Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers

Ferreyra, Darío D.; Reynoso, Eugenia; Cordero, Paula; Spesia, Mariana B.; Alvarez, M. Gabriela; Milanesio, M. Elisa; Durantini, Edgardo N.

doi:10.1016/j.jphotobiol.2016.02.021

Cited by 43 publications

(66 citation statements)

References 33 publications

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“…The killing of microbial cells with aPDI is rapid (seconds) while the action of antibiotics can take hours or days, giving a potential advantage against fast-spreading infections such as necrotizing fasciitis. Moreover the broad-spectrum nature of aPDI means that treatment can be instituted before the infectious agents have been identified [13]. Although many infections can occur deep inside the body, it is now possible to deliver both PS and light to almost any anatomical region, via endoscopes and narrow-diameter interstitially-inserted needles and fiber optics [14].…”

Section: Antimicrobial Photodynamic Inactivationmentioning

confidence: 99%

Antimicrobial photodynamic inactivation: a bright new technique to kill resistant microbes

Hamblin

2016

Current Opinion in Microbiology

580

342

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Photodynamic therapy (PDT) uses photosensitizers (non-toxic dyes) that are activated by absorption of visible light to form reactive oxygen species (including singlet oxygen) that can oxidize biomolecules and destroy cells. Antimicrobial photodynamic inactivation (aPDI) can treat localized infections. aPDI neither causes any resistance to develop in microbes, nor is affected by existing drug resistance status. We discuss some recent developments in aPDI. New photosensitizers including polycationic conjugates, stable synthetic bacteriochlorins and functionalized fullerenes are described. The microbial killing by aPDI can be synergistically potentiated (several logs) by harmless inorganic salts via photochemistry. Genetically engineered bioluminescent microbial cells allow PDT to treat infections in animal models. Photoantimicrobials have a promising future in the face of the unrelenting increase in antibiotic resistance.

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Section: Antimicrobial Photodynamic Inactivationmentioning

confidence: 99%

Antimicrobial photodynamic inactivation: a bright new technique to kill resistant microbes

Hamblin

2016

Current Opinion in Microbiology

580

342

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“…The phthalocyanine ZnPPc 4+ mainly absorbs at 678 nm in DMF, while the chlorin TAPC shows an intense band at 421 nm and another less pronounced at 650 nm (Figure ). Previously, PBS suspensions of planktonic S aureus treated with 1 μM TAPC and irradiated for 15 minutes achieve complete eradication . Moreover, the phthalocyanine ZnPPc 4+ is also an efficient photosensitizer to kill planktonic bacterial cells .…”

Section: Discussionmentioning

confidence: 99%

“…On the other hand, the effects of PDI on the structure of S aureus biofilm were observed by microscopy. Previously, TAPC was found to have particularly high binding affinity for S aureus planktonic cells and exhibited the red fluorescence typical of chlorin derivatives . Staphylococcus aureus biofilm also shows red fluorescence distributed on bacteria after photodynamic treatment with this photosensitizer.…”

Section: Discussionmentioning

confidence: 99%

“…After that, acrylic discs with 48 hours biofilm were placed in PBS (2 mL) and incubated with 5 μM photosensitizer (TAPC or ZnPPc 4+ ). According to previous examinations, this concentration allowed observing differences between controls and PDI‐treated biofilms. After 15 minutes of incubation in dark at 37°C on rotatory shaker (100 rpm), plate was irradiated with visible light for different time periods.…”

Section: Methodsmentioning

confidence: 98%

“…Chlorin TAPC has four tertiary amine groups as substituents attached to alkyl chain of three carbon atoms in the periphery of macrocycle. This link confers high mobility to the amine groups, which can be protonated at physiological pH . On the other hand, the structure of the phthalocyanine derivative ZnPPc 4+ presents four cationic centres isolated from the phthalocyanine macrocycle by ether bonds .…”

Section: Introductionmentioning

confidence: 99%

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Photodynamic inactivation to prevent and disrupt Staphylococcus aureus biofilm under different media conditions

Reynoso

Ferreyra

Durantini

et al. 2019

Photoderm Photoimm Photomed

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Objective The goal of this work was to investigate the photodynamic activity of 5,10,15,20‐tetrakis[4‐(3‐N,N‐dimethylaminopropoxy)phenyl]chlorin (TAPC) and zinc(II) 2,9,16,23‐tetrakis[4‐(N‐methylpyridyloxy)]phthalocyanine iodide (ZnPPc4+) as photosensitizers to inactivate Staphylococcus aureus biofilms and prevent their formations in different culture media. Methods We incubated S aureus biofilms in different culture media: tryptic soy (TS), nutrient (N), Müeller Hinton (MH) broth, TS with glucose 2 and 5% (w/v) with 5 μM ZnPPc4+ or TAPC and irradiated with visible light (350‐800 nm). Photodynamic inactivation (PDI) was determined by count of colony forming units (CFU) and crystal violet method. Furthermore, we studied PDI effect on biofilm development in TS broth. Finally, we examined the effects of PDI on the structure of S aureus biofilm. Results Greater inactivation was achieved, using TAPC or ZnPPc4+, when S aureus biofilm was grown in N or MH broths rather than in TS. Besides, glucose addition to the medium decreases the ability to develop biofilm and increase the photoinactivation capacity. Prevention of 3 log biofilm developments was obtained when S aureus cultures were treated with TAPC (10 μM) and 108 J/cm2 in TS broth and the number of CFU was counted after 24 hours. Moreover, microscopy studies demonstrated modifications in biofilm architecture. Conclusions These results indicate that TAPC and ZnPPc4+ may be promising photosensitizers for photodynamic inactivation of S aureus biofilms or to prevent their formation.

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Proton‐Dependent Switching of a Novel Amino Chlorin Derivative as a Fluorescent Probe and Photosensitizer for Acidic Media

Heredia

Durantini

Sarotti

et al. 2018

Chemistry A European J

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A novel chlorin derivative (TPCF -NMe ) has been synthesized as a syn adduct of a pyrrolidine-fused chlorin bearing a C-linked N,N-dimethylaminophenyl residue. The absorption spectrum of TPCF -NMe is essentially identical to that of TPCF in N,N-dimethylformamide, indicating a very weak interaction between the chlorin macrocycle and the amine group in the ground state. However, the fluorescence emission of the chlorin moiety in TPCF -NMe is effectively quenched by the attached amine unit. Moreover, TPCF -NMe is unable to attain a triplet excited state or to photosensitize singlet molecular oxygen. Spectroscopic and redox properties indicate that intramolecular photoinduced electron transfer can take place from the N,N-dimethylaminophenyl group to the chlorin macrocycle. Thus, in an acid medium, protonation of the amino group leads to a considerable increase in the fluorescence emission, triplet excited-state formation, and singlet molecular oxygen production. Photodynamic inactivation of Escherichia coli sensitized by TPCF -NMe is negligible at neutral pH. However, this chlorin becomes highly effective in inactivating E. coli cells under acidic conditions. Therefore, these results indicate that TPCF -NMe is an interesting molecular structure, in which protonation of the amino group can be used as an off/on molecular switch activating red fluorescence emission and photodynamic activity capable of eradicating bacteria.

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Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers

Cited by 43 publications

References 33 publications

Antimicrobial photodynamic inactivation: a bright new technique to kill resistant microbes

Antimicrobial photodynamic inactivation: a bright new technique to kill resistant microbes

Photodynamic inactivation to prevent and disrupt Staphylococcus aureus biofilm under different media conditions

Proton‐Dependent Switching of a Novel Amino Chlorin Derivative as a Fluorescent Probe and Photosensitizer for Acidic Media

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