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Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties

Year 2020, Volume: 16 Issue: 4, 367 - 372, 30.12.2020

Abstract

In this study, it is desired to apply Sono-photodynamic Therapy (SPDT) method to create a more effective therapeutic outcome. For this purpose, a new palladium phthalocyanine (PdPc) (2) was synthesized and characterized by standard spectroscopy methods. Then it's photochemical and photophysical properties were determined in DMSO. Singlet oxygen quantum yield of the complex (2) was calculated by both PDT and SPDT method. The SPDT method (∆ =0.90) was found to be more effective than the PDT method (∆ =0.74), to obtain high singlet oxygen quantum yield. All the results show that, SPDT improves the therapeutic effects and the new PdPc can be a potential photosensitizer in PDT / or SPDT.

Supporting Institution

Yildiz Technical University

Thanks

Thanks to Prof. Dr. Ali Erdoğmuş from Yildiz Technical University for his contributions.

References

  • 1. Shen, X.M., Zheng, B.Y., Huang, X.R.,Wang, L., Huang J.D. 2013. First silicon (IV) phthalocyanine-nucleoside conjugates with high photodynamic activity. Dalton Transaction, 42 (29), 10398 – 10403.
  • 2. Hışır, A, Köse, G. G., Atmaca, G.Y., Erdogmus, A., Karaoglan, G.K. 2018. Novel carboxylic acid terminated silicon (IV) and zinc (II) phthalocyanine photosensitizers: Synthesis, photophysical and photochemical studies. Journal Porphyrins and Phthalocyanines, 22, 1010–1021.
  • 3. Liu, Y., Wang, P., Liu, Q., Wang, X. 2016. Sinoporphyrin sodium triggered sono-photodynamic effects on breast cancer both in vitro and in vivo. Ultrasonics Sonochemistry, 31, 437–448
  • 4. Dolmans, D.E., Fukumura, D., Jain, R.K. 2003. Photodynamic therapy for cancer. Nature Reviews Cancer, 3, 380–387.
  • 5. Yumita, N., Nishigaki, R., Umemura, K., Umemura, S.i. 1989. Hematoporphyrin as a sensitizer of cell-damaging effect of ultrasound. Cancer Science, 80, 219– 222.
  • 6. Trendowski, M. 2014. The Promise of Sonodynamic Therapy. Cancer Metastasis Reviewer. 33, 143–160.
  • 7. KÖKEN.,E. C. Doktorate thesis. Adnan Menderes University. Ehrlich Asit Tümör Hücreleri Üzerinde Kloraluminyum Ftalosiyanin ve Dosetakselin Sonodinamik Etkilerinin Araştirilmasi, 2014, Aydın.
  • 8. Chen, H., Zhou, X., Gao,Y., Zheng, B., Tang, F., Huang, J. 2014. Recent progress in development of new sonosensitizers for sonodynamic cancer therapy. Drug Discovery Today, 19, 502-509.
  • 9. D.Costley, C.M. Ewan, C. Fowley, A.P. McHale, J.Atchison, N.Nomikou, J. F. Callan. 2015. Treating cancer with sonodynamic therapy: A review. International Journal of Hyperthermia, 31(2)107–117.
  • 10. Hai-Jun, Xiao-Bin Zhou, Ai-Lan Wang , Bi-Yuan Zheng , Chih-Kuang Yeh , Jian-Dong Huang. 2018. Synthesis and biological characterization of novel rose bengal derivatives with improved amphiphilicity for sono-photodynamic therapy. European Journal of Medicinal Chemistry,145, 86-95.
  • 11. Li.,Q., Liu.Q., Wang, P., Feng, X., Wang, H., Wang, X. 2014. The effects of Ce6-mediated sono-photodynamic therapy on cell migration, apoptosis and autophagy in mouse mammary 4T1 cell line. Ultrasonics, 54, 4, 981-989.
  • 12. Jin.,Z.H. , Miyoshi, N ., Ishiguro, K., Umemura, S ., Kawabata, K ., Yumita, N ., Sakata, I. , Takaoka,K ., Udagawa ,T., Nakajima ,S.,Tajiri ,H. , Ueda, K. , Fukuda, M. , Kumakiri, M. 2000. Combination Effect of Photodynamic and Sonodynamic Therapy on Experimental Skin Squamous Cell Carcinoma in C3H/HeN Mice. Journal of Dermatol, 27, 294.
  • 13. Kolarova, H., Tomankova, K., Bajgar, R., Kolar, P., Kubinek, R. 2009. Photodynamic and Sonodynamic Treatment by Phthalocyanine on Cancer Cell Lines. Ultrasound Medicinal Biology, 35, 1397.
  • 14. Kessel D, Lo J, Jeffers R, Fowlkes, J.B., Cain, C. 1995. Modes of photodynamic vs. sonodynamic cytotoxicity. Journal of Photochemistry and Photobiology B Biology 28(3):219-21.
  • 15. Wang,X., Zhang, W., Xu,Z., Luo,Y., Mitchell, D., Ralph W. 2009. Moss. Sonodynamic and Photodynamic Therapy in Advanced Breast Carcinoma: A Report of 3 Cases. Integrative Cancer Therapies, 8, 3, 283–287.
  • 16. Atmaca, G.Y., Dizman,C., Eren,T., Erdoğmuş,A. 2015. Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,137, 244-249.
  • 17. Kırbaç,E., Atmaca, G.Y., Erdoğmuş,A. 2014. Novel highly soluble fluoro, chloro, bromo-phenoxy-phenoxy substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties. Journal of Organometalic Chemistry, 752, 115-122.
  • 18. Laeter ,J. R. D., Böhlke, J. K., Bıèvre, P. D., Hıdaka, H., Peıser, H. S., Rosman, K. J. R., Taylor, P. D. P. 2003. Atomıc Weıghts Of The Elements:Revıew 2000. Pure and Applied Chemistry 75, 683–800.
  • 19. Atmaca, G.Y., Erdoǧmuş, A. 2019. Synthesis of new water soluble silicon phthalocyanine substituted by linker sulfur atom and photophysicochemical studies for photodynamic therapy. Journal of Porphyrins and Phthalocyanines 23, 1398-1405.
  • 20. Tayfuroglu, O., Kılıçarslan, F.A., Atmaca,G.Y., Erdogmus, A. 2018. Synthesis, characterization of new phthalocyanines and investigation of photophysical, photochemical properties and theoretical studies. Journal of Porphyrins and Phthalocyanines, 22, 250-265.
  • 21. Guzel,E., Arslan,B, Atmaca, G.Y., Nebioglu, M., Erdogmus, A. 2019. High Photosensitized Singlet Oxygen Generating Zinc and Chloroindium Phthalocyanines Bearing (4‐isopropylbenzyl) oxy Groups as Potential Agents for Photophysicochemical. Chemistry Select , 4, 2, 515-520.
  • 22. Güzel, E. 2019. Dual-purpose zinc and silicon complexes of 1,2,3-triazole group substituted phthalocyanine photosensitizers: synthesis and evaluation of photophysical, singlet oxygen generation, electrochemical and photovoltaic properties. Royal Society of Chemistry. 9, 10854-10864.
  • 23. Sen, P., Dumludağ, F., Salih, B.,Özkaya, A.R., Bekaroğlu, Ö. 2011. Synthesis and electrochemical, electrochromic and electrical properties of novel s-triazine bridged trinuclear Zn(II), Cu(II) and Lu(III) and a tris double-decker Lu(III) phthalocyanines. Synthetic Metals, 161, 13:14, 1245-1254.
  • 24. Koca, B., Hamuryudan, E., Catak, S., Erdoğmuş, A., Monari, A., Aviyente,V. 2019. Exploring the Photophysics of Polyfluorinated Phthalocyanine Derivatives as Potential Theranostic Agents. Journal of Physical Chemistry C, 123, 40, 24417-24425.
  • 25. Chauke,V., Durmuş,M., Nyokon, T. 2007. Photochemistry, photophysics and nonlinear optical parameters of phenoxy and tert-butylphenoxy substituted indium (III) phthalocyanines. Journal of Photochemistry and Photobiology A: Chemistry 192 (2-3), 179-187.
  • 26. Sen, P., Managa, M., Nyokong, T. 2019. New type of metal-free and Zinc(II), In(III), Ga(III) phthalocyanines carrying biologically active substituents: Synthesis and photophysicochemical properties and photodynamic therapy activity. Inorganica Chimica Acta, 491,1-8.
Year 2020, Volume: 16 Issue: 4, 367 - 372, 30.12.2020

Abstract

References

  • 1. Shen, X.M., Zheng, B.Y., Huang, X.R.,Wang, L., Huang J.D. 2013. First silicon (IV) phthalocyanine-nucleoside conjugates with high photodynamic activity. Dalton Transaction, 42 (29), 10398 – 10403.
  • 2. Hışır, A, Köse, G. G., Atmaca, G.Y., Erdogmus, A., Karaoglan, G.K. 2018. Novel carboxylic acid terminated silicon (IV) and zinc (II) phthalocyanine photosensitizers: Synthesis, photophysical and photochemical studies. Journal Porphyrins and Phthalocyanines, 22, 1010–1021.
  • 3. Liu, Y., Wang, P., Liu, Q., Wang, X. 2016. Sinoporphyrin sodium triggered sono-photodynamic effects on breast cancer both in vitro and in vivo. Ultrasonics Sonochemistry, 31, 437–448
  • 4. Dolmans, D.E., Fukumura, D., Jain, R.K. 2003. Photodynamic therapy for cancer. Nature Reviews Cancer, 3, 380–387.
  • 5. Yumita, N., Nishigaki, R., Umemura, K., Umemura, S.i. 1989. Hematoporphyrin as a sensitizer of cell-damaging effect of ultrasound. Cancer Science, 80, 219– 222.
  • 6. Trendowski, M. 2014. The Promise of Sonodynamic Therapy. Cancer Metastasis Reviewer. 33, 143–160.
  • 7. KÖKEN.,E. C. Doktorate thesis. Adnan Menderes University. Ehrlich Asit Tümör Hücreleri Üzerinde Kloraluminyum Ftalosiyanin ve Dosetakselin Sonodinamik Etkilerinin Araştirilmasi, 2014, Aydın.
  • 8. Chen, H., Zhou, X., Gao,Y., Zheng, B., Tang, F., Huang, J. 2014. Recent progress in development of new sonosensitizers for sonodynamic cancer therapy. Drug Discovery Today, 19, 502-509.
  • 9. D.Costley, C.M. Ewan, C. Fowley, A.P. McHale, J.Atchison, N.Nomikou, J. F. Callan. 2015. Treating cancer with sonodynamic therapy: A review. International Journal of Hyperthermia, 31(2)107–117.
  • 10. Hai-Jun, Xiao-Bin Zhou, Ai-Lan Wang , Bi-Yuan Zheng , Chih-Kuang Yeh , Jian-Dong Huang. 2018. Synthesis and biological characterization of novel rose bengal derivatives with improved amphiphilicity for sono-photodynamic therapy. European Journal of Medicinal Chemistry,145, 86-95.
  • 11. Li.,Q., Liu.Q., Wang, P., Feng, X., Wang, H., Wang, X. 2014. The effects of Ce6-mediated sono-photodynamic therapy on cell migration, apoptosis and autophagy in mouse mammary 4T1 cell line. Ultrasonics, 54, 4, 981-989.
  • 12. Jin.,Z.H. , Miyoshi, N ., Ishiguro, K., Umemura, S ., Kawabata, K ., Yumita, N ., Sakata, I. , Takaoka,K ., Udagawa ,T., Nakajima ,S.,Tajiri ,H. , Ueda, K. , Fukuda, M. , Kumakiri, M. 2000. Combination Effect of Photodynamic and Sonodynamic Therapy on Experimental Skin Squamous Cell Carcinoma in C3H/HeN Mice. Journal of Dermatol, 27, 294.
  • 13. Kolarova, H., Tomankova, K., Bajgar, R., Kolar, P., Kubinek, R. 2009. Photodynamic and Sonodynamic Treatment by Phthalocyanine on Cancer Cell Lines. Ultrasound Medicinal Biology, 35, 1397.
  • 14. Kessel D, Lo J, Jeffers R, Fowlkes, J.B., Cain, C. 1995. Modes of photodynamic vs. sonodynamic cytotoxicity. Journal of Photochemistry and Photobiology B Biology 28(3):219-21.
  • 15. Wang,X., Zhang, W., Xu,Z., Luo,Y., Mitchell, D., Ralph W. 2009. Moss. Sonodynamic and Photodynamic Therapy in Advanced Breast Carcinoma: A Report of 3 Cases. Integrative Cancer Therapies, 8, 3, 283–287.
  • 16. Atmaca, G.Y., Dizman,C., Eren,T., Erdoğmuş,A. 2015. Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,137, 244-249.
  • 17. Kırbaç,E., Atmaca, G.Y., Erdoğmuş,A. 2014. Novel highly soluble fluoro, chloro, bromo-phenoxy-phenoxy substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties. Journal of Organometalic Chemistry, 752, 115-122.
  • 18. Laeter ,J. R. D., Böhlke, J. K., Bıèvre, P. D., Hıdaka, H., Peıser, H. S., Rosman, K. J. R., Taylor, P. D. P. 2003. Atomıc Weıghts Of The Elements:Revıew 2000. Pure and Applied Chemistry 75, 683–800.
  • 19. Atmaca, G.Y., Erdoǧmuş, A. 2019. Synthesis of new water soluble silicon phthalocyanine substituted by linker sulfur atom and photophysicochemical studies for photodynamic therapy. Journal of Porphyrins and Phthalocyanines 23, 1398-1405.
  • 20. Tayfuroglu, O., Kılıçarslan, F.A., Atmaca,G.Y., Erdogmus, A. 2018. Synthesis, characterization of new phthalocyanines and investigation of photophysical, photochemical properties and theoretical studies. Journal of Porphyrins and Phthalocyanines, 22, 250-265.
  • 21. Guzel,E., Arslan,B, Atmaca, G.Y., Nebioglu, M., Erdogmus, A. 2019. High Photosensitized Singlet Oxygen Generating Zinc and Chloroindium Phthalocyanines Bearing (4‐isopropylbenzyl) oxy Groups as Potential Agents for Photophysicochemical. Chemistry Select , 4, 2, 515-520.
  • 22. Güzel, E. 2019. Dual-purpose zinc and silicon complexes of 1,2,3-triazole group substituted phthalocyanine photosensitizers: synthesis and evaluation of photophysical, singlet oxygen generation, electrochemical and photovoltaic properties. Royal Society of Chemistry. 9, 10854-10864.
  • 23. Sen, P., Dumludağ, F., Salih, B.,Özkaya, A.R., Bekaroğlu, Ö. 2011. Synthesis and electrochemical, electrochromic and electrical properties of novel s-triazine bridged trinuclear Zn(II), Cu(II) and Lu(III) and a tris double-decker Lu(III) phthalocyanines. Synthetic Metals, 161, 13:14, 1245-1254.
  • 24. Koca, B., Hamuryudan, E., Catak, S., Erdoğmuş, A., Monari, A., Aviyente,V. 2019. Exploring the Photophysics of Polyfluorinated Phthalocyanine Derivatives as Potential Theranostic Agents. Journal of Physical Chemistry C, 123, 40, 24417-24425.
  • 25. Chauke,V., Durmuş,M., Nyokon, T. 2007. Photochemistry, photophysics and nonlinear optical parameters of phenoxy and tert-butylphenoxy substituted indium (III) phthalocyanines. Journal of Photochemistry and Photobiology A: Chemistry 192 (2-3), 179-187.
  • 26. Sen, P., Managa, M., Nyokong, T. 2019. New type of metal-free and Zinc(II), In(III), Ga(III) phthalocyanines carrying biologically active substituents: Synthesis and photophysicochemical properties and photodynamic therapy activity. Inorganica Chimica Acta, 491,1-8.
There are 26 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Göknur Yaşa Atmaca

Publication Date December 30, 2020
Published in Issue Year 2020 Volume: 16 Issue: 4

Cite

APA Yaşa Atmaca, G. (2020). Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties. Celal Bayar Üniversitesi Fen Bilimleri Dergisi, 16(4), 367-372.
AMA Yaşa Atmaca G. Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties. CBUJOS. December 2020;16(4):367-372.
Chicago Yaşa Atmaca, Göknur. “Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 16, no. 4 (December 2020): 367-72.
EndNote Yaşa Atmaca G (December 1, 2020) Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 16 4 367–372.
IEEE G. Yaşa Atmaca, “Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties”, CBUJOS, vol. 16, no. 4, pp. 367–372, 2020.
ISNAD Yaşa Atmaca, Göknur. “Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 16/4 (December 2020), 367-372.
JAMA Yaşa Atmaca G. Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties. CBUJOS. 2020;16:367–372.
MLA Yaşa Atmaca, Göknur. “Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi, vol. 16, no. 4, 2020, pp. 367-72.
Vancouver Yaşa Atmaca G. Synthesis of Palladium Phthalocyanine and Investigation of Sono-Photodynamic Therapy Properties. CBUJOS. 2020;16(4):367-72.