Water-soluble self-assembled butadiyne-bridged bisporphyrin: A potential two-photon-absorbing photosensitizer for photodynamic therapy

被引:61
作者
Dy, Joanne T. [1 ]
Ogawa, Kazuya [1 ]
Satake, Akiharu [1 ]
Ishizumi, Atsushi [1 ]
Kobuke, Yoshiaki [1 ]
机构
[1] Nara Inst Sci & Technol, Grad Sch Mat Sci, Nara 6300101, Japan
关键词
photodynamic therapy; porphyrins; self-assembly; singlet oxygen; two-photon absorption;
D O I
10.1002/chem.200601205
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have synthesized a novel, two-photon-absorbing photosensitizer for two-photon-absorption photodynamic therapy (2PA-PDT). The molecule is a butadiyne-bridged porphyrin dimer terminated with two water-soluble porphyrin monomers connected through Zn-imidazolyl self-assembly and covalently linked through olefin metathesis. It has an effective two-photon-absorption (2PA) cross-section value, sigma((2)), of 33 000 4600 GM with 5-ns pulses at 890 nm measured by using the open-aperture Z-scan technique. The compound was found to generate singlet oxygen, cytotoxic for tumor cells in photodynamic therapy (PDT), under 2PA conditions by conducting photobleaching experiments with anthracene-9,10-dipropionic acid sodium salt (ADPA).
引用
收藏
页码:3491 / 3500
页数:10
相关论文
共 73 条
  • [1] Design of organic molecules with large two-photon absorption cross sections
    Albota, M
    Beljonne, D
    Brédas, JL
    Ehrlich, JE
    Fu, JY
    Heikal, AA
    Hess, SE
    Kogej, T
    Levin, MD
    Marder, SR
    McCord-Maughon, D
    Perry, JW
    Röckel, H
    Rumi, M
    Subramaniam, C
    Webb, WW
    Wu, XL
    Xu, C
    [J]. SCIENCE, 1998, 281 (5383) : 1653 - 1656
  • [2] CONJUGATED PORPHYRIN LADDERS
    ANDERSON, HL
    [J]. INORGANIC CHEMISTRY, 1994, 33 (05) : 972 - 981
  • [3] Two-photon photosensitized production of singlet oxygen: Optical and optoacoustic characterization of absolute two-photon absorption cross sections for standard sensitizers in different solvents
    Arnbjerg, Jacob
    Johnsen, Mette
    Frederiksen, Peter K.
    Braslavsky, Silvia E.
    Ogilby, Peter R.
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (23) : 7375 - 7385
  • [4] Bhawalkar J D, 1997, J Clin Laser Med Surg, V15, P201
  • [5] Nonlinear multiphoton processes in organic and polymeric materials
    Bhawalkar, JD
    He, GS
    Prasad, PN
    [J]. REPORTS ON PROGRESS IN PHYSICS, 1996, 59 (09) : 1041 - 1070
  • [6] Fluorescence resonance energy transfer in a novel two-photon absorbing system
    Brousmiche, DW
    Serin, JM
    Fréchet, JMJ
    He, GS
    Lin, TC
    Chung, SJ
    Prasad, PN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) : 1448 - 1449
  • [7] ZP8, a neuronal zinc sensor with improved dynamic range; Imaging zinc in hippocampal slices with two-photon microscopy
    Chang, CJ
    Nolan, EM
    Jaworski, J
    Okamoto, KI
    Hayashi, Y
    Sheng, M
    Lippard, SJ
    [J]. INORGANIC CHEMISTRY, 2004, 43 (21) : 6774 - 6779
  • [8] Two-photon three-dimensional microfabrication of poly(dimethylsiloxane) elastomers
    Coenjarts, CA
    Ober, CK
    [J]. CHEMISTRY OF MATERIALS, 2004, 16 (26) : 5556 - 5558
  • [9] PHOTOREACTIONS OF MACROCYCLIC DYES BOUND TO HUMAN-SERUM-ALBUMIN
    DAVILA, J
    HARRIMAN, A
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1990, 51 (01) : 9 - 19
  • [10] Use of two-photon excitation for erasable-rewritable three-dimensional bit optical data storage in a photorefractive polymer
    Day, D
    Gu, M
    [J]. OPTICS LETTERS, 1999, 24 (14) : 948 - 950