Charge dependence of cellular uptake and selective antitumor activity of porphyrazines

Journal of Medicinal Chemistry

Volumn 48, Issue 26, 2005, Pages 8125-8133

  Hammer, Neal D ^a,c   Lee, Sangwan ^b   Vesper, Benjamin J ^b   Elseth, Kim M ^a,c   Hoffman, Brian M ^b   Barrett, Anthony G M ^d   Radosevich, James A ^a,c  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c JESSE BROWN VA MEDICAL CENTER   (United States)

^d IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; MACROCYCLIC COMPOUND; NITROGEN; PHTHALOCYANINE; PORPHYRAZINE DERIVATIVE; PORPHYRIN; TETRAAZAPORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOCOMPATIBILITY; CANCER CELL CULTURE; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG UPTAKE; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; LUNG ADENOCARCINOMA; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE; CELL LINE, TUMOR; CELL PROLIFERATION; CROWN COMPOUNDS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MICROSCOPY, CONFOCAL; PHOTOSENSITIZING AGENTS; PORPHYRINS;

EID: 29744464313     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050466y     Document Type: Article

References (47)

1. Kessel, D.; Dougherty, T. J. Agents Used in Photodynamic Therapy. Rev. Contemp. Pharmacother. 1999, 10, 19-24.
2. Dolmans, D. E. J. G. J.; Fukumura, D.; Jain, R. K. Photodynamic Therapy for Cancer. Nat. Rev. Cancer 2003, 3, 380-387.
3. Bonnett, R. Photosensitizers of the Porphyrin and Phthalocyanine Series for Photodynamic Therapy. Chem. Soc. Rev. 1995, 19-33.
4. Pandey, R. K.; Zheng, G. Porphyrins as Photosensitizers in Photodynamic Therapy. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000; Vol. 6, pp 157-227.
5. Jiang, H.; Iftimia N. V.; Xu, Y.; Eggert J. A.; Fajardo L. L.; Klove K. L. Near-Infrared Optical Imaging of the Breast with Model-Based Reconstruction. Acad. Radiol. 2002, 9, 186-194.
6. Weissleder, R.; Ntziachristos, V. Shedding Light onto Live Molecular Targets. Nat. Med. 2003, 9, 123-128.
7. Sevick-Muraca, E. M.; Godavarty, A.; Houston, J. P.; Thompson, A. B.; Roy, R. Near-Infrared Imaging with Fluorescent Contrast Agents. In Fluorescence in Biomedicine; Pogue, B. W., Mycek, M., Eds.; Marcel Dekker: New York, 2003; pp 445-527.
8. Chance, B.; Alfano, R. R.; Tromberg, B. J.; Tamura, M.; Sevick-Muraca, E. M.; Eds. Proceedings of the SPIE International Conference on Optical Tomography and Spectroscopy of Tissue V; January 26-29, 2003, San Jose, CA
9. [In Proc. SPIE-Int. Soc. Opt. Eng. 2003, 4955].
10. Quaresima, V.; Matcher, S. J.; Ferrari, M. Identification and Quantification of Intrinsic Optical Contrast for Near-Infrared Mammography. Photochem. Photobiol. 1998, 67, 4-14.
11. Troy, T. L.; Page, D. L.; Sevick-Muraca, E. M. Optical Properties of Normal and Diseased Breast Tissues: Prognosis for Optical Mammography. J. Biomed. Opt. 1996, 1, 342-355.
12. de Haller, E. B. Time-Resolved Transillumination and Optical Tomography. J. Biomed. Opt. 1996, 1, 7-17.
13. MacDonald, I. J.; Dougherty, T. J. Basic Principles of Photodynamic Therapy. J. Porphyrins Phthalocyanines 2001, 5, 105-129.
14. Allen, C. M.; Sharman, W. M.; Van Lier, J. E. Current Status of Phthalocyanines in the Photodynamic Therapy of Cancer. J. Porphyrins Phthalocyanines 2001, 5, 161-169.
15. Liu, W.; Jensen, T. J.; Fronczek, F. R.; Hammer, R. P.; Smith, K. M.; Vicente, M. G. H. Synthesis and Cellular Studies of Nonaggregated Water-Soluble Phthalocyanines. J. Med. Chem. 2005, 48, 1033-1048.
16. Chowdhary, R. K.; Sheriff, I.; Dolphin, D. Drug Release Characteristics of Lipid Based Benzoporphyrin Derivative. J. Pharm. Pharm. Sci. 2003, 6, 13-19.
17. Pandey, R. K. Synthetic strategies in designing porphyrin-based photosensitizers for photodynamic therapy. In CAC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; pp 144-1-144-21.
18. Sessler, J. L.; Seidel, D. Synthetic Expanded Porphyrin Chemistry. Angew. Chem., Int. Ed. 2003, 42, 5134-5175.
19. Michel, S. L. J.; Baum, S.; Barrett, A. G. M.; Hoffman, B. M. Peripherally Functionalized Porphyrazines: Novel Metallomacrocycles with Broad, Untapped Potential. Prog. Inorg. Chem. 2001, 50, 473-590.
20. Cook, A. S.; Williams, D. B. G.; White, A. J. P.; Williams, D. J.; Lange, S. J.; Barrett, A. G. M.; Hoffman, B. M. Enantiomerically Pure "Winged" Spirane Porphyrazinoctaols. Angew. Chem., Int. Ed. Engl. 1997, 36, 760-761.
21. Sibert, J. W.; Baumann, T. F.; Williams, D. J.; White, A. J. P.; Barrett, A. G. M.; Hoffman, B. M. Gemini Porphyrazines: The Synthesis and Characterization of Metal-Capped cis- and trans-Porphyrazine Tetrathiolates. J. Am. Chem. Soc. 1996, 118, 10487-10493.
22. Lange, S. J.; Nie, H.; Stern, C. L.; Barrett, A. G. M.; Hoffman, B. M. Peripheral Palladium(II) and Platinum(II) Complexes of Bis(dimethylamino) porphyrazine. Inorg. Chem. 1998, 37, 6435-6443.
23. Forsyth, T. P.; Williams, D. B. G.; Montalban, A. G.; Stern, C. L.; Barrett, A. G. M.; Hoffman, B. M. A Facile and Regioselective Synthesis of Trans-Heterofunctionalized Porphyrazine Derivatives. J. Org. Chem. 1998, 63, 331-336.
24. Linben, T. G.; Hanack, M. Synthesis, Separation and Characterization of Unsymmetrically Substituted Phthalocyanines. Chem. Ber. 1994, 127, 2051-2057.
25. 2h Symmetry. Chem. Lett. 1992, 2031-2034.
26. Stihler, P.; Hauschel, B.; Hanack, M. Synthesis of a Bisdienophilic Phthalocyanine and of Precursors for Repetitive Diels-Alder Reactions Based on Hemiporphyrazines and Phthalocyanines. Chem. Ber. 1997, 130, 801-806.
27. Leznoff, C. C.; Svirskaya, P. I.; Khouw, B.; Cerny, R. L.; Seymour, P.; Lever, A. B. P. Syntheses of Monometalated and Unsymmetrically Substituted Binuclear Phthalocyanines and a Pentanuclear Phthalocyanine by Solution and Polymer Support Methods. J. Org. Chem. 1991, 56, 82-90.
28. Lee, S.; Stackow, R.; Foote, C. S.; Barrett, A. G. M.; Hoffman, B. M. Tuning the Singlet Oxygen Quantum Yield of Near-IR-Absorbing Porphyrazines. Photochem. Photobiol. 2003, 77, 18-21.
29. Carvalho, V. C. M.; Melo, C. A. S.; Bagnato, V. S.; Perussi, J. R. Comparison of the Effects of Cationic and Anionic Porphyrins in Tumor Cells Under Illumination of Argon Ion Laser. Laser Phys. 2002, 12, 1314-1319.
30. Ruck, A.; Kollner, T.; Dietrich, A.; Strauss, W.; Schneckenburger, H. Fluorescence Formation During Photodynamic Therapy in the Nucleus of Cells Incubated with Cationic and Anionic Water-Soluble Photosensitizers. J. Photochem. Photobiol., B: Biol. 1992, 12, 403-412.
31. Juarranz, A.; Villanueva, A.; Diaz, V.; Canete, M. Photodynamic Effects of the Cationic Porphyrin, Mesotetra(4N-methylpyridyl)-porphyine, on Microtubules of HeLa Cells. J. Photochem. Photobiol., B: Biol. 1995, 27, 47-53.
32. Ehrlich, L. A.; Skrdla, P. J.; Jarrell, W.; Sibert, J. W.; Armstrong, N. R.; Saavedra, S. S.; Barrett, A. G. M.; Hoffman, B. M. Preparation of Polyetherol-Appended Sulfur Porphyrazines and Investigations of Peripheral Metal Ion Binding in Polar Solutions. Inorg. Chem. 2000, 39, 3963-3969.
33. Lee, S.; White, A. J. P.; Williams, D. J.; Barrett, A. G. M.; Hoffman, B. M. Synthesis of Near-IR Absorbing/Emitting Porphyrazine Derivatives with Tunable Solubility. J. Org. Chem. 2001, 66, 461-465.
34. Davison, A.; Holm, R. H. Metal Complexes Derived from cis-1,2-dicyano-1,2-ethylenedithiolate and Bis(trifluoromethyl)-1,2-dithiete. Inorg. Synth. 1967, 10, 8-26.
35. The HpD concentration was calculated using an assigned molecular weight of 600.
36. Giard, D. J.; Aaronson, S. A.; Todaro, G. J.; Arnstein, P.; Kersey, J. H.; Dosik, H.; Parks, W. P. In Vitro Cultivation of Human Tumors: Establishment of Cell Lines Derived from a Series of Solid Tumors. J. Natl. Cancer Inst. 1973, 51, 1417-1423.
37. Lieber, M.; Smith, B.; Szakal, A.; Nelson-Rees, W.; Todaro, G. A Continuous Tumor-Cell Line from a Human Lung Carcinoma with Properties of Type II Alveolar Epithelial Cells. Int. J. Cancer. 1976, 17, 62-70.
38. Girardi, A. J.; Weinstein, D.; Moorhead, P. S. SV40 Transformation of Human Diploid Cells. A Parallel Study of Viral and Karyologic Parameters. Ann. Med. Exp. Biol. Fenn. 1966, 44, 242-254.
39. Hayflick, L.; Moorhead, P. S. The Serial Cultivation of Human Diploid Cell Strains. Exp. Cell Res. 1961, 25, 585-621.
40. Hayflick, L. The Limited in Vitro Lifetime of Human Diploid Cell Strains. Exp. Cell Res. 1965, 37, 614-636.
41. Dougherty, T. J. Photodynamic Therapy (PDT) of Malignant-Tumors. Crit. Rev. Oncol. Hematol. 1984, 2, 83-116.
42. Little, F. M.; Gomer, C. J.; Hyman, S.; Apuzzo, M. L. J. Observations in Studies of Quantitative Kinetics of Tritium Labeled Hematoporphyrin Derivatives (HpDI and HpDII) in the Normal and Neoplastic Rat Brain Model. J. Neuro-Oncol. 1984, 2, 361-370.
43. Williams, R. M.; Zipfel, W. R.; Webb, W. W. Multiphoton Microscopy in Biological Research. Curr. Opin. Chem. Biol. 2001, 5, 603-608.
44. So, P. T. C.; Dong, C. Y.; Masters, B. R.; Berland, K. M. Two-Photon Excitation Fluorescence Microscopy. Annu. Rev. Biomed. Eng. 2000, 2, 399-429.
45. Denk, W.; Piston, D. W.; Webb, W. W. Two-Photon Molecular Excitation in Laser-Scanning Microscopy. In Handbook of Biological Confocal Microscopy; Pawley, J. B., Ed.; Plenum Press: New York, 1995; pp 445-458.
46. Haugland, R. P. Chapter 12: Probes for Organelles. In Handbook of Fluorescent Probes and Research Products, 9th ed.; Haugland, R. P., Spence, M. T. Z.; Johnson, I. D., Gregory, J., Eds.; Molecular Probes: Eugene, OR, 2002; pp 469-502.
47. Tanielian, C.; Schweitzer, C.; Mechin, R.; Wolff, C. Quantum Yield of Singlet Oxygen Production by Monomeric and Aggregated Forms of Hematoporphyrin Derivative. Free Radical Biol. Med. 2001, 30, 208-212.