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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

Yıl 2017, Cilt: 5 Sayı: 3, 1 - 9, 01.10.2017
https://doi.org/10.21541/apjes.329065

Öz

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.

Kaynakça

  • 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

Yıl 2017, Cilt: 5 Sayı: 3, 1 - 9, 01.10.2017
https://doi.org/10.21541/apjes.329065

Öz

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.

Kaynakça

  • 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.
Toplam 32 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Ali Arslantas

Mehmet Salih Ağırtaş

Yayımlanma Tarihi 1 Ekim 2017
Gönderilme Tarihi 17 Temmuz 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 5 Sayı: 3

Kaynak Göster

IEEE A. Arslantas ve 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, c. 5, sy. 3, ss. 1–9, 2017, doi: 10.21541/apjes.329065.