Photooxidation and phototoxicity of π-extended squaraines

Journal of Medicinal Chemistry

Volumn 53, Issue 5, 2010, Pages 2188-2196

  Rapozzi, Valentina ^a   Beverina, Luca ^b   Salice, Patrizio ^b   Pagani, Giorgio A ^b   Camerin, Monica ^c   Xodo, Luigi E ^a  

^a UNIVERSITY OF UDINE   (Italy)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

^c UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BIS SQUARAINE; CASPASE 3; CASPASE 7; HYDROCARBON; HYDROPEROXIDE; MALONALDEHYDE; PEROXIDE; SQUARAINE; SQUARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL DEATH; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; CYTOPLASM; DRUG DESIGN; ENZYME ASSAY; FLUORESCENCE ACTIVATED CELL SORTING; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPID PEROXIDATION; PHOTOOXIDATION; PHOTOTOXICITY;

ANTINEOPLASTIC AGENTS; BENZOTHIAZOLES; CELL PROLIFERATION; CYCLOBUTANES; DERMATITIS, PHOTOTOXIC; FLOW CYTOMETRY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HELA CELLS; HUMANS; INHIBITORY CONCENTRATION 50; LIPID PEROXIDES; MICROSCOPY, CONFOCAL; PHOTOSENSITIZING AGENTS; THIOBARBITURIC ACID REACTIVE SUBSTANCES;

EID: 77949379072     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901727j     Document Type: Article

References (37)

1. Sprenger, G. E.; Ziegenebein, W. Cyclobutenediylium Dyes. Angew. Chem., Int. Ed. Engl. 1968, 7, 530-535.
2. Maahas, G.; Hegenberg, P. Syntheses and derivatives of squaric acid. Angew. Chem., Int. Ed. Engl. 1966, 5, 888-893.
3. Keil, D.; Hartmann, H. Synthesis and characterization of a new class of unsymmetrical squaraine dyes. Dyes Pigm. 2001, 49,161-179.
4. Schmidt, A. H. Oxocarbons; West, R., Ed.; Academic Press: New York, 1980; p 185.
5. Santos, P. F.; Reis, L. V.; Almeida, P.; Serrano, J. P.; Oliveira, A. S.; Vieira-Ferreira, L. F. Efficiency of single oxygen generation of aminosquarylium cyanines. J. Photochem. Photobiol, A 2004, 163,267-1169
6. Ramaiah, D.; Eckert, I.; Arun, K. T.; Weidenfeiler, L.; Epe, B. Squaraine dyes for photodynamic therapy : Study of their cytotoxicity and genotoxicity in bacteria and mammalin cells. Photochem. Photobiol. 2002, 76, 672-677.
7. Ramaiah, D. A.; Joy, N.; Chandrasekar, N. V.; Eldho, S. D.; George, M. V. Halogenated squaraine dyes as potential photochemotherapeutic agents. Synthesis and study of photophysical properties and quantum efficiencies of single oxygen generation. Photochem. Photobiol. 1997, 65, 783-790.
8. Ramaiah, D.; Eckert, I.; Arun, K. T.; Weidenfeiler, L.; Epe, B. Squaraine dyes for photodynamic therapy: Mechanism of cytotoxicity and DNA damage induced by halogenated squaraine dyes plus light (> 600 nm). Photochem. Photobiol. 2004, 79, 99-104.
9. Sreejith, S.; Divya, K. P.; Ajayaghosh, A. A near-infrared squaraine dye as a latent ratiometric fluorophore for the detection of aminothiol content in blood plasma. Angew. Chem., Int. Ed. Engl. 2008, 47, 7883-7887.
10. Dolmans, D. E.; Fukumura, D.; Jain, R. K. Photodynamic therapy for cancer. Nat. Rev. Cancer 2003, 3, 380-387.
11. Castano, A. P.; Mroz, P.; Hamblin, M.R.. Photodynamic therapy and anti-tumour immunity. Nat. Rev. Cancer 2006, 6, 535-545.
12. Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, P.; Peng, Q. Photodinamic Therapy. J. Natl. Cancer Inst. 1998, 90, 889-905.
13. Miller, J. Chemistry behind the News-Photodynamic Therapy: The Sensitization of Cancer Cells to Light. J. Chem. Educ. 1999,76, 592-594.
14. Pervaiz, S. Reactive oxygen-dependent production of novel photochemotherapeutic agents. FASEB J. 2001, 15, 612-617.
15. Josefsen, L. B.; Boyle, R. W. Photodynamic therapy and the development of metal-based photosensitisers. Met. Based Drugs 2008,276109-276133.
16. Castano, A. P.; Demidova, T. N.; Hamblin, M. R. Mechanisms in photodynamic therapy: Part one-photosensitizers, photochemistry and cellular localization. Photodiagn. Photodyn. Ther. 2004, 1, 279-293.
17. Castano, A. P.; Demidova, T. N.; Hamblin, M. R. Mechanisms in photodynamic therapy: part three-photosensitizers pharmacokinetics, biodistribution, tumor localization and modes of tumor destruction. Photodiagn. Photodyn. Ther. 2005, 2, 91-106.
18. Allison, R. R.; Downie, G. H.; Cuenca, R.; Hu, X. H.; Childs, C. J.; Sibata, C. H. Photosensitizers in clinical PDT. Photodiagn. Photodyn. Ther. 2004, 1, 17-41.
19. Sessler, J. L.; Miller, R. A. Texaphyrins: New drugs eith diverse clinical applications in radiation and photodynamic therapy. Biochem. Pharmacol. 2000, 59, 733-739
20. Comuzzi, C.; Cogoi, S.; Overhand, M.; van der marel, G. A.; Overkleeft, H. S.; Xodo, L. E. Synthesis and biological evaluation of new pentaphyrin macrocycles for photodynamic therapy. J. Med. Chem. 2006, 49, 196-204.
21. Rapozzi, V.; Lombardo, C.; Cogoi, S.; Comuzzi, C.; Xodo, L. E. Small interfering RNA-mediated silencing of glutathione S-transferasi Al sensitizes hepatic carcinoma cells to photodynamic therapy with pentaphyrins. ChemMedChem 2008, 3, 565-568.
22. Rapozzi, V.; Miculan, M.; Xodo, L. E. Evidence that photoactivated pheophorbide a causes in human cancer cells a photodynamic effect involving lipid peroxidation. Cancer Biol. Ther. 2009, 14, 1-10.
23. Taquet, J. P.; Frochot, C.; Manneville, V.; Barberi-Heyob, M. Phthalocyanines covalently bound to biomolecules for a targeted photodynamic therapy. Curr. Med. Chem. 2007, 14, 1673-1687.
24. Juarranz, A.; Jaen, P.; Sanz-Rodriguez, F.; Cuevas, J.; Gonzales, S. Photodynamic therapy of cancer. Basic principles and applications. Clin. Transl. Oncol. 2008, 10, 148-154.
25. Josefsen, L. B.; Boyle, R.W. Photodynamic therapy: Novel thirdgeneration photosensitizers one step closer? Br. J. Pharmacol. 2008, 154, 1-3.
26. Gayathri Devi, D.; Cibin, T. R.; Ramaiah, D.; Abraham, A. J. Bis (3,5-diiodo-2,4,6-trihydroxyphenyl) squaraine: a novel candidate in photodynamic therapy for skin cancer models in vivo. Photochem. Photobiol, B 2008, 92, 153-159.
27. Yagi, S.; Ohta, T.; Akagi, N.; Nakazumi, H. The synthesis and optical properties of bis-squarylium dyes bearing arene and thiophene spacers. Dyes Pigm. 2008, 77, 525-536.
28. Foote, C. S.; Lin, J. W.-P. Chemistry of singlet oxygen. VI. Photooxygenation of enamines: Evidence for an intermediate. Tetrahedron Lett. 1968, 9 (29), 3267-3270.
29. Mazur, S.; Foote, C. S. Chemistry of singlet oxygen. IX. Stable dioxetane from photooxygenation of tetramethoxyethylene. J. Am. Chem. Soc. 1970, 92 (10), 3225-3226.
30. Foote, C.; Wexler, S.; Ando, W. Chemistry of Singlet Oxygen. III. Product Selectivity. Tetrahedron Lett. 1965, 46, 4111-4118.
31. Marine, S.; Clemons, J. Determination of limonene oxidation products using SPME and GC-MS. J. Chromatogr. Sci. 2003, 41(1), 31-35.
32. Mikaia, A.; Stein, S. E.; Zaikin,V.; Zhu, D.; Milman, B.; Babishok, V.; Zenkevich, I.; Linstrom, P.; Mirokhin, Y.; Tchekhovskoi, D.; Mallard, W. G.; Sparkman, O. D.; Sparkman, J. A. NIST/EPA/ NIH Mass Spectral Library-Version 2.0d; National Institute of Standards and Technology: Gaithersburg, MD, 2005.
33. Kawakami, M.; Suzuki, M.; Kawai, H.; Ogawa, K.; Shishido, T. A self-sensitized photoreaction of rhodacyanine dye, MKT 077. Tetrahedron Lett. 1998, 39 (13), 1763-1766.
34. Hoebeke, M.; Piette, J.; van de Vorst, A. Photosensitized production of singlet oxygen by merocyanine 540 bound to liposomes. J. Photochem. Photobiol., B: Biol. 1991, 9 (3-4), 281-294.
35. Wong, S. H. Y.; Knight, J. A.; Hopfer, S. M.; Zaharia, O.; Leach, G N.; Sunderman, F. W. Lipoperoxides in plasma as measured by liquid-chromatographic separation of malondialdehyde-thiobarbituric acid adduct. Clin. Chem. 1987, 33,214-220.
36. Koopman, G.; Reutelingsperger, C. P. M.; Kuijten, G. A. M.; Keehnen, R. M. J.; Palsvan, S. T.; Oers, M. H. J. Annexin V for flow cytometric detection of phosphatidylserine expression on B cells undergoing apoptosis. Blood 1994, 84, 1415-1420.
37. Ziegler, U.; Groscurth, P. Morphological features of cell death. News Physiol. Sci. 2004, 19, 124-128.