Influence of charge and metal coordination of meso-substituted porphyrins on bacterial photoinactivation

Zoltan, Tamara; Vargas, Franklin; López, Verónica Rodríguez; Chávez, Valery; Rivas, Carlos; Ramírez, Alvaro

doi:10.1016/j.saa.2014.07.053

Cited by 39 publications

(14 citation statements)

References 39 publications

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“…Both TPPS4 and TMPyP4 were localized in the nucleus of C. albicans cells . There have been a few papers where the aPDI effects of TPPS4 have been studied (mostly against bacteria) [30, 41, 42] but the surprising effectiveness found in our study was not reported. There is a paper comparing the localization of TPPS4 and TMPyP4 in CT26 mouse cancer cells.…”

Section: Discussioncontrasting

confidence: 55%

Potentiation by potassium iodide reveals that the anionic porphyrin TPPS4 is a surprisingly effective photosensitizer for antimicrobial photodynamic inactivation

Huang

El-Hussein

Xuan

et al. 2018

Journal of Photochemistry and Photobiology B: Biology

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We recently reported that addition of the non-toxic salt, potassium iodide can potentiate antimicrobial photodynamic inactivation of a broad-spectrum of microorganisms, producing many extra logs of killing. If the photosensitizer (PS) can bind to the microbial cells, then delivering light in the presence of KI produces short-lived reactive iodine species, while if the cells are added after light the killing is caused by molecular iodine produced as a result of singlet oxygen-mediated oxidation of iodide. In an attempt to show the importance of PS-bacterial binding, we compared two charged porphyrins, TPPS4 (thought to be anionic and not able to bind to Gram-negative bacteria) and TMPyP4 (considered cationic and well able to bind to bacteria). As expected TPPS4+light did not kill Gram-negative Escherichia coli, but surprisingly when 100mM KI was added, it was highly effective (eradication at 200nM+10J/cm of 415nm light). TPPS4 was more effective than TMPyP4 in eradicating the Gram-positive bacteria, methicillin-resistant Staphylococcus aureus and the fungal yeast Candida albicans (regardless of KI). TPPS4 was also highly active against E. coli after a centrifugation step when KI was added, suggesting that the supposedly anionic porphyrin bound to bacteria and Candida. This was confirmed by uptake experiments. We compared the phthalocyanine tetrasulfonate derivative (ClAlPCS4), which did not bind to bacteria or allow KI-mediated killing of E. coli after a spin, suggesting it was truly anionic. We conclude that TPPS4 behaves as if it has some cationic character in the presence of bacteria, which may be related to its delivery from suppliers in the form of a dihydrochloride salt.

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Section: Discussioncontrasting

confidence: 55%

Potentiation by potassium iodide reveals that the anionic porphyrin TPPS4 is a surprisingly effective photosensitizer for antimicrobial photodynamic inactivation

Huang

El-Hussein

Xuan

et al. 2018

Journal of Photochemistry and Photobiology B: Biology

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“…The results indicate that (Ph-Zn, Ph-Mn, Ph-Al, Ph-V) had a quantum yield higher than (1, Ph). This difference could be related to an increase of relaxation of excited states in macromolecule; moreover, the insertion of these metals inside the ring generated more stability for the generation of singlet oxygen [25,41,42]. In general, the Φ ∆ of (1-7) were lower for the paramagnetic metals than for the diamagnetic ones, and this is in line with previous studies, which showed that porphyrins containing paramagnetic ions were very poor photosensitizers [24,26].…”

Section: Singlet Oxygen Quantum Yieldsupporting

confidence: 86%

In Vitro Anti-Leishmanial Effect of Metallic Meso-Substituted Porphyrin Derivatives against Leishmania braziliensis and Leishmania panamensis Promastigotes Properties

et al. 2020

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In this study, a family of porphyrins based on 5,10,15,20-Tetrakis(4-ethylphenyl)porphyrin (1, Ph) and six metallo-derivatives (Zn2+(2, Ph-Zn), Sn4+(3, Ph-Sn), Mn2+ (4, Ph-Mn), Ni2+ (5, Ph-Ni), Al3+ (6, Ph-Al), and V3+ (7, Ph-V)) were tested as photosensitizers for photodynamic therapy against Leishmania braziliensis and panamensis. The singlet oxygen quantum yield value (ΦΔ) for (1–7) was measured using 1,3-diphenylisobenzofuran (DPBF) as a singlet oxygen trapping agent and 5,10,15,20-(tetraphenyl)-porphyrin (H2TPP) as a reference standard; besides, parasite viability was estimated by the MTT assay. After metal insertion into the porphyrin core, the ΦΔ increased from 0.76–0.90 and cell viability changed considerably. The ΦΔ and metal type changed the cytotoxic activity. Finally, (2) showed both the highest ΦΔ (0.90) and the best photodynamic activity against the parasites studied (IC50 of 1.2 μM).

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“…Complexes TPyEtAcPNi and TPyEtAcPZn have moderate activity, while TNPS 4 , TNPZnS 4 and TPyEtAcP lower PDI activity. This work demonstrated that the production of ROS and structural deformations due to peripheral substituents and metal coordination positively enhanced the PDI activity of the complexes studied …”

Section: Types Of Porphyrin Based Compounds For Anti‐microbial Pdi Trmentioning

confidence: 70%

A Perspective on the Trends and Challenges Facing Porphyrin‐Based Anti‐Microbial Materials

Gan

Gao

et al. 2016

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The emergence of multidrug resistant bacterium threatens to unravel global healthcare systems, built up over centuries of medical research and development. Current antibiotics have little resistance against this onslaught as bacterium strains can quickly evolve effective defense mechanisms. Fortunately, alternative therapies exist and, at the forefront of research lays the photodynamic inhibition approach mediated by porphyrin based photosensitizers. This review will focus on the development of various porphyrins compounds and their incorporation as small molecules, into polymers, fibers and thin films as practical therapeutic agents, utilizing photodynamic therapy to inhibit a wide spectrum of bacterium. The use of photodynamic therapy of these porphyrin molecules are discussed and evaluated according to their electronic and bulk material effect on different bacterium strains. This review also provides an insight into the general direction and challenges facing porphyrins and derivatives as full-fledged therapeutic agents and what needs to be further done in order to be bestowed their rightful and equal status in modern medicine, similar to the very first antibiotic; penicillin itself. It is hoped that, with this perspective, new paradigms and strategies in the application of porphyrins and derivatives will progressively flourish and lead to advances against disease.

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Influence of charge and metal coordination of meso-substituted porphyrins on bacterial photoinactivation

Cited by 39 publications

References 39 publications

Potentiation by potassium iodide reveals that the anionic porphyrin TPPS4 is a surprisingly effective photosensitizer for antimicrobial photodynamic inactivation

Potentiation by potassium iodide reveals that the anionic porphyrin TPPS4 is a surprisingly effective photosensitizer for antimicrobial photodynamic inactivation

In Vitro Anti-Leishmanial Effect of Metallic Meso-Substituted Porphyrin Derivatives against Leishmania braziliensis and Leishmania panamensis Promastigotes Properties

A Perspective on the Trends and Challenges Facing Porphyrin‐Based Anti‐Microbial Materials

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