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DNA-binding and spectroscopic studies of cobalt (II) compound containing 2, 10, 16, 24-tetrakis 4-(2-phenoxy-1, 3-dioxo-2, 3-dihydro-1H-inden-2-yloxy) phthalonitrile

Year 2017, Volume: 5 Issue: 3, 1 - 9, 01.10.2017
https://doi.org/10.21541/apjes.329065

Abstract

In this study, binding activities of the
previously synthesized
cobalt
(II) compound (PcCo) with
calf thymus-DNA containing 2, 10, 16, 24-tetrakis 4-(2-phenoxy-1,
3-dioxo-2, 3-dihydro-1H-inden-2-yloxy) phthalonitrile were investigated to
determine binding activities by using UV-Vis absorption, fluorescence titration
methods.
Absorption titration spectra of PcCo in DMF give peaks at about 670 nm
for Q-band absorption and about 340 nm for B-band absorption in the absence of
calf thymus-DNA. Emission intensities of PcCo
in presence of calf thymus-DNA, PcCo gives
emission at about 545 nm. Thermal
denaturation profile study was systematically studied by UV/Vis spectroscopic
technique and melting point temperaturewas found around 7.87 oC
for Co (II) phthalocyanine compound.  The
reduction oxidation behavior of PcCo with
calf thymus-DNA was investigated using cyclic voltammetry (CV).
Cathodic peak potential and anodic peak
potential for PcCo were recorded to be 0.84, -0.36 V for EPc and 0.88 V, 0.15
V, and -0.69 V EPa. The cyclic
voltammetric results show one half- reversible reduction oxidation wave. The
shift in Epc and Epa potentials indicates that PcCo shows strong interaction with calf thymus-DNA. Further to
understand binding activities of PcCo
with calf thymus-DNA was studied by using electrophoresis technique. Electrophoresis
findings showed that there is decrease in the intensity of CT-DNA bands. All the findings show that PcCo interacts strongly with DNA
molecule via an intercaltion binding.

References

  • C.C. Leznoff, A.B.P. Lever, ´´Phthalocyanines Properties and Applications´´ New York, Wiley-VCH, New York, Vol. 4, pp-79-181, 1996.
  • N.B. McKeown, ´´Phthalocyanines Materials: Synthesis, Structure and Functions´´ Cambridge, MA: Cambridge University Press. 1998.
  • M.S. Agırtas, A. Altındal, B. Salih, S. Saydam, O. ´´Bekaroglu, Synthesis, characterization, and electrochemical and electrical properties of novel mono and ball-type mettalophthalocyanines with four 9,9-bis(4-hydroxyphenyl)fluorine´´ Dalton Trans., Vol. 40, pp. 3315-3324, 2011.
  • Y. Peng, H. Zhang, H. Wu, B. Huang, L. Gan, Z. Chen, ´´The synthesis and photophysical properties of zinc (II) phthalocyanine bearing poly (aryl benzyl ether) dendritic substituents´´ Dyes and Pigments, Vol. 87, pp. 10–16, 2010.
  • M.S. Agırtas, ´´Synthesis and characterization of novel symmetrical pthalocyanines substituted with four benzo [d]>[1,3] dioxol-5-ylmethoxy groups´´ Inorg.chim. Acta., Vol. 360, pp. 2499-2502, 2007.
  • J-D. Wang, M-J. Lin, S-F. Wu, Y. Lin, ´´15-Bis (2,2,4-trimethylpentoxy)phthalocyanine, a trans-form nonperipheral disubstituted phthalocyanines synthesis by the cross condensation method´´ J. Organomet. Chem., Vol. 691, pp. 5074-5076, 2006.
  • M. Kandaz, O. Bekaroglu, ´´Synthesis and characterization of novel actakis (2-aminophenoxy and aminophenylsulfanyl)-substituted metallophthalocyanines´´ Chem. Ber./Recueli., Vol. 130, pp. 1833-1836, 1997.
  • N. Nombona, E. Antunes, T. Nyokong, ´´The sysnthesis and fluorescence behavviour of phthalocyanines unsymmetrically substituted with naphthol and carboxy groupss´´ Dyes and Pigments, Vol.86, pp. 68-73, 2010.
  • O. Bekaroglu, ´´Ball-type phthalocyanines: synthesis and properties´´ Struct. Bond., Vol. 135, pp. 105-136, 2010.
  • G. Keser Karaoglan, G. Gumrukcu, A. Koca, A. Gul, ´´The synthesis, characterizatio, electrochemical and spectroelectrochemical properties of a novel, cationic, water-soluble Zn phthalocyanine extended conjugation´´ Dyes and Pigments, Vol. 88, pp. 247-256, 2011.
  • A.G. Gurek, V. Ahsen, A. Gul, O. Bekaroglu, ´´Synthesis and characterization of a new copper (II) phthalocyaninato substituted with four 15-membered tetraazamacrocycles and its water soluble pentanuclear complexes´´ J. Chem. Soc., Dalton Trans., pp. 3367-3371, 1991.
  • E. Ben-Hur, R.C. Hoeben, H. Van Ormondt, T.M.A.R. Dubbelman, J. Van Steveninck, ´´Inactivation of retroviruses by phthalocyanines: the effects of sulphonation, metal ligand and fluoride´´ J. Photochem. Photobiol. B: Biol., Vol. 13, pp. 145-152, 1992.
  • J.D. Spikes, ´´Phthalocyanines as photosensitizers in biological systems Phthalocyanines as photosensitizers in biological systems and for the photodynamic therapy of tumors´´ Photochem. Photobiol., Vol. 43, pp. 691-699, 1986.
  • J. Ferlay, I. Soerjomatarm, R. Dikshit, R. Eser, C. Mathers, M. Rebelo, D.M. Parkin, D. Forman, F. Bray, ´´Cancer incidence and mortality worlwide: sources, methods and major patterns in Globocan´´ Int. J. Canc., Vol. 136, pp. 359-86, 2015.
  • R. Gul, A. Badshah, A. Khan, A. Junaid, M.K. Rauf, ´´Preliminary investigation of anticancer activitiy by determining the DNA binding and antioxidant potency of new ferrocene incorporated N,N’,N’’-trisubstituted phenylgunidines´´ Spectrochim Acta Part A Mol. Biomol. Spect., Vol. 117, pp. 264-9, 2014.
  • C. Uslan, B.S. Sesalan, ´´The synthesis, photochemical and biological properties of new silicon phthalocyanines´´ Inorg. Chim. Acta, Vol. 394, pp. 353-62, 2013.
  • T. Keles, B. Barut, Z. Biyiklioglu, A. Özel, ´´A comparative study on DNA/BSA binding, DNA phorocleavage and antioxidant activities of water soluble peripherally and non-peripherally tetra-3-pyridin-3-ylpropoxy-substituted Mn (III), Cu (II) phthalocyanines´´ Dyes and Pigments, doi: 10.1016/j.dyepig. 2016.12.045, 2017.
  • S.M. Pradeepa, H.S. Bhojya Naik, B. Vinay Kumar, K. Indira Priyadarsini, A. Barik, S. Jayakumar, ´´Synthesis and characterization of cobalt(II), nickel(II) and copper(II)-based potential photosensitizers: Evaluation of their DNA binding profile, cleavage and Photocytotoxicity´´ Inorg. Chim. Acta, Vol. 428, pp. 138-46, 2015.
  • B. Zheng, X. Shen, D. Zhao, Y. Cai, M. Ke, J. Huang, ´´Silicon (IV) phthalocyanines substituted axially with different nucleoside moieties. Effects of nucleoside type on the photosensitizing efficiencies and in vitro photodynamic activities´´ J. Photochem. Photobiol. B: Biol., Vol. 159, pp. 196-204, 2016.
  • L. Xodo, S. Cogoi, V. Rapozzi, ´´Photosensitizers binding to nucleic acids as anticanceragents´´ Fut. Med. Chem., Vol. 8, pp. 179-94, 2016.
  • M.S. Ağırtaş, İ. Gümüş, M. S. İzgi, ´´Designing of new thermo stabile phthalocyanines: synthesis, characterization, and thermal studies´´ Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, Vol. 42, pp. 1327-1333, 2012.
  • J. Bolger, A. Gourdon, E. Ishow, J. P. Launay, ´´Mononuclear and Binuclear Tetrapyrido[3,2-a:2‘,3‘-c:3‘‘,2‘‘-h:2‘‘‘,3‘‘‘-j]phenazine (tpphz) Ruthenium and Osmium Complexes´´Inorg. Chem., Vol.35, pp. 2937–2944, 1996.
  • A. S. Azza, M. S. Mohamed, ´´DNA binding, spectrocopic and antimicrobial studies of palladium (II) complexes containin 2,2o-bipyridin and 1-phenypiperazine´´ Spectrochim. Acta Part A Mol. Biomol. Spect., Vol. 96, pp. 586-593, 2012.
  • M. Özçesmeci, Ö. B. Ecevit, S. Sürgün, E. Humuryudan, ´´Tetracationic fluorinated zinc (ii) phthalocyanine: Synthesis, characterization and DNA-binding properties´´ Dyes and Pigments, Vol. 96, pp. 52-58, 2013.
  • P.R. Reddy, A. Shilpa, N. Raju, P. Raghavaiah, ´´Synthesis, structure, DNA binding and cleavage properties of ternaryamino acid Schiff base-phen/bipy C(II) complexes´´ J. Inorg. Bioochem., Vol. 105, pp. 1603-1612, 2011.
  • A. Apilux, O. Tabata MChailapakul, ´´Electrochemical bihaviors of native and thermal denatured fish DNA in the presence of cytosine derivatives and porphyrin by cyclic voltammetry using boron-drobed diamond electrode´´ Bioelectrochemistry, Vol. 70, pp. 435-439, 2007.
  • N. Demirezen, D. Tarınc, D. Polat, M. Cesme, A. Golcu, M. Tumer, ´´Synthesis of trimethoprim metal complexes: Spectral, electrochmical, thermal, DNA-binding and surface morp hology studies´´ Spectrochimica Acta Part A, Vol. 94, pp. 243-255, 2012.
  • X-W. Liu, Y-M. Shen, Z-X. Li, X. Zhong, Y-D. Chen, S-B. Zhang, ´´Study on DNA binding behavior and light switch effect of new coumarin-derived Ru (II) complexes´´ Spectrochim. Acta Part: Mol. Biomol. Specrt., Vol. 149, pp. 150-156, 2015.
  • C. Ozluer, H. E. Satana Kara, ´´In vitro DNA binding studies of anticancer drug idarubicin using spectroscopic techniques´´ J. Photochem. Photobiol. B., Vol. 138, pp. 36–42, 2014.
  • A. Özel, B. Barut, Ü. Demirbaş, Z. Biyiklioglu, ´´Invetigation of DNA binding, DNA photocleavage, topoisomerase I inhibition and antioxidant activities of water soluble titanium (IV) phthalocyanine compounds´´ J. Photoch. Photobiol. B. Biology, Vol. 157, pp.32-38, 2016.
  • S. Mahadevan, M. Palaniandavar, ´´Spectroscopic and voltametric studies on copper complexes of 2,9-dimethyl-1,10-phenanthrolines bound to calf thymus DNA´´ J. Inorg. Chem., Vol. 37, pp. 693-706, 1998.
  • M. Sirajuddin, S. Ali, A. Badshah, ´´Drug-DNA interactions and their study by UV-Visible, fluorescence spectroscopies and cyclic voltametry´´ J. Photochem. Photobiol. B. Biology, Vol. 124, pp. 1-19, 2013.

2, 10, 16, 24-Tetrakis 4- (2-fenoksi-l, 3-diokso-2,3-dihidro-lH-inden-2-iloksi) ftalonitril içeren kobalt (II) bileşiğinin DNA bağlanmasının spektroskopik yöntemler ile araştırılması

Year 2017, Volume: 5 Issue: 3, 1 - 9, 01.10.2017
https://doi.org/10.21541/apjes.329065

Abstract

2,10, 16, 24-tetrakis 4-
(2-fenoksi-1,3-diokso-2,3-dihidro-lH-inden-2-iloksi) ftalonitril içeren önceden
sentezlenmiş kobalt (II) bileşiğinin (PcCo)
CT-DNA ile bağlanma özellikleri UV/Vis absorpsiyon, floresan titrasyonu
yöntemleri kullanılarak bağlanma özelliklerini belirlemek için araştırıldı.
Termal denatürasyon profili çalışması UV-Vis spektroskopik tekniği ile
sistematik olarak incelenmiş ve Co (II) ftalosiyanin bileşiği için erime
noktası sıcaklık değeri 7.87 oC civarında bulunmuştur. CT-DNA
yokluğunda ve varlığında PcCo'in
redüksiyon oksidasyon davranışı, dönüşümlü voltametri (CV) ile incelendi.
Dönüşümlü (cyclic) voltametri sonuçlar, bir yarı-tersinir redaksiyon oksidasyon
dalgasını göstermektedir. Epc ve Epa potansiyelindeki değişim, PcCo'in CT-DNA'yla güçlü etkileşim gösterdiğini
önermektedir. PcCo'in CT-DNA ile
olan etkileşimi ayrıca jel elektroforez yöntemi kullanılarak araştırılmıştır.
Jel elektroforezi sonuçları, CT-DNA bantlarının yoğunluğunda azalma olduğunu
gösterdi. Tüm bulgular, PcCo ile
CT-DNA molekülü arasındaki etkileşimin interkalatif bağlanma türü olduğunu
göstermektedir.

References

  • C.C. Leznoff, A.B.P. Lever, ´´Phthalocyanines Properties and Applications´´ New York, Wiley-VCH, New York, Vol. 4, pp-79-181, 1996.
  • N.B. McKeown, ´´Phthalocyanines Materials: Synthesis, Structure and Functions´´ Cambridge, MA: Cambridge University Press. 1998.
  • M.S. Agırtas, A. Altındal, B. Salih, S. Saydam, O. ´´Bekaroglu, Synthesis, characterization, and electrochemical and electrical properties of novel mono and ball-type mettalophthalocyanines with four 9,9-bis(4-hydroxyphenyl)fluorine´´ Dalton Trans., Vol. 40, pp. 3315-3324, 2011.
  • Y. Peng, H. Zhang, H. Wu, B. Huang, L. Gan, Z. Chen, ´´The synthesis and photophysical properties of zinc (II) phthalocyanine bearing poly (aryl benzyl ether) dendritic substituents´´ Dyes and Pigments, Vol. 87, pp. 10–16, 2010.
  • M.S. Agırtas, ´´Synthesis and characterization of novel symmetrical pthalocyanines substituted with four benzo [d]>[1,3] dioxol-5-ylmethoxy groups´´ Inorg.chim. Acta., Vol. 360, pp. 2499-2502, 2007.
  • J-D. Wang, M-J. Lin, S-F. Wu, Y. Lin, ´´15-Bis (2,2,4-trimethylpentoxy)phthalocyanine, a trans-form nonperipheral disubstituted phthalocyanines synthesis by the cross condensation method´´ J. Organomet. Chem., Vol. 691, pp. 5074-5076, 2006.
  • M. Kandaz, O. Bekaroglu, ´´Synthesis and characterization of novel actakis (2-aminophenoxy and aminophenylsulfanyl)-substituted metallophthalocyanines´´ Chem. Ber./Recueli., Vol. 130, pp. 1833-1836, 1997.
  • N. Nombona, E. Antunes, T. Nyokong, ´´The sysnthesis and fluorescence behavviour of phthalocyanines unsymmetrically substituted with naphthol and carboxy groupss´´ Dyes and Pigments, Vol.86, pp. 68-73, 2010.
  • O. Bekaroglu, ´´Ball-type phthalocyanines: synthesis and properties´´ Struct. Bond., Vol. 135, pp. 105-136, 2010.
  • G. Keser Karaoglan, G. Gumrukcu, A. Koca, A. Gul, ´´The synthesis, characterizatio, electrochemical and spectroelectrochemical properties of a novel, cationic, water-soluble Zn phthalocyanine extended conjugation´´ Dyes and Pigments, Vol. 88, pp. 247-256, 2011.
  • A.G. Gurek, V. Ahsen, A. Gul, O. Bekaroglu, ´´Synthesis and characterization of a new copper (II) phthalocyaninato substituted with four 15-membered tetraazamacrocycles and its water soluble pentanuclear complexes´´ J. Chem. Soc., Dalton Trans., pp. 3367-3371, 1991.
  • E. Ben-Hur, R.C. Hoeben, H. Van Ormondt, T.M.A.R. Dubbelman, J. Van Steveninck, ´´Inactivation of retroviruses by phthalocyanines: the effects of sulphonation, metal ligand and fluoride´´ J. Photochem. Photobiol. B: Biol., Vol. 13, pp. 145-152, 1992.
  • J.D. Spikes, ´´Phthalocyanines as photosensitizers in biological systems Phthalocyanines as photosensitizers in biological systems and for the photodynamic therapy of tumors´´ Photochem. Photobiol., Vol. 43, pp. 691-699, 1986.
  • J. Ferlay, I. Soerjomatarm, R. Dikshit, R. Eser, C. Mathers, M. Rebelo, D.M. Parkin, D. Forman, F. Bray, ´´Cancer incidence and mortality worlwide: sources, methods and major patterns in Globocan´´ Int. J. Canc., Vol. 136, pp. 359-86, 2015.
  • R. Gul, A. Badshah, A. Khan, A. Junaid, M.K. Rauf, ´´Preliminary investigation of anticancer activitiy by determining the DNA binding and antioxidant potency of new ferrocene incorporated N,N’,N’’-trisubstituted phenylgunidines´´ Spectrochim Acta Part A Mol. Biomol. Spect., Vol. 117, pp. 264-9, 2014.
  • C. Uslan, B.S. Sesalan, ´´The synthesis, photochemical and biological properties of new silicon phthalocyanines´´ Inorg. Chim. Acta, Vol. 394, pp. 353-62, 2013.
  • T. Keles, B. Barut, Z. Biyiklioglu, A. Özel, ´´A comparative study on DNA/BSA binding, DNA phorocleavage and antioxidant activities of water soluble peripherally and non-peripherally tetra-3-pyridin-3-ylpropoxy-substituted Mn (III), Cu (II) phthalocyanines´´ Dyes and Pigments, doi: 10.1016/j.dyepig. 2016.12.045, 2017.
  • S.M. Pradeepa, H.S. Bhojya Naik, B. Vinay Kumar, K. Indira Priyadarsini, A. Barik, S. Jayakumar, ´´Synthesis and characterization of cobalt(II), nickel(II) and copper(II)-based potential photosensitizers: Evaluation of their DNA binding profile, cleavage and Photocytotoxicity´´ Inorg. Chim. Acta, Vol. 428, pp. 138-46, 2015.
  • B. Zheng, X. Shen, D. Zhao, Y. Cai, M. Ke, J. Huang, ´´Silicon (IV) phthalocyanines substituted axially with different nucleoside moieties. Effects of nucleoside type on the photosensitizing efficiencies and in vitro photodynamic activities´´ J. Photochem. Photobiol. B: Biol., Vol. 159, pp. 196-204, 2016.
  • L. Xodo, S. Cogoi, V. Rapozzi, ´´Photosensitizers binding to nucleic acids as anticanceragents´´ Fut. Med. Chem., Vol. 8, pp. 179-94, 2016.
  • M.S. Ağırtaş, İ. Gümüş, M. S. İzgi, ´´Designing of new thermo stabile phthalocyanines: synthesis, characterization, and thermal studies´´ Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, Vol. 42, pp. 1327-1333, 2012.
  • J. Bolger, A. Gourdon, E. Ishow, J. P. Launay, ´´Mononuclear and Binuclear Tetrapyrido[3,2-a:2‘,3‘-c:3‘‘,2‘‘-h:2‘‘‘,3‘‘‘-j]phenazine (tpphz) Ruthenium and Osmium Complexes´´Inorg. Chem., Vol.35, pp. 2937–2944, 1996.
  • A. S. Azza, M. S. Mohamed, ´´DNA binding, spectrocopic and antimicrobial studies of palladium (II) complexes containin 2,2o-bipyridin and 1-phenypiperazine´´ Spectrochim. Acta Part A Mol. Biomol. Spect., Vol. 96, pp. 586-593, 2012.
  • M. Özçesmeci, Ö. B. Ecevit, S. Sürgün, E. Humuryudan, ´´Tetracationic fluorinated zinc (ii) phthalocyanine: Synthesis, characterization and DNA-binding properties´´ Dyes and Pigments, Vol. 96, pp. 52-58, 2013.
  • P.R. Reddy, A. Shilpa, N. Raju, P. Raghavaiah, ´´Synthesis, structure, DNA binding and cleavage properties of ternaryamino acid Schiff base-phen/bipy C(II) complexes´´ J. Inorg. Bioochem., Vol. 105, pp. 1603-1612, 2011.
  • A. Apilux, O. Tabata MChailapakul, ´´Electrochemical bihaviors of native and thermal denatured fish DNA in the presence of cytosine derivatives and porphyrin by cyclic voltammetry using boron-drobed diamond electrode´´ Bioelectrochemistry, Vol. 70, pp. 435-439, 2007.
  • N. Demirezen, D. Tarınc, D. Polat, M. Cesme, A. Golcu, M. Tumer, ´´Synthesis of trimethoprim metal complexes: Spectral, electrochmical, thermal, DNA-binding and surface morp hology studies´´ Spectrochimica Acta Part A, Vol. 94, pp. 243-255, 2012.
  • X-W. Liu, Y-M. Shen, Z-X. Li, X. Zhong, Y-D. Chen, S-B. Zhang, ´´Study on DNA binding behavior and light switch effect of new coumarin-derived Ru (II) complexes´´ Spectrochim. Acta Part: Mol. Biomol. Specrt., Vol. 149, pp. 150-156, 2015.
  • C. Ozluer, H. E. Satana Kara, ´´In vitro DNA binding studies of anticancer drug idarubicin using spectroscopic techniques´´ J. Photochem. Photobiol. B., Vol. 138, pp. 36–42, 2014.
  • A. Özel, B. Barut, Ü. Demirbaş, Z. Biyiklioglu, ´´Invetigation of DNA binding, DNA photocleavage, topoisomerase I inhibition and antioxidant activities of water soluble titanium (IV) phthalocyanine compounds´´ J. Photoch. Photobiol. B. Biology, Vol. 157, pp.32-38, 2016.
  • S. Mahadevan, M. Palaniandavar, ´´Spectroscopic and voltametric studies on copper complexes of 2,9-dimethyl-1,10-phenanthrolines bound to calf thymus DNA´´ J. Inorg. Chem., Vol. 37, pp. 693-706, 1998.
  • M. Sirajuddin, S. Ali, A. Badshah, ´´Drug-DNA interactions and their study by UV-Visible, fluorescence spectroscopies and cyclic voltametry´´ J. Photochem. Photobiol. B. Biology, Vol. 124, pp. 1-19, 2013.
There are 32 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Ali Arslantas

Mehmet Salih Ağırtaş

Publication Date October 1, 2017
Submission Date July 17, 2017
Published in Issue Year 2017 Volume: 5 Issue: 3

Cite

IEEE A. Arslantas and M. S. Ağırtaş, “2, 10, 16, 24-Tetrakis 4- (2-fenoksi-l, 3-diokso-2,3-dihidro-lH-inden-2-iloksi) ftalonitril içeren kobalt (II) bileşiğinin DNA bağlanmasının spektroskopik yöntemler ile araştırılması”, APJES, vol. 5, no. 3, pp. 1–9, 2017, doi: 10.21541/apjes.329065.