (a) Sadamoto, R.; Nobuyuki, T.; Aida, T. J. Am. Chem. Soc. 1996, 118, 3978.
19. (b) Gorman, C. B.; Smith, J. C.; Hager, M. W.; Parkhurst, B. L.; Sierzputowska-Gracz, H.; Haney, C. A. J. Am. Chem. Soc. 1999, 121, 9958.
20. (c) Camps, X.; Dietel, E.; Hirsch, A.; Pyo, S.; Echegoyen, L.; Hackbarth, S.; Roder, R. Chem. - Eur. J. 1999, 5, 2362.
21. (d) Capitosti, G. J.; Cramer, S. J.; Rajesh, C. S.; Modarelli, D. A. Org. Lett. 2001, 3, 1645.
22. (e) Rajesh, C. S.; Capitosti, G. J.; Cramer, S. J.; Modarelli, D. A. J. Phys. Chem. B 2001, 105, 10175.
23. (f) Toba, R.; Quintela, J. M.; Peinador, C.; Roman, E.; Kaifer, A. E. Chem. Commun. 2001, 857.
24. (g) Ghaddar, T. H.; Wishart, J. F.; Thompson, D. W.; Whitesell, J. K.; Fox, M. A. J. Am. Chem. Soc. 2002, 124, 8285.
25. (g) Lor, M.; Thielemans, J.; Viaene, L.; Cotlet, M.; Hofkens, J.; Weil, T.; Hampel, C.; Mullen, K.; Verhoeven, J. W.; Van der Auweraer, M.; De Schryver, F. C. J. Am. Chem. Soc. 2002, 124, 9918.
26. (a) Bar-Haim, A.; Klafter, J. J. Lumin. 1998, 76, 197.
27. (b) Adronov, A.; Gilat, S. L.; Fréchet, J. M. J.; Ohta, K.; Neuwahl, F. V. R.; Fleming, G. R. J. Am. Chem. Soc. 2000, 122, 1175.
28. (c) Balzani, V.; Juris, A. Coord. Chem. Rev. 2001, 211, 97.
29. (d) Adronov, A.; Robello, D. R.; Fréchet, J. M. J. J. Polym. Sci., A 2001, 39, 1366.
30. (a) Bhyrappa, P.; Young, J. K.; Moore, J. S.; Suslick, K. S. J. Am. Chem. Soc. 1996, 118, 5708.
31. (b) Bhyrappa, P.; Vaijayanthimala, G.; Suslick, K. S. J. Am. Chem. Soc. 1999, 121, 262.
32. (c) Kimura, M.; Shiba, T.; Yamazaki, M.; Hanabusa, K.; Shirai, H.; Kobayashi, N. J. Am. Chem. Soc. 2001, 123, 5636-5642.
33. (d) Hecht, S.; Fréchet, J. M. J. J. Am. Chem. Soc. 2001, 123, 6959.
34. (e) Davis, A. V.; Driffield, M.; Smith, D. K. Org. Lett. 2001, 3, 3075.
35. (f) Uyemura, M.; Aida, T. J. Am. Chem. Soc. 2002, 124, 11392.
36. (g) Zhang, J. L.; Zhou, H. B.; Huang, J. S.; Che, C. M. Chem. - Eur. J. 2002, 8, 1554.
37. (i) Twyman, L. J.; King, A. S. H.; Martin, I. K. Chem. Soc. Rev. 2002, 31, 69 and references therein.
38. (a) Jin, R. H.; Aida, T.; Inoue, S. Chem. Commun. 1993, 1260.
39. (b) Dandliker, P. J.; Diederich, F.; Gisselbrecht, J. P.; Louati, A.; Gross, M. Angew. Chem., Int. Ed. Engl. 1996, 34, 2725.
40. (c) Tomoyose, Y.; Jiang, D. L.; Jin, R. H.; Aida, T.; Yamashita, T.; Horie, K.; Yashima, E.; Okamoto, Y. Macromolecules 1996, 29, 5236.
41. (d) Collman, J. P.; Fu, L.; Zingg, A.; Diederich, F. Chem. Commun. 1997, 193.
42. (e) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773.
43. (f) Pollak, K. W.; Sanford, E. M.; Fréchet, J. M. J. J. Mater. Chem. 1998, 8, 519.
44. (g) Tomioka, N.; Takasu, D.; Takahashi, T.; Aida, T. Angew. Chem., Int. Ed. 1998, 37, 1531.
45. (i) Weyermann, P.; Diederich, F. J. Chem. Soc., Perkin Trans. 1 2000, 4231.
46. (j) Matos, M. S.; Hofkens, J.; Verheijen, W.; De Schryver, F. C.; Hecht, S.; Pollak, K. W.; Fréchet, J. M. J.; Forier, B.; Dehaen, W. Macromolecules 2000, 33, 2967.
47. (k) Weyermann, P.; Diederich, F. Helv. Chim. Acta 2002, 85, 599.
48. (l) Van Doorslaer, S.; Zingg, A.; Schweiger, A.; Diederich, F. ChemPhysChem 2002, 3, 65.
49. (a) Issbemer, J.; Vögtle, F.; De Cola, L.; Balzani, V. Chem. - Eur. J. 1997, 3, 706.
50. (b) Kawa, M.; Fréchet, J. M. J. Chem. Mater. 1998, 10, 286.
51. (c) Gorman, C. B.; Hager, M. W.; Parkhurst, B. L.; Smith, J. C. Macromolecules 1998, 31, 815.
52. (d) Cardona, C. M.; Kaifer, A. E. J. Am. Chem. Soc. 1998, 120, 4023.
53. (e) Vögtle, F.; Plevoets, M.; Nieger, M.; Azzellini, G. C.; Credi, A.; De Cola, L.; De Marchis, V.; Venturi, M.; Balzani, V. J. Am. Chem. Soc. 1999, 121, 6290.
54. (f) Gorman, C. B.; Smith, J. C. J. Am. Chem. Soc. 2000, 122, 9342.
55. (g) Koenig, S.; Muller, L.; Smith, D. K. Chem. - Eur. J. 2001, 7, 979.
56. (i) Stone, D. L.; Smith, D. K.; McGrail, P. T. J. Am. Chem. Soc. 2002, 124, 856.
57. (j) Goldsmith, J. I.; Takada, K.; Abruna, H. D. J. Phys. Chem. B 2002, 106, 8504.
58. (a) Vinogradov, S. A.; Wilson, D. F. Adv. Exp. Med. Biol. 1997, 428, 657.
59. (b) Vinogradov, S. A.; Lo, L. W.; Wilson, D. F. Chem. - Eur. J. 1999, 5, 1338.
60. (c) Vinogradov, S. A.; Wilson, D. F. Chem. - Eur. J. 2000, 6, 2456.
61. (d) Rozhkov, V.; Wilson, D. F.; Vinogradov, S. Macromolecules 2002, 35, 1991.
62. Lash, T. D. Syntheses of novel porphyrinoid chromophores. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000.
63. Handbook of Fluorescent Probes and Research Products, Web edition at: http://www.probes.com/handbook/Ch. 21; Molecular Probes, Inc.
64. (a) Hägerhäll, C. Biochim. Biophys. Acta 1997, 1320, 107.
65. (b) Galkin, A. S.; Grivennikova, V. G.; Vinogradov, A. D. FEBS Lett. 1999, 451, 157.
66. Senge, M. O.; Highly substituted porphyrins. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000.
67. Lash, T. D. J. Porphyrins Phthalocyanines 2001, 5, 267.
68. Hambright, P. Chemistry of water soluble porphyrins. In The Porphyrin Handbook, Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000.
69. Valiotti, A.; Adeyemo, A.; Williams, R. F. X.; Ricks, L.; North, J.; Hambright, P. J. Inorg. Nucl. Chem. 1981, 43, 2653.
70. (a) Medforth, C. J.; Smith, K. M. Tetrahedron Lett. 1990, 31, 5583.
71. (b) Barkigia, K. M.: Berber, M. D.; Fajer, J.; Medforth, C. J.; Renner, M. W.; Smith, K. M. J. Am. Chem. Soc. 1990, 112, 8851.
72. (c) Takeda, J.; Ohya, T.; Sato, M. Inorg. Chem. 1992, 31, 2877.
73. Kohata, K.; Higashio, H.; Yamaguchi, Y.; Koketsu, M.; Odashima, T. Bull. Chem. Soc. Jpn. 1994, 67, 668.
74. A series of Pd tetrabenzoporphyrin dendrimers for in vivo oxygen imaging were recently synthesized: Rietveld, I.; Kim, E.; Vinogradov, S. Tetrahedron 2003, in press.
75. Finikova, O.; Cheprakov, A.; Carroll, P.; Dalosto S., Vinogradov, S. Inorg. Chem. 2002, 41, 6944.
76. (a) Stone, A.; Fleisher, E. B. J. Am. Chem. Soc. 1968, 90, 2735.
77. (b) Cheng, B.; Munro, O. Q.; Marques, H. M.; Scheidt, W. R. J. Am. Chem. Soc. 1997, 119, 10732.
78. Cheng, R. J.; Chen, Y. R.; Wang, S. L.; Cheng, C. Y. Polyhedron 1993, 12, 1353.
79. (a) Gentemann, S.; Medforth, C. J.; Forsyth, T. P.; Nurco, D. J.; Smith, K. M.; Fajer, J.; Holten, D. J. Am. Chem. Soc. 1994, 116, 7363.
80. (b) Gentemann, S.; Medforth, C. J.; Ema, T.; Nelson, N. Y.; Smith, K. M.; Fajer, J.; Holten, D. Chem. Phys. Lett. 1995, 245, 441.
81. (c) Sazanovich, I. V.; Galievsky, V. A.; van Hoek, A.; Schaafsma, T. J.; Malinovskii, V. L.; Holten, D.; Chirvony, V. S. J. Phys. Chem. B 2001, 105, 7818.
82. (a) Kimura, M.; Nakada, K.; Yamaguchi, Y.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Commun. 1997, 1215.
83. (b) Brewis, M.; Clarkson, G. J.; Goddard, V.; Helliwell, M.; Holder, A. M.; McKeown, N. B. Angew. Chem., Int. Ed. 1998, 37, 1092.
84. (c) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. - Eur. J. 1999, 5, 3495.
85. (d) Brewis, M.; Helliwell, M.; McKeown, N. B.; Reynolds, S.; Shawcross, A. Tetrahedron Lett. 2001, 42, 813.
86. Adler, A. D.; Longo, F. R.; Shergalis, W. D. J. Am. Chem. Soc. 1964, 86, 3145.
87. Twyman, L.; Beezer, A. E.; Mitchell, J. C. Tetrahedron Lett. 1994, 35, 4423.
88. (a) Ito, S.; Murashima, T.; Uno, H.; Ono, N. Chem. Commun. 1998, 1661.
89. (b) Ito, S.; Uno, H.; Murashima, T.; Ono, N. Tetrahedron Lett. 2001, 42, 45.
90. Finikova, O.; Cheprakov, A.; Beletskaya, I.; Vinogradov, S. Chem. Commun. 2001, 261.
91. (a) Newkome, G. R.; Lin, X. Macromolecules 1991, 24, 1443.
92. (b) Newkome, G. R.; Lin, X.: Young, J. K. Synlett 1992, 53.
93. Nicholls, A.; Sharp, K. A.; Honig, H. Proteins 1991, 11, 281.
94. Mitchell, P.; Moyle J. Nature 1967, 213, 137.
95. Rigaud, J. L.; Pitard, B.; Levy, D. Biochim. Biophys. Acta 1995, 1231, 223.
96. Driessen, A. J.M.; De Vrij, W.; Konings, W. N. Eur. J. Biochem. 1986, 154, 617.
97. Molecular diameter was determined by taking a few measurements across the calculated dendrimer molecule and averaging the obtained distances.
98. Harold, F. M.; Baarda, J. R. J. Bacteriol. 1967, 94, 53.
99. Urry, D. W.; Goodall, M. C.; Glickson, J. D.; Mayers, D. F. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1907.
100. Seybold, P. G.; Gouterman, M. J. Mol. Spectrosc. 1969, 31, 1.
101. (a) Haake, G.; Struve, D.; Montforts, F. P. Tetrahedron Lett. 1994, 35, 9703.
102. (b) Abel, Y.; Haake, E.; Haake, G.; Schmidt, W.; Struve, D.; Walter, A.; Montforts, F. P. Helv. Chim. Acta 1998, 81, 1978.
103. (c) Hopkins, P. B.; Fush, P. L. J. Org. Chem. 1978, 43, 1208.
104. Perlman, W. M. Tetrahedron Lett. 1967, 17, 1663.