Phthalocyanines functionalized with 2-methyl-5-nitro-1H-imidazolylethoxy and 1,4,7-trioxanonyl moieties and the effect of metronidazole substitution on photocytotoxicity

Journal of Inorganic Biochemistry

Volumn 127, Issue , 2013, Pages 62-72

  Wierzchowski, Marcin ^a   Sobotta, Lukasz ^a   Skupin Mrugalska, Paulina ^a   Kruk, Justyna ^a   Jusiak, Weronika ^a   Yee, Michael ^b   Konopka, Krystyna ^b   Düzgüneş, Nejat ^b   Tykarska, Ewa ^a   Gdaniec, Maria ^c   Mielcarek, Jadwiga ^a   Goslinski, Tomasz ^a  

^a POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

^b UNIVERSITY OF THE PACIFIC   (United States)

^c ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Photocytotoxicity; Photodynamic therapy; Photosensitizer; Phthalocyanine; Singlet oxygen

Indexed keywords

[1,4,8,11,15,18 HEXAKIS(1,4,7 TRIOXANONYL) 22 [2 (2 METHYL 5 NITRO 1H IMIDAZOL 1 YL)ETHOXY]PHTHALOCYANINE]MAGNESIUM; [1,4,8,11,15,18,22,25 OCTAKIS(1,4,7 TRIOXANONYL)PHTHALOCYANINE] MAGNESIUM; [1,4,8,11,15,18,22,25 OCTAKIS(1,4,7 TRIOXANONYL)PHTHALOCYANINE] MAGNESIUM ZINC; [1,8,18,25 TETRAKIS[2 (2 METHYL 5 NITRO 1H IMIDAZOL 1 YL)ETOXY] PHTHALOCYANINE]MAGNESIUM; PHOTOSENSITIZING AGENT; PHTHALOCYANINE DERIVATIVE; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; HUMAN; HUMAN CELL; MOUTH SQUAMOUS CELL CARCINOMA; PHOTOTOXICITY; QUANTUM YIELD;

PHOTOCYTOTOXICITY; PHOTODYNAMIC THERAPY; PHOTOSENSITIZER; PHTHALOCYANINE; SINGLET OXYGEN;

CELL LINE, TUMOR; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; HUMANS; INDOLES; METRONIDAZOLE; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; PHOTOSENSITIZING AGENTS;

EID: 84884388233     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2013.06.012     Document Type: Article

References (65)

1. R.R. Allison, and C.H. Sibata Photodiagn. Photodyn. Ther. 7 2010 61 75
2. S. Yano, S. Hirohara, M. Obata, Y. Hagiya, S. Ogura, A. Ikeda, H. Kataoka, M. Tanaka, and T. Joh J. Photochem. Photobiol. C 12 2011 46 67
3. M. Ethirajan, Y. Chen, P. Joshi, and R.K. Pandey Chem. Soc. Rev. 40 2011 340 362
4. K. Konopka, and T. Goslinski J. Dent. Res. 86 2007 694 707
5. G.D. Weinstein, J.L. McCullough, J.S. Nelson, M.W. Berns, and A. McCormick J. Invest. Dermatol. 96 1991 573 578
6. I. Kozak, L. Cheng, D.E. Cochran, and W.R. Freeman Br. J. Ophthalmol. 90 2006 1152 1156
7. Z.A. Carneiro, J.C.B. de Moraes, F.P. Rodrigues, R.G. de Lima, C. Curti, Z.N. da Rocha, M. Paulo, L.M. Bendhack, A.C. Tedesco, A.L.B. Formiga, and R.S. da Silva J. Inorg. Biochem. 105 2011 1035 1043
8. T. Goslinski, T. Osmalek, K. Konopka, M. Wierzchowski, P. Fita, and J. Mielcarek Polyhedron 30 2011 1538 1546
9. H. Isago, H. Fujita, and T. Sugimori J. Inorg. Biochem. 117 2012 111 117
10. A.P. Castano, T.N. Demidova, and M.R. Hamblin Photodiagn. Photodyn. Ther. 2 2005 1 23
11. T.J. Dougherty, C.J. Gomer, B.W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan, and Q. Peng J. Natl. Cancer Inst. 90 1998 889 905
12. K. Nawalany, A. Rusin, M. Kepczynski, P. Filipczak, M. Kumorek, B. Kozik, H. Weitman, B. Ehrenberg, Z. Krawczyk, and M. Nowakowska Int. J. Pharm. 430 2012 129 140
13. R.R. Allison, V.S. Bagnato, R. Cuenca, G.H. Downie, and C.H. Sibata Future Oncol. 2 2006 53 71
14. E. Paszko, C. Ehrhardt, M.O. Senge, D.P. Kelleher, and J.V. Reynolds Photodiagn. Photodyn. Ther. 8 2011 14 29
15. R.F. Donnelly, P.A. McCarron, and D. Woolfson Recent Pat. Drug Deliv. Formul. 3 2009 1 7
16. W.A. Denny Lancet Oncol. 1 2000 25 29
17. P. Wardman Clin. Oncol. 19 2007 397 417
18. A. Schreiber, M. Krause, D. Zips, A. Dörfler, K. Richter, S. Vettermann, C. Petersen, B. Beuthien-Baumann, D. Thümmler, and M. Baumann Strahlenther. Onkol. 180 2004 375 382
19. G.I. Sengee, N. Badraa, and Y.K. Shim Phthalocyanines 13 2009 818 822
20. P. Mroz, J. Bhaumik, D.K. Dogutan, Z. Aly, Z. Kamal, L. Khalid, H.L. Kee, D.F. Bocian, D. Holten, J.S. Lindsey, and M.R. Hamblin Cancer Lett. 282 2009 63 76
21. S. Nakajima, T. Fujii, N. Murakami, T. Aburano, I. Sakata, Y. Nakae, and T. Takemura Cancer Lett. 181 2002 173 178
22. S. Lijewski, J. Piskorz, M. Kucińska, M. Wierzchowski, K. Czerniak, H. Billert, M. Murias, J. Mielcarek, and T. Goslinski Inorg. Chem. Commun. 29 2013 97 100
23. E. Hamuryudan Dye. Pigment. 68 2006 151 157
24. F. Dumoulin, M. Durmuş, V. Ahsen, and T. Nyokong Coord. Chem. Rev. 254 2010 2792 2847
25. E. Aǧar, S. Şaşmaz, K. İbrahim, and B. Karabulut Dye. Pigment. 35 1997 269 278
26. P.C. Lo, S. Wang, A. Zeug, M. Meyer, B. Röder, and D.K.P. Ng Tetrahedron Lett. 44 2003 1967 1970
27. A. Wang, L. Long, and C. Zhang Tetrahedron 68 2012 2433 2451
28. F. Lv, B. Cao, Y. Cui, and T. Liu Molecules 17 2012 6348 6361
29. D. Wöhrle, G. Schnurpfeil, S.G. Makarov, A. Kazarin, and O.N. Suvorova Macroheterocycles 5 2012 191 202
30. N. Kobayashi, and A.B.P. Lever J. Am. Chem. Soc. 109 1987 7433 7441
31. O.E. Sielcken, M.M. Van Tilborg, M.F.M. Roks, R. Hendriks, W. Drenth, and R.J.M. Nolte J. Am. Chem. Soc. 109 1987 4261 4265
32. W. Szczolko, L. Sobotta, P. Fita, T. Koczorowski, M. Mikus, M. Gdaniec, A. Orzechowska, K. Burda, S. Sobiak, M. Wierzchowski, J. Mielcarek, E. Tykarska, and T. Goslinski Tetrahedron Lett. 53 2012 2040 2044
33. Agilent Technologies CrysAlis PRO Software 2010 Agilent Technologies Yarnton, Oxfordshire, England
34. G.M. Sheldrick Acta Crystallogr. A64 2008 112 122
35. T. Goslinski, T. Osmalek, and J. Mielcarek Polyhedron 28 2009 3839 3843
36. I. Seotsanyana-Mokhosi, N. Kuznetsova, and T. Nyokong J. Photochem. Photobiol. A 140 2001 215 222
37. J. Piskorz, P. Skupin, S. Lijewski, M. Korpusinski, M. Sciepura, K. Konopka, S. Sobiak, T. Goslinski, and J. Mielcarek J. Fluorine Chem. 135 2012 265 271
38. K. Matsumoto, M. Horikoshi, K. Rikimaru, and S. Enomoto J. Oral Pathol. Med. 18 1989 498 501
39. S.S. Prime, S.V.R. Nixon, I.J. Crane, A. Stone, J.B. Matthews, N.J. Maitland, L. Remnant, S.K. Powell, S.M. Game, and C. Scully J. Pathol. 160 1990 259 269
40. R.D. Fields, and M.V. Lancaster Am. Biotechnol. Lab. 11 1993 48 50
41. K. Konopka, E. Pretzer, P.L. Felgner, and N. Düzgüneş Biochim. Biophys. Acta 1312 1996 186 196
42. N. Düzgüneş Methods Enzymol. 367 2003 23 27
43. I. Sircar, M. Hoefle, and R.E. Maxwell J. Med. Chem. 26 1983 1020 1027
44. T.P. Forsyth, D. Bradley, G. Williams, A.G. Montalban, C.L. Stern, A.G.M. Barrett, and B.M. Hoffman J. Org. Chem. 63 1998 331 336
45. G.C. Eastmond, I. Paprotny, R.A. Pethrick, and F. Santamaria-Mendia Macromolecules 39 2006 7534 7548
46. R.P. Linstead, and M. Whalley J. Chem. Soc. 1952 4839 4846
47. S.L.J. Michel, B.M. Hoffman, S.M. Baum, and A.G.M. Barrett K.D. Karlin, Peripherally Functionalized Porphyrazines: Novel Metallomacrocycles With Broad, Untapped Potential Prog. Inorg. Chem. 50 2001 J. Wiley & Sons New York 473 590
48. J. Vacus, G. Memetzidis, P. Doppelt, and J. Simon J. Chem. Soc. Chem. Commun. 1994 697 698
49. K. Kameyama, M. Morisue, A. Satake, and Y. Kobuke Angew. Chem. Int. Ed. 44 2005 4763 4766
50. L. Niu, C. Zhong, Z. Chen, Z. Zhang, Z. Li, F. Zhang, and Y. Tang Chin. Sci. Bull. 54 2009 1169 1175
51. D.S. Terekhov, K.J.M. Nolan, C.R. McArthur, and C.C. Leznoff J. Org. Chem. 61 1996 3034 3040
52. M. Kobayashi, K. Satoh, K. Sawada, and J. Porphyrins Phthalocyanines 16 2012 359 369
53. W. Chidawanyika, E. Antunes, and T. Nyokong J. Photochem. Photobiol. A 195 2008 183 190
54. W. Spiller, H. Kliesch, D. Wöhrle, S. Hackbarth, B. Röder, and G. Schnurpfeil J. Porphyrins Phthalocyanines 2 1998 145 158
55. M.P. Cormick, M. Rovera, and E.N. Durantini J. Photochem. Photobiol. A 194 2008 220 229
56. A. Ogunsipe, M. Durmuş, D. Atilla, A.G. Gürekc, V. Ahsenc, and T. Nyokong Synth. Met. 158 2008 839 847
57. X. Shen, W. Lu, G. Feng, Y. Yao, and W. Chen J. Mol. Catal. A Chem. 298 2009 17 22
58. J.H. Howard, and G.D. Mendenhall Can. J. Chem. 53 1975 2199 2201
59. J.P. Celli, B.Q. Spring, I. Rizvi, C.L. Evans, K.S. Samkoe, S. Verma, B.W. Pogue, and T. Hasan Chem. Rev. 110 2010 2795 2838
60. S. Lee, R. Stackow, C.S. Foote, A.G.M. Barrett, and B.M. Hoffman Photochem. Photobiol. 77 2003 18 21
61. K. Ishii, H. Itoya, H. Miwa, M. Fujitsuka, O. Ito, and N. Kobayashi J. Phys. Chem. A 109 2005 5781 5787
62. J. Kossanyi, and D. Chahraoui Int. J. Photoenergy 2 2000 9 15
63. A.S.L. Derycke, and P.A.M. deWitte Adv. Drug Delivery Rev. 56 2004 17 30
64. A. Petri, D. Yova, E. Alexandratou, M. Kyriazi, and M. Rallis Photodiagn. Photodyn. Ther. 9 2012 344 354
65. B. Görlach, M. Dachter, T. Glaser, K. Albert, and M. Hanack Chem. Eur. J. 7 2001 2459 2465