Novel Functional Axially Substituted Silicon (IV) Phthalocyanine Derivative and its Photochemical Properties

Year 2022, Volume: 9 Issue: 2, 545 - 552, 31.05.2022

Hülya Yanık , Gülçin Ekineker

https://doi.org/10.18596/jotcsa.995902

Abstract

Photodynamic therapy is a highly specific and clinically approved method in which a non-toxic photosensitizer drug is administered to the patient for cancer treatment. Phthalocyanines with their long wavelength absorption and fluorescence from 650 to 800 nm can be used as photosensitizers for photodynamic therapy and are used in clinical trials. In this study, functional novel axially substituted silicon (IV) phthalocyanine (PS-2) was synthesized. Unsubstituted dichlorosilicon (IV) phthalocyanine was synthesized from 1,3-diiminoisoindoline via cyclotetramerization. The axial substitution reaction was carried out using dichlorosilicon (IV) phthalocyanine and excess of N-Boc-ethanolamine. Structural characterization of this novel PS-2 by FT-IR, mass, 1H NMR and UV-Vis spectroscopy were performed. Photochemical properties (photo degradation quantum yields (d) and singlet oxygen quantum yield () of PS-2, which are the first steps for cancer treatment, were investigated.

Keywords

Photodynamic therapy, Singlet Oxygen Quantum Yield, Silicon(IV) Phthalocyanine

Thanks

Authors would like to thank Meltem Göksel who contributed to the preparation of this publication.

References

• 1. Anonymous. Cancer [Internet]. WHO. 2021 [cited 2022 Mar 19].
• 2. Wayteck L, Breckpot K, Demeester J, De Smedt SC, Raemdonck K. A personalized view on cancer immunotherapy. Cancer Letters. 2014 Sep;352(1):113–25.
• 3. Kübler AC. Photodynamic therapy. Medical Laser Application. 2005 May;20(1):37–45.
• 4. Yurt F, Ocakoglu K, Ince M, Colak SG, Er O, Soylu HM, et al. Photodynamic therapy and nuclear imaging activities of zinc phthalocyanine-integrated TiO 2 nanoparticles in breast and cervical tumors. Chem Biol Drug Des. 2018 Mar;91(3):789–96.
• 5. Juzeniene A, Juzenas P, Iani V, Moan J. Topical Application of 5-Aminolevulinic Acid and its Methylester, Hexylester and Octylester Derivatives: Considerations for Dosimetry in Mouse Skin Model¶. Photochemistry and Photobiology. 2007 May 1;76(3):329–34.
• 6. Ogunsipe A, Chen J-Y, Nyokong T. Photophysical and photochemical studies of zinc( ii ) phthalocyanine derivatives—effects of substituents and solvents. New J Chem. 2004;28(7):822–7.
• 7. Kessel D, Oleinick NL. Photodynamic Therapy and Cell Death Pathways. In: Gomer CJ, editor. Photodynamic Therapy [Internet]. Totowa, NJ: Humana Press; 2010 [cited 2022 Mar 19]. p. 35–46. (Methods in Molecular Biology; vol. 635).
• 8. Lo P-C, Rodríguez-Morgade MS, Pandey RK, Ng DKP, Torres T, Dumoulin F. The unique features and promises of phthalocyanines as advanced photosensitisers for photodynamic therapy of cancer. Chem Soc Rev. 2020;49(4):1041–56.
• 9. Ekineker G, Göksel M. Synthesis of both peripheral and non-peripheral substituted metal-free phthalocyanines and characterization. Tetrahedron. 2020 Jan;76(5):130878.
• 10. Göksel M, Durmuş M, Biyiklioglu Z. Synthesis and photodynamic activities of novel silicon( iv ) phthalocyanines axially substituted with water soluble groups against HeLa cancer cell line. Dalton Trans. 2021;50(7):2570–84.
• 11. Tarhouni M, Durand D, Önal E, Aggad D, İşci Ü, Ekineker G, et al. Triphenylphosphonium-substituted phthalocyanine: Design, synthetic strategy, photoproperties and photodynamic activity. J Porphyrins Phthalocyanines. 2018 Jul;22(07):552–61.
• 12. Bartlett MA, Mark K, Sundermeyer J. Synthesis, spectroscopy and singlet oxygen quantum yield of a non-aggregating hexadecamethyl-substituted phthalocyanine silicon(IV) derivative. Inorganic Chemistry Communications. 2018 Dec;98:41–3.
• 13. Barut B, Demirbaş Ü, Özel A, Kantekin H. Novel water soluble morpholine substituted Zn(II) phthalocyanine: Synthesis, characterization, DNA/BSA binding, DNA photocleavage and topoisomerase I inhibition. International Journal of Biological Macromolecules. 2017 Dec;105:499–508.
• 14. Skupin-Mrugalska P, Szczolko W, Gierlich P, Konopka K, Goslinski T, Mielcarek J, et al. Physicochemical properties of liposome-incorporated 2-(morpholin-4-yl)ethoxy phthalocyanines and their photodynamic activity against oral cancer cells. Journal of Photochemistry and Photobiology A: Chemistry. 2018 Feb;353:445–57.
• 15. Lowery MK, Starshak AJ, Esposito JN, Krueger PC, Kenney ME. Dichloro(phthalocyanino)silicon. Inorg Chem. 1965 Jan;4(1):128–128.
• 16. Derrin D, Armarego W, Perrin D. Purification of Laboratory Chemicals. 1980.
• 17. Yanık H, Aydın D, Durmuş M, Ahsen V. Peripheral and non-peripheral tetrasubstituted aluminium, gallium and indium phthalocyanines: Synthesis, photophysics and photochemistry. Journal of Photochemistry and Photobiology A: Chemistry. 2009 Jul;206(1):18–26.
• 18. Spiller W, Kliesch H, Wöhrle D, Hackbarth S, Röder B, Schnurpfeil G. Singlet Oxygen Quantum Yields of Different Photosensitizers in Polar Solvents and Micellar Solutions. J Porphyrins Phthalocyanines. 1998 Mar;02(02):145–58.
• 19. Gülmez AD, Göksel M, Durmuş M. Silicon(IV) phthalocyanine-biotin conjugates: Synthesis, photophysicochemical properties and in vitro biological activity for photodynamic therapy. J Porphyrins Phthalocyanines. 2017 Jul;21(07n08):547–54.
• 20. Atmaca GY, Dizman C, Eren T, Erdoğmuş A. Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2015 Feb;137:244–9.