Light induced antimicrobial properties of a brominated boron difluoride (BF2) chelated tetraarylazadipyrromethene photosensitizer

Journal of Medicinal Chemistry

Volumn 53, Issue 20, 2010, Pages 7337-7343

  Frimannsson, Daniel O ^a   Grossi, Marco ^a   Murtagh, Julie ^a   Paradisi, Francesca ^a   Oshea, Donal F ^a  

^a University College Dublin   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; BORON DERIVATIVE; BROMINATED BORON DIFLUORIDE; CHELATING AGENT; PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BORON; COORDINATION COMPOUND; PYRROLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CANDIDA ALBICANS; CELL COUNT; CELL VIABILITY; CONTROLLED STUDY; DRUG EFFICACY; DRUG RESPONSE; ESCHERICHIA COLI; FUNGAL VIRULENCE; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; PHOTODYNAMIC THERAPY; STAPHYLOCOCCUS AUREUS; YEAST; CHEMISTRY; DRUG EFFECTS; HUMAN; LIGHT; PHOTOCHEMOTHERAPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BORON; BORON COMPOUNDS; CANDIDA ALBICANS; CELL LINE, TUMOR; COORDINATION COMPLEXES; ESCHERICHIA COLI; HUMANS; LIGHT; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PYRROLES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77958477243     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100585j     Document Type: Article

References (33)

1. Coates, A.; Hu, Y.; Bax, R.; Page, C. The future challenges facing the development of new antimicrobial drugs Nat. Rev. Drug Discovery 2002, 1, 895-910
2. Mulvey, M. R.; Simor, A. E. Antimicrobial resistance in hospitals: how concerned should we be? Can. Med. Assoc. J. 2009, 180, 408-415
3. Wainwright, M. Photodynamic antimicrobial chemotherapy (PACT) J. Antimicrob. Chemother. 1998, 42, 13-28
4. Maisch, T. Antimicrobial photodynamic therapy: useful in the future? Lasers Med. Sci. 2007, 22, 83-91
5. Bertolini, G.; Rossi, F.; Valduga, G.; Jori, G.; Lier, J. Photosensitizing activity of water- and lipid-soluble phthalocyanines on Escherichia coli FEMS Microbiol. Lett. 1990, 71, 149-155
6. Nitzan, Y.; Gutterman, M.; Malik, Z.; Ehrenberg, B. Inactivation of Gram-negative bacteria by photosensitized porphyrins Photochem. Photobiol. 1992, 55, 89-96
7. Merchat, M.; Bertolini, G.; Giacomini, P.; Villanueva, A.; Jori, G. Meso-substituted cationic porphyrins as efficient photosensitizers of Gram-positive and Gram-negative bacteria J. Photochem. Photobiol., B 1996, 32, 153-157 (Pubitemid 26127371)
8. Maisch, T. A new strategy to destroy antibiotic resistant microorganisms: antimicrobial photodynamic therapy Mini-Rev. Med. Chem. 2009, 9, 974-983
9. Hamblin, M. R.; ODonnell, D. A.; Murthy, N.; Contag, C. H.; Hasan, T. Rapid control of wound infections by targeted photodynamic therapy monitored by in vivo bioluminescence imaging Photochem. Photobiol. 2002, 75, 51-57
10. Hamblin, M. R.; Zahra, T.; Contag, C. H.; McManus, A. T.; Hasan, T. Optical monitoring and treatment of potentially lethal wound infections in vivo J. Infect. Dis. 2003, 187, 1717-1725
11. Tegos, G. P.; Anbe, M.; Yang, C.; Demidova, T. N.; Satti, M.; Mroz, P.; Janjua, S.; Gad, F.; Hamblin, M. R. Protease-stable polycationic photosensitizer conjugates between polyethyleneimine and chlorin(e6) for broad-spectrum antimicrobial photoinactivation Antimicrob. Agents Chemother. 2006, 50, 1402-1410
12. Dai, T.; Tegos, G. P.; Zhiyentayev, T.; Mylonakis, E.; Hamblin, M. R. Photodynamic therapy for methicillin-resistant Staphylococcus aureus infection in a mouse skin abrasion model Lasers Surg. Med. 2010, 42, 38-44
13. Dosselli, R.; Gobbo, M.; Bolognini, E.; Campestrini, S.; Reddi, E. Porphyrin-apidaecin conjugate as a new broad spectrum antibacterial agent ACS Med. Chem. Lett. 2010, 1, 35-38
14. Maisch, T.; Bosl, C.; Szeimies, R.-M.; Lehn, N.; Abels, C. Photodynamic effects of novel XF porphyrin derivatives on prokaryotic and eukaryotic cells Antimicrob. Agents Chemother. 2005, 49, 1542-1552
15. Mohr, H.; Lambrecht, B.; Selz, A. Photodynamic virus inactivation of blood components Immunol. Invest. 1995, 24, 73-85
16. Wainwright, M.; Mohr, H.; Walker, W. H. Phenothiazinium derivatives for pathogen inactivation in blood products J. Photochem. Photobiol., B 2007, 86, 45-58
17. Zolfaghari, P. S.; Packer, S.; Singer, M.; Nair, S. P.; Bennett, J.; Street, C.; Wilson, M. In vivo killing of Staphylococcus aureus using a light-activated antimicrobial agent BMC Microbiol. 2009, 9, 27
18. Teichert, M. C.; Jones, J. W.; Usacheva, M. N.; Biel, M. A. Treatment of oral candidiasis with methylene blue-mediated photodynamic therapy in an immunodeficient murine model Oral Surg., Oral Med., Oral Pathol. Oral Radiol., Endodontol. 2002, 93, 155-160
19. Wilson, M. Lethal photosensitisation of oral bacteria and its potential application in the photodynamic therapy of oral infections Photochem. Photobiol. Sci. 2004, 3, 412-418
20. Wilson, M.; Dobson, J.; Harvey, W. Sensitization of oral bacteria to killing by low-power laser radiation Curr. Microbiol. 1992, 25, 77-81
21. Wong, T. W.; Wang, Y. Y.; Sheu, H. M.; Chuang, Y. C. Bactericidal effects of toluidine blue-mediated photodynamic action on Vibrio vulnificus Antimicrob. Agents Chemother. 2005, 49, 895-902
22. http://clinicaltrials.gov/ct2/show/study/NCT00825760.
23. Foley, J. W.; Song, X.; Demidova, T. N.; Jalil, F.; Hamblin, M. R. Synthesis and properties of benzo[ a ]phenoxazinium chalcogen analogues as novel broad-spectrum antimicrobial photosensitizers J. Med. Chem. 2006, 49, 5291-5299
24. Akilov, O. E.; Kosaka, S.; ORiordan, K.; Song, X.; Sherwood, M.; Flotte, T. J.; Foley, J. W.; Hasan, T. The role of photosensitizer molecular charge and structure on the efficacy of photodynamic therapy against Leishmania parasites Chem. Biol. 2006, 13, 839-847
25. Gorman, A.; Killoran, J.; OShea, C.; Kenna, T.; Gallagher, W. M.; OShea, D. F. In vitro demonstration of the heavy-atom effect for photodynamic therapy J. Am. Chem. Soc. 2004, 126, 10619-10631
26. Gallagher, W. M.; Allen, L. T.; OShea, C.; Kenna, T.; Hall, M.; Gorman, A.; Killoran, J.; OShea, D. F. A potent nonporphyrin class of photodynamic therapeutic agent: cellular localisation, cytotoxic potential and influence of hypoxia Br. J. Cancer 2005, 92, 1702-1710
27. 2-chelated tetraaryl-azadipyrromethene agents Br. J. Cancer 2009, 101, 1565-1573
28. McDonnell, S. O.; Hall, M. J.; Allen, L. T.; Byrne, A.; Gallagher, W. M.; OShea, D. F. Supramolecular photonic therapeutic agents J. Am. Chem. Soc. 2005, 127, 16360-16361
29. 2-chelated tetraarylazadipyrromethenes Org. Biomol. Chem. 2010, 8, 522-525
30. Wainright, M. Methylene blue derivatives - suitable photoantimicrobials for blood product disinfection Int. J. Antimicrob. Agents 2000, 16, 381-394
31. Kawai, M.; Yamada, S.; Ishidoshiro, A.; Oyamada, Y.; Ito, H.; Yamagisgi, J. Cell-wall thickness: possible mechanism of acriflavine resistance in meticillin-resistant Staphylococcus aureus J. Med. Microbiol. 2009, 58, 331-336
32. Zeina, B.; Greenman, J.; Purcell, W. M.; Das, B. Killing of cutaneous microbial species by photodynamic therapy Br. J. Dermatol. 2001, 144, 274-278
33. Jett, B. D.; Hatter, K. L.; Huycke, M. M.; Gilmore, M. S. Simplified agar plate method for quantifying viable bacteria BioTechniques 1997, 23, 648-650