Photodynamic efficiency of porphyrins encapsulated in polysilsesquioxanes

Chemical Papers

Volumn 66, Issue 4, 2012, Pages 269-277

  Rychtarikova, Renata ^a   Šabata, Stanislav ^a   Hetflejš, Jiři ^a   Kuncova, Gabriela ^a  

^a INSTITUTE OF CHEMICAL PROCESS FUNDAMENTALS   (Czech Republic)

Author keywords

Absorbance; Bacteria; Fluorescence; Immobilisation; Photoinactivation; Porphyrin; Specific surface area

Indexed keywords

EID: 84862676300     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-012-0153-3     Document Type: Article

References (52)

1. Alves, E., Costa, L., Carvalho, C. M. B., Tome, J. P. C., Faustino, M. A., Neves, M. G. P. M. S., Tome, A. C., Cavaleiro, J. A. S., Cunha, A., & Almeida, A. (2009). Charge effect on the photoinactivation of Gram-negative and Grampositive bacteria by cationic meso-substituted porphyrins. BMC Microbiology, 9, 70. DOI: 10.1186/1471-2180-9-70.
2. Arabei, S. M., Pavich, T. A., & Solov'ev, K. N. (2001). The influence of the conditions of sol-gel synthesis on the absorption and fluorescence spectra of porphyrin molecules in silicate matrices. Journal of Applied Spectroscopy, 68, 66-72. DOI: 10.1023/a:1019261002923. (Pubitemid 33306129)
3. Biazzotto, J. C., Vidoto, E. A., Nascimento, O. R., Iamamoto, Y., & Serra, O. A. (2002). Iron(III)-tetra-oureaphenylporphyrinosilica obtained by a sol-gel process: a study of EPR, surface area and catalytic activity. Journal of Non-Crystalline Solids, 304, 101-108. DOI: 10.1016/s0022-3093(02)01010-4. (Pubitemid 34466936)
4. Brevet, D., Gary-Bobo, M., Raehm, L., Richeter, S., Hocine, O., Amro, K., Loock, B., Couleaud, P., Frochot, C., Morère, A., Maillard, P., Garcia, M., & Durand, J. O. (2009). Manosetargeted mesoporous silica nanoparticles for photodynamic therapy. Chemical Communications, 2009, 1475-1477. DOI: 10.1039/b900427k.
5. Brinker, C. J., & Scherer, G. W. (1990). Sol-gel science: The physics and chemistry of sol-gel processing. New York, NY, USA: Academic Press.
6. Caminos, D. A., & Durantini, E. N. (2006). Photodynamic inactivation of Escherichia coli immobilized on agar surfaces by a tricationic porphyrin. Bioorganic & Medicinal Chemistry, 14, 4253-4259. DOI: 10.1016/j.bmc.2006.01. 058.
7. Caminos, D. A., Spesia, M. B., Pons, P., & Durantini, E. N. (2008). Mechanisms of Escherichia coli photodynamic inactivation by an amphiphilic tricationic porphyrin and 5, 10, 15, 20-tetra(N, N, N-trimethylammoniumphenyl) porphyrin. Photochemical & Photobiological Sciences, 2008, 1071-1078. DOI: 10.1039/b804965c.
8. Carvalho, C. M. B., Gomes, A. T. P. C., Fernandes, S. C. D., Prata, A. C. B., Almeida, M. A., Cunha, M. A., Tome, J. P. C., Faustino, M. A. F., Neves, M. G. P. M. S., Tome, A. C., Cavaleiro, J. A. S., Lin, Z., Rainho, J. P., & Rocha, J. (2007). Photoinactivation of bacteria in wastewater by porphyrins: Bacterial β-galactosidase activity and leucineuptake as methods to monitor the process. Journal of Photochemistry and Photobiology B: Biology, 88, 112-118. DOI: 10.1016/j.jphotobiol.2007.04.015. (Pubitemid 47382614)
9. 2 generation properties of porphyrin molecules immobilized in oxidized nano-porous silicon matrix. Journal of Photochemistry and Photobiology A: Chemistry, 181, 106-113. DOI: 10.1016/j.jphotochem.2005.11.008.
10. Chirvony, V. S., Bolotin, V. I., Ovejero, J., Matveeva, E. S., Dzhagarov, B. M., Albella, J., & Parkhutin, V. P. (2007). Luminescence properties of the porphyrin/porous silicon composites. Physica Status Solidi (A), 204, 1523-1527. DOI: 10.1002/pssa.200674414. (Pubitemid 47120022)
11. Collins, T. L., Markus, E. A., Hassett, D. J., & Robinson, J. B. (2010). The effect of a cationic porphyrin on Pseudomonas aeruginosa biofilms. Current Microbiology, 61, 411-416. DOI: 10.1007/s00284-010-9629-y.
12. Cormick, M. P., Alvarez, M. G., Rovera, M., & Durantini, E. N. (2009). Photodynamic inactivation of Candida albicans sensitized by tri- and tetra-cationic porphyrin derivatives. European Journal of Medicinal Chemistry, 44, 1592-1599. DOI: 10.1016/j.ejmech.2008.07.026.
13. Cormick, M. P., Quiroga, E. D., Bertolotti, S. G., Alvarez, M. G., & Durantini, E. N. (2011). Mechanistic insight of the photodynamic effect induced by tri- and tetra-cationic porphyrins on Candida albicans cells. Photochemistry & Photobiology Sciences, 2011, 1556-1561. DOI: 10.1039/c1pp05074e.
14. Costa, L., Alves, E., Carvalho, C. M. B., Tome, J. P. C., Faustino, M. A. F., Neves, M. G. P.M. S., Tome, A. C., Cavaleiro, J.A. S., Cunha, Ǎ., & Almeida, A. (2008). Sewage bacteriophage photoinactivation by cationic porphyrins: a study of charge effect. Photochemical & Photobiological Sciences, 2008, 415-422. DOI: 10.1039/b712749a. (Pubitemid 351490298)
15. Costa, L., Carvalho, C. M. B., Faustino, M. A. F., Neves, M. G. P. M. S., Tome, J. P. C., Tome, A. C., Cavaleiro, J. A. S., Cunha, Ǎ., & Almeida, A. (2010). Sewage bacteriophage photoinactivation by cationic porphyrins: influence of light parameters. Photochemical & Photobiological Sciences, 2010, 1126-1133. DOI: 10.1039/c0pp00051e.
16. Da̧browski, J. M., Pereira, M. M., Arnaut, L. G., Monteiro, C. J. P., Peixoto, A. F., Karocki, A., Urbánska, K., & Stochel, G. (2007). Synthesis, photophysical studies and anticancer activity of a new halogenated water-soluble porphyrin. Photochemistry and Photobiology Sciences, 83, 897-903. DOI: 10.1111/j.1751-1097.2007.00073.x. (Pubitemid 47087375)
17. Dargiewicz, J., Makarska, M., & Radzki, S. (2002). Spectroscopic characterization of water-soluble cationic porphyrins in sol-gel silica matrices and coatings. Colloids and Surface A: Physicochemical and Engineering Aspects, 208, 159-165. DOI: 10.1016/s0927-7757(02)00142-5. (Pubitemid 34828356)
18. +. Journal of Bacteriology, 180, 4314-4318. (Pubitemid 28373542)
19. Figueira, F., Cavaleiro, J. A. S., & Tome, J. P. C. (2011). Silica nanoparticles functionalized with porphyrins and analogs for biomedical studies. Journal of Porhyrins and Phthalocyanines, 15, 517-533. DOI: 10.1142/s1088424611003653.
20. Fueda, Y., Hashimoto, M., Nobuhara, K., Yokoi, H., Komiya, Y., Shiragami, T., Matsumoto, J., Kawano, K., Suzuki, S., & Yasuda, M. (2005). Visible-light bactericidal effect of silica gel-supported porphyrinatoantimony(V) catalyst on Legionella species occurring in the living environmental fields. Biocontrol Science, 10, 55-60. (Pubitemid 40895872)
21. Fueda, Y., Suzuki, H., Komiya, Y., Asakura, Y., Shiragami, T., Matsumoto, J., Yokoi, H., & Yasuda, M. (2006). Bactericidal effect of silica gel-supported porphyrinatophosphorus(V) catalysts on Escherichia coli under visible-light irradiation. Bulletin of the Chemical Society of Japan, 79, 1420-1425. DOI: 10.1246/bcsj.79.1420. (Pubitemid 44681179)
22. Garcia-Sanchez, M. A., de la Luz, V., Coahuila-Hernandez, M. I., Rojas-Gonzales, F., Tello-Solis, S. R., & Campero, A. (2011). Effects of the structure of entrapped substituted porphyrins on the textural characteristics of silica networks. Journal of Photochemistry & Photobiology A: Chemistry, 223, 172-181. DOI: 10.1016/j.photochem.2011.08.015.
23. Gomes, M. C., Woranovicz-Barreira, S. M., Faustino, M. A. F., Fernandes, R., Neves, M. G. P. M. S., Tome, A. C., Gomes, N. C. M., Almeida, A., Cavaleiro, J. A. S., Cunha, Ǎ., & Tome, J. P. C. (2011). Photodynamic inactivation of Penicillium chrysogenum conidia by cationic porphyrins. Photochemical & Photobiological Sciences, 2011, 1735-1743. DOI: 10.1039/c1pp05174a.
24. Hocine, O., Gary-Bobo, M., Brevet, D., Maynadier, M., Fontanel, S., Raehm, L., Richeter, S., Loock, B., Couleaud, P., Frochot, C., Charnay, C., Derrien, G., Smaïhi, M., Sahmoune, A., Morère, A., Maillard, P., Garcia, M., & Durand, J. O. (2011). Silicalites and mesoporous silica nanoparticles for photodynamic therapy. International Journal of Pharmaceutics, 402, 221-230. DOI: 10.1016/j.ijpharm.2010.10.004.
25. Jemli, M., Alouini, Z., Sabbahi, S., & Gueddari, M. (2002). Destruction of fecal bacteria in wastewater by three photosensitizers. Journal of Environmental Monitoring, 2002, 511-516. DOI: 10.1039/b204637g. (Pubitemid 34864579)
26. Jori, G. (2006). Photodynamic therapy of microbial infections: State of the art and perspectives. Journal of Environmental Pathology, Toxicology and Oncology, 25, 505-520.
27. Jori, G., Camerin, M., Soncin, M., Guidolin, L., & Coppellotti, O. (2011a). Antimicrobial photodynamic therapy: Basic principles. In M. R. Hamblin, & G. Jori (Eds.), Photodynamic inactivation of microbial pathogens: Medical and environmental applications (pp. 3-14). London, UK: Royal Society of Chemistry. DOI: 10.1039/9781849733083-00001.
28. Jori, G., Fabris, C., Soncin, M., Ferro, S., Coppellotti, O., Dei, D., Fantetti, L., Chiti, G., & Roneucci, G. (2006). Photodynamic therapy in the treatment of microbial infections: Basic principles and perspective applications. Lasers in Surgery and Medicine, 38, 468-481. DOI: 10.1002/lsm.20361.
29. Jori, G., Magaraggia, M., Fabris, C., Soncin, M., Camerin, M., Tallandini, L., Coppellotti, O., & Guidolin, L. (2011b). Photodynamic inactivation of microbial pathogens: Disinfection of water and prevention of water-borne diseases. Journal of Environmental Pathology, Toxicology and Oncology, 30, 261-271.
30. Ko, Y. J., Yun, K. J., Kang, M. S., Park, J., Lee, K. T., Park, S. B., & Shin, J. H. (2007). Synthesis and in vitro photodynamic activities of water-soluble fluorinated tetrapyridylporphyrins as tumor photosensitizers. Bioorganic & Medicinal Chemistry Letters, 17, 2789-2794. DOI: 10.1016/j.bmcl.2007.02.083. (Pubitemid 46636253)
31. Koenig K., & Schneckenburger, H. (2004). Laser-induced autofluorescence for medical diagnosis. Journal of Fluorescence, 4, 17-40, DOI: 10.1007/bf01876650.
32. Loy, D. A., Jamison, G. M., Baugher, B. M., Russick, E. M., Assink, R. A., Prabakar, S., & Shea, K. J. (1995). Alkylenebridged polysilsesquioxane aerogels: highly porous hybrid organic-inorganic materials. Journal of Non-Crystalline Solids, 186, 44-53. DOI: 10.1016/0022-3093(95)00032-1.
33. Lukasik, K. V., & Ludescher, R. D. (2006). Molecular mobility in water and glycerol plasticized cold- and hotcast gelatin films. Food Hydrocolloids, 20, 96-105. DOI: 10.1016/j.foodhyd.2005.03.007. (Pubitemid 41116840)
34. Lukšiene, Z. (2005). New approach to inactivation of harmful and pathogenic microorganisms by photosensitization. Food Technology & Biotechnology, 43, 411-418.
35. Magaraggia, M., Marigo, L., Pagnan, A., Jori, G., & Visona, A. (2007). Porphyrin-photosensitized processes in the prevention of arterial restenosis. Cardiovascular & Hematological Agents in Medical Chemistry, 5, 278-288. (Pubitemid 47595738)
36. Maisch, T., Szeimies, R. M., Jori, G., & Abels, C. (2004). Antibacterial photodynamic therapy in dermatology. Photochemical & Photobiological Sciences, 3, 907-917. DOI: 10.1039/b407622b. (Pubitemid 39504589)
37. Mosinger, J., Losinska, K., Abrhamova, T., Veiserova, S., Mička, Z., Němcova, I., & Mosinger, B. (2000). Determination of singlet oxygen production and antibacterial effect of nonpolar porphyrins in heterogeneous systems. Analytical Letters, 33, 1091-1104. DOI: 10.1080/00032710008543111. (Pubitemid 30212592)
38. Oliveira, A., Almeida, A., Carvalho, C. M. B., Tome, J. P. C., Faustino, M. A. F., Neves, M. G. P.M. S., Tome, A. C., Cavaleiro, J. A. S., & Cunha, Ǎ. (2009). Porphyrin derivatives as photosensitizers for the inactivation of Bacillus cereus endospores. Journal of Applied Microbiology, 106, 1086-1995. DOI: 10.1111/j.1365-2672.2009.04168.x.
39. Ou, Z. M., Yao, H., & Kimura, K. (2007). Preparation and optical properties of organic nanoparticles of porphyrins without self-aggregation. Journal of Photochemistry and Photobiology A: Chemistry, 189, 7-14. DOI: 10.1016/j.jphotochem.2006.12.042.
40. Oviatt, H. W., Shea, K. J., & Small, J. H. (1993). Alkylenebridged silsesquioxane sol-gel synthesis and xerogel characterization. Molecular requirements for porosity. Chemistry of Materials, 5, 943-950. DOI: 10.1021/cm00031a012.
41. Rychtarikova, R. (2011). Antimicrobial effects of immobilized porphyrins. Ph.D. thesis. Prague, Czech Republic: Institute of Chemical Technology.
42. Rychtarikova, R., & Kuncova, G. (2011). Assessment of antimicrobial activity via computational tresholding of colours. Chemické Listy, 105, 493-498.
43. Rychtarikova, R., Sabata, S., Hetflejs, J., & Kuncova, G. (2012). Composites with photosensitive 5, 10, 15, 20-tetrakis(Nmethylpyridinium- 4-yl)porphyrin entrapped into silica gels. Journal of Sol-Gel Science and Technology, 61, 119-125. DOI: 10.1007/s10971-011-2600-y.
44. Šabata, S., Hetflejš, J., Rychtarikova, R., Kuncova, G., Lang, K., & Kubat, P. (2009). Immobilization of porphyrins in poly(hydroxymethyl)siloxane. Chemical Papers, 63, 438-444. DOI: 10.2478/s11696-009-0037-3.
45. Sigler, K., Chaloupka, J., Brozmanova, J., Stadler, N., & Höfer, M. (1999). Oxidative stress in microorganisms-I. Microbial vs. higher cells-damage and defenses in relation to cell aging and death. Folia Microbiologica, 44, 587-624. DOI: 10.1007/bf02825650. (Pubitemid 129551998)
46. Simon, V., Devaux, C., Darmon, A., Donnet, T., Thienot, E., Germain, M., Honnorat, J., Duval, A., Pottier, A., Borghi, E., Levy, L., & Marrill, J. (2010). Pp IX silica nanoparticles demonstrate differential interactions with in vitro tumor cell lines and in vivo mouse models of human cancers. Photochemistry and Photobiology, 86, 213-222. DOI: 10.1111/j.1751-1097.2009. 00620.x.
47. Strawbridge, I., & James, P. F. (1986). Thin silica films prepared by dip coating. Journal of Non-Crystalline Solids, 82, 366-372. DOI: 10.1016/0022-3093(86)90153-5.
48. Ulatowska-Jarza, A., Zychowicz, J., Hołowacz, I., Bauer, J., Razik, J., Wieliczko, A., Podbielska, H., Müller, G., Strȩk, W., & Bindig, U. (2006). Antimicrobial PDT with chlorophyll-derived photosensitizer and semiconductor laser. Medical Laser Application, 21, 177-183. DOI: 10.1016/j.mla.2006.05.003. (Pubitemid 44255804)
49. Vergeldt, F. J., Koehorst, R. B. M., van Hoek, A., & Schaafsma, T. J. (1995). Intramolecular interactions in the ground and excited-state of tetrakis(N-methylpyridyl)porphyrins. The Journal of Physical Chemistry, 99, 4397-4405. DOI: 10.1021/j100013a007.
50. Yokoi, H., Shiragami, T., Hirose, J., Kawauchi, T., Hinoue, K., Fueda, Y., Nobuhara, K., Akazaki, I., & Yasuda, M. (2003). Bactericidal effect of a silica gel-supported porphyrinatoantimony( V) complex under visible light irradiation. World Journal of Microbiology and Biotechnology, 19, 559-563. DOI: 10.1023/a:1025104032318. (Pubitemid 37089990)
51. Yoshida, A., Kakegawa, N., & Ogawa, M. (2003). Adsorption of cationic porphyrin onto mesoporous silicas. Research on Chemical Intermediates, 29, 721-731. DOI: 10.1163/156856 703322601735.
52. Zhu, J., Wang, H., Liao, L., Zhao, L., Zhou, L., Yu, M., Wang, Y., Liu, B., & Yu, C. (2011). Small mesoporous silica nanoparticles as carriers for enhanced photodynamic therapy. Chemistry -An Asian Journal, 6, 2332-2338. DOI: 10.1002/asia.201100064.