Synthesis and properties of benzo[a]phenoxazinium chalcogen analogues as novel broad-spectrum antimicrobial photosensitizers

Journal of Medicinal Chemistry

Volumn 49, Issue 17, 2006, Pages 5291-5299

  Foley, James W ^a   Song, Xiangzhi ^a   Demidova, Tatiana N ^b,c   Jilal, Fatima ^b,d   Hamblin, Michael R ^b,e,f  

^a HARVARD UNIVERSITY   (United States)

^b MASSACHUSETTS GENERAL HOSPITAL   (United States)

^c TUFTS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d AGA KHAN UNIVERSITY HOSPITAL   (Pakistan)

^e HARVARD MEDICAL SCHOOL   (United States)

^f HARVARD MIT DIVISION OF HEALTH SCIENCES AND TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (ETHYLAMINO) 9 DIETHYLAMINOBENZO[A]PHENOXAZINIUM; BENZO[A]PHENOXAZINIUM CHALCOGEN DERIVATIVE; CHALCOGEN; DYE; OXYGEN; PHENOXAZINE DERIVATIVE; PHOTOSENSITIZING AGENT; SELENAZINIUM DERIVATIVE; SELENIUM; SULFUR; THIAZINE DERIVATIVE; THIAZINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CELL KILLING; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; FUNGUS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; INFECTION; LIGHT ABSORPTION; LIPOPHILICITY; NONHUMAN; PHOTODYNAMIC THERAPY; PHOTOSENSITIVITY; QUANTUM YIELD; RED LIGHT; SOLUBILITY;

ANTI-INFECTIVE AGENTS; BINDING SITES; CANDIDA ALBICANS; CELL PROLIFERATION; CHALCOGENS; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; OXAZINES; PHOTOSENSITIZING AGENTS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33747502536     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060153i     Document Type: Article

References (49)

1. Dougherty, T. J. Photosensitizers: Therapy and Detection of Malignant-Tumors. Photochem. Photobiol 1987, 45, 879-889.
2. Castano, A. P.; Demidova, T. N.; Hamblin, M. R. Mechanisms in photodynamic therapy: part one-photosensitizers, photochemistry and cellular localization. Photodiagnosis Photodyn. Ther. 2004, 1, 279-293.
3. Castano, A. P.; Demidova, T. N.; Hamblin, M. R. Mechanisms in photodynamic therapy: part two-cellular signaling, cell metabolism and modes of cell death. Photodiagnosis Photodyn. Ther. 2005, 2, 1-23.
4. Castano, A. P.; Demidova, T. N.; Hamblin, M. R. Mechanisms in photodynamic therapy: part three:- photosensitizer pharmpocokinetics, biodistribution, tumor localization and modes of tumor destruction. Photodiagnosis Photodyn. Ther. 2005, 2, 91-106.
5. Detty, M. R.; Gibson, S. L.; Wagner, S. J. Current clinical and preclinical photosensitizers for use in photodynamic therapy. J. Med. Chem. 2004, 47, 3897-3915.
6. Michl, J.; Bonacic-Koutecky, V. Electronic Aspects of Organic Photochemistry, 1st ed.; John Wiley & Sons: New York, 1990.
7. Moan, J.; Peng, Q. An outline of the hundred-year history of PDT. Anticancer Res. 2003, 23, 3591-3600.
8. Dolmans, D.; Fukumura, D.; Jain, R. K. Photodynamic therapy for cancer. Nat. Rev. Cancer 2003, 3, 380-387.
9. Lin, C.-W. Photodynamic therapy of malignant tumors: recent developments. Cancer Cells (Cold Spring Harbor) 1992, 3, 437-444.
10. Henderson, B. W.; Dougherty, T. J. How does photodynamic therapy work? Photochem. Photobiol. 1992, 55, 145-157.
11. Lin, C. W.; Shulok, J. R.; Wong, Y. K.; Schanbacher, C. F.; Cincotta, L.; Foley, J. W. Photosensitization, uptake, and retention of phenoxazine nile blue derivatives in human bladder-carcinoma cells. Cancer Res. 1991, 51, 1109-1116.
12. Cincotta, L.; Foley, J. W.; Cincotta, A. H. Novel red absorbing benzo[a]phenoxazinium and benzo[a]phenothiazinium photosensitizers: In vitro evaluation. Photochem. Photobiol. 1987, 46, 751-758.
13. Lewis, M. R.; Sloviter, H. A.; Goland, P. P. In vivo staining and retardation of growth of sarcomata in mice. Anat. Rec. 1946, 95, 89-96.
14. Lewis, M. R.; Goland, P. P.; Sloviter, H. A. The Action of Oxazine Dyes on Tumors in Mice. Cancer Res. 1949, 9, 736-740.
15. Cincotta, A. H.; Cincotta, L.; Foley, J. W. Novel benzophenothiazinium photosensitizers: preliminary in vivo results. SPIE 1990, 1203, 202-210.
16. Cincotta, L.; Foley, J. W.; Maceachern, T.; Lampros, E.; Cincotta, A. H. Novel photodynamic effects of a benzophenothiazine on 2 different murine sarcomas. Cancer Res. 1994, 54, 1249-1258.
17. Frimberger, A. E.; Moore, A. S.; Cincotta, L.; Cotter, S. M.; Foley, J. W. Photodynamic therapy of naturally occurring tumors in animals using a novel benzophenothiazine photosensitizer. Clin. Cancer Res. 1998, 4, 2207-2218.
18. Cincotta, L.; Foley, J. W.; Cincotta, A. H. Phototoxicity, redox behavior, and pharmacokinetics of benzophenoxazine analogs in Emt-6 murine sarcoma-cells. Cancer Res. 1993, 53, 2571-2580.
19. Hamblin, M. R.; Hasan, T. Photodynamic therapy: A new antimicrobial approach to infectious disease? Photochem. Photobiol. Sci. 2004, 3, 436-450.
20. Malik, Z.; Ladan, H.; Nitzan, Y. Photodynamic inactivation of Gram-negative bacteria: Problems and possible solutions. J. Photochem. Photobiol., B 1992, 14, 262-266.
21. Nitzan, Y.; Gutterman, M.; Malik, Z.; Ehrenberg, B. Inactivation of Gram-negative bacteria by photosensitized porphyrins. Photochem. Photobiol. 1992, 55, 89-96.
22. Demidova, T. N.; Hamblin, M. R. Effect of cell-photo sensitize: binding and cell density on microbial photoinactivation. Antimicrob. Agents Chemother. 2005, 49, 2329-2335.
23. 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.
24. Voet, D.; Voet, J. G. Biochemistry, 1st ed.; John Wiley & Sons: New York, 1990.
25. Hamouda, T.; Shih, A. Y.; Baker, J. R. A rapid staining technique for the detection of the initiation of germination of bacterial spores. Lett. Appl. Microbiol 2002, 34, 86-90.
26. Phoenix, D. A.; Harris, F. Phenothiazinium-based photosensitizers: antibacterials of the future? Trends Mol. Med. 2003, 9, 283-285.
27. http://www.ondinebiopharma.com/periodontal_disease_therapy.php. 2005.
28. http://www.denfotex.com/.2005.
29. Foley, J. W.; Cincotta, L. Photo-inactivation of Cancer Cells. U.S. Patent 4,962,197, 1990.
30. Nikas, D. C.; Foley, J. W.; Black, P. M. Fluorescent imaging in a glioma model in vivo. Lasers Surg. Med. 2001, 29, 11-17.
31. Clapp, R. C.; English, J. P.; Fellows, C. E.; Forsythe, J.; Grotz, R. E.; Shepherd, R. G. Chemotherapeutic dyes. 5. Benzo[a]phenothiazines and benzo[a]phenazines. J. Am. Chem. Soc. 1952, 74, 1994-1996.
32. Magde, D.; Brannon, J. H.; Cremers, T. L.; Olmsted, J. Absolute luminescence yield of cresyl violet: Standard for the red. J. Phys. Chem. 1979, 83, 696-699.
33. Tanielian, C.; Wolff, C.; Esch, M. Singlet oxygen production in water: Aggregation and charge-transfer effects. J. Phys. Chem. 1996, 100, 6555-6560.
34. Gregory, P.; Thorp, D. Electronic absorption-spectra of 2-substituted-4-Nn-diethylamino-4′-nitroazobenzene dyes and their monoacid cations: Applicability of Dewar rules to these and related dyestuffs. J. Chem. Soc., Perkin Trans. 1 1979, 8, 1990-2000.
35. Griffiths, J. Colour and Constitution of Organic Molecules, 1st ed.; Academic Press: New York, 1976; p 264.
36. 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.
37. Groves, J. T.; Lindenau, S. M.; Haywood, B. J.; Knol, J. A.; Schultz, J. S. Synthesis of seleno-toluidine blue. J. Med. Chem. 1974, 17, 902-904.
38. Detty, M. R.; Merkel, P. B. Chalcogenapyrylium dyes as potential photochemotherapeutic agents: Solution studies of heavy-atom effects on triplet yields, quantum efficiencies of singlet oxygen generation, rates of reaction with singlet oxygen, and emission quantum yields. J. Am. Chem. Soc. 1990, 112, 3845-3855.
39. Bergmann, K.; O'Konski, C. T. A spectroscopic study of methylene blue monomer, dimer, and complexes with monillonite. J. Phys. Chem. 1963, 67, 2169-2175.
40. Henderson, B. W.; Miller, A. C. Effects of scavengers of reactive oxygen and radical species on cell-survival following photodynamic treatment in vitro: Comparison to ionizing-radiation. Radiat. Res. 1986, 108, 196-205.
41. Hamanoue, K.; Nakayama, T.; Tsujimoto, I.; Miki, S.; Ushida, K. Further studies on the nature of the lowest excited triplet states of haloanthraquinones: triplet-triplet absorption and phosphorescence spectra of the α-halo(1-bromo,1-bromo-5-chloro,1,5-dibromo,1-bromo-8-chloro, 1,8-dibromo) and β-halo(2-bromo) compounds. J. Phys. Chem. 1995, 99, 5802-5808.
42. Atkins, P. W. Quanta, A Handbook of Concepts, 2nd ed.; Oxford University Press: Oxford, England, 1991; p 339.
43. Lien, E. J.; Hansch, C.; Anderson, S. M. Structure-activity correlations for antibacterial agents on gram-positive and gram-negative cells. J. Med. Chem. 1968, 11, 430-441.
44. Cincotta, L.; Foley, J. W.; Cincotta, A. H. Novel phenothiazinuium photosensitizers for photodynamic therapy. SPIE 1988, 997, 145-153.
45. Broder, K. W.; Moise, P. A.; Schultz, R. O.; Forrest, A.; Schentag, J. J. Clinical experience with linezolid in conjunction with wound coverage techniques for skin and soft-tissue infections and postoperative osteomyelitis. Ann. Plastic Surgery 2004, 52, 385-390.
46. Russo, T. A.; Johnson, J. R. Medical and economic impact of extraintestinal infections due to Escherichia coli: Focus on an increasingly important endemic problem. Microbes Infect. 2003, 5, 449-456.
47. Shinagawa, N.; Hirata, K.; Katsuramaki, T.; Hata, F.; Ushijima, Y.; Ushida, T.; Tanimura, H.; Taniguchi, K.; Aikawa, N.; Yo, K.; Yamaue, H.; Ohnishi, H.; Takayama, T.; Sato, T.; Kato, K.; Tanaka, N.; Iwagaki, H.; Yura, J.; Fuchimoto, S.; Manabe, T.; Takeyama, H.; Kimura, H.; Hasegawa, M.; Takeuchi, H.; Yasui, Y.; Taniguchi, M.; Sueda, T.; Takesue, Y.; Mashita, K.; Hiyama, E.; Ishikawa, S.; Yokoyama, T.; Mizuno, A.; Ikeda, S.; Yasunami, Y.; Kubo, S.; Takada, N.; Suzuki, Y.; Fujimoto, M. Bacteria isolated from surgical infections and its susceptibilities to antimicrobial agents-special references to bacteria isolated between April 2003 and March 2004. Jpn. J. Antibiot. 2005, 58, 123-158.
48. Still, J. M.; Law, E. J.; Belcher, K. E.; Spencer, S. A. A Comparison of susceptibility to 5 antifungal agents of yeast cultures from burn patients. Burns 1995, 21, 167-170.
49. Chen, Y. C.; Chang, S. C.; Sun, C. C.; Yang, L. S.; Hsieh, W. C.; Luh, K. T. Secular trends in the epidemiology of nosocomial fungal infections at a teaching hospital in Taiwan, 1981 to 1993. Infection Control and Hospital Epidemiology 1997, 18, 369-375.