Water-soluble bis(imidazolylporphyrin) self-assemblies with large two-photon absorption cross sections as potential agents for photodynamic therapy

Journal of Medicinal Chemistry

Volumn 49, Issue 7, 2006, Pages 2276-2283

  Ogawa, Kazuya ^a   Hasegawa, Hideki ^a   Inaba, Yusuke ^a   Kobuke, Yoshiaki ^a   Inouye, Hideyuki ^a   Kanemitsu, Yoshihiko ^a   Kohno, Eiji ^b   Hirano, Toru ^b   Ogura, Shun Ichiro ^c   Okura, Ichiro ^c  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b HAMAMATSU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; BIS(IMIDAZOLYLPORPHYRIN); BISACETYLENE; IMIDAZOLE DERIVATIVE; MONOACETYLENE; PORPHYRIN DERIVATIVE; PROTOPORPHYRIN; SINGLET OXYGEN; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG CONJUGATION; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IRRADIATION; LIGHT ABSORPTION; LUMINESCENCE; MEASUREMENT; PHOTODYNAMIC THERAPY;

ACETYLENE; HELA CELLS; HUMANS; IMIDAZOLES; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PORPHYRINS; SINGLET OXYGEN; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 33645718814     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm051072+     Document Type: Article

References (40)

1. (a) Bonnett, R. Chemical Aspects of Photodynamic Therapy; Gordon and Breach Science Publishers: Amsterdam, 2000.
2. (b) MacDonald, I. J.; Dougherty, T. J. Basic principles of photodynamic therapy. J. Porphyrins Phthalocyanines 2001, 5, 105-129.
3. Electrooptics Handbook: Waynant, R. W., Ediger, M. N., Eds.; McGraw-Hill: New York, 1993; Chapter 24.
4. Kershaw, S. In Characterization Techniques and Tabulations for Organic Nonlinear Optical Materials; Kuzyk, M. G., Dirk, C. W., Eds.; Marcel Dekker: New York, 1998; Chapter 7.
5. (a) Bhawalkar, J. D.; Kumar, N. D.; Zhao, C. F.; Prasad, P. N. Two-photon photodynamic therapy. J. Clin. Laser Med. Surg. 1997, 15, 201-204.
6. (b) Wachter, E. A.; Partridge, W. P.; Fisher, W. G.; Dees, H. C.; Petersen, M. G. Simultaneous two-photon excitation of photodynamic therapy agents. Proc. SPIE-Int. Soc. Opt. Eng. 1998, 5269, 68-75.
7. (c) Liu, J.; Zhao, Y. W.; Zhao, J. Q.; Xia, A. D.; Jiang, L. J.; Wu, S.; Ma, L.; Dong, Y. Q.; Gu, Y. H. Two-photon excitation studies of hypocrellins for photodynamic therapy. J. Photochem. Photobiol. B 2002, 68, 156-164.
8. (a) Kobuke, Y.; Miyaji, H. Supramolecular organization of imidazolyl-porphyrin to a slipped cofacial dimer J. Am. Chem. Soc. 1994, 116, 4111-4112.
9. (b) Ogawa, K.; Kobuke, Y. Formation of a giant supramolecular porphyrin array by self-coordination. Angew. Chem., Int. Ed. 2000, 39, 4070-4073.
10. (c) Ogawa, K.; Zhang, T.; Yoshihara, K1; Kobuke, Y. Large third-order optical nonlinearity of self-assembled porphyrin oligomers. J. Am. Chem. Soc. 2002, 124, 22-23.
11. (d) Nomoto, A.; Kobuke, Y. Photocurrent generation system incorporated with antenna function. Chem. Commun. 2002, 1104-1105.
12. (e) Takahahshi, R.; Kobuke, Y. Hexameric macroring of gable-porphyrins as a light-harvesting antenna mimic. J. Am. Chem. Soc. 2003, 125, 2372-2373.
13. (f) Kobuke, Y.; Ogawa, K. Porphyrin supramolecules toward artificial photosynthesis and molecular photonic/electronic materials. Bull. Chem. Soc. Jpn. 2003, 76, 689-708.
14. (g) Ogawa, K.; Ohashi, A.; Kobuke, Y.; Kamada, K.; Ohta, K. Strong two-photon absorption of self-assembled butadiyne-linked bisporphyrin. J. Am. Chem. Soc. 2003, 125, 13356-13357.
15. (h) Kuramochi, Y.; Satake, A.; Kobuke, Y. Light-harvesting macroring accommodating a tetrapodal ligand based on complementary and cooperative coordinations. J. Am. Chem. Soc. 2004, 126, 8668-8669.
16. (i) Ozeki, H.; Nomoto, A.; Ogawa, K.; Kobuke, Y.; Murakami, M.; Hosoda, K.; Ohtani, M.; Nakashima, S.; Miyasaka, H.; Okada, T. Role of special pair in charge-separating event in photosynthesis. Chem. Eur. J. 2004, 10, 6393-6401.
17. (j) Hwang, I.-W.; Park, M.; Ahn, T. K.; Yoon, Z. S.; Ko, D. M.; Kim, D.; Ito, F.; Ishibashi, Y.; Khan, S. R.; Nagasawa, Y.; Miyasaka, H.; Ikeda, C.; Takahashi, R.; Ogawa, K.; Satake, A.; Kobuke, Y. Excitation energy migration in self-assembled cyclic zinc(II) porphyrin arrays: A close mimicry of natural light harvesting system. Chem. Eur. J. 2005, 11, 3753-3761.
18. (k) Ogawa, K.; Ohashi, A.; Kobuke, Y.; Kamada, K.; Ohta, K. Two-photon absorption properties of self-assemblies of butadiyne-linked bis-(imidazolylporphyrin). J. Phys. Chem. B 2005, 109, 22003-22012.
19. Goyan, R. L.; Cramb, D. T. Near-infrared two-photon excitation of protoporphyrin IX: Photodynamics and photoproduct generation. Photochem. Photobiol. 2000, 72, 821-827.
20. 2+) in aqueous micellar media. Inorg. Chem. 1989, 28, 2125-2131.
21. (b) Schneider, H.-J.; Wang, M. Ligand-porphyrin complexes: Quantitative evaluation of stacking and ionic contributions. J. Org. Chem. 1994, 59, 7464-7472. Further, hydrophobic and π-π interactions between porphyrins in water must be strong and assist the dimer formation.
22. Ohashi, A.; Satake, A.; Kobuke, Y. Covalent linking of coordination-organized slipped cofacial porphyrin dimers. Bull. Chem. Soc. Jpn. 2004, 77, 365-374.
23. (a) Lin, V. S.-Y.; DiMagno, S. G.; Therien, M. J. Highly conjugated, acetylenyl bridged porphyrins: New models for light-harvesting antenna systems. Science 1994, 264, 1105-1111.
24. (b) Lin, V. S.-Y.; Therien, M. J. The role of porphyrin-to-porphyrin linkage topology in the extensive modulation of the absorptive and emissive properties of a series of ethynyl- and butadiynyl-bridged bis- and tris-(porphinato)zinc chromophores. Chem. Eur. J. 1995, 1, 645-651.
25. (c) Angiolillo, P. J.; Uyeda, H. T.; Duncan, T. V.; Therien, M. J. Impact of electronic asymmetry on photoexcited triplet-state spin distributions in conjugated porphyrin oligomers probed via EPR spectroscopy. J. Phys. Chem. B 2004, 108, 11893-11903.
26. (a) Abbotto, A.; Beverina, L.; Bozio, R.; Facchetti, A.; Ferrante, C; Pagani, G. A.; Pedron, D.; Signorini, R. Novel heterocycle-based two-photon absorbing dyes Org. Lett. 2002, 4, 1495-1498.
27. (b) Kim, O. K.; Lee, K. S,; Woo, H. Y.; Kim, K. S.; He, G. S.; Swiatkiewicz, J.; Prasad, P. N. Two-photon absorption and excited-state energy-transfer properties of a new multibranched molecule. Chem. Mater. 2001, 13, 4071-4076.
28. (c) Chung, S. J.; Kim, K. S.; Lin, T. C.; He, G. S.; Swiatkiewicz, J.; Prasad, P. N. Cooperative enhancement of two-photon absorption in multi-branched structures. J. Phys. Chem. B 1999, 103, 10741-10745.
29. (d) Kamada, K.; Ohta, K.; Iwase, Y.; Kondo, K. Two-photon absorption properties of symmetric substituted diacetylene: Drastic enhancement of the cross section near the one-photon absorption peak. Chem. Phys. Lett. 2003, 372, 386-393.
30. (e) Abbotto, A.; Beverina, L.; Bozio, R.; Facchetti, A.; Ferrante, C.; Pagani, G. A.; Pedron, D.; Signorini, R. Novel heteroaromatic-based multi-branched dyes with enhanced two-photon absorption activity. Chem. Commun. 2003, 2144-2145.
31. (f) Belfield, K. D.; Liu, Y.; Negres, R. A.; Fan, M.; Pan, G.; Hagan, D. J.; Hernandez, F. E. Two-photon photochromism of an organic material for holographic recording. Chem Mater. 2002, 14, 3663-3667.
32. (g) Porrès, L.; Mongin, O.; Katan, C.; Chariot, M.; Pons, T.; Mertz, J.; Blanchard-Desce, M. Enhanced two-photon absorption with novel octupolar propeller-shaped fluorophores derived from triphenylamine. Org. Lett. 2004, 6, 47-50.
33. (h) Karotki, A.; Drobizhev, M.; Dzenis, Y.; Taylor, P. N.; Anderson, H. L.; Rebane, A. Dramatic enhancement of intrinsic two-photon absorption in a conjugated porphyrin dimer. Phys. Chem. Chem. Phys. 2004, 6, 7-10.
34. (i) Drobizhev, M.; Stepanenko, Y.; Dzenis, Y.; Karotki, A.; Rebane, A.; Taylor, P. N.; Anderson, H. L. Understanding strong two-photon absorption in π-conjugated porphyrin dimers via double-resonance enhancement in a three-level model. J. Am. Chem. Soc. 2004, 126, 15352-15353.
35. (a) Rodgers, M. A. J.; Snowden, P. T. J. Am. Chem. Soc. 1982, 104, 5541.
36. (b) Ogilby, P. R.; Foote, C. S. Chemistry of singlet oxygen. 42. Effect of solvent, solvent isotopic substitution, and temperature on the lifetime of singlet molecular oxygen (1.DELTA.g). J. Am. Chem. Soc. 1983, 105, 3423-3430.
37. (c) Frederiksen, P. K.; Mcllroy, S. P.; Nielsen, C. B.; Nikolajsen, L.; Skovsen, E.; Jørgensen, M.; Mikkelsen, K. V.; Ogilby, P. R. Two-photon photosensitized production of singlet oxygen in water. J. Am. Chem. Soc. 2005, 127, 255-269.
38. Wang, Q. M.; Bruce, D. W. One-step synthesis of β, meso-unsubstituted dipyrromethane. Synlett. 1995, 1267-1268.
39. Sheik-Bahae, M.; Said, A. A.; Wei, T.-H.; Hagan, D. G.; van Stryland, E. W. Sensitive measurement of optical nonlinearities using a single beam. IEEE J. Quantum Electron. 1990, 26, 760-769.
40. Oda, K.; Ogura, S.; Okura, I. Preparation of a water-soluble fluorinated zinc phthalocyanine and its effect for photodynamic therapy. J. Photochem. Photobiol. B: Biol. 2000, 59, 20-25.