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An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group

Year 2022, Volume: 9 Issue: 1, 19 - 25, 30.03.2022
https://doi.org/10.17350/HJSE19030000251

Abstract

The tetra substituted Zn(II) phthalocyanine complex having the dicyanophenoxy)-3-methoxybenzoic acid group had been obtained from 4-(3, 4-dicyanophenoxy)-3-methoxybenzoic acid and analyzed with the application of FT-IR, NMR, UV/Vis techniques in compliance with reported literature. The interacting property of Pc4 by CT-DNA was examined with absorption bands, emission titrations, melting temperature, viscosity, and gel electrophoresis procedures. The obtained findings from these techniques demonstrated that the complex containing the dicyanophenoxy)-3-methoxybenzoic acid binds to the DNA by means of intercalation attachment mechanisms.

Supporting Institution

This research was supported by the Commission of Scientific Research Project of Karabük University.

Project Number

KBÜBAP-18-DS-046.

References

  • 1. Yılmaz F, Ozer M, Kani I, Bekaroglu O. Catalytic activity of a thermoregulated, phase-separable Pd(II)-perfluoroalkylphthalocyanine complex in an organic/fluorous biphasic system: hydrogenation of olefins. Catalysis Letters 130 (2009) 642-647.
  • 2. Leznoff CC, Lever ABP. Phthalocyanines Properties and Applications. VCH Publisher, New York, Vol. 2, 1993.
  • 3. Leznoff CC, Lever ABP. Phthalocyanines Properties and Applications. VCH Publisher, New York, Vol. 1, 1989.
  • 4. Parra V, Bouvet M, Brunet J, Rodríguez-Mendez ML, Saja JA. On the effect of ammonia and wet atmospheres on the conducting properties of different lutetium bisphthalocyanine thin films. Thin Solid Films 516 (2008) 9012-9019. 5. Bouvet M. Phthalocyanine-based field-effect transistors as gas sensor. Analytical and Bioanalytical Chemistry 384 (2006) 366-373.
  • 6. Rosenthal I. Phthalocyanines as photodynamic sensitizer. Photochemistry and hotobiology 53 (1991) 859-870.
  • 7. Leznoff CC, Lever ABP. Phthalocyanines, Properties and Applications. VCH Publisher, New York, 1996.
  • 8. Hadjiliadis ND, Sletten E. Metal complex–DNA interactions. Wiley-Blackwell, New York, 2009.
  • 9. Van Holst M, M.P. Grant MP, Aldrich-Wright J. Metallointercalators- Synthesis and Techniques to Probe Their Interactions with Biomolecules. Springer Wien, New York, 2011.
  • 10. Lukyanets EA. Phthalocyanines as photosensitizers in the photodynamic therapy of cancer. Journal of Porphyrins and Phthalocyanines 3 (1999) 424–432.
  • 11. Vummidi BR, Noreen F, Alzeer J, Moelling K, Luedtke NW. Photodynamic agents with anti-metastatic activities. ACS Chemical Biology 8 (2013) 1737–1746.
  • 12. Yildiz BT, Sezgin T, Cakar ZP, Uslan C, Sesalan BS. The use of novel photobleachable phthalocyanines to image DNA. Synthetic Metals 161 (2011) 1720–1724.
  • 13. Amitha GS, Vasudevan S. DNA/BSA binding studies of peripherally tetra substituted neutral azophenoxy zinc phthalocyanine. Polyhedron 175 (2020) 114208
  • 14. Ali A, Bhattacharya S. DNA binders in clinical trials and chemotherapy. Bioorganic Medicinal Chemistry 22 (2014) 4506–4521.
  • 15. Alam MDF, Varshney S, Khan MA, Laskar AA, Younus H. In vitro DNA binding studies of therapeutic and prophylactic drug citral. International Journal of Biological Macromolecules 113 (2018) 300–8.
  • 16. Palchaudhuri R, Hergenrother PJ. DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action. Current. Opinion in biotechnology 18 (2007) 497–503.
  • 17. Bağda E, Yabaş E,Bağda E. Analytical approaches for clarification of DNA-double deckerphthalocyanine binding mechanism: As an alternative anticancer chemotherapeutic. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 172 (2017) 199–204
  • 18. Rescifina A, Zagni C, Varrica MG, Pistarà V, Corsaro A. Recent advances in small organic molecules as DNA intercalating agents: synthesis, activity, and modeling. European journal of medicinal chemistry 74 (2014) 95–115.
  • 19. Ozluer C, Satana Kara HE. In vitro DNA binding studies of anticancer drug idarubicin using spectroscopic techniques. Journal of photochemistry and photobiology. B, Biology 138 (2014) 36–42.
  • 20. Williams AK, Dasilva SC, Bhatta A, Rawal B, Liu M, Korobkova EA. Determination of the drug-DNA binding modes using fluorescence-based assays. Analytical Biochemistry 411 (2012) 66–73.
  • 21. Özkay Y, Işıkdağ İ, İncesu Z, Akalın G. Synthesis of 2-substituted-N-[4-(1-methyl-4,5-diphenyl-1H-imidazole-2-yl)phenyl]acetamide derivatives and evaluation of their anticancer activity. European Journal of Medicinal Chemistry 45 (2010) 3320–3328.
  • 22. Uslan C, Sesalan BŞ. The synthesis, photochemical and biological properties of new silicon phthalocyanines. Inorganica Chimica Acta 394 (2013) 353–362.
  • 23. Özgül G, Taştemel A, Özkaya AR, Bulut M. Synthesis, characterization and comparative electrochemistry of beta and alpha tetra-[4-oxy-3-methoxybenzoic acid]-substituted Zn(II), Co(II) and Cu(II) phthalocyanines. Polyhedron 85 (2015) 181-189.
  • 24. Wolfe A, Shimer GH, Meehan T. Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry 26 (1987) 6392–6396.
  • 25. Liu X-W, Shen Y-M, Li Z-X, Zhong X, Chen Y-D, Zhang S-B. Study on DNA binding behavior and light switch effect of new coumarin-derived Ru(II) complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 149 (2015) 150–156.
  • 26. Barton JK, Goldberg JM, Kumar CV, Turro NJ. Binding modes and base specificity of tris(phenanthroline)ruthenium(II) enantiomers with nucleic acids: tuning the stereoselectivity Journal of American Chemical 108 (1986) 2081–2088.
  • 27. Shoukry AA, Mohamed MS. DNA-binding, spectroscopic and antimicrobial studies of palladium(II) complexes containing 2,20 -bipyridine and 1-phenylpiperazine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 586–593.
Year 2022, Volume: 9 Issue: 1, 19 - 25, 30.03.2022
https://doi.org/10.17350/HJSE19030000251

Abstract

Project Number

KBÜBAP-18-DS-046.

References

  • 1. Yılmaz F, Ozer M, Kani I, Bekaroglu O. Catalytic activity of a thermoregulated, phase-separable Pd(II)-perfluoroalkylphthalocyanine complex in an organic/fluorous biphasic system: hydrogenation of olefins. Catalysis Letters 130 (2009) 642-647.
  • 2. Leznoff CC, Lever ABP. Phthalocyanines Properties and Applications. VCH Publisher, New York, Vol. 2, 1993.
  • 3. Leznoff CC, Lever ABP. Phthalocyanines Properties and Applications. VCH Publisher, New York, Vol. 1, 1989.
  • 4. Parra V, Bouvet M, Brunet J, Rodríguez-Mendez ML, Saja JA. On the effect of ammonia and wet atmospheres on the conducting properties of different lutetium bisphthalocyanine thin films. Thin Solid Films 516 (2008) 9012-9019. 5. Bouvet M. Phthalocyanine-based field-effect transistors as gas sensor. Analytical and Bioanalytical Chemistry 384 (2006) 366-373.
  • 6. Rosenthal I. Phthalocyanines as photodynamic sensitizer. Photochemistry and hotobiology 53 (1991) 859-870.
  • 7. Leznoff CC, Lever ABP. Phthalocyanines, Properties and Applications. VCH Publisher, New York, 1996.
  • 8. Hadjiliadis ND, Sletten E. Metal complex–DNA interactions. Wiley-Blackwell, New York, 2009.
  • 9. Van Holst M, M.P. Grant MP, Aldrich-Wright J. Metallointercalators- Synthesis and Techniques to Probe Their Interactions with Biomolecules. Springer Wien, New York, 2011.
  • 10. Lukyanets EA. Phthalocyanines as photosensitizers in the photodynamic therapy of cancer. Journal of Porphyrins and Phthalocyanines 3 (1999) 424–432.
  • 11. Vummidi BR, Noreen F, Alzeer J, Moelling K, Luedtke NW. Photodynamic agents with anti-metastatic activities. ACS Chemical Biology 8 (2013) 1737–1746.
  • 12. Yildiz BT, Sezgin T, Cakar ZP, Uslan C, Sesalan BS. The use of novel photobleachable phthalocyanines to image DNA. Synthetic Metals 161 (2011) 1720–1724.
  • 13. Amitha GS, Vasudevan S. DNA/BSA binding studies of peripherally tetra substituted neutral azophenoxy zinc phthalocyanine. Polyhedron 175 (2020) 114208
  • 14. Ali A, Bhattacharya S. DNA binders in clinical trials and chemotherapy. Bioorganic Medicinal Chemistry 22 (2014) 4506–4521.
  • 15. Alam MDF, Varshney S, Khan MA, Laskar AA, Younus H. In vitro DNA binding studies of therapeutic and prophylactic drug citral. International Journal of Biological Macromolecules 113 (2018) 300–8.
  • 16. Palchaudhuri R, Hergenrother PJ. DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action. Current. Opinion in biotechnology 18 (2007) 497–503.
  • 17. Bağda E, Yabaş E,Bağda E. Analytical approaches for clarification of DNA-double deckerphthalocyanine binding mechanism: As an alternative anticancer chemotherapeutic. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 172 (2017) 199–204
  • 18. Rescifina A, Zagni C, Varrica MG, Pistarà V, Corsaro A. Recent advances in small organic molecules as DNA intercalating agents: synthesis, activity, and modeling. European journal of medicinal chemistry 74 (2014) 95–115.
  • 19. Ozluer C, Satana Kara HE. In vitro DNA binding studies of anticancer drug idarubicin using spectroscopic techniques. Journal of photochemistry and photobiology. B, Biology 138 (2014) 36–42.
  • 20. Williams AK, Dasilva SC, Bhatta A, Rawal B, Liu M, Korobkova EA. Determination of the drug-DNA binding modes using fluorescence-based assays. Analytical Biochemistry 411 (2012) 66–73.
  • 21. Özkay Y, Işıkdağ İ, İncesu Z, Akalın G. Synthesis of 2-substituted-N-[4-(1-methyl-4,5-diphenyl-1H-imidazole-2-yl)phenyl]acetamide derivatives and evaluation of their anticancer activity. European Journal of Medicinal Chemistry 45 (2010) 3320–3328.
  • 22. Uslan C, Sesalan BŞ. The synthesis, photochemical and biological properties of new silicon phthalocyanines. Inorganica Chimica Acta 394 (2013) 353–362.
  • 23. Özgül G, Taştemel A, Özkaya AR, Bulut M. Synthesis, characterization and comparative electrochemistry of beta and alpha tetra-[4-oxy-3-methoxybenzoic acid]-substituted Zn(II), Co(II) and Cu(II) phthalocyanines. Polyhedron 85 (2015) 181-189.
  • 24. Wolfe A, Shimer GH, Meehan T. Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry 26 (1987) 6392–6396.
  • 25. Liu X-W, Shen Y-M, Li Z-X, Zhong X, Chen Y-D, Zhang S-B. Study on DNA binding behavior and light switch effect of new coumarin-derived Ru(II) complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 149 (2015) 150–156.
  • 26. Barton JK, Goldberg JM, Kumar CV, Turro NJ. Binding modes and base specificity of tris(phenanthroline)ruthenium(II) enantiomers with nucleic acids: tuning the stereoselectivity Journal of American Chemical 108 (1986) 2081–2088.
  • 27. Shoukry AA, Mohamed MS. DNA-binding, spectroscopic and antimicrobial studies of palladium(II) complexes containing 2,20 -bipyridine and 1-phenylpiperazine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 586–593.
There are 26 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Zekeriya Ballı 0000-0002-8311-5916

Mehmet Salih Ağırtaş 0000-0003-1296-2066

Ali Arslantas 0000-0002-0847-9015

Project Number KBÜBAP-18-DS-046.
Publication Date March 30, 2022
Submission Date October 18, 2021
Published in Issue Year 2022 Volume: 9 Issue: 1

Cite

Vancouver Ballı Z, Ağırtaş MS, Arslantas A. An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group. Hittite J Sci Eng. 2022;9(1):19-25.

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