Tetracationic fluorinated zinc(ii)phthalocyanine: Synthesis, characterization and DNA-binding properties

作者: Mukaddes Özçeşmeci , Özgür Bülent Ecevit , Serdar Sürgün , Esin Hamuryudan

DOI: 10.1016/J.DYEPIG.2012.06.018

关键词: Fluorine-19 NMRPhthalonitrileZincMethyl iodideProton NMRDerivative (chemistry)PhthalocyanineFluorescence spectroscopyChemistryPhotochemistryPolymer chemistry

摘要: Abstract Selective replacement of the p-fluorine atom 4-(2′,3′,4′,5′,6′-pentafluorobenzyloxy) phthalonitrile with N,N-dimethylaminoetanethiol gave 4-[2′,3′,5′,6′-tetrafluoro-4′-(2-dimethylaminoetanethio)benzyloxy]phthalonitrile. A peripherally tetra-substituted zinc(II) phthalocyanine was achieved by tetramerization new perfluorobenzyloxyphthalonitrile in presence zinc acetate. The derivative quaternized methyl iodide to afford a water-soluble product. compounds were characterized using elemental analyses, 1H NMR, 19F UV–vis and FT-IR spectroscopy mass spectrometry. interaction between calf thymus DNA investigated tris buffer (pH 7.4) absorption fluorescence spectroscopy. Upon addition phthalocyanine, change thermal denaturation profile observed.

参考文章(42)
Wilfred Louis Florio Armarego, Douglas Dalzell Perrin, D. R Perrin, Purification of laboratory chemicals ,(1966)
Sueleyman Guersoy, Ali Cihan, Makbule B. Kocak, Oezer Bekaroglu, Synthesis of New Metal-Free and Metal-Containing Phthalocyanines with Tertiary or Quaternary Aminoethyl Substituents. ChemInform. ,vol. 32, ,(2001) , 10.1002/CHIN.200144186
Selma Ünlü, Meryem N. Yaraşır, Mehmet Kandaz, Atıf Koca, Bekir Salih, Synthesis, spectroscopy and electrochemical properties of highly soluble fluoro containing phthalocyanines Polyhedron. ,vol. 27, pp. 2805- 2810 ,(2008) , 10.1016/J.POLY.2008.05.036
An-Ming Zhang, Jing Huang, Xiao-Cheng Weng, Jin-Xi Li, Li-Ge Ren, Zhi-Bin Song, Xiao-Qin Xiong, Xiang Zhou, Xiao-Ping Cao, Yan Zhou, A water-soluble, octacationic zinc phthalocyanine as molecular probe for nucleic acid secondary structure. Chemistry & Biodiversity. ,vol. 4, pp. 215- 223 ,(2007) , 10.1002/CBDV.200790026
Pavel Kubát, Kamil Lang, Pavel Anzenbacher Jr., Karolina Jursíková, Vladimír Král, Benjamin Ehrenberg, Interaction of novel cationic meso-tetraphenylporphyrins in the ground and excited states with DNA and nucleotides Journal of The Chemical Society-perkin Transactions 1. pp. 933- 941 ,(2000) , 10.1039/A909466K
Jie Fu, Xi-you Li, Dennis K. P. Ng, Chi Wu, Encapsulation of phthalocyanines in biodegradable poly(sebacic anhydride) nanoparticles Langmuir. ,vol. 18, pp. 3843- 3847 ,(2002) , 10.1021/LA011764A
Atıf Koca, Ali Rıza Özkaya, Mukaddes Selçukoğlu, Esin Hamuryudan, Electrochemical and spectroelectrochemical characterization of the phthalocyanines with pentafluorobenzyloxy substituents Electrochimica Acta. ,vol. 52, pp. 2683- 2690 ,(2007) , 10.1016/J.ELECTACTA.2006.09.025
Canan Uslan, B. Şebnem Sesalan, Synthesis of novel DNA-interacting phthalocyanines Dyes and Pigments. ,vol. 94, pp. 127- 135 ,(2012) , 10.1016/J.DYEPIG.2011.12.003
Jiafei Mao, Yangmiao Zhang, Jianhui Zhu, Changli Zhang, Zijian Guo, Molecular combo of photodynamic therapeutic agent silicon(IV) phthalocyanine and anticancer drug cisplatin Chemical Communications. pp. 908- 910 ,(2009) , 10.1039/B817968A