Photodynamic Therapy Using Novel Zinc Phthalocyanine Derivatives and a Diode Laser for Superficial Tumors in Experimental Animals — Oak Academic Publishing
Research ArticleOpen AccessGoogle Scholar indexed
Photodynamic Therapy Using Novel Zinc Phthalocyanine Derivatives and a Diode Laser for Superficial Tumors in Experimental Animals
Department of Bioorganic Chemistry, Faculty of Pharmaceutical Sciences, Aichi-Gakuin University, Nagoya, Japan
,
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Nagoya, Japan
,
Department of Bioorganic Chemistry, Faculty of Pharmaceutical Sciences, Aichi-Gakuin University, Nagoya, Japan
,
Department of Bioorganic Chemistry, Faculty of Pharmaceutical Sciences, Aichi-Gakuin University, Nagoya, Japan
,
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Nagoya, Japan
,
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Nagoya, Japan
,
Department of Bioorganic Chemistry, Faculty of Pharmaceutical Sciences, Aichi-Gakuin University, Nagoya, Japan
1 Department of Bioorganic Chemistry, Faculty of Pharmaceutical Sciences, Aichi-Gakuin University, Nagoya, Japan
2 Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Nagoya, Japan
3 Department of Bioorganic Chemistry, Faculty of Pharmaceutical Sciences, Aichi-Gakuin University, Nagoya, Japan
4 Department of Bioorganic Chemistry, Faculty of Pharmaceutical Sciences, Aichi-Gakuin University, Nagoya, Japan
5 Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Nagoya, Japan
6 Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Nagoya, Japan
7 Department of Bioorganic Chemistry, Faculty of Pharmaceutical Sciences, Aichi-Gakuin University, Nagoya, Japan
Photodynamictherapy (PDT) using a photo sensitizing agent and several light sources has been shown to have nonspecific and noninvasive effects on superficial cancers. Phthalocyanine (Pc) derivatives as novel photosensitizers, trifluoroethoxy-coatedzinc Pcconjugated with β -cyclodextrin ( β CD-4TFEO-Pc) was synthesized and its photodynamic effect in vitro and in vivo was evaluated. β CD-4TFEO-Pc alone was completely non-cytotoxic even at high concentrations, and showed excellentphotodynamic effects in B16-F10 and HT-1080 celllines. The in vivo antitumor effect of β CD-4TFEO-Pc against B16-F10 cells transplanted on to the chorioallantoic membranes of chickembryos was 52.7%, but that of laserirradiation alone and photosensitizer alone was <7% at thedose of 50 μg pereggand 100 J/cm 2 (50 mW). These data suggest that β CD-4TFEO-Pc is a useful photosensitizer for the treatment of superficial cancers. If a high-power LED with optimal wavelength is developed, excellent treatment of superficial cancers could be achieved by applying β CD-4TFEO-Pc for PDT.
Anand, S., Ortel, B.J., Pereira, S.P., Hasan, T. and Maytin, E.V. (2012) Biomodulatory Approaches to Photodynamic Therapy for Solid Tumors. Cancer Letters, 326, 8-16. http://dx.doi.org/10.1016/j.canlet.2012.07.026
Baldea, I. and Filip, A.G. (2012) Photodynamic Therapy in Melanoma—An Update. Journal of Physiology and Pharmacology, 63, 109-118. http://www.jpp.krakow.pl/journal/archive/04_12/pdf/109_04_12_article.pdf
Ikeda, N., Usuda, J., Kato, H., Ishizumi, T., Ichinose, S., Otani, K., Honda, H., Furukawa, K., Okunaka, T. and Tsutsui, H. (2011) New Aspects of Photodynamic Therapy for Central Type Early Stage Lung Cancer. Lasers in Surgery and Medicine, 43, 749-754. http://dx.doi.org/10.1002/lsm.21091
Mimura, S., Narahara, H., Otani, T. and Okuda, S. (1999) Progress of Photodynamic Therapy in Gastric Cancer. Diagnostic and Therapeutic Endoscopy, 5, 175-182. http://dx.doi.org/10.1155/dte.5.175
Tanaka, M., Kinoshita, M., Yoshihara, Y., Shinomiya, N., Seki, S., Nemoto, K., Hirayama, T., Dai, T., Huang, L., Hamblin, M.R. and Morimoto, Y. (2012) Optimal Photosensitizers for Photodynamic Therapy of Infections Should Kill Bacteria but Spare Neutrophils. Photochemistry and Photobiology, 88, 227-232. http://dx.doi.org/10.1111/j.1751-1097.2011.01005.x
Allison, R. R. and Moghissi, K. (2013) Photodynamic Therapy (pdt): Pdt Mechanisms. Clinical Endo- scopy, 46, 24-29. http://dx.doi.org/10.5946/ce.2013.46.1.24
Saini, R. and Poh, C.F. (2013) Photodynamic Therapy: A Review and Its Prospective Role in the Management of Oral Potentially Malignant Disorders. Oral Diseases, 19, 440-451. http://dx.doi.org/10.1111/odi.12003
Opitz, I., Krueger, T., Pan, Y., Altermatt, H.J., Wagnieres, G. and Ris, H.B. (2006) Preclinical Comparison of Mthpc and Verteporfin for Intracavitary Photodynamic Therapy of Malignant Pleural Mesothelioma. European Surgical Research, 38, 333-339. http://dx.doi.org/10.1159/000094028
Huggett, M.T., Jermyn, M., Gillams, A., Illing, R., Mosse, S., Novelli, M., Kent, E., Bown, S.G., Hasan, T., Pogue, B.W. and Pereira, S.P. (2014) Phase i/ii Study of Verteporfin Photodynamic Therapy in Locally Advanced Pancreatic Cancer. British Journal of Cancer, 110, 1698-1704. http://dx.doi.org/10.1038/bjc.2014.95
Tanaka, M., Uchibayashi, T., Obata, T. and Sasaki, T. (1995) Photodynamic Therapy of Photofrin ii and Excimer Dye Laser on Experimental Tumors. Cancer Letters, 90, 163-169. http://dx.doi.org/10.1016/0304-3835(95)03699-W
Magaraggia, M., Marigo, L., Pagnan, A., Jori, G. and Visona, A. (2007) Porphyrin-Photosensitized Processes: Their Applications in the Prevention of Arterial Restenosis. Cardiovascular & Hematological Agents in Medicinal Chemistry, 5, 278-288. http://dx.doi.org/10.2174/187152507782109908
Van Lier, J.E. and Spikes, J.D. (1989) The Chemistry, Photophysics and Photosensitizing Properties of Phthalocyanines. Ciba Foundation Symposium, 146, 17-26.
Gorman, S.A., Brown, S.B. and Griffiths, J. (2006) An Overview of Synthetic Approaches to Porphyrin, Phthalocyanine, and Phenothiazine Photosensitizers for Photodynamic Therapy. Journal of Environmental Pathology, Toxicology and Oncology, 25, 79-108. http://dx.doi.org/10.1615/JEnvironPatholToxicolOncol.v25.i1-2.50
Yoshiyama, H., Shibata, N., Sato, T., Nakamura, S. and Toru, T. (2008) Synthesis and Properties of Trifluoroethoxy-Coated Binuclear Phthalocyanine. Chemical Communications, 7, 1977-1979. http://dx.doi.org/10.1039/b800918j
Reddy, M.R., Shibata, N., Kondo, Y., Nakamura, S. and Toru, T. (2006) Design, Synthesis, and Spectroscopic Investigation of Zinc Dodecakis(trifluoroethoxy)phthalocyanines Conjugated with Deoxyribonucleosides. Angewandte Chemie International Edition, 45, 8163-8166. http://dx.doi.org/10.1002/anie.200603590
Yoshiyama, H., Shibata, N., Sato, T., Nakamura, S. and Toru, T. (2009) Synthesis of Trifluoroethoxy-Coated Binuclear Phthalocyanines with Click Spacers and Investigation of Their Clamshell Behaviour. Organic & Biomolecular Chemistry, 7, 2265-2269. http://dx.doi.org/10.1039/b902905b
Das, B., Tokunaga, E., Tanaka, M., Sasaki, T. and Shibata, N. (2010) Perfluoroisopropyl Zinc Phthalocyanines Conjugated with Deoxyribonucleosides: Synthesis, Photophysical Properties and in Vitro Photodynamic Activities. European Journal of Organic Chemistry, 2010, 2878-2884. http://dx.doi.org/10.1002/ejoc.201000179
Uchida, H., Sasaki, T., Tanaka, M., Endo, Y., Nitta, K., Nishikawa, K., Chuman, H., Fukuma, H. and Matsumoto, K. (1987) Response to Antitumor Agents of Murine Transplantable Tumors Implanted onto Chorioallantoic Membrane of Chick Embryo. Japanese Journal of Cancer Research, 78, 729-736.
Nishikawa, K., Sasaki, T., Tanaka, M., Uchida, H., Endo, Y., Fukuma, H., Chuman, H., Beppu, Y., Matsumoto, K. and Nitta, K. (1987) Experimental Model for Predicting Metastatic Ability of Tumors Using Chick Embryo. Japanese Journal of Clinical Oncology, 17, 319-325.
Shoin, K., Yamashita, J., Enkaku, F., Sasaki, T., Tanaka, M. and Endo, Y. (1991) Chick Embryo Assay as Chemosensitivity Test for Malignant Glioma. Cancer Science, 82, 1165-1170. http://dx.doi.org/10.1111/j.1349-7006.1991.tb01772.x
Tanaka, M., Matsuda, A., Terao, T. and Sasaki, T. (1992) Antitumor Activity of a Novel Nucleoside, 2'-C-cyano-2'-deoxy-1-β-D-arabinofuranosylcytosine (CNDAC) against Murine and Human Tumors. Cancer Letters, 64, 67-74. http://dx.doi.org/10.1016/0304-3835(92)90024-P
Yoshida, T., Tokashiki, R., Ito, H., Shimizu, A., Nakamura, K., Hiramatsu, H., Tsukahara, K., Shimizu, S., Takata, D., Okamoto, I. and Suzuki, M. (2008) Therapeutic Effects of a New Photosensitizer for Photodynamic Therapy of Early Head and Neck Cancer in Relation to Tissue Concentration. Auris Nasus Larynx, 35, 545-551. http://dx.doi.org/10.1016/j.anl.2007.10.008
Loftsson, T. and Masson, M. (2001) Cyclodextrins in Topical Drug Formulations: Theory and Practice. International Journal of Pharmaceutics, 225, 15-30. http://dx.doi.org/10.1016/S0378-5173(01)00761-X
Carrier, R.L., Miller, L.A. and Ahmed, I. (2007) The Utility of Cyclodextrins for Enhancing Oral Bioavailability. Journal of Controlled Release, 123, 78-99. http://dx.doi.org/10.1016/j.jconrel.2007.07.018
Sharma, K.V., Bowers, N. and Davids, L.M. (2011) Photodynamic Therapy-Induced Killing Is Enhanced in Depigmented Metastatic Melanoma Cells. Cell Biology International, 35, 939-944. http://dx.doi.org/10.1042/CBI20110103
Calzavara-Pinton, P.G. (1995) Repetitive Photodynamic Therapy with Topical Delta-Aminolevulinic Acid as an Appropriate Approach to the Routine Treatment of Superficial Non-Melanoma Skin Tumours. Journal of Photochemistry and Photobiology B, 29, 53-57. http://dx.doi.org/10.1016/1011-1344(95)90253-8
Tanaka, M., Tatsuzawa, Y., Uchida, H., Watanabe, Y. and Sasaki, T. (1993) Chemosensitivity Testing of Advanced Lung Cancer by the Chick Embryo Assay. Annals of Cancer Research and Therapy, 2, 217-222. http://dx.doi.org/10.4993/acrt1992.2.217