Porphysome nanoparticles: Tailoring treatments with nature’s pigments

MacDonald, Thomas D.; Zheng, Gang

doi:10.1515/plm-2013-0059

Cited by 7 publications

(4 citation statements)

References 83 publications

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“…“ptersomes”, which we aim to report in the near future. Porphyrin-based conjugation routes have already emerged for porphysome nanovesicles with use in photothermal therapy. − …”

Section: Discussionmentioning

confidence: 99%

Lipophilic Decyl Chain–Pterin Conjugates with Sensitizer Properties

et al. 2017

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A new series of decyl chain [-(CH)CH] pterin conjugates have been investigated by photochemical and photophysical methods, and with theoretical solubility calculations. To synthesize the pterins, a nucleophilic substitution (S2) reaction was used for the regioselective coupling of the alkyl chain to the O site over the N site. However, the O-alkylated pterin converts to N-alkylated pterin under basic conditions, pointing to a kinetic product in the former and a thermodynamic product in the latter. Two additional adducts were also obtained from an N-amine condensation of DMF solvent molecule as byproducts. In comparison to the natural product pterin, the alkyl chain pterins possess reduced fluorescence quantum yields (Φ) and increased singlet oxygen quantum yields (Φ). It is shown that the DMF-condensed pterins were more photostable compared to the N- and O-alkylated pterins bearing a free amine group. The alkyl chain pterins efficiently intercalate in large unilamellar vesicles, which is a good indicator of their potential use as photosensitizers in biomembranes. Our study serves as a starting point where the synthesis can be expanded to produce a wider series of lipophilic, photooxidatively active pterins.

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“…“ptersomes”, which we aim to report in the near future. Porphyrin-based conjugation routes have already emerged for porphysome nanovesicles with use in photothermal therapy. − …”

Section: Discussionmentioning

confidence: 99%

Lipophilic Decyl Chain–Pterin Conjugates with Sensitizer Properties

et al. 2017

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“…This structural similarity further reduces chances of systemic rejection or severe allergic reactions by the human body . In addition to PDI, in recent years, there are significant advances in the porphyrin related materials in the class of porphysomes which are self‐assembled porphyrin‐phospholipid bilayers into nanovesicles, porphyrin functionalized graphene oxide, and porphyrin conjugated nanoparticles, for the purpose of diverse biophotonic applications such as photothermal therapy (PTT), photoacoustic tomography imaging, and optical frequency domain imaging . Unlike PDI, PTT works on the principle of targeted tissue ablation via thermal necrosis in the presence of PSs that exhibit excellent photon to thermal energy conversion upon localized laser irradiation.…”

Section: Introductionmentioning

confidence: 99%

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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“…12,13 Amphiphilic porphyrin derivatives appear as very promising scaffolds since they can self-assemble into supramolecular structures 5 with adjustable photophysical properties and biomedical outcomes. 14 Among the amphiphilic porphyrins that have been designed so far for the development of photo-activatable drug delivery systems, the phospholipid-porphyrin (PL-Por) conjugates initially proposed by Gang Zheng's group 9,15,16 belong to the most versatile compounds for biomedical applications. These conjugates are made of pyropheophorbide-a or bacteriochlorophyll-a photosensitizers (PSs) linked to the sn2 hydroxyl group of 1-lysophosphatidylcholine (C16) via an esterification reaction.…”

Section: Introductionmentioning

confidence: 99%