Water soluble peripheral and non-peripheral tetrasubstituted zinc phthalocyanines: Synthesis, photochemistry and bovine serum albumin binding behavior

Abstract The new peripherally and non-peripherally tetra-1,3-bis[3-(diethylamino)phenoxy]propan-2-ol substituted zinc(II) phthalocyanine complexes (2a and 3a) and their quaternized amphiphilic derivatives (2b and 3b) have been synthesized and characterized using UV–vis, FT-IR, 1H-NMR, 13C-NMR, MS spectroscopic data and elemental analysis for the first time. The quaternized complexes (2b and 3b) show excellent solubility in water and DMSO which makes them potential photosensitizers for use in photodynamic therapy (PDT) of cancer. The photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of these novel phthalocyanines are investigated in dimethylsulfoxide (DMSO) for non-quaternized complexes and in DMSO, phosphate buffered solution (PBS) or PBS+triton X-100 (TX) solution for quaternized complexes. In this study, the effects of the aggregation of the molecules, quaternization, position of the substituents (peripherally or non-peripherally) and nature of the solvents (DMSO, PBS or PBS+triton X-100) on the photochemical parameters of the zinc (II) phthalocyanines are also reported. In addition, a spectroscopic investigation of the binding behavior of the quaternized zinc(II) phthalocyanine complexes to bovine serum albumin (BSA) is also presented in this work.

[1]  J. Mosinger,et al.  Photophysical properties of porphyrinoid sensitizers non-covalently bound to host molecules; models for photodynamic therapy , 2004 .

[2]  W. Fong,et al.  Phthalocyanine-polyamine conjugates as highly efficient photosensitizers for photodynamic therapy. , 2011, Journal of medicinal chemistry.

[3]  Tebello Nyokong,et al.  Metallophthalocyanine-based molecular materials as catalysts for electrochemical reactions , 2010 .

[4]  S. Gibson,et al.  Current clinical and preclinical photosensitizers for use in photodynamic therapy. , 2004, Journal of medicinal chemistry.

[5]  E. Durantini,et al.  Synthesis, properties, and photodynamic inactivation of Escherichia coli using a cationic and a noncharged Zn(II) pyridyloxyphthalocyanine derivatives. , 2005, Bioorganic & medicinal chemistry.

[6]  T. Fujimoto,et al.  Chromic materials. Part 1.—Liquid-crystalline behaviour and electrochromism in bis(octakis-n-alkylphthalocyaninato)lutetium(III) complexes , 1994 .

[7]  H. Dinçer,et al.  A novel route to 4-chloro-5-alkyl-phthalonitrile and phthalocyanines derived from it , 2004 .

[8]  E. Agostinelli,et al.  Polyamines: fundamental characters in chemistry and biology , 2010, Amino Acids.

[9]  F. Rüker,et al.  The Three Recombinant Domains of Human Serum Albumin , 1999, The Journal of Biological Chemistry.

[10]  A. Tedesco,et al.  HPLC-FLD methods to quantify chloroaluminum phthalocyanine in nanoparticles, plasma and tissue: application in pharmacokinetic and biodistribution studies. , 2011, Journal of pharmaceutical and biomedical analysis.

[11]  M. Tabak,et al.  Fluorescence and optical absorption study of interaction of two water soluble porphyrins with bovine serum albumin. The role of albumin and porphyrin aggregation , 1996 .

[12]  T. Nyokong,et al.  Synthesis and photophysical properties of 1,1'-binaphthol substituted phthalocyanines , 2010 .

[13]  I Rosenthal,et al.  PHTHALOCYANINES AS PHOTODYNAMIC SENSITIZERS * , 1991, Photochemistry and photobiology.

[14]  A. Wunder,et al.  Albumin-based drug carriers: comparison between serum albumins of different species on pharmacokinetics and tumor uptake of the conjugate. , 1999, Anti-cancer drugs.

[15]  A. Koca,et al.  SYNTHESIS, ELECTROCHEMICAL AND SPECTROELECTROCHEMICAL CHARACTERIZATION OF NOVEL SOLUBLE PHTHALOCYANINES BEARING CHLORO AND QUATERNIZABLE BULKY SUBSTITUENTS ON PERIPHERAL POSITIONS , 2012 .

[16]  L. Valli.  Phthalocyanine-based Langmuir-Blodgett films as chemical sensors. , 2005, Advances in colloid and interface science.

[17]  D. Dei,et al.  Synthesis of a new water-soluble octa-cationic phthalocyanine derivative for PDT , 2000 .

[18]  Y. Gök,et al.  Synthesis and characterization of new metal-free and nickel(II) phthalocyanines containing tetraazatrioxa macrotricyclic moieties , 2007 .

[19]  H. Kantekin,et al.  Microwave-assisted synthesis and characterization of new soluble metal-free and metallophthalocyanines substituted with four tetrathiamacrocycles through oxy bridges , 2008 .

[20]  Yuyuan Yao,et al.  The role of multiwalled carbon nanotubes in enhancing the catalytic activity of cobalt tetraaminophthalocyanine for oxidation of conjugated dyes , 2009 .

[21]  Tebello Nyokong,et al.  Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines , 2007 .

[22]  M. Durmuş,et al.  Synthesis, photophysical, photochemical and electrochemical properties of crown ether bearing coumarin substituted phthalocyanines , 2012 .

[23]  J. V. van Lier,et al.  Metal complexes as photo- and radiosensitizers. , 1999, Chemical reviews.

[24]  Z. Bıyıklıoğlu.  Novel water-soluble metal-free and metallophthalocyanines: Synthesis, spectroscopic characterization and aggregation properties , 2011 .

[25]  J. V. van Lier,et al.  Targeted photodynamic therapy via receptor mediated delivery systems. , 2004, Advanced drug delivery reviews.

[26]  A. Koca,et al.  Synthesis, electrochemical, in situ spectroelectrochemical and in situ electrocolorimetric characterization of new metal-free and metallophthalocyanines substituted with 4-{2-[2-(1-naphthyloxy)ethoxy]ethoxy} groups , 2010 .

[27]  M. Vicente,et al.  Syntheses and properties of a series of cationic water-soluble phthalocyanines. , 2008, Journal of medicinal chemistry.

[28]  T. Nyokong,et al.  The synthesis and photophysicochemical behaviour of novel water-soluble cationic indium(III) phthalocyanine , 2009 .

[29]  M. Cook,et al.  Synthesis of novel cationic amphiphilic phthalocyanine derivatives for next generation photosensitizer using photodynamic therapy of cancer , 2005 .

[30]  Qingping Wang,et al.  A spectroscopic study of the interaction of octacarboxylic metal phthalocyanine with bovine serum albumin , 2008 .

[31]  Z. Öztürk,et al.  Phthalocyanines as sensitive coatings for QCM sensors operating in liquids for the detection of organic compounds , 2010 .

[32]  N. Brasseur,et al.  Hydroxyphthalocyanines as potential photodynamic agents for cancer therapy. , 1998, Journal of medicinal chemistry.

[33]  A. Koca,et al.  Synthesis, electrochemical, in situ spectroelectrochemical and in situ electrocolorimetric characterization of new phthalocyanines peripherally fused to four flexible crown ether moieties , 2009 .

[34]  Yasin Arslanoğlu,et al.  Synthesis and derivatization of near-IR absorbing titanylphthalocyanines with dimethylaminoethylsulfanyl substituents , 2007 .

[35]  Lei Duan,et al.  Preparation and in vitro photodynamic activity of amphiphilic zinc(II) phthalocyanines substituted with 2-(dimethylamino)ethylthio moieties and their N-alkylated derivatives. , 2010, Bioorganic & medicinal chemistry.

[36]  Thomas J. Dougherty,et al.  Basic principles of photodynamic therapy , 2001 .

[37]  Steven L. Murov,et al.  Handbook of photochemistry , 1973 .

[38]  M. Kang,et al.  A near-infrared dye for dye-sensitized solar cell: Catecholate-functionalized zinc phthalocyanine , 2012 .

[39]  H. Kantekin,et al.  The synthesis, using microwave irradiation and characterization of novel, organosoluble metal-free and metallophthalocyanines substituted with flexible crown ether moieties , 2009 .

[40]  Cihat Tasaltin,et al.  Synthesis and DMMP sensing properties of fluoroalkyloxy and fluoroaryloxy substituted phthalocyanines in acoustic sensors , 2010 .

[41]  M. Durmuş,et al.  Tetra-2-[2-(dimethylamino)ethoxy]ethoxy substituted zinc phthalocyanines and their quaternized analoques: Synthesis, characterization, photophysical and photochemical properties , 2011 .

[42]  Zekeriya Bıyıklıoğlu,et al.  Synthesis and spectroscopic properties of a series of octacationic water-soluble phthalocyanines , 2011 .

[43]  A. Koca,et al.  Water soluble novel phthalocyanines containing dodeca-amino groups , 2008 .

[44]  G. G. Stokes.  "J." , 1890, The New Yale Book of Quotations.

[45]  D. Kearns,et al.  Role of singlet oxygen in some chemiluminescence and enzyme oxidation reactions. , 1974, The Journal of physical chemistry.

[46]  Yuyuan Yao,et al.  Highly efficient decomposition of organic dyes by aqueous-fiber phase transfer and in situ catalytic oxidation using fiber-supported cobalt phthalocyanine. , 2007, Environmental science & technology.

[47]  H. Kantekin,et al.  The synthesis and characterization of new organosoluble long chain-substituted metal-free and metallophthalocyanines by microwave irradiation , 2008 .

[48]  M. Ağırtaş,et al.  Novel metal (II) phthalocyanines with 3,4,5-trimethoxybenzyloxy-substituents: Synthesis, characterization, aggregation behaviour and antioxidant activity , 2013 .

[49]  M. Kenney,et al.  Electronic and redox properties of stacked-ring silicon phthalocyanines from molecular orbital theory , 1985 .

[50]  Tebello Nyokong,et al.  Synthetic pathways to water-soluble phthalocyanines and close analogs , 2010 .

[51]  A. Tedesco,et al.  Photophysical studies of zinc phthalocyanine and chloroaluminum phthalocyanine incorporated into liposomes in the presence of additives. , 2004, Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas.

[52]  W. Cheng,et al.  Fabrication and Performance of Copper Phthalocyanine/Squaraine Dye/Perylene Composite with Bulk Heterojunctions by the Solution Blending Process , 2012 .

[53]  T. Nyokong,et al.  Synthesis and solvent effects on the electronic absorption and fluorescence spectral properties of substituted zinc phthalocyanines , 2007 .

[54]  D C Carter,et al.  Structure of serum albumin. , 1994, Advances in protein chemistry.

[55]  R. Pandey.  Recent advances in photodynamic therapy , 2000 .

[56]  F. Lamarche,et al.  Polyamine conjugates of meso-tritolylporphyrin and protoporphyrin IX: potential agents for photodynamic therapy of cancers. , 2006, Bioorganic & medicinal chemistry.

[57]  T. Torres,et al.  The phthalocyanine approach to second harmonic generation , 1997 .

[58]  M. Durmuş,et al.  Coumarino-12-crown-4 bearing phthalocyanine photosensitizers for singlet oxygen production , 2011 .

[59]  M. Durmuş,et al.  Synthesis, photophysical and photochemical properties of crown ether substituted zinc phthalocyanines , 2009 .

[60]  T. Nyokong,et al.  Photophysical and photochemical studies of zinc(II) phthalocyanine derivatives—effects of substituents and solvents , 2004 .

[61]  A. Koca,et al.  Synthesis and electrochemical investigation of phthalocyanines with dendritic bulky ethereal substituents , 2012 .

[62]  C. M. Allen,et al.  Current status of phthalocyanines in the photodynamic therapy of cancer , 2001 .

[63]  H. Konami,et al.  Inter-ring overlap integrals in dimer complexes of phthalocyanines and porphyrins , 1990 .

[64]  H. Kantekin,et al.  Metal-free and metallophthalocyanines appending with eight 12-crown-4 ethers , 2010 .

[65]  V. Ahsen,et al.  Synthesis, photophysical and photochemical properties of substituted zinc phthalocyanines. , 2007, Dalton transactions.

[66]  Tayyaba Hasan,et al.  Development and applications of photo-triggered theranostic agents. , 2010, Advanced drug delivery reviews.

[67]  N. McKeown.  Phthalocyanine Materials: Synthesis, Structure and Function , 1998 .