Synthesis and Characterization of Novel Water-Soluble Tetra-Substituted Zn(II) Phthalocyanine Containing Triazole and Galactose Moieties

Synthesis and Characterization of Novel Water-Soluble Tetra-Substituted Zn(II) Phthalocyanine Containing Triazole and Galactose Moieties

In this study, new water-soluble non-peripheral tetra-substituted zinc complex of phthalocyanine which is contain galactose moieties was synthesized. ZnPc-I was prepared from the galactose substituted dicyano compound by the cyclotetramerization reaction. This dicyano compound was synthesized by Click reaction between 3-(pent-4-yn-1-yloxy)phthalonitrile and 6-azido-6-deoxy1,2:3,4-di-O-isopropylidene-α-D-galactopyranose. ZnPc-II was obtained by hydrolysis of the protected isopropylidene groups in ZnPc-I in TFA and water mixture. The galactose linked Zn(II) phthalocyanine was achieved to dissolve in common polar solvents and water. All of the new compounds were characterized by elemental analysis, 1H NMR, 13C NMR, IR, UV–vis and MS spectral data.

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  • C. C. Leznoff, A. B. P. Lever (Eds.), “Phthalocyanines—Properties and Applications,” Vols. 1–4, VCH, New York, 1989.
  • N. Farajzadeh, G. Kösoğlu, M. Erdem, G. Eryürek, M. Burkut Koçak, “Nonlinear optical properties of peripheral symmetrically and non-symmetrically 4-(trifluoromethoxy)phenoxy substituted zinc phthalocyanines,” Synthetic Metals, vol. 266, pp. 116440, 2020.
  • Y. Baygu, R. Capan, M. Erdogan, C. Ozkaya, Acikbas, Kabay, Y. Gok, “Synthesis, characterization and chemical sensor properties of a novel Zn(II) phthalocyanine containing 15-membered dioxa-dithia macrocycle moiety,” Synthetic Metals, vol. 280, pp. 116870, 2021.
  • A. J. Duro, G. de la Torre, J. Barbera, J. L. Serrano, T. Torres, “Synthesis and Liquid-Crystal Behavior of Metal-Free and Metal-Containing Phthalocyanines Substituted with Long-Chain Amide Groups,” Chemistry of Materials, vol. 8, no. 5, pp. 1061, 1996.
  • B. Yıldız, B. S. Arslan, E. Güzel, M. Nebioglu, N. Menges, I. Sisman, M. K. Sener, “Non-aggregating zinc phthalocyanine sensitizer with bulky diphenylphenoxy donor groups and pyrazole-3-carboxylic acid anchoring group for coadsorbent-free dye-sensitized solar cells,” Solar Energy, vol. 226, pp. 173–179, 2021.
  • L. Valli, “Phthalocyanine-based Langmuir–Blodgett films as chemical sensors,” Advances in Colloid and Interface Science, vol. 116, no. 1-3, pp. 13-44, 2005.
  • T. Nyokong, V. Ahsen (Eds.), “Photosensitizers in Medicine, Environment and Security,” Springer, Dordrecht Heidelberg London New York, 2012.
  • C. Hopper, “Photodynamic therapy: a clinical reality in the treatment of cancer,” The Lancet Oncology, vol. 1, pp. 212-219, 2000.
  • Y. Uruma, L. Sivasamy, P. M. Y. Yoong, K. Onuma, Y. Omura, M. Doe, M. Osaki, F. Okada, “Synthesis and biological evaluation of glucose conjugated phthalocyanine as a second-generation photosensitizer,” Bioorganic & Medicinal Chemistry, vol. 27, no. 15, pp. 3279-3284, 2019.
  • H. T., Akçay, M. Piskin, Ü. Demirbas, R. Bayrak, M. Durmus, E. Menteşe, H. Kantekin, “Novel triazole bearing zinc(II) and magnesium(II) metallo-phthalocyanines: Synthesis, characterization, photophysical and photochemical properties,” Journal of Organometallic Chemistry, vol. 745-746, pp. 379-386, 2013.
  • G. Reddy, E. D. Enrico Della Gaspera, L. A. Jones, L. Giribabu, “Self-assembly of a symmetrical dimethoxyphenyl substituted Zn(II) phthalocyanine into nanoparticles with enhanced NIR absorbance for singlet oxygen generation,” Journal of Photochemistry & Photobiology, A: Chemistry, vol. 408, pp. 113123, 2021.
  • A. Ogunsipe, T. Nyokong, “Photophysical and photochemical studies of sulphonated non-transition metal phthalocyanines in aqueous and non-aqueous media,” Journal of Photochemistry & Photobiology, A: Chemistry, vol. 173, no. 2, pp. 211, 2005.
  • Z. Iqbal, M. Hanack, T. Ziegler, “Synthesis of an octasubstituted galactose zinc(II) phthalocyanine,” Tetrahedron Letters, vol. 50, no. 8, pp. 873–875, 2009.
  • A. O. Ribeiro, J. P. C. Tomé, M. G. P. M. S. Neves, A. C. Tomé, J. A. S. Cavaleiro, Y. Iamamoto, T. Torres, “[1,2,3,4-Tetrakis(α/β-d-galactopyranos-6-yl)phthalocyaninato]zinc(II): a water-soluble phthalocyanine,” Tetrahedron Letters, vol. 47, no. 52, pp. 9177–9180, 2006.
  • T. K. Horne, M. J. Cronjé, “Novel carbohydrate-substituted metallo-porphyrazine comparison for cancer tissue-type specificity during PDT,” Journal of Photochemistry and Photobiology B: Biology, vol. 173, pp. 412-422, 2017.
  • A. M. Otto, “Warburg effect(s)—a biographical sketch of Otto Warburg and his impacts on tumor metabolism,” Cancer and Metabolism, vol. 4, no. 5, pp. 1-8, 2016.
  • M. V. Liberti, J. W. Locasale, “The Warburg effect: how does it benefit cancer cells?,” Trends in Biochemical Sciences, vol. 41, no. 3, pp. 211–218. 2016.
  • R. Huisgen, “1,3-Dipolar Cycloadditions Past and Future,” Angewandte Chemie International Edition, vol. 2, pp. 565-598, 1963.
  • H. C. Kolb, M. G. Finn, K. B. Shapless, “Click Chemistry: Diverse Chemical Function from a Few Good Reactions,” Angewandte Chemie International Edition, vol. 40, pp. 2004-2021, 2001.
  • Y. Baygu, B. Yıldız, N. Kabay, Y. Gök, “Novel magnesium and zinc porphyrazines containing galactose moieties: synthesis via click reaction and characterization,” Inorganic Chemistry Communications, vol. 71, pp. 35-40, 2016.
  • F. Bächle, N. Siemens, T. Ziegler, ”Glycoconjugated Phthalocyanines as Photosensitizers for PDT – Overcoming Aggregation in Solution," European Journal of Organic Chemistry, vol. 2019, pp. 7089-7116, 2019.
  • D. D. Perin, W. L. F. Armarego, D. R. Perin, “Purification of Laboratory Chemicals,” 2nd ed., Pergamon Press, New York, 1985.
  • Z. Kanat, H. Dinçer, “The synthesis and characterization of nonperipherally tetra terminal alkynyl substituted phthalocyanines and glycoconjugation via the click reaction,” Dalton Transactions, vol. 43, pp. 8654–8663, 2014.
  • J. A. F. Joosten, B. Evers, R. P. van Summeren, J. P. Kamerling, J. F. G Vliegenthart, “Synthesis of β-D-Galp-(1→4)-β-D-GlcpNAc-(1→2)-α-D-Manp-(1→O)(CH2)7CH3 Mimics to Explore the Substrate Specificity of Sialyltransferases and trans-Sialidases,” European Journal of Organic Chemistry, vol. 18, no. 6, pp. 3569-3586, 2003.
  • A. R. M. Soares, J. P. C., Tomé, M. G. P. M. S. Neves, A. C. Tomé, J. A. S. Cavaleiro, T. Torres, “Synthesis of water-soluble phthalocyanines bearing four or eight D-galactose units,” Carbohydrate Research, vol. 344, no. 4, pp. 507–510, 2009.