Synthesis and photophysical properties of a new cationic water-soluble Zn phthalocyanine

Journal of Photochemistry and Photobiology B: Biology

Volumn 41, Issue 3, 1997, Pages 227-232

  Fernández, Daniel A ^a   Awruch, Josefina ^b   Dicelio, Lelia E ^a  

^a Instituto de Quimica Fisica de los Materiales Medio Ambiente y Energia   (Argentina)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Cationic phthalocyanine; Phthalocyanine; Zinc

Indexed keywords

DYE; PHOTOSENSITIZING AGENT; PHTHALOCYANINE ZINC; SINGLET OXYGEN;

ABSORPTION SPECTROSCOPY; AQUEOUS SOLUTION; ARTICLE; DIMERIZATION; DRUG SYNTHESIS; HYDROPHOBICITY; LIGHT ABSORPTION; PHOTOCHEMISTRY; PHOTODYNAMIC THERAPY; PRIORITY JOURNAL;

CATIONS; DIMERIZATION; FLUORESCENCE; FLUORESCENT DYES; INDOLES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXYGEN; RADIATION-SENSITIZING AGENTS; SINGLET OXYGEN; SOLUBILITY; WATER; ZINC;

EID: 0039752406     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(97)00106-1     Document Type: Article

References (36)

1. M.T. Foultier, V. Vonarx-Coinsman, L. Morlet, L.X. de Brito, N. Robillard and T. Patrice, Photodynamic therapy of cancers, in G. Jori, R.H. Pottier, M.A.J. Rodgers and T.G. Truscott (eds.), Photobiology in Medicine, Plenum Press, New York, 1994, pp. 177.
2. J.D. Spikes, Phthalocyanines as photosensitizers in biological systems and for the photodynamic therapy of tumors, Photochem. Photobiol. 43 (1986) 691-699.
3. I. Rosenthal, Phthalocyanines as Photodynamic Sensitizers. Photochem. Photobiol. 53 (1991) 859-870.
4. B. Paquette and J.E. van Lier, Phthalocyanines and related compounds: Structure-activity relationship, in B.W. Henderson and T.J. Dougherty (eds.), Photodynamic Therapy, Marcel Dekker, New York, 1992, pp. 145.
5. T.S. Mang, C. Mcginnis, C. Liebow, U.O. Nseyo, D.H. Crean and T. Dougherty, Fluorescense detection of tumors - early diagnosis of microscopic lesions in preclinical studies, Cancer 71 (1993) 269-272.
6. A. Rück, G. Beck, R. Bachor, N. Akgün, M.H. Gschwend and R. Steiner, Dynamic fluorescence changes during photodynamic therapy in vivo and in vitro of hydrophilic Al (III) phthalocyanine tetrasulphonate and lipophilic Zn (II) phthalocyanine administered in liposomes, J. Photochem. Photobiol. B: Biol. 36 (1996) 127-134.
7. R.W. Boyle and D. Dolphin, Structure and biodistribution relationships of photodynamic sensitizers, Photochem. Photobiol. 64 (1996) 469-485.
8. A. Villanueva, The cationic meso-substituted porphyrins: An interesting group of photosensitizers, J. Photochem. Photobiol. B: Biol. 18 (1993) 295-296.
9. M. Merchat, G. Bertolini, P. Giacomini, A. Villanueva and G. Jori, Meso-substituted cationic porphyrins as efficient photosensitizers of Gram-positive and Gram-negative bacteria, J. Photochem. Photobiol. B: Biol. 32 (1996) 153-157.
10. D. Wöhrle, J. Gitzel, I. Okura and S. Aono, Photoredox properties of tetra-2,3-pyridinoporphyrazines (29H,31H-tetrapyrido[2,3-b:2′,3′-g:2″,3″-l: 2′″,3′″-q]-porphyrazine), J. Chem. Soc.. Perkin Trans. 2 (1985) 1171-1178.
11. A.K. Sobbi, D. Wöhrle and D. Schlettwein, Photochemical stability of various porphyrins in solution as thin film electrodes, J. Chem. Soc., Perkin Trans. 2, (1993) 481-494.
12. D.D. Perrin and W.L.F. Armarego, Purification of Laboratory Chemicals, Pergamon Press, Oxford, Third edition, 1988.
13. R.M. Negri, A. Zalts, E.A. San Román, P.P. Aramendía and S.E. Braslavsky, Carboxylated Zinc Phthalocyanine, influence of dimerization on the spectroscopic properties. An absorption, emission and thermal lensing study, Photochem. Photobiol. 53 (1991) 317-322.
14. D.A. Fernández, L.E. Dicelio and J. Awruch, Synthesis and properties of two new N-alkyl substituted phthalocyanines, J. Heterocycl. Chem. 32 (1995) 519-522.
15. M. Kubista, R. Sjöback and B. Albinsson, Determination of equilibrium constants by chemometric analysis of spectroscopic data. Anal. Chem. 65 (1993) 994-998.
16. D.A. Fernández, J. Awruch and L.E. Dicelio, Photophysical and Aggregation Studies of t-Butyl-Substituted Phthalocyanines, Photochem. Photobiol. 63 (1996) 784-792.
17. C.A. Parker, Photoluminescence of Solutions, Elsevier, Amsterdam, 1968.
18. S. Nonell i Marrugat, Ph.D. Thesis, Max-Planck-Institut für Strahlenchemie Mülheim/Ruhr, 1988.
19. P.E. Aramendía, R.W. Redmond, S. Nonell, W. Schuster, S.E. Braslavsky, K. Schaffner and E. Vogel, Photophysical properties of porphycenes: Potential photodynamic therapy agents, Photochem. Photobiol. 44 (1986) 555-559.
20. F. Wilkinson, W.P. Helman and A.B. Ross, Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution, J. Phys. Chem. Ref. Data 22 (1993) 113-262.
21. H.Z. Sommer, H.I. Lipp and L.L. Jackson, Alkylation of amines. A general exhaustive alkylation method for the synthesis of quaternary ammonium compounds, J. Org. Chem. 36 (1971) 824-828.
22. P. Haisch and M. Hanack, Synthesis of unsymmetrically-substituted Nickel, Palladium and Platinum phthalocyanines. Synthesis (1995) 1251-1256.
23. M. Sommerauer, C. Rager and M. Hanack, Separation of 2(3), 9(10), 16(17), 23(24) tetrasubstituted phthalocyanines with newly developed HPLC phases, J. Am. Chem. Soc. 118 (1996) 10085-10093.
24. E. Baranowska, R. Ostazewski, J. Jurczack, R.H. Fokkens and N.M.M. Nibbering, Fast atom bombardment mass spectra of some N,N′-tetramethyl diazacoronands diiodides, Org. Mass Spectrom. 24 (1989) 431-434.
25. K.G. Furton and C.F. Poole, Fast atom bombardment mass spectra of some tetra-n-butylammonium salts, Org. Mass Spectrom. 22 (1987) 377-378.
26. A. Harriman and M. Richoux, Attempted photoproduction of hydrogen using sulphophthalocyanines as chromophores for three-components systems, J. Chem. Soc. Faraday Trans. 2, 76 (1980) 1618-1626.
27. M.J. Stillman and T. Nyokong, Absorption and magnetic circular dichroism spectral properties of phthalocyanines Part 1: Complexes of the dianion Pc(-2), in C.C. Leznoff and A.B.P. Lever (eds.), Phthalocyanines: Properties and Applications, VCH. New York, 1989, pp. 133-289.
28. M.G. Lagorio, L.E. Dicelio and E.A. San Román, Visible and near-IR spectroscopic and photochemical characterization of substituted metallo-phthalocyanines, J. Photochem. Photobiol. A: Chem. 72 (1993) 153-161.
29. J.A. Darwent, P. Douglas, A. Harriman, G. Porter and M. Richoux, Metal phthalocyanines and porphyrins as photosensitizers for reduction of water to hydrogen, Coord. Chem. Rev. 44 (1982) 83-126.
30. T. Shen, Z. Yuan and H. Xu, Fluorescent properties of phthalocyanines, Dyes and Pigments 11 (1989) 77-80.
31. T. Zhang and H. Xu, Influence of halogenation and aggregation on photosensitizing properties of zinc phthalocyanine (ZnPC), J. Chem. Soc. Faraday Trans. 89 (1993) 3347-3351.
32. B.D. Rihter, M.E. Kenney, W.E. Ford and M.A. Rodgers, Synthesis and photoproperties of diamagnetic octabutoxyphthalocyanines with deep red optical absorbance, J. Am. Chem. Soc. 112 (1990) 8064-8070.
33. M.E. Daraio, P.F. Aramendía, E.A. San Román and S.E. Braslavsky, Carboxylated zinc-phthalocyanines-II. Dimerization and singlet molecular oxygen sensitization in hexadecyltrimethylammonium bromide micelles, Photochem. Photobiol. 54 (1991) 367-373.
34. A.U. Kahn, The discovery of the chemical evolution of singlet oxygen. Some current chemical, photochemical, and biological applications, Int. J. Quantum Chem. 39 (1991) 251-267.
35. S.L. Murov, Handbook of Photochemistry, Marcel Dekker Inc., New York, 1973.
36. J.R. Darwent, I. McCubbin and G. Porter, Photoreduction of methyl viologen sensitized by sulphonated phthalocyanines in micellar solutions, J. Chem. Soc. Faraday Trans. 2, 78 (1982) 903-910.