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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.

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

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.

Details

Primary Language English
Subjects Basic Sciences
Journal Section Research Article
Authors

Zekeriya BALLI
0000-0002-8311-5916
Türkiye


Mehmet Salih AĞIRTAŞ
VAN YÜZÜNCÜ YIL ÜNİVERSİTESİ
0000-0003-1296-2066
Türkiye


Ali ARSLANTAS (Primary Author)
IZMIR BAKIRCAY UNIVERSITY
0000-0002-0847-9015
Türkiye

Supporting Institution This research was supported by the Commission of Scientific Research Project of Karabük University.
Project Number KBÜBAP-18-DS-046.
Publication Date March 30, 2022
Application Date October 18, 2021
Acceptance Date March 13, 2022
Published in Issue Year 2022, Volume 9, Issue 1

Cite

Bibtex @research article { hjse1009490, journal = {Hittite Journal of Science and Engineering}, issn = {}, eissn = {2148-4171}, address = {Hitit Üniversitesi Mühendislik Fakültesi Kuzey Kampüsü Çevre Yolu Bulvarı 19030 Çorum / TÜRKİYE}, publisher = {Hitit University}, year = {2022}, volume = {9}, pages = {19 - 25}, doi = {10.17350/HJSE19030000251}, title = {An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group}, key = {cite}, author = {Ballı, Zekeriya and Ağırtaş, Mehmet Salih and Arslantas, Ali} }
APA Ballı, Z. , Ağırtaş, M. S. & Arslantas, A. (2022). An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group . Hittite Journal of Science and Engineering , 9 (1) , 19-25 . DOI: 10.17350/HJSE19030000251
MLA Ballı, Z. , Ağırtaş, M. S. , Arslantas, A. "An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group" . Hittite Journal of Science and Engineering 9 (2022 ): 19-25 <https://dergipark.org.tr/en/pub/hjse/issue/69208/1009490>
Chicago Ballı, Z. , Ağırtaş, M. S. , Arslantas, A. "An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group". Hittite Journal of Science and Engineering 9 (2022 ): 19-25
RIS TY - JOUR T1 - An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group AU - Zekeriya Ballı , Mehmet Salih Ağırtaş , Ali Arslantas Y1 - 2022 PY - 2022 N1 - doi: 10.17350/HJSE19030000251 DO - 10.17350/HJSE19030000251 T2 - Hittite Journal of Science and Engineering JF - Journal JO - JOR SP - 19 EP - 25 VL - 9 IS - 1 SN - -2148-4171 M3 - doi: 10.17350/HJSE19030000251 UR - https://doi.org/10.17350/HJSE19030000251 Y2 - 2022 ER -
EndNote %0 Hittite Journal of Science and Engineering An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group %A Zekeriya Ballı , Mehmet Salih Ağırtaş , Ali Arslantas %T An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group %D 2022 %J Hittite Journal of Science and Engineering %P -2148-4171 %V 9 %N 1 %R doi: 10.17350/HJSE19030000251 %U 10.17350/HJSE19030000251
ISNAD Ballı, Zekeriya , Ağırtaş, Mehmet Salih , Arslantas, Ali . "An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group". Hittite Journal of Science and Engineering 9 / 1 (March 2022): 19-25 . https://doi.org/10.17350/HJSE19030000251
AMA Ballı Z. , Ağırtaş M. S. , 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.
Vancouver Ballı Z. , Ağırtaş M. S. , Arslantas A. An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group. Hittite Journal of Science and Engineering. 2022; 9(1): 19-25.
IEEE Z. Ballı , M. S. Ağırtaş and A. Arslantas , "An Investigating on DNA Binding Activity of Zn(II) Phthalocyanine Complex Having Tetra Substituted Phenoxy-3-methoxybenzoic Acid Group", Hittite Journal of Science and Engineering, vol. 9, no. 1, pp. 19-25, Mar. 2022, doi:10.17350/HJSE19030000251