Meso-substituted cationic porphyrins as efficient photosensitizers of gram-positive and gram-negative bacteria

Merchat, Michèle; G, Bertolini; Giacomini, P; Villanueva, Ángeles; Jori, Giulio

doi:10.1016/1011-1344(95)07147-4

Cited by 372 publications

(280 citation statements)

References 7 publications

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“…These findings agree with numerous reports in the literature that demonstrate that PS with one (or preferably more cationic groups) are efficient antimicrobial PS. [62][63][64][65][66] Quaternary nitrogen based groups are superior to primary, secondary or tertiary amino groups as the positive charge is less dependent on the pH of the surrounding media, or the pK a of the molecules that the PS is interacting with. Microbial cells possess overall negative charges and it is thought that cationic PS bind to these groups on the outer layers of the cell surface.…”

Section: Fullerenes For Antimicrobial Photoinactivationmentioning

confidence: 99%

Photodynamic therapy with fullerenes

Mróz

Tegos

Gali

et al. 2007

Photochem Photobiol Sci

274

209

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Fullerenes are a class of closed-cage nanomaterials made exclusively from carbon atoms. A great deal of attention has been focused on developing medical uses of these unique molecules especially when they are derivatized with functional groups to make them soluble and therefore able to interact with biological systems. Due to their extended π-conjugation they absorb visible light, have a high triplet yield and can generate reactive oxygen species upon illumination, suggesting a possible role of fullerenes in photodynamic therapy. Depending on the functional groups introduced into the molecule, fullerenes can effectively photoinactivate either or both pathogenic microbial cells and malignant cancer cells. The mechanism appears to involve superoxide anion as well as singlet oxygen, and under the right conditions fullerenes may have advantages over clinically applied photosensitizers for mediating photodynamic therapy of certain diseases.

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Section: Fullerenes For Antimicrobial Photoinactivationmentioning

confidence: 99%

Photodynamic therapy with fullerenes

Mróz

Tegos

Gali

et al. 2007

Photochem Photobiol Sci

274

209

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“…Various classes of chemical compounds, including phenothiazines, phthalocyanines, and porphyrines, with photoactive properties have been successfully tested as photoinactivating agents against Grampositive and Gram-negative bacteria (8)(9)(10)(11). Photosensitization mechanisms are initiated by the absorption of light by a given photosensitizer (12).…”

mentioning

confidence: 99%

“…This highly reactive oxygen initiates further oxidative reactions in the proximate environment, such as the bacterial cell wall, lipid membranes, enzymes, or nucleic acids (16,17). Therefore, the photodynamic inactivation of bacteria is based on the concept that a photosensitizer can accumulate to a significant extent in or at the cytoplasmic membrane, which is the critical target for irreversible damage in bacteria after irradiation (8).…”

mentioning

confidence: 99%

The role of singlet oxygen and oxygen concentration in photodynamic inactivation of bacteria

Maisch¹,

Baier²,

Franz³

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

375

289

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New antibacterial strategies are required in view of the increasing resistance of bacteria to antibiotics. One promising technique involves the photodynamic inactivation of bacteria. Upon exposure to light, a photosensitizer in bacteria can generate singlet oxygen, which oxidizes proteins or lipids, leading to bacteria death. To elucidate the oxidative processes that occur during killing of bacteria, Staphylococcus aureus was incubated with a standard photosensitizer, and the generation and decay of singlet oxygen was detected directly by its luminescence at 1,270 nm. At low bacterial concentrations, the time-resolved luminescence of singlet oxygen showed a decay time of 6 ؎ 2 s, which is an intermediate time for singlet oxygen decay in phospholipids of membranes (14 ؎ 2 s) and in the surrounding water (3.5 ؎ 0.5 s). Obviously, at low bacterial concentrations, singlet oxygen had sufficient access to water outside of S. aureus by diffusion. Thus, singlet oxygen seems to be generated in the outer cell wall areas or in adjacent cytoplasmic membranes of S. aureus. In addition, the detection of singlet oxygen luminescence can be used as a sensor of intracellular oxygen concentration. When singlet oxygen luminescence was measured at higher bacterial concentrations, the decay time increased significantly, up to Ϸ40 s, because of oxygen depletion at these concentrations. This observation is an important indicator that oxygen supply is a crucial factor in the efficacy of photodynamic inactivation of bacteria, and will be of particular significance should this approach be used against multiresistant bacteria.luminescence ͉ oxygen depletion ͉ Staphylococcus aureus

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“…There are a number of compounds that can act as photosensitizers. The positively charged phthalocyanines, especially, have been studied regarding their bactericidal effect to G-bacteria (Merchat et al, 1996;Minnock et al, 1996). Porphyrins have also been shown to be effective sensitizers for the inactivation of microbes (Malik et al, 1990;Merchat et al, 1996;Reddi et al, 2002).…”

Section: Introductionmentioning

confidence: 99%

“…The positively charged phthalocyanines, especially, have been studied regarding their bactericidal effect to G-bacteria (Merchat et al, 1996;Minnock et al, 1996). Porphyrins have also been shown to be effective sensitizers for the inactivation of microbes (Malik et al, 1990;Merchat et al, 1996;Reddi et al, 2002). Higher sensitivity of cyanobacteria to ROS, contrary to green algae, is known from several studies on hydrogen peroxide, which also belongs to the group of ROS (Barroin and Feuillade, 1986).…”

Section: Introductionmentioning

confidence: 99%

Photodynamic therapy against cyanobacteria

Drábková

Maršálek

Admiraal

2007

Environmental Toxicology

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This study explores the use of photosensitizers and reactive oxygen species (ROS) to limit growth of cyanobacteria. We chose 12 phthalocyanines, tetraphenol porphyrine, and methylene blue as compounds producing singlet oxygen. Hydrogen peroxide was chosen as another source of ROS. These compounds were tested using algal toxicity tests in microplates on three cultures of green algae (Pseudokirchneriella subcapitata, Scenedesmus quadricauda, and Chlorella kessleri) and on three cultures of cyanobacteria (Synechococcus nidulans, Microcystis incerta, and Anabaena sp.). Results indicate that photosensitizers and singlet oxygen could be highly toxic for some selected phytoplankton species. Green alga Scenedesmus quadricauda was highly sensitive (EC50 ¼ 0.07 mg/L) to compounds producing singlet oxygen, although it was not sensitive to hydrogen peroxide, which was about 10 times more toxic for cyanobacteria. We conclude that the compounds producing hydroxyl radical species seems to be more promising to treat cyanobacterial blooms than the compounds producing the singlet oxygen. # 2007 Wiley Periodicals, Inc. Environ Toxicol 22: 112-115, 2007.

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Meso-substituted cationic porphyrins as efficient photosensitizers of gram-positive and gram-negative bacteria

Cited by 372 publications

References 7 publications

Photodynamic therapy with fullerenes

Photodynamic therapy with fullerenes

The role of singlet oxygen and oxygen concentration in photodynamic inactivation of bacteria

Photodynamic therapy against cyanobacteria

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