Antioxidant properties of water-soluble phthalocyanines containing quinoline 5-sulfonic acid groups

Antioxidant properties of water-soluble phthalocyanines containing quinoline 5-sulfonic acid groups

In the present study, the antioxidant properties of peripherally and nonperipherally water-soluble tetra(quinoline 5-sulfonic acid) substituted metal-free (1, 2), Zn(II) (3, 4), Co(II) (5, 6), and Mn(III)Cl (7, 8) phthalocyanine(Pc) derivatives were reported. In order to determine the antioxidant properties of the Pc compounds, three different commonly known antioxidant methods were used: DPPH (α,α-diphenyl-β -picrylhydrazyl) radical scavenging, ferrous ion chelating, and reducing power assays. Compound 6 showed the best DPPH activity among the other tested compounds except for the standards. The ferrous ion chelating IC50 value of compound 7 was nearly as good as that of the EDTA standard. The reducing power activity results indicated that the tested Pc compounds were as sensitive as standard reducing agents such as butylated hydroxytoluene and ascorbic acid. Overall, all tested compounds showed good antioxidant properties and it may be suggested that they could be used as new positive controls for reducing power assays in the future works.

___

  • 1. Sindhi V, Gupta V, Sharma K, Bhatnagar S, Kumari R et al. Potential applications of antioxidants-A review. Journal of Pharmacy Research 2013; 7: 828-835. doi: 10.1016/j.jopr.2013.10.001
  • 2. Maia AM, Baby AR, Yasaka WJ, Suenaga E, Kaneko TM et al. Validation of HPLC stability-indicating method for vitamin C in semisolid pharmaceutical/cosmetic preparations with glutathione and sodium metabisulfite as antioxidants. Talanta 2007; 71: 639-643. doi: 10.1016/j.talanta.2006.05.006
  • 3. Fatima K, Masood N, Luqman S. Quenching of singlet oxygen by natural and synthetic antioxidants and assessment of electronic UV/Visible absorption spectra for alleviating or enhancing the efficacy of photodynamic therapy. Biomedical Research and Therapy 2016; 3 (2): 514-527. doi: 10.7603/s40730-016-0008-6
  • 4. Williams GM, Iatropoulos MJ, Whysner J. Safety assessment of butylated hydroxyanisole and butylated hydroxytoluene as antioxidant food additives. Food and Chemical Toxicology 1999; 37: 1027-1038. doi: 10.1016/S0278- 6915(99)00085-X
  • 5. Yabaş E, Bağda E, Bağda E. The water soluble ball-type phthalocyanine as new potential anticancer drugs. Dyes and Pigments 2015; 120: 220-227. doi: 10.1016/j.dyepig.2015.03.038
  • 6. Ağırtas MS, Karatas C, Sadin Ö. Synthesis of some metallophthalocyanines with dimethyl 5-(phenoxy)-isophthalate substituents and evaluation of their antioxidant-antibacterial activities. Spectrochimica Acta A Molecular and Biomolecular Spectroscopy 2015; 135: 20-24. doi: 10.1016/j.saa.2014.06.139
  • 7. Aydın M, Alıcı EH, Bilgiçli AT, Yarasir MN, Arabaci G. Synthesis, characterization, aggregation, fluorescence and antioxidant properties of bearing (4-(methylthio)phenylthio) tetra substituted phthalocyanines. Inorganica Chimica Acta 2017; 464: 1-10. doi: 10.1016/j.ica.2017.04.038
  • 8. Kostova I, Balkansky S. Metal complexes of biologically active ligands as potential antioxidants. Current Medicinal Chemistry 2013; 20 (36): 4508-4539. doi: 10.2174/09298673113206660288
  • 9. Kobayashi N, Furuyama T, Satoh K. Rationally designed phthalocyanines having their main absorption band beyond 1000 nm. Journal of the American Chemical Society 2011; 133: 19642-19645. doi: 10.1021/ja208481q
  • 10. Günsel A, Yarasir MN, Kandaz M, Koca A. Synthesis, H- or J-type aggregations, electrochemistry and in situ spectroelectrochemistry of metal ion sensing lead(II) phthalocyanines. Polyhedron 2010; 29: 3394-3404. doi: 10.1016/j.poly.2010.09.035
  • 11. Günsel A, Güzel E, Bilgiçli AT, Yaşa Atmaca G, Erdoğmuş A et al. Synthesis and investigation of photophysicochemical properties of novel ketone-substituted gallium (III) and indium (III) phthalocyanines with high singlet oxygen yield for photodynamic therapy. Journal of Luminescence 2017; 192: 888-892. doi: 10.1016/j.jlumin.2017.08.014
  • 12. Yıldırım N, Bilgiçli AT, Alici EH, Arabacı G, Yarasir MN. Formation, characterization, aggregation, fluorescence and antioxidant properties of novel tetrasubstituted metal-free and metallophthalocyanines bearing (4- (methylthio)phenoxy) moieties. Journal of Molecular Structure 2017; 1144: 66-79. doi: 10.1016/j.molstruc.2017.05.006
  • 13. Ağırtaş MS, Gümüş I, Okumus V, Dundar A. Design of novel binuclear phthalocyanines formed by dioxyphenyl bridges: synthesis and investigation of thermal and antioxidant properties. Zeitschrift für anorganische und allgemeine Chemie 2012; 638: 1868-1872. doi: 10.1002/zaac.201200220
  • 14. Günsel A, Kocabaş S, Bilgiçli AT, Güney S, Kandaz M. Synthesis, photophysical and electrochemical properties of water–soluble phthalocyanines bearing 8-hydroxyquinoline-5-sulfonicacid derivatives. Journal of Luminescence 2016; 176: 387-396. doi: 10.1016/j.jlumin.2016.03.036
  • 15. Günsel A, Bilgiçli AT, Kırbaç E, Güney S, Kandaz M. Water soluble quarternizable gallium and indium phthalocyanines bearing quinoline 5-sulfonic acid: synthesis, aggregation, photophysical and electrochemical studies. Journal of Photochemistry and Photobiology A Chemistry 2015; 310: 155-164. doi: 10.1016/j.jphotochem.2015.05.018
  • 16. Güzel E, Günsel A, Bilgiçli AT, Yaşa Atmaca G, Erdoğmuş A et al. Synthesis and photophysicochemical properties of novel thiadiazole-substituted zinc (II), gallium (III) and silicon (IV) phthalocyanines for photodynamic therapy. Inorganica Chimica Acta 2017; 467: 169-176. doi: 10.1016/j.ica.2017.07.058
  • 17. Goksel M, Biyiklioglu Z, Durmus M. The water soluble axially disubstituted silicon phthalocyanines: photophysicochemical properties and in vitro studies. Journal of Biological Inorganic Chemistry 2017; 22 (6): 953-967. doi: 10.1007/s00775-017-1473-0
  • 18. Ozel A, Barut B, Demirbas U, Biyiklioglu Z. Investigation of DNA binding, DNA photocleavage, topoisomerase I inhibition and antioxidant activities of water soluble titanium(IV) phthalocyanine compounds. Journal of Photochemistry and Photobiology B: Biology 2016; 157: 32-38. doi: 10.1016/j.jphotobiol.2016.02.005
  • 19. Blois MS. Antioxidant determination by the use of stable free radicals. Nature 1958; 181: 1199-1200. doi: 10.1038/1811199a0
  • 20. Dinis TCP, Madeira, V.M.C., Almeida, L.M. Action of phenolic derivatives (acetaminophen, salicylate, and 5- aminosalicylate) as inhibitors of membrane lipid-peroxidation and as peroxyl radical scavengers. Archives of Biochemistry and Biophysics 1994; 315 (1): 161-169. doi: 10.1006/abbi.1994.1485
  • 21. Oyaizu M. Studies on products of browning reaction: antioxidant activity of products of browning reaction prepared from glucosamine. Japanese Journal of Nutrition and Dietetics 1986; 44: 307-315. doi: 10.5264/eiyogakuzashi.44.307
  • 22. David JM, Barreisors ALBS, Povid JP. Antioxidant phenylpropanoid esters of triterpenes from Diodea lasiophylla. Pharmaceutical Biology 2004; 42: 36-38. doi: 10.1080/13880200490505447
  • 23. Edamatsu R, Mori A, Fujita Y, Yasuhara E. Effects of the interaction of tannins with co-existing substances 6. Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chemical and Pharmaceutical Bulletin 1989; 37: 2016-2027. doi: 10.1248/cpb.37.2016
  • 24. Alici EH, Günsel A, Akin M, Bilgiçli AT, Arabaci G et al. Synthesis, characterization, antioxidant and antibacterial properties of non-peripherally and peripherally tetra-substituted phthalocyanines. Journal of Coordination Chemistry 2018; 71 (19): 3077-3089. doi: 10.1080/00958972.2018.1511778
  • 25. Keleş T, Barut B, Biyiklioglu Z, Özel A. A comparative study on DNA/BSA binding, DNA photocleavage and antioxidant activities of water soluble peripherally and non-peripherally tetra-3-pyridin-3-ylpropoxy-substituted Mn(III), Cu(II) phthalocyanines. Dyes and Pigments 2017; 139: 575-586. doi: 10.1016/j.dyepig.2016.12.045
  • 26. Swaran JSF. Structural chemical and biological aspects of antioxidants for strategies against metal and metalloid exposure. Oxidative Medicine and Cellular Longevity 2009; 2: 191-206. doi: 10.4161/oxim.2.4.9112
  • 27. Kantar C, Akal H, Kaya B, Islamoğlu F, Türk M et al. Novel phthalocyanines containing resorcinol azo dyes; synthesis, determination of pKa values, antioxidant, antibacterial and anticancer activity. Journal of Organometallic Chemistry 2015; 783: 28-39. doi: 10.1016/j.jorganchem.2014.12.042
  • 28. Ferreira ICFR, Baptista P, Vilas-Boas M, Barros L. Free-radical scavenging capacity and reducing power of wild edible mushrooms from northeast Portugal: individual cap and stipe activity. Food Chemistry 2007; 100: 1511-1516. doi: 10.1016/j.foodchem.2005.11.043
  • 29. Farajzadeh N, Karaoğlu HP, Akin M, Saki N, Koçak MB. Antimicrobial and antioxidant properties of novel octasubstituted phthalocyanines bearing (trifluoromethoxy) phenoxy groups on peripheral positions. Journal of Porphyrins and Phthalocyanines 2019; 23: 91-102. doi: 10.1142/S1088424619500068