Dendrimers with tetrabenzoporphyrin cores: Near infrared phosphors for in vivo oxygen imaging

Tetrahedron

Volumn 59, Issue 22, 2003, Pages 3821-3831

  Rietveld, Ivo B ^a   Kim, Evelyn ^a   Vinogradov, Sergei A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Dendrimer; Dendritic encapsulation; Laterally extended porphyrin; Luminescence; Non invasive imaging; Oxygen; Phosphorescence; Porphyrin; Quenching

Indexed keywords

DENDRIMER; MACROGOL; OXYGEN; PHOSPHORUS; POLYGLUTAMIC ACID; PORPHYRIN DERIVATIVE; PROTEIN; SERUM ALBUMIN; TETRABENZOPORPHYRIN; UNCLASSIFIED DRUG; WATER;

ANALYTICAL PARAMETERS; ARTICLE; COMPLEX FORMATION; ENCAPSULATION; IMAGING; IN VIVO STUDY; INFRARED RADIATION; LIPOPHILICITY; OPTICS; PRIORITY JOURNAL; PROTEIN BINDING; SOLUBILITY; SYNTHESIS;

EID: 0037737942     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00432-0     Document Type: Article

References (88)

1. For selected reviews, see: (a) Smith D.K., Diederich F. Chem. Eur. J. 4:1998;1353-1361.
2. (b) Fischer M., Vögtle F. Angew. Chem. Int. Ed. 38:1999;885-905.
3. (c) Vögtle F., Gestermann S., Hesse R., Schwierz H., Windisch B. Prog. Polym. Sci. 25:2000;987-1041.
4. (d) Dykes G.M. J. Chem. Tech. Biotech. 76:2001;903-918.
5. (e) Grayson S.K., Fréchet J.M.J. Chem. Rev. 101:2001;3819-3867.
6. (a) Krause W., Hackmann-Schlichter N., Maier F., Muller R. Dendrimers in diagnostics. In Dendrimers II. Architecture, Nanostructure and Supramolecular Chemistry. Topics in Current Chemistry; Vögtle, F. Ed.; Springer: New York, 2000; Vol. 210, pp 261-308.
7. (b) Stiriba S.E., Frey H., Haag R. Angew. Chem. Int. Ed. 41:2002;1329-1334.
8. (a) Hecht S., Fréchet J.M.J. Angew. Chem. Int. Ed. 40:2001;74-91.
9. (b) Gorman C.B., Smith J.C. Acc. Chem. Res. 34:2001;60-71.
10. For a review, see: Demas J.N., DeGraff B.A., Coleman P.B. Anal. Chem. 71:1999;793A-800A.
11. (a) Vanerkooi J.M., Maniara G., Green T.J., Wilson D.F. J. Biol. Chem. 262:1987;5476-5482.
12. (b) Wilson D.F., Rumsey W.L., Green T.J., Vanderkooi J.M. J. Biol. Chem. 263:1988;2712-2718.
13. (c) Rumsey W.L., Vanderkooi J.M., Wilson D.F. Science. 241:1988;1649.
14. (a) Pawlowski M., Wilson D.F. Adv. Exp. Med. Biol. 316:1992;179-185
15. (b) Wilson D.F., Cerniglia G. Cancer Res. 52:1992;3988-3992.
16. (c) Vinogradov S.A., Lo L.-W., Jenkins W.T., Evans S.M., Koch C., Wilson D.F. Biophys. J. 70:1996;1609-1617.
17. (d) Shonat R.D., Wachman E.S., Niu W.H., Koretsky A.P., Farkas D.L. Biophys. J. 73:1997;1223-1231.
18. (e) Howlett R.A., Hogan M.C. J. Appl. Physiol. 91:2001;632-636.
19. (f) Bonanno J.A., Stickel T., Nguyen T., Biehl T., Carter D., Benjamin W.J., Soni P.S. Invest. Ophthalmol. Visual Sci. 43:2002;371-376.
20. (g) Smith L.M., Golub A.S., Pittman R.N. Microcirculation. 9:2002;389-395.
21. 2O Fogg P.G.T., Gerrard W. Solubility of Gases in Liquids. 2001;Wiley, New York.
22. (a) Issberner J., Vögtle F., De Cola L., Balzani V. Chem. Eur. J. 3:1997;706-712.
23. (b) 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. 121:1999;6290-6298.
24. (a) Jin R.H., Aida T., Inoue S. J. Chem. Soc., Chem. Commun. 1993;1260-1262.
25. (b) Sadamoto R., Nobuyuki T., Aida T. J. Am. Chem. Soc. 118:1996;3978-3979.
26. (c) Pollak K.W., Leon J.W., Fréchet J.M.J., Maskus M., Abruna H.D. Chem. Mater. 10:1998;30-38.
27. (d) 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. 33:2000;2967-2973.
28. (e) Riley J.M., Alkan S., Chen A.D., Shapiro M., Khan W.A., Murphy W.R., Hanson J.E. Macromolecules. 34:2001;1797-1809.
29. (f) Cardona C.M., Wilkes T., Ong W., Kaifer A.E., McCarley T.D., Pandey S., Baker G.A., Kane M.N., Baker S.N., Bright F.V. J. Phys. Chem. B. 106:2002;8649-8656.
30. (a) Diederich F., Felber B. Proc. Natl Acad. Sci. USA. 99:2002;4778-4781. and references therein.
31. (b) Van Doorslaer S., Zingg A., Schweiger A., Diederich F. ChemPhysChem. 3:2002;659-667.
32. (c) Weyermann P., Diederich F., Gisselbrecht J.P., Boudon C., Gross M. Helv. Chim. Acta. 85:2002;571-598.
33. (d) Weyermann P., Diederich F. Helv. Chim. Acta. 85:2002;599-617.
34. (e) Zingg A., Felber B., Gramlich V., Fu L., Collman J.P., Diederich F. Helv. Chim. Acta. 85:2002;333-351.
35. (f) Uyemura M., Aida T. J. Am. Chem. Soc. 124:2002;11392-11403.
36. (a) Capitosti G.J., Cramer S.J., Rajesh C.S., Modarelli D.A. Org. Lett. 3:2001;1645-1648.
37. (b) Rajesh C.S., Capitosti G.J., Cramer S.J., Modarelli D.A. J. Phys. Chem. B. 105:2001;10175-10188.
38. (a) Bhyrappa P., Young J.K., Moore J.S., Suslick K.S. J. Am. Chem. Soc. 118:1996;5708-5711.
39. (b) Bhyrappa P., Vaijayanthimala G., Suslick K.S. J. Am. Chem. Soc. 121:1999;262-263.
40. (c) Kimura M., Shiba T., Yamazaki M., Hanabusa K., Shirai H., Kobayashi N. J. Am. Chem. Soc. 123:2001;5636-5642.
41. (d) Zhang J.L., Zhou H.B., Huang J.S., Che C.M. Chem. Eur. J. 8:2002;1554-1562.
42. (a) Jiang D.L., Aida T. J. Am. Chem. Soc. 120:1998;10895-10901.
43. (b) Choi M.S., Aida T., Yamazaki T., Yamazaki I. Chem. Eur. J. 8:2002;2668-2678.
44. (c) Onitsuka K., Kitajima H., Fujimoto M., Iuchi A., Takei F., Takahashi S. Chem. Commun. 2002;2576-2577.
45. (a) Vinogradov S.A., Wilson D.F. Adv. Exp. Med. Biol. 428:1997;657-662.
46. (b) Vinogradov S.A., Lo L.W., Wilson D.F. Chem. Eur. J. 5:1999;1338-1347.
47. (a) Rozhkov V.V., Wilson D.F., Vinogradov S.A. Polym. Mater. Sci. Eng. 2001;601-603.
48. (b) Rozhkov V., Wilson D., Vinogradov S. Macromolecules. 35:2002;1991-1993.
49. Adler A.D., Longo F.R., Shergalis W.D. J. Am. Chem. Soc. 86:1964;3145-3149.
50. Lindsey J.S., Schreiman I.C., Hsu H.C., Kearney P.C., Marguerettaz A.M. J. Org. Chem. 52:1987;827-836.
51. Eastwood D., Gouterman M.J. Mol. Spectr. 35:1970;359-375.
52. (a) Papkovsky D.B., Ponomarev G.V., Trettnak W., Oleary P. Anal. Chem. 67:1995;4112-4117.
53. (b) Papkovsky D.B., Ponomarev G.V., Wolfbeis O.S. Spectrochim. Acta A-Mol. Biomol. Spectr. 52:1996;1629-1638.
54. (a) Vinogradov S.A., Wilson D.F. J. Chem. Soc., Perkin Trans. 2. 1994;103-111.
55. (b) Vinogradov S.A., Wilson D.F. Adv. Exp. Med. Biol. 411:1997;597-603.
56. (a) Kimura M., Nakada K., Yamaguchi Y., Hanabusa K., Shirai H., Kobayashi N. Chem. Commun. 1997;1215-1216.
57. (b) Brewis M., Clarkson G.J., Goddard V., Helliwell M., Holder A.M., McKeown N.B. Angew. Chem. Int. Ed. 37:1998;1092-1094.
58. (c) Kimura M., Sugihara Y., Muto T., Hanabusa K., Shirai H., Kobayashi N. Chem. Eur. J. 5:1999;3495-3500.
59. (d) Brewis M., Helliwell M., McKeown N.B., Reynolds S., Shawcross A. Tetrahedron Lett. 42:2001;813-816.
60. For review see: Lash, T.D. In The Porphyrin Handbook. Syntheses of novel porphyrinoid chromophores; Kadish, K. M., Smith, K. M., Guilard. R., Ed.; Academic: New York. 2000; Vol. 2, pp 125-199.
61. (a) Kopranenkov V.N., Dashkevich S.N., Luk'yanets E.A. J. Gen. Chem. (Russ). 51:1981;2165-2168.
62. (b) Remy D.E. Tetrahedron Lett. 24:1983;1452-1454.
63. (a) Vicente M.G.H., Tome A.C., Walter A., Cavaleiro J.A.S. Tetrahedron Lett. 38:1997;3639-3642.
64. (b) Ito S., Murashima T., Uno H., Ono N. Chem. Commun. 1998;1661-1662.
65. (c) Ito S., Uno H., Murashima T., Ono N. Tetrahedron Lett. 42:2001;45-47.
66. (d) Finikova O., Cheprakov A., Beletskaya I., Vinogradov S. Chem. Commun. 2001;261-262.
67. Ichimura K., Sakuragi M., Morii H., Yatsuike M., Fukui M., Ohno O. Inorg. Chim. Acta. 182:1991;83-86.
68. Vinogradov S.A., Wilson D.F. Tetrahedron Lett. 39:1998;8935-8938.
69. (a) Dandliker P.J., Diederich F., Gisselbrecht J.P., Louati A., Gross M. Angew. Chem. Int. Ed. Engl. 34:1996;2725-2728.
70. (b) Dandliker P.J., Diederich F., Zingg A., Gisselbrecht J.P., Gross M., Louati A., Sanford E. Helv. Chim. Acta. 80:1997;1773-1801.
71. (a) Liu M., Kono K., Fréchet J.M.J. J. Polym. Sci. A Polym. Chem. 37:1999;3492-3503.
72. (b) Liu M., Kono K., Fréchet J.M.J. J. Controlled Release. 65:2000;121-131.
73. Twyman L., Beezer A.E., Mitchell J.C. Tetrahedron Lett. 35:1994;4423-4424.
74. For examples see: (a) Maiti N.C., Mazumdar S., Periasamy N. J. Phys. Chem. B. 102:1998;1528-1538.
75. (b) Khairutdinov R.F., Serpone N. J. Phys. Chem. B. 1999;761-769. and references therein.
76. (a) Cheng R.J., Chen Y.R., Wang S.L., Cheng C.Y. Polyhedron. 12:1993;1353-1360.
77. (b) Finikova O.S., Cheprakov A.V., Carroll P.J., Dalosto S., Vinogradov S.A. Inorg. Chem. 41:2002;6944-6946.
78. Callis J.B., Knowles J.M., Gouterman M. J. Phys. Chem. 77:1973;154-156.
79. 2 scavenger for aqueous solutions.
80. Tomoyose Y., Jiang D.L., Jin R.H., Aida T., Yamashita T., Horie K., Yashima E., Okamoto Y. Macromolecules. 29:1996;5236-5238.
81. 14.
82. (a) Phillips D. Analyst. 119:1994;543-550.
83. (b) Borissevitch I.E., Tominaga T.T., Imasato H., Tabak M.J. Luminescence. 69:1996;65-76.
84. Dunphy I., Vinogradov S.A., Wilson D.F. Analyt. Biochem. 310:2002;191-198.
85. Vinogradov S.A., Fernandez-Seara M.A., Dugan B.W., Wilson D.F. Rev. Sci. Instrum. 72:2001;3396-3406.
86. Koch, C. J. Canadian Patent 1992, June 30, 1304449.
87. Seybold P.G., Gouterman M. J. Mol. Spectrosc. 31:1969;1.
88. Quimby D.J., Longo F.R. J. Am. Chem. Soc. 97:1975;5111-5117.