Evaluation of antibacterial properties of novel phthalocyanines against Escherichia coli - Comparison of analytical methods

Journal of Photochemistry and Photobiology B: Biology

Volumn 138, Issue , 2014, Pages 230-239

  Mikula, Premysl ^a   Kalhotka, Libor ^b   Jancula, Daniel ^a   Zezulka, Stepan ^a   Korinkova, Radka ^c   Cerny, Jiri ^c   Marsalek, Blahoslav ^a   Toman, Petr ^d  

^a INSTITUTE OF BOTANY   (Czech Republic)

^b MENDEL UNIVERSITY IN BRNO   (Czech Republic)

^c Centre for Organic Chemistry Ltd   (Czech Republic)

^d INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Czech Republic)

Author keywords

Antibacterial effect; Binding affinity; Cell membrane integrity; Cultivation techniques; Flow cytometry; Photosensitizers; Phthalocyanines; Singlet oxygen

Indexed keywords

PHTHALOCYANINE DERIVATIVE; SINGLET OXYGEN; ANTIINFECTIVE AGENT; INDOLE DERIVATIVE; PHOTOSENSITIZING AGENT; PHTHALOCYANINE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL CELL; BACTERIAL MEMBRANE; BACTERIAL STRAIN; BACTERIUM CULTURE; BINDING AFFINITY; CELL COUNT; CONTROLLED STUDY; DRUG STRUCTURE; ESCHERICHIA COLI; FLOW CYTOMETRY; ILLUMINATION; INTERMETHOD COMPARISON; NONHUMAN; PRIORITY JOURNAL; WHITE LIGHT; CHEMISTRY; DRUG EFFECTS; EVALUATION STUDY; LIGHT; METABOLISM;

ANTI-BACTERIAL AGENTS; ESCHERICHIA COLI; FLOW CYTOMETRY; INDOLES; LIGHT; PHOTOSENSITIZING AGENTS; SINGLET OXYGEN;

EID: 84903740456     PISSN: 10111344     EISSN: 18732682     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2014.04.014     Document Type: Article

References (50)

1. L.S. Bicalho, J.P. Longo, C.E.O. Cavalcanti, A.R. Simioni, A.L. Bocca, M.D.M.D. Santos, A.C. Tedesco, and R.B. Azevedo Photodynamic therapy leads to complete remission of tongue tumors and inhibits metastases to regional lymph nodes J. Biomed. Nanotechnol. 9 2013 811 818
2. T.K. Horne, H. Abrahamse, and M.J. Cronje Investigating the efficiency of novel metallo-phthalocyanine PDT-induced cell death in MCF-7 breast cancer cells Photodiag. Photodyn. Ther. 9 2012 215 224
3. K. Maduray, B. Odhav, and T. Nyokong In vitro photodynamic effect of aluminum tetrasulfophthalocyanines on melanoma skin cancer and healthy normal skin cells Photodiag. Photodyn. Ther. 9 2012 32 39
4. K. Sutoris, J. Rakusan, M. Karaskova, J. Mattova, J. Benes, M. Nekvasil, P. Jezek, M. Zadinova, P. Pouckova, and D. Vetvicka Novel topical photodynamic therapy of prostate carcinoma using hydroxy-aluminum phthalocyanine entrapped in liposomes Anticancer Res. 33 2013 1563 1568
5. J. Dobson, and M. Wilson Sensitization of oral bacteria in biofilms to killing by light from a low-power laser Arch. Oral Biol. 37 1992 883 887
6. S. Wood, B. Nattress, J. Kirkham, R. Shore, S. Brookes, J. Griffiths, and C. Robinson An in vitro study of the use of photodynamic therapy for the treatment of natural oral plaque biofilms formed in vivo J. Photochem. Photobiol. B-Biol. 50 1999 1 7 (Pubitemid 29360960)
7. M. Drabkova, B. Marsalek, and W. Admiraal Photodynamic therapy against cyanobacteria Environ. Toxicol. 22 2007 112 115
8. D. Jancula, M. Drabkova, J. Cerny, M. Karaskova, R. Korinkova, J. Rakusan, and B. Marsalek Algicidal activity of phthalocyanines - Screening of 31 compounds Environ. Toxicol. 23 2008 218 223 (Pubitemid 351458211)
9. D. Jancula, B. Marsalek, Z. Novotna, J. Cerny, M. Karaskova, and J. Rakusan In search of the main properties of phthalocyanines participating in toxicity against cyanobacteria Chemosphere 77 2009 1520 1525
10. R. Bonnett, M.A. Krysteva, I.G. Lalov, and S.V. Artarsky Water disinfection using photosensitizers immobilized on chitosan Water Res. 40 2006 1269 1275 (Pubitemid 43374905)
11. N. Masilela, P. Kleyi, Z. Tshentu, G. Priniotakis, P. Westbroek, and T. Nyokong Photodynamic inactivation of Staphylococcus aureus using low symmetrically substituted phthalocyanines supported on a polystyrene polymer fiber Dyes Pigment. 96 2013 500 508
12. J. Mosinger, K. Lang, P. Kubat, J. Sykora, M. Hof, L. Plistil, and B. Mosinger Photofunctional polyurethane nanofabrics doped by zinc tetraphenylporphyrin and zinc phthalocyanine photosensitizers J. Fluoresc. 19 2009 705 713
13. M.J. Allen, S.C. Edberg, and D.J. Reasoner Heterotrophic plate count bacteria - what is their significance in drinking water? Int. J. Food Microbiol. 92 2004 265 274 (Pubitemid 38625562)
14. M. Berney, M. Vital, I. Hulshoff, H.U. Weilenmann, T. Egli, and F. Hammes Rapid, cultivation-independent assessment of microbial viability in drinking water Water Res. 42 2008 4010 4018
15. F. Hammes, M. Berney, Y.Y. Wang, M. Vital, O. Koster, and T. Egli Flow-cytometric total bacterial cell counts as a descriptive microbiological parameter for drinking water treatment processes Water Res. 42 2008 269 277
16. H.M. Shapiro Practical Flow Cytometry fourth ed. 2003 John Wiley & Sons Inc Hoboken, New Jersey
17. D. Marie, F. Partensky, S. Jacquet, and D. Vaulot Enumeration and cell cycle analysis of natural populations of marine picoplankton by flow cytometry using the nucleic acid stain SYBR Green I Appl. Environ. Microbiol. 63 1997 186 193
18. F. Hammes, and T. Egli Cytometric methods for measuring bacteria in water: advantages, pitfalls and applications Anal. Bioanal. Chem. 397 2010 1083 1095
19. F.A. Hammes, and T. Egli New method for assimilable organic carbon determination using flow-cytometric enumeration and a natural microbial consortium as inoculum Environ. Sci. Technol. 39 2005 3289 3294 (Pubitemid 40638270)
20. R.T. Noble, and J.A. Fuhrman Use of SYBR Green I for rapid epifluorescence counts of marine viruses and bacteria Aquat. Microb. Ecol. 14 1998 113 118 (Pubitemid 128474827)
21. G. Nebe-von-Caron, P.J. Stephens, C.J. Hewitt, J.R. Powell, and R.A. Badley Analysis of bacterial function by multi-colour fluorescence flow cytometry and single cell sorting J. Microbiol. Methods 42 2000 97 114
22. S. Barbesti, S. Citterio, M. Labra, M.D. Baroni, M.G. Neri, and S. Sgorbati Two and three-color fluorescence flow cytometric analysis of immunoidentified viable bacteria Cytometry 40 2000 214 218 (Pubitemid 30441524)
23. G. Gregori, S. Citterio, A. Ghiani, M. Labra, S. Sgorbati, S. Brown, and M. Denis Resolution of viable and membrane-compromised bacteria in freshwater and marine waters based on analytical flow cytometry and nucleic acid double staining Appl. Environ. Microbiol. 67 2001 4662 4670 (Pubitemid 33646098)
24. J. Cerny, M. Karaskova, J. Rakusan, and S. Nespurek Reactive oxygen species produced by irradiation of some phthalocyanine derivatives J. Photochem. Photobiol. A-Chem. 210 2010 82 88
25. J. Mosinger, and B. Mosinger Photodynamic sensitizers assay - rapid and sensitive iodometric measurement Experientia 51 1995 106 109
26. A.D. Becke A new mixing of Hartree-Fock and local density-functional theories J. Chem. Phys. 98 1993 1372 1377
27. C.T. Lee, W.T. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density Phys. Rev. B 37 1988 785 789
28. B.H. Besler, K.M. Merz, and P.A. Kollman Atomic charges derived from semiempirical methods J. Comput. Chem. 11 1990 431 439
29. U.C. Singh, and P.A. Kollman An approach to computing electrostatic charges for molecules J. Comput. Chem. 5 1984 129 145
30. A. Minnock, D.I. Vernon, J. Schofield, J. Griffiths, J.H. Parish, and S.B. Brown Photoinactivation of bacteria. Use of a cationic water-soluble zinc phthalocyanine to photoinactivate both gram-negative and gram-positive bacteria J. Photochem. Photobiol. B-Biol. 32 1996 159 164 (Pubitemid 26127372)
31. G. Jori, C. Fabris, M. Soncin, S. Ferro, O. Coppellotti, D. Dei, L. Fantetti, G. Chiti, and G. Roncucci Photodynamic therapy in the treatment of microbial infections: Basic principles and perspective applications Lasers Surg. Med. 38 2006 468 481
32. W.C.M.A. Melo, L.F. Castro, R.M.M.T.S. Dal'Mas, and J.R. Perussi Effectiveness of photodynamic therapy on Gram-negative bacteria A. Mendez-Vilas, Science Against Microbial Pathogens: Communicating Current Research and Technological Advances 2011 Formatex Research Center pp. 662-667
33. J.A. Lacey, and D. Phillips The photosensitisation of Escherichia coli using disulphonated aluminium phthalocyanine J. Photochem. Photobiol. A-Chem. 142 2001 145 150 (Pubitemid 33618456)
34. M. Merchat, J.D. Spikes, G. Bertoloni, and G. Jori Studies on the mechanism of bacteria photosensitization by meso-substituted cationic porphyrins J. Photochem. Photobiol. B-Biol. 35 1996 149 157 (Pubitemid 26383615)
35. M.G. Strakhovskaya, Y.N. Antonenko, A.A. Pashkovskaya, E.A. Kotova, V. Kireev, V.G. Zhukhovitsky, N.A. Kuznetsova, O.A. Yuzhakova, V.M. Negrimovsky, and A.B. Rubin Electrostatic binding of substituted metal phthalocyanines to enterobacterial cells: Its role in photodynamic inactivation Biochem.-Moscow 74 2009 1305 1314
36. A. Minnock, D.I. Vernon, J. Schofield, J. Griffiths, J.H. Parish, and S.B. Brown Mechanism of uptake of a cationic water-soluble pyridinium zinc phthalocyanine across the outer membrane of Escherichia coli Antimicrob. Agents Chemother. 44 2000 522 527 (Pubitemid 30117935)
37. V. Mantareva, V. Kussovski, I. Angelov, D. Woehrle, R. Dimitrov, E. Popova, and S. Dimitrov Non-aggregated Ga(III)-phthalocyanines in the photodynamic inactivation of planktonic and biofilm cultures of pathogenic microorganisms Photochem. Photobiol. Sci. 10 2011 91 102
38. V. Kussovski, V. Mantareva, I. Angelov, P. Orozova, D. Wohrle, G. Schnurpfeil, E. Borisova, and L. Avramov Photodynamic inactivation of Aeromonas hydrophila by cationic phthalocyanines with different hydrophobicity FEMS Microbiol. Lett. 294 2009 133 140
39. Y. Nitzan, and H. Ashkenazi Photoinactivation of Acinetobacter baumannii and Escherichia coli B by a cationic hydrophilic porphyrin at various light wavelengths Curr. Microbiol. 42 2001 408 414 (Pubitemid 32428934)
40. J.B. Pereira, E.F.A. Carvalho, M.A.F. Faustino, R. Fernandes, M.G.M.P.S. Neves, J.A.S. Cavaleiro, N.C.M. Gomes, A. Cunha, A. Almeida, and J.P.C. Tome Phthalocyanine thio-pyridinium derivatives as antibacterial photosensitizers Photochem. Photobiol. 88 2012 537 547
41. T. Maisch, J. Baier, B. Franz, M. Maier, M. Landthaler, R.M. Szeimies, and W. Baumler The role of singlet oxygen and oxygen concentration in photodynamic inactivation of bacteria Proc. Natl. Acad. Sci. USA 104 2007 7223 7228 (Pubitemid 47186036)
42. A. Segalla, C.D. Borsarelli, S.E. Braslavsky, J.D. Spikes, G. Roncucci, D. Dei, G. Chiti, G. Jori, and E. Reddi Photophysical, photochemical and antibacterial photosensitizing properties of a novel octacationic Zn(II)-phthalocyanine Photochem. Photobiol. Sci. 1 2002 641 648 (Pubitemid 37069778)
43. D.A. Makarov, N.A. Kuznetsova, O.A. Yuzhakova, L.P. Savina, O.L. Kaliya, E.A. Lukyanets, V.M. Negrimovsky, and M.G. Strakhovskaya Effects of the degree of substitution on the physicochemical properties and photodynamic activity of zinc and aluminum phthalocyanine polycations Russ. J. Phys. Chem. A 83 2009 1044 1050
44. S. Moeno, and T. Nyokong Solvent and central metal effects on the photophysical and photochemical properties of peripherally tetra mercaptopyridine substituted metallophthalocyanines J. Photochem. Photobiol. A-Chem. 203 2009 204 210
45. T. Nyokong Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines Coord. Chem. Rev. 251 2007 1707 1722
46. D.A. Makarov, O.A. Yuzhakova, L.K. Slivka, N.A. Kuznetsova, V.M. Negrimovsky, O.L. Kaliya, and E.A. Lukyanets Cationic Zn and Al phthalocyanines: synthesis, spectroscopy and photosensitizing properties J. Porphyr. Phthalocyanines 11 2007 586 595
47. J.D. Oliver Recent findings on the viable but nonculturable state in pathogenic bacteria FEMS Microbiol. Rev. 34 2010 415 425
48. SLMB, Method No. 333.1 - determining the total cell count and ratios of high and low nucleic acid content cells in freshwater using flow cytometry, in: the Swiss Food Book (Schweizierische Lebensmittelbuch), Federal Office of Public Health, Switzerland, 2012.
49. F. Hammes, T. Broger, H.U. Weilenmann, M. Vital, J. Helbing, U. Bosshart, P. Huber, R.P. Odermatt, and B. Sonnleitner Development and laboratory-scale testing of a fully automated online flow cytometer for drinking water analysis Cytom. Part A 81A 2012 508 516
50. M. Vital, F. Hammes, and T. Egli Competition of Escherichia coli O157 with a drinking water bacterial community at low nutrient concentrations Water Res. 46 2012 6279 6290