Study on DNA Binding Properties of Nickle (II) Phthalocyanine Compound with 2-Isopropyl-5- Methylphenoxy Substituents.

Study on DNA Binding Properties of Nickle (II) Phthalocyanine Compound with 2-Isopropyl-5- Methylphenoxy Substituents.

I n this study, previously synthesized Ni (II) phthalocyanine compound bearing 2,10,16,24-tetrakis(2-isopropyl-5-methylphenoxy group was chosen for its interaction with calf thymus-DNA. Calf thymus-DNA was used to determine DNA binding properties of Ni (II) phthalocyanine compound. The DNA binding activities of Ni (II) phthalocyanine compound bearing 2-isopropyl-5-methylphenoxy substituent was investigated by using absorption titration, fluorescence emission, cyclic voltammetry, gel elctrophoresis in Tris-HCl buffer at pH 7.0. In addition to above methods, melting point and viscosity experiment were performed to determine the DNA intercation of the compound in Tris-HCl buffer solution. The results showed that Ni (II) phthalocyanine compound binds strongly to calf thymus-DNA via intercalation binding

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  • 1. Leznoff CC, Lever ABP. Phthalocyanine: Properties and Applications. VCH publishers, New York, pp. 1-4, 1996.
  • 2. Agirtas MS, Karatas C, Gümüş S. Synthesis, Aggregation Behavior, and Electronic properties of some metallophthalocyanines with 2-Isopropyl-5- methylphenoxy substituents. Z Anorg Allg Chem 641(7) (2015) 1334-1339.
  • 3. Agirtas MS, Karatas C, Özdemir S. Synthesis of some metallophthalocyanines with dimethyl 5-(phenoxy)- isophthalate substituents and evaluation of their antioxidant-antibacterial activities. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 135 (2015) 20-24.
  • 4. McKeown NB. Phthalocyanines Materials: Synthesis, Structure and Functions. Cambridge, MA: Cambridge University Press, 1998.
  • 5. Agirtas MS, Altındal A, Salih B, Saydam S, Bekaroglu Ö. Synthesis, characterization, and electrochemical and electrical properties of novel mono and ball-type metallophthalocyanines with four 9,9-bis(4-hydroxyphenyl) fluorine. Daltons Trans 40 (2011) 3315- 24.
  • 6. Peng Y, Zhang H, Wu H, Huang B, Gan L, Chen Z. The sysnthesis and photophysical properties of zinc (II) phthalocyanine bearing poly (aryl benzyl ether) dendritic substituents. Dyes and Pigments 87 (2010) 10-16.
  • 7. Jori G. photosensitized processes in vivo: proposed phototherapeutic applications. J Photoch Photobio 52 (1990) 439-443.
  • 8. Eshkourfu R, Cobeljic B, Vujcic M, Turel I, Pevec A, Sepcic K, Zec M, Radulovic S, Srdic-Radic T, Mitic D, Andjelkovic K, Sladic D. Synthesis, characterization, cytotoxic activity and DNA binding properties of the novel dinuclear cobalt (II) complex with the condensation product of 2-acetylpyrine and malonic acid dihydrazide. Inorg Biochem 105 (2011) 1196-1203.
  • 9. Uslan C, Sesalan BS. Synthesis of novel DNA-interacting phthalocyanines. Dyes and Pigments 94 (2012) 127-135.
  • 10. Janjua NK, Shaheen A, Yaqup A, Perveen F, Sabahat S, Mumtaz M, Yacob C, Ba LA, Mohammed HA. FlavonoidDNA binding studies and thermodynamic parameters. Spectrochim Acta A 79 (2011) 1600-1604.
  • 11. Palchaudhuri R, Hergenrother PJ. DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action. Curr Opin Biotechnol 18 (2007) 497-503.
  • 12. Wolfe A, Shimer GH, Meehan T. Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry 26 (1987) 6392-6396.
  • 13. Lopez Zeballos NC, Gauna GA, Garcia Vior MC, Awruch J, Dicelio LE. Interaction of cationic phthalocyanines with DNA. Importance of the substituents. J Photochem Photobiol B Biology 136 (2014) 29-33.
  • 14. Özçesmeci M, Ecevit ÖB, Sürgün S. Humuryudan S. Tetracationic fluorinated zinc (ii) phthalocyanine: Synthesis, characterization and DNA-binding properties E. Hamuryudan, Dyes and Pigments 96 (2013) 52-58.
  • 15. Apilux A, Tabata MChailapakul O. 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 70 (2007) 435-439.
  • 16. Demirezen N, Tarınc D, Polat D, Cesme M, Golcu A, Tumer M. Synthesis of trimethoprim metal complexes: Spectral, electrochmical, thermal, DNA-binding and surface morp hology studies. Spectrochimica Acta Part A 94 (2012) 243- 255.
  • 17. Reddy PR, Shilpa A, Raju N, Raghavaiah P. Synthesis, structure, DNA binding and cleavage properties of ternaryamino acid Schiff base-phen/bipy C(II) complexes. J Inorg Bioochem 105 (2011) 1603-1612.
  • 18. 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: Molecular and Biomolecular Specrtoscopy 149 (2015) 150-156.
  • 19. Ozluer C, Satana Kara HE. In vitro DNA binding studies of anticancer drug idarubicin using spectroscopic techniques. J Photochem Photobiol B 138 (2014) 36–42.
  • 20. Pradeepa SM, Bhojya Naik HS, Vinay Kumar B, Indira Priyadarsini K, Barik A, Prabhakara MC. DNA binding, photoactivated DNA cleavage and cytotoxic activity of Cu(II) and Co(II) based Schiff-base azo ptotosensitizers. Spectrochim Acta A 141 (2015) 141:34–42.
  • 21. Özel A, Barut B, Demirbaş Ü, Biyiklioglu Z. Invetigation of DNA binding, DNA photocleavage, topoisomerase I inhibition and antioxidant activities of water soluble titanium (IV) phthalocyanine compounds. J Photoch and Photobiol B Biology 157 (2016) 32-38.
  • 22. Mahadevan S, Palaniandavar M. Spectroscopic and voltametric studies on copper complexes of 2,9-dimethyl1,10-phenanthrolines bound to calf thymus DNA. J Inorg Chem 37 (1998) 693-706.
  • 23. Sirajuddin M, Ali S, Badshah A. Drug-DNA interactions and their study by UV-Visible, fluorescence spectroscopies and cyclic voltametry. J Photochem Photobiol B Biology 124 (2013) 1-19.
  • 24. Song YM, Yang PJ, Yang ML, Kang JW, Qin SQ, Lu BQ. Spectroscopic and voltammetric studies of the cobalt (II) complexe of morin bound to calf thymus DNA. Transition Met Chem 28 (2003) 712- 721.
  • 25. Zhang SS, Niu SY, Qu B, Jie GB, Xu H, Ding CF. Studies on the interaction mechanism between hexakis(imidazole) manganese (II) terephthalate and DNA and preparation of DNA electrochemical sensor. J Inorg Biochem 99 (2005) 2340-2347.
  • 26. Cater MT, Rodriguez M, Bard AJ. Voltammetric studies of the interaction of metal chelated with DNA. 2. Trischelated complexes of cobalt (III) and iron (II) with 1,10-phenanthroline and 2, 20- bipryridine. J Am Chem Soc 111 (1989) 8901-8911.
  • 27. Pravin P, Utthra PP, Kumaravel G, Raman N. Effective DNA binding and cleavage tendencies of malonic acid coupled transition metal complexes. J Mol Struc 1123 (2016) 162- 70.
  • 28. Keleş T, Barut B, Biyiklioglu Z, Özel A. A comparative study on DNA/BSA binding, DNA pA 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(II), Cu (II). Dyes and Pigments 2017; doi: 10.1016/j.dyepig. 2016.12.045.
  • 29. Azza A S, Mohamed MS. DNA binding, spectrocopic and antimicrobial studies of palladium (II) complexes containin 2,2o-bipyridin and 1-phenypiperazine. Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 96 (2012) 586-593.
  • 30. Hassani L, Hakimian F, Safaei E, Fazzeli Z. Antibacterial effect of cationic porphyrazines and anionic phthalocyanine and their interaction with plasmid DNA. J Mol Struc 1052 (2013) 221-227.
  • 31. Al-Mogren MM, Alaghaz MA, Ebrahem EA. Synthesis, spectroscopic, molecular orbital calculation, cytotoxic, molecular docking of DNA binding and DNA cleavage studies of of transition metal complexes with N-benzylidene–N´- salicylidene-1,1-diaminopropane. Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 114 (2013) 695-707.