Natural product photoantimicrobials

Current Bioactive Compounds

Volumn 3, Issue 4, 2007, Pages 252-261

  Wainwright, Mark ^a  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

Anthraquinone; Antimicrobial; Furocoumarin; Isoquinoline; Perylenequinonoid; Photosensitiser; Porphyrin; Singlet oxygen

Indexed keywords

ALOE EMODIN; AMINOLEVULINIC ACID; AMOTOSALEN; ANGELICIN; ANTHRAQUINONE DERIVATIVE; ANTIINFECTIVE AGENT; BENZOPORPHYRIN DERIVATIVE; BERBERINE; DAMNACANTHAL; DNA; EMODIN; FUROCOUMARIN; HYPERICIN; HYPOCRELLIN B; ISOQUINOLINE ALKALOID; LIPOSOME; METHOXSALEN; NATURAL PRODUCT; PERYLENEQUINONE DERIVATIVE; PHOTOFRIN; PHOTOSENSITIZING AGENT; PORPHYRIN; PROTOPORPHYRIN; PSORALEN DERIVATIVE; QUINONE DERIVATIVE; RIBOFLAVIN; SANGUINARINE; SINGLET OXYGEN; TRIOXYSALEN; UNINDEXED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; BACTERIAL INFECTION; CLINICAL TRIAL; DRUG DESIGN; DRUG DNA BINDING; DRUG EFFICACY; DRUG FORMULATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; LYMPHOMA; MYCOSIS; NONHUMAN; PHOTODYNAMIC THERAPY; PRIORITY JOURNAL; PSORIASIS; PUVA; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 37549038161     PISSN: 15734072     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340707783220202     Document Type: Review

References (65)

1. Arnason, J.T., Guerin, B., Kraml, M.M., Mehta, B., Redmond, R.W., Scaiano, J.C. (1992) Phototoxic and photochemical properties of sanguinarine. Photochem. Photobiol., 55, 35-38.
2. Bai, L.P., Zhao, Z.Z., Cai, Z., Jiang, Z.H. (2006) DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine. Bioorg. Med. Chem., 14, 5439-5445.
3. Banfi, S., Caruso, E., Buccafurni, L., Battini, V., Zazzaron, S., Barbieri, P., Orlandi, V. (2006) Antibacterial activity of tetraaryl-porphyrin photosensitizers: An in vitro study on Gram negative and Gram positive bacteria. J. Photochem. Photobiol. B: Biol., 85, 28-382.
4. Bertoloni, G., Sacchetto, R., Jori, G., Vernon, D.I., Brown, S.B. (1993) Protoporphyrin photosensitization of Enterococcus hirae and Candida albicans cells. Lasers Life Sci., 5, 267-275.
5. Bintsis, T., Litopoulou-Tzanetaki, E., Davies, R., Robinson, R.K. (2000) The antimicrobial effects of long-wave ultra-violet light and furocoumarins on some micro-organisms that occur in cheese brines. Food Microbiol., 17, 687-695.
6. Calzavara-Pinton, P.G., Venturini, M., Capezzera, R., Sala, R., Zane, C. (2004) Photodynamic therapy of interdigital mycoses of the feet with topical application of 5-aminolevulinic acid. Photodermatol. Photoimmunol. Photomed., 20 (2004), pp. 144-147.
7. Carré, V, Gaud, O., Sylvain,I., Bourdon, O., Spiro, M., Blais, J., Granet, R., Krausz, P., Guilloton, M. (1999) Fungicidal properties of meso-arylglycosylporphyrins: influence of sugar substituents on photoinduced damage in the yeast Saccharomyces cerevisiae. J. Photochem. Photobiol. B. Biol., 48, 57-62.
8. Chukwujekwu, J.C., Coombes, P.H., Mulholland, D.A., van Staden, J. (2006) Emodin, an antibacterial anthraquinone from the roots of Cassia occidentalis. South African J. Bot., 72, 295-297.
9. Cimino, G.D., Gamper, H.B., Isaacs, S.T., Hearst, J.E. (1985) Psoralens as photoactive probes of nucleic acid structure and function: organic chemistry, photochemistry, and biochemistry. Ann. Rev. Biochem., 54, 1151-1193.
10. Corash, L. (2000) Inactivation of viruses, bacteria, protozoa and leukocytes in platelet and red cell concentrates. Vox Sang., 78, 205-210.
11. Crnolatac, I., Huygens, A., van Aerschot, A., Busson, R., Rozenski, J., de Witte, P.A.M. (2005) Synthesis, in vitro cellular uptake and pboto-induced antiproliferative effects of lipophilic hypericin acid derivatives. Bioorg. Med. Chem., 13, 6347-6353.
12. Cushman, M., Mohan, P., Smith, E.C.R. (1984) Synthesis and biological activity of structural analogues of the anticancer benzophenanthridine alkaloid nitidine chloride. J. Med. Chem., 27, 544-547.
13. Dai, R., Yamazaki, T., Yamazaki, I., Song, P.S. (1995) Initial spectroscopic characterization of the ciliate photoreceptor stentorian. Biochim. Biophys. Acta - Bioenerg., 1231, 58-68.
14. Dardare, N., Platz, M.S. (2002) Binding affinities of commonly employed sanitizers of viral inactivation. Photochem. Photobiol., 75, 561-564.
15. Dietel, W., Pottier, R., Pfister, W., Schleier, P., Zinner, K. (2006) 5-Aminolaevulinic acid (ALA) induced formation of different fluorescent porphyrins: a study of the biosynthesis of porphyrnis by bacteria of the human digestive tract. J. Photochem. Photobiol. B. Biol., 86, 77-86.
16. Dinkins, M.B., Stallknecht, D.E., Howerth, E.W., Brackett, B.G. (2001) Photosensitive chemical and laser light treatments decrease epizootic hemorrhagic disease virus associated with in vitro produced bovine embryos. Theriogenol., 55, 1639-1655.
17. Diwu, Z., Lown, J.W. (1993) Photosensitization with anticancer agents 17. EPR studies of photodynamic action of hypericin: Formation of semiquinone radical and activated oxygen species on illumination. Free Radio. Biol. Med., 14, 209-215.
18. Diwu, Z., Lown, J.W. (1994) Phototherapeutic potential of alternative photosensitizers to porphyrins. Pharmacol. Ther., 63, 1-35.
19. Diwu, Z., Zimmermann, J., Meyer, T., Lown, J.W. (1994) Design, synthesis and investigation of mechanisms of action of novel protein kinase C inhibitors: perylenequinonoid pigments. Biochem. Pharmacol., 47, 373-385.
20. Ferro, S., Ricchelli, F., Mancini, G., Tognon, G., Jori, G. (2006) Inactivation of methicillin-resistant Staphylococcus aureus (MRSA) by liposome-delivered photosensitising agents. J. Photochem. Photobiol. B: Biol., 83, 98-104.
21. Giuliana, G., Pizzo, G., Milici, M.E., Giangreco, R. (1999) In vitro activities of antimicrobial agents against Candida species. Oral Surg. Oral Med. Oral Pathol. Oral Radiol. Endodontol., 87, 4449.
22. TM PRT system for pathogen reduction of platelets and plasma: An overview of current status and future trends. Transfus. Apher. Sci., 35, 5-17.
23. Grenby, T.H. (1995) The use of sanguinarine in mouthwashes and toothpaste compared with some other antimicrobial agents. Br. Dent. J., 178, 254-258.
24. Guedes, R.C., Eriksson, L.A. (2006) Effects of halogen substitution on the photochemical properties of hypericin. J. Photochem. Photobiol. A: Chem., 178, 41-49.
25. Hardwick, C.C., Herivel, T.R., Hernandez, S.C., Ruane, P.H., Goodrich, R.P. (2004) Separation, identification and quantification of riboflavin and its photoproducts in blood products using HLPC with fluorescence detection: a method to support pathogen-reduction technology. Photochem. Photobiol., 80, 609-615.
26. Hatano, T., Kusuda, M., Inada, K., Ogawa, T., Shiota, S., Tsuchiya, T., Yoshida, T. (2005) Effects of tannins and related polyphenols on methicillin-resistant Staphylococcus aureus. Phytochemistry, 66, 2047-2055.
27. Hudson, J.B., Harris, L., Towers, G.H.N. (1993) The importance of light in the anti-HIV effect of hypericin. Antiviral Res., 20, 173-178.
28. Hudson, J.B., Lopez-Bazzocchi, I., Towers, G.H.N. (1991) Antiviral activities of hypericin. Antiviral Res., 15, 101-112.
29. Ito, T. (1981) Photodynamic action of haematorphyrin on yeast cell: a kinetic approach. Photochem. Photobiol., 34, 521-524.
30. Iwasa, K., Kim, H.S., Wataya, Y., Lee, D.U. (1998) Antimalarial activity and structure-activity relationships of protoberberine alkaloids. Eur. J. Med. Chem., 33, 65-69.
31. Jones, S.G., Young, A.R., Truscott, T.G. (1993) Singlet oxygen yields of furocoumarins and related molecules - the effect of excitation wavelength. J. Photochem. Photobiol. B. Biol., 21, 223-227.
32. Kuete, V., Nguemeving, J.R., Beng, V.P., Azebaze, A.G.P., Etoa, F.X., Meyer, M., Bodo, B., Nkengfack, A.E. (2007) Antimicrobial activity of the methanolic extracts and compounds from Vismia laurentii De Wild (Guttiferae). J. Ethnopharmacol., 109, 372-379.
33. Lee, C.F., Lee, C.J., Chen, C.T., Huang, C.T. (2004) δ-Aminolaevulinic acid mediated photodynamic antimicrobial chcmotherapy on Pseudomonas aeruginosa planktonic and biofilm cultures. J. Photochem. Photobiol. B: Biol., 75, 21-25.
34. Lee, H.Y., Zhou, Z.X., Chen, S., Zhang, M.H., Shen, T. (2006) New long-wavelength ethanolamino-substituted hypocrellin: photodynamic activity and toxicity to MGC803 cancer cell. Dyes Pigments, 68, 1-10.
35. Liang, M., Zhang, W., Hu, J., Liu, R., Zhang, C. (2006) Simultaneous analysis of alkaloids from Zanthoxylum nitidum by high performance liquid chromatography-diode array detector-electrospray tandem mass spectrometry. J. Pharm. Biomed. Anal., 42, 178-183.
36. Maiti, M., Chaterjee, A. (1995) Production of singlet oxygen by sanguinarine and berberine. Curr. Sci., 68, 734-736.
37. Marrot, L., Labarussiat, A., Perez, P., Meunier, J.R. (2006) Use of the yeast Saccharomyces cerevisiae as a pre-screening approach for assessment of chemical-induced phototoxicity. Toxicol. In Vitro, 20, 1040-1050.
38. Miolo, G., Tomanin, R., De Rossi, A., Dall'Acqua, F., Zacchello, F., Scarpa, M. (1994) Antiretroviral activity of furocoumarins plus UVA light detected by a replication-defective retrovirus. J. Photochem. Photobiol. B. Biol., 26, 241-247.
39. Miyake, A., Harumoto, T., Iio, H. (2001) Defence function of pigment granules in Stentor coeruleus. Eur. J. Protistol., 37, 77-88.
40. Newton, S.M., Lau, C., Gurcha, S.S., Besra, G.S., Wright, C.W. (2002) The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria Canadensis. J. Ethnopharmacol., 79, 57-67.
41. North, J., Coombs, R., Levy, J. (1994) Photodynamic inactivation of free and cell-associated HIV-1 using the photosensitizer, benzoporphyrin derivative. J. Acq. Immun. Defic. Synd., 7, 891-898.
42. Nunez Montoya, S.C., Comini, L.R., Sarmiento, M., Becerra, C., Albesa, I., Arguello, G.A., Cabrera, J.L. (2005) Natural anthraquinones probed as Type I and Type II photosensitizers: singlet oxygen and superoxide anion production. J. Photochem. Photobiol. B: Biol., 78:77-83.
43. O'Neill, J., Wilson, M., Wainwright, M. (2003) Comparative antistreptococcal activity of a range of photobactericidal agents. J. Chemother., 15, 329-334.
44. O'Riordan, K., Sharlin, D.S., Gross, J., Chang, S., Errabelli, D., Akilov, O.E., Kosaka, S., Nau, G.J., Hasan, T. (2006) Photoinactivation of mycobacteria in vitro and in a new murine model of localized Mycobacterium bovis BCG-induced granulomatous infection. Antimicrob. Chemother., 50, 1828-1834.
45. Pant, B., Kato, Y., Kumagai, T., Matsuoka, T., Sugiyama, M. (1997) Blepharismin produced by a protozoan Blepharisma functions as an antibiotic effective against methicillin-resistant Staphylococcus aureus. FEMS Microbiol. Lett., 155, 67-71.
46. Pelletier, J.P.R., Transue, S., Snyder, E.L. (2006) Pathogen inactivation techniques. Best Prac. Res. Clin. Haematol., 19, 205-242.
47. Policard, A. (1924) Etude sur les aspects offers par des tumeurs experimentales examinees a la lumicre de Wood. C.R. Soc. Biol., 91, 1423-1424.
48. Rajendran, M., Inbaraj, J., Gandhidasan, R., Murugesan, R. (2004) Photodynamic action of damnacanthal and nordamnacanthal J. Photochem. Photobiol. A. Chem., 162, 615-623.
49. Sardari, S., Mori, Y., Horita, K., Micetich, R.G., Nishibe, S., Daneshtalab, M. (1999) Synthesis and antifungal activity of coumarins and angular furanocoumarins. Bioorg. Med. Chem. 7, 1933-1940.
50. Schinazi, R.F., Chu, C.K., Babu, J.R., Oswald, B.J., Saalmann, V., Cannon, D.L., Eriksson, B.F.H., Nasr, M. (1990) Anthraquinones as a new class of antiviral agents against human immunodeficiency virus. Antiviral Res., 13, 265-272.
51. Schmeller, T., Latz-Brüning, B., Wink, M. (1997) Biochemical activities of berberine, palmatine and sanguinarine mediating chemical defence against microorganisms and herbivores. Phytochem., 44, 257-266.
52. Seghatchian, J., de Sousa, G. (2006) Pathogen-reduction systems for blood components: The current position and future trends. Transfus. Apher. Sci., 35, 189-196.
53. Shen, L., Ji, H.F., Zhang, H.Y. (2006) Anion of hypericin is crucial to understanding the photosensitive features of the pigment. Bioorg. Med. Chem. Lett., 16, 1414-1417.
54. Singh, D.N., Verma, N., Raghuwanshi, S., Shukla, P.K., Kulshreshtha, D.K. (2006) Antifungal anthraquinones from Saprosma fragrans. Bioorg. Med. Chem. Lett., 16, 4512-4514.
55. Solheim, B.G., Seghatchian, J. (2006) Update on pathogen reduction technology for therapeutic plasma: An overview. Transfus. Apher. Sci., 35, 83-90.
56. Spitzner, D., Höfle, G., Klein, I., Pohlan, S., Ammermann, D., Jaenicke, L. (1998) On the structure of oxyblepharismin and its formation from blepharismin. Tetrahedron Lett., 39, 4003-4006.
57. Szocs, K., Gabor, F., Csik, G., Fidy, J. (1999) δ-Aminolaevulinic acid-induced porphyrin synthesis and photodynamic inactivation of Escherichia coli. J. Photochem. Photobiol. B. Biol., 50, 8-17.
58. Ulatowska-Jarza, A., Zychowicz, J., Hołowacz, I., Bauer, J., Razik, J., Wieliczko, A., Podbielska, H., Müller, G., Strek, W., Bindig, U. (2006) Antimicrobial PDT with chlorophyll-derived photosensitizer and semiconductor laser. Med. Laser App., 21, 177-183.
59. van der Meulen, F.W., Ibrahim, K., Sterenborg, H.J.C.M., Alphen, L.V., Maikoe, A., Dankert, J. (1997) Photodynamic destruction of Haemophilus parainfluenzae by endogenously produced porphyrin. J. Photochem. Photobiol. B: Biol., 40, 204-208.
60. Wainwright, M. (2001) Acridine - a forgotten antimicrobial chromophore. J. Antimicrob. Chemother., 47, 1-13.
61. Wainwright, M. (2004) Photoantimicrobials - a PACT against resistance and infection. Drugs Future, 29, 85-93.
62. Yon-Min, P., Wijesekera, T.P., Dolphin, D. (1991) A convenient synthetic route to the bacteriochlorin chromophore. Tetrahedron Lett., 32, 2875-2878.
63. Zhao, Y., Xie, J., Zhao, J. (2005) The photosensitization activity of a water-soluble carboxylate of hypocrellin B. Dyes Pigments, 66, 61-68.
64. Zhao, Y., Zhao, J. (2004) Preparation of a novel hypocrellin derivative and its photochemical, photophysical properties. Dyes Pigments, 63, 175-179.
65. Zoladek, T., Nguyen, B.N., Jagiello, I., Graczyk, A., Rytka, J. (1997) Diamino acid derivatives of porphyrins penetrate into yeast cells, induce photodamage, but have no mutagenic effect. Photochem. Photobiol., 66, 253-259.