Pd tetrabenzoporphyrin-dendrimers - Near infrared phosphors for oxygen measurements by phosphorescence quenching

Proceedings of SPIE - The International Society for Optical Engineering

Volumn 4626, Issue , 2002, Pages 193-200

  Vinogradov, Sergei A ^a   Kim, Evelyn ^a   Wilson, David F ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Dendrimer; Dendritic encapsulation; Lifetime distribution; Luminescence; Non invasive imaging; Oxygen; Phosphorescence; Porphyrin; Quenching

Indexed keywords

DENDRIMERS; MEDICAL IMAGING; OXYGEN SENSORS; PHOSPHORESCENCE; PORPHYRINS; QUENCHING; TISSUE;

OXYGENATION;

PHOSPHORS;

EID: 0036405264     PISSN: 0277786X     EISSN: None     Source Type: Conference Proceeding    
DOI: 10.1117/12.472081     Document Type: Conference Paper

References (40)

1. 2 sensing using luminescence quenching by dye-doped polymeric sensors see: J.N. Demas, B.A. DeGraff, and P.B. Coleman, "Oxygen sensors based on luminescence quenching," Anal. Chem., 71, p. 793A, 1999.
2. J.M. Vanerkooi, G. Maniara, T.J. Green, and D.F. Wilson, "An optical method for measurement of dioxygen concentration based on quenching of phosphorescence," J. Biol. Chem, 262, p. 5476, 1987; D.F. Wilson, W.L. Rumsey, T.J. Green, and J.M. Vanderkooi, "The oxygen dependence of mitochondrial oxidative phosphorylation measured by a new optical method for measuring oxygen.," J. Biol. Chem., 263, 2712, 1988.
3. J.M. Vanerkooi, G. Maniara, T.J. Green, and D.F. Wilson, "An optical method for measurement of dioxygen concentration based on quenching of phosphorescence," J. Biol. Chem, 262, p. 5476, 1987; D.F. Wilson, W.L. Rumsey, T.J. Green, and J.M. Vanderkooi, "The oxygen dependence of mitochondrial oxidative phosphorylation measured by a new optical method for measuring oxygen.," J. Biol. Chem., 263, 2712, 1988.
4. J.B. Callis, J.M. Knowles, and M. Gouterman, "Porphyrins. XXVI. Triplet excimer quenching of free base Zinc, Palladium, and Platinum Complexes," J. Phys. Chem., 77, p. 154, 1973.
5. 2.
6. W.L. Rumsey, J.M. Vanderkooi, and D.F. Wilson, "Imaging of phosphorescence: A novel method for measuring the distribution of oxygen in perfused tissue.," Science, 241, p. 1649, 1988; D.F. Wilson and G. Cerniglia, "Localization of tumors and evaluation of their state of oxygenation by phosphorescence imaging," Cancer Research, 52, p. 3988, 1992; R.D. Shonat, D.F. Wilson, C.E. Riva, and M. Pawlowski, "Oxygen distribution in the retinal and choroidal vessels of the cat as measured by a new phosphorescence imaging method," Applied Optics, 33, p. 3711, 1992.
7. W.L. Rumsey, J.M. Vanderkooi, and D.F. Wilson, "Imaging of phosphorescence: A novel method for measuring the distribution of oxygen in perfused tissue.," Science, 241, p. 1649, 1988; D.F. Wilson and G. Cerniglia, "Localization of tumors and evaluation of their state of oxygenation by phosphorescence imaging," Cancer Research, 52, p. 3988, 1992; R.D. Shonat, D.F. Wilson, C.E. Riva, and M. Pawlowski, "Oxygen distribution in the retinal and choroidal vessels of the cat as measured by a new phosphorescence imaging method," Applied Optics, 33, p. 3711, 1992.
8. W.L. Rumsey, J.M. Vanderkooi, and D.F. Wilson, "Imaging of phosphorescence: A novel method for measuring the distribution of oxygen in perfused tissue.," Science, 241, p. 1649, 1988; D.F. Wilson and G. Cerniglia, "Localization of tumors and evaluation of their state of oxygenation by phosphorescence imaging," Cancer Research, 52, p. 3988, 1992; R.D. Shonat, D.F. Wilson, C.E. Riva, and M. Pawlowski, "Oxygen distribution in the retinal and choroidal vessels of the cat as measured by a new phosphorescence imaging method," Applied Optics, 33, p. 3711, 1992.
9. S.A. Vinogradov, L.-W. Lo, W.T. Jenkins, S.M. Evans, C. Koch, and D.F. Wilson, "Noninvasive imaging of distribution of oxygen in tissue in vivo using near-infrared phosphors," Biophys. J., 70, p. 1609, 1996.
10. S.A. Vinogradov and D.F. Wilson, "Phosphorescence lifetime analysis with a quadratic-programming algorithm for determining quencher distributions in heterogeneous systems," Biophys. J., 67, p. 2048, 1994; S.A. Vinogradov, M.A. Fernandez-Seara, B.W. Dugan, and D.F. Wilson, "Frequency domain instrument for measuring phosphorescence lifetime distributions in heterogeneous samples," Rev. Sci. Instrum., 72, p. 3396, 2001.
11. S.A. Vinogradov and D.F. Wilson, "Phosphorescence lifetime analysis with a quadratic-programming algorithm for determining quencher distributions in heterogeneous systems," Biophys. J., 67, p. 2048, 1994; S.A. Vinogradov, M.A. Fernandez-Seara, B.W. Dugan, and D.F. Wilson, "Frequency domain instrument for measuring phosphorescence lifetime distributions in heterogeneous samples," Rev. Sci. Instrum., 72, p. 3396, 2001.
12. Ideally "uniform" decay is single-exponential, with lifetime distribution is given by a δ-function.
13. S.A. Vinogradov and D.F. Wilson, "Dendritic" porphyrins - new protected phosphors for oxygen measurements," Adv. Exp. Med. Biol., 428, p. 657, 1997; S.A. Vinogradov, L.W. Lo, and D.F. Wilson, "Dendritic polyglutamic porphyrins: probing porphyrin protection by oxygen-dependent quenching of phosphorescence," Chem. Eur. J., 5, p. 1338, 1999.
14. S.A. Vinogradov and D.F. Wilson, "Dendritic" porphyrins - new protected phosphors for oxygen measurements," Adv. Exp. Med. Biol., 428, p. 657, 1997; S.A. Vinogradov, L.W. Lo, and D.F. Wilson, "Dendritic polyglutamic porphyrins: probing porphyrin protection by oxygen-dependent quenching of phosphorescence," Chem. Eur. J., 5, p. 1338, 1999.
15. V.V. Rozhkov, D.F. Wilson, and S.A. Vinogradov, "Tuning oxygen quenching constants using dendritic encapsulation of phosphorescent Pd-porphyrins," Polym. Mater. Sci. Eng., p. 601, 2001; V.V. Rozhkov, D.F. Wilson, S.A. Vinogradov, "Phosphorescent Pd porphyrin dendrimers: tuning core accessibility by varying hydrophobicity of dendritic matrix," Macromolecules, in press.
16. V.V. Rozhkov, D.F. Wilson, and S.A. Vinogradov, "Tuning oxygen quenching constants using dendritic encapsulation of phosphorescent Pd-porphyrins," Polym. Mater. Sci. Eng., p. 601, 2001; V.V. Rozhkov, D.F. Wilson, S.A. Vinogradov, "Phosphorescent Pd porphyrin dendrimers: tuning core accessibility by varying hydrophobicity of dendritic matrix," Macromolecules, in press.
17. D.K. Smith and F. Diederich, "Functional dendrimers: unique biological mimcs," Chem. Eur. J., 4, p. 1353, 1998; F. Vögtle, S. Gestermann, R. Hesse, H. Schwierz, and B. Windisch, "Functional dendrimers," Progr. Polym. Sci., 25, p. 987, 2000; C.B. Gorman and J.C. Smith, "Structure-property relationships in dendritic encapsulation," Acc. Chem. Res, 34, p. 60, 2001; S. Hecht and J.M.J. Fréchet, "Dendritic encapsulation of function: Applying nature's site isolation principles from biomimetics to materials science," Angew. Chem. Int. Ed., 40, p. 74, 2001.
18. D.K. Smith and F. Diederich, "Functional dendrimers: unique biological mimcs," Chem. Eur. J., 4, p. 1353, 1998; F. Vögtle, S. Gestermann, R. Hesse, H. Schwierz, and B. Windisch, "Functional dendrimers," Progr. Polym. Sci., 25, p. 987, 2000; C.B. Gorman and J.C. Smith, "Structure-property relationships in dendritic encapsulation," Acc. Chem. Res, 34, p. 60, 2001; S. Hecht and J.M.J. Fréchet, "Dendritic encapsulation of function: Applying nature's site isolation principles from biomimetics to materials science," Angew. Chem. Int. Ed., 40, p. 74, 2001.
19. D.K. Smith and F. Diederich, "Functional dendrimers: unique biological mimcs," Chem. Eur. J., 4, p. 1353, 1998; F. Vögtle, S. Gestermann, R. Hesse, H. Schwierz, and B. Windisch, "Functional dendrimers," Progr. Polym. Sci., 25, p. 987, 2000; C.B. Gorman and J.C. Smith, "Structure-property relationships in dendritic encapsulation," Acc. Chem. Res, 34, p. 60, 2001; S. Hecht and J.M.J. Fréchet, "Dendritic encapsulation of function: Applying nature's site isolation principles from biomimetics to materials science," Angew. Chem. Int. Ed., 40, p. 74, 2001.
20. D.K. Smith and F. Diederich, "Functional dendrimers: unique biological mimcs," Chem. Eur. J., 4, p. 1353, 1998; F. Vögtle, S. Gestermann, R. Hesse, H. Schwierz, and B. Windisch, "Functional dendrimers," Progr. Polym. Sci., 25, p. 987, 2000; C.B. Gorman and J.C. Smith, "Structure-property relationships in dendritic encapsulation," Acc. Chem. Res, 34, p. 60, 2001; S. Hecht and J.M.J. Fréchet, "Dendritic encapsulation of function: Applying nature's site isolation principles from biomimetics to materials science," Angew. Chem. Int. Ed., 40, p. 74, 2001.
21. D. Eastwood and M. Gouterman, "Porphyrins. XVIII. Luminescence of (Co), (Ni), Pd, Pt Complexes," J. Mol. Spectr., 35, p. 359, 1970.
22. D.B. Papkovsky, G.V. Ponomarev, W. Trettnak, and P. Oleary, "Phosphorescent complexes of porphyrin ketones: optical-properties and application to oxygen sensing," Anal. Chem., 67, p. 4112, 1995; D.B. Papkovsky, G.V. Ponomarev, and O.S. Wolfbeis, "Longwave luminescent porphyrin probes," Spectr. Acta Part A-Mol. Biomol. Spectr., 52, p. 1629, 1996.
23. D.B. Papkovsky, G.V. Ponomarev, W. Trettnak, and P. Oleary, "Phosphorescent complexes of porphyrin ketones: optical-properties and application to oxygen sensing," Anal. Chem., 67, p. 4112, 1995; D.B. Papkovsky, G.V. Ponomarev, and O.S. Wolfbeis, "Longwave luminescent porphyrin probes," Spectr. Acta Part A-Mol. Biomol. Spectr., 52, p. 1629, 1996.
24. S.A. Vinogradov and D.F. Wilson, "Extended porphyrins - New IR phosphors for oxygen measurements," Adv. Exp. Med. Biol., 411, p. 597, 1997; S.A. Vinogradov and D.F. Wilson, "Metallotetrabenzoporphyrins. New phosphorescent probes for oxygen measurements," J. Chem. Soc., Perkin Trans. II, p. 103, 1994.
25. S.A. Vinogradov and D.F. Wilson, "Extended porphyrins - New IR phosphors for oxygen measurements," Adv. Exp. Med. Biol., 411, p. 597, 1997; S.A. Vinogradov and D.F. Wilson, "Metallotetrabenzoporphyrins. New phosphorescent probes for oxygen measurements," J. Chem. Soc., Perkin Trans. II, p. 103, 1994.
26. S.A. Vinogradov, L.-W. Lo, W.T. Jenkins, S.M. Evans, C. Koch, and D.F. Wilson, "Noninvasive imaging of the distribution in oxygen in tissue in vivo using near-infrared phosphors," Biophys. J., 70, p. 1609, 1996.
27. S.A. Vinogradov, and D.F. Wilson (unpublished).
28. For review of methods see, for example: L. Edwards, M. Gouterman, and C.B. Rose, "Synthesis and vapor spectra of Zinc tetrabenzoporphyrin," J. Am. Chem. Soc., 98, p. 7638, 1976.
29. V.N. Kopranenkov, S.N. Dashkevich, and E.A. Luk'yanets, "meso-Tetraarylporphyrins," J. Gen. Chem. (Russ), 51, p. 2165, 1981; D.E. Remy, "A versatile synthesis of tetrabenzoporphyrins," Tetr. Lett., 24, p. 1452, 1983.
30. V.N. Kopranenkov, S.N. Dashkevich, and E.A. Luk'yanets, "meso-Tetraarylporphyrins," J. Gen. Chem. (Russ), 51, p. 2165, 1981; D.E. Remy, "A versatile synthesis of tetrabenzoporphyrins," Tetr. Lett., 24, p. 1452, 1983.
31. K. Ichimura, M. Sakuragi, H. Morii, M. Yasuike, M. Fukui, and O. Ohno, "Reinvestigation of synthetic methods for Zn meso-tetraphenyltetrabenzoporphyrin," Inorg. Chim. Acta, 176, p. 31, 1990.
32. M.G.H. Vicente, A.C. Tome, A. Walter, and J.A.S. Cavaleiro, "Synthesis and cycloaddition reactions of pyrrole-fused 3-sulfolenes: a new versatile route to tetrabenzoporphyrins," Tetr. Lett., 38, p. 3639, 1997.
33. S. Ito, T. Murashima, H. Uno, and N. Oho, "A new synthesis of benzoporphyrins using 4,7-dihydro-4,7-ethano-2H-isoindole as a synthon of isoindole," Chem. Commun., p. 1661, 1998; S. Ito, H. Uno, T. Murashima, and N. Ono, "Synthesis of benzoporphyrins functionalized with octaester groups," Tetr. Lett., 42, p. 45, 2001.
34. S. Ito, T. Murashima, H. Uno, and N. Oho, "A new synthesis of benzoporphyrins using 4,7-dihydro-4,7-ethano-2H-isoindole as a synthon of isoindole," Chem. Commun., p. 1661, 1998; S. Ito, H. Uno, T. Murashima, and N. Ono, "Synthesis of benzoporphyrins functionalized with octaester groups," Tetr. Lett., 42, p. 45, 2001.
35. O. Finikova, A. Cheprakov, I. Beletskaya, and S. Vinogradov, "An expedient synthesis of substituted tetraaryltetrabenzoporphyrins," Chem. Commun., p. 261, 2001.
36. K. Ichimura, M. Sakuragi, H. Morii, M. Yatsuike, M. Fukui, and O. Ohno, "Unequivocal synthesis of meso-tetraphenyltetrabenzoporphine," Inorg. Chim. Acta, 182, p. 83, 1991.
37. S.A. Vinogradov and D.F. Wilson, "Palladium catalyzed carbonylation of Br-substituted porphyrins," Tetr. Lett., 39, p. 8935, 1998.
38. The phosphorescence lifetimes and oxygen quenching constants were measured using equipment and methods described in: S.A. Vinogradov and D.F. Wilson, "Recursive maximum entropy algorithm and its application to the luminescence lifetime distribution recovery," Appl. Spectr., 54, p. 849, 2000; S.A. Vinogradov, M.A. Fernandez-Seara, B.W. Dugan, and D.F. Wilson, "Frequency domain instrument for measuring phosphorescence lifetime distributions in heterogeneous samples," Rev. Sci. Instrum., 72, p. 3396, 2001.
39. The phosphorescence lifetimes and oxygen quenching constants were measured using equipment and methods described in: S.A. Vinogradov and D.F. Wilson, "Recursive maximum entropy algorithm and its application to the luminescence lifetime distribution recovery," Appl. Spectr., 54, p. 849, 2000; S.A. Vinogradov, M.A. Fernandez-Seara, B.W. Dugan, and D.F. Wilson, "Frequency domain instrument for measuring phosphorescence lifetime distributions in heterogeneous samples," Rev. Sci. Instrum., 72, p. 3396, 2001.
40. The phosphorescence quantum yields were measured as described in ref. 15.