Perylenebisimide-fullerene dyads as heavy atom free triplet photosensitizers with unique singlet oxygen generation efficiencies

Gündüz, Ezel Öztürk; Eserci, Hande; Okutan, Elif

doi:10.1016/j.jphotochem.2019.112022

Cited by 14 publications

(7 citation statements)

References 51 publications

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“…The ability of perylene compounds to photogenerate singlet oxygen is well known. Both perylene itself [ 104 ], and perylene-3,4,9,10-tetracarboxylic acid diimides, are efficient in this process [ 105 , 106 ]. The BODIPY-perylene dyad is an effective photosensitizer of 1 O 2 formation [ 107 ].…”

Section: Perylene-based Rigid Amphipathic Photosensitizersmentioning

confidence: 99%

Photosensitizing Antivirals

et al. 2021

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Antiviral action of various photosensitizers is already summarized in several comprehensive reviews, and various mechanisms have been proposed for it. However, a critical consideration of the matter of the area is complicated, since the exact mechanisms are very difficult to explore and clarify, and most publications are of an empirical and “phenomenological” nature, reporting a dependence of the antiviral action on illumination, or a correlation of activity with the photophysical properties of the substances. Of particular interest is substance-assisted photogeneration of highly reactive singlet oxygen (1O2). The damaging action of 1O2 on the lipids of the viral envelope can probably lead to a loss of the ability of the lipid bilayer of enveloped viruses to fuse with the lipid membrane of the host cell. Thus, lipid bilayer-affine 1O2 photosensitizers have prospects as broad-spectrum antivirals against enveloped viruses. In this short review, we want to point out the main types of antiviral photosensitizers with potential affinity to the lipid bilayer and summarize the data on new compounds over the past three years. Further understanding of the data in the field will spur a targeted search for substances with antiviral activity against enveloped viruses among photosensitizers able to bind to the lipid membranes.

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Section: Perylene-based Rigid Amphipathic Photosensitizersmentioning

confidence: 99%

Photosensitizing Antivirals

et al. 2021

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“…A number of works have shown an enhancement in the optical and photosensitizing properties of fullerene-based photosensitizers. For example, several fullerene dyads, triads, and tetrads with visible to near-infrared light-absorbing groups have been reported [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ]. However, due to the low solubility of C 60 , its functionalization is usually arduous, especially when introducing functional groups, which may lead to even lower solubility.…”

Section: Introductionmentioning

confidence: 99%

S/Se-Terchalcogenophene-C60 Dyads: Synthesis and Characterization of Optical and Photosensitizing Properties

et al. 2023

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Fullerenes have been long investigated for application as singlet oxygen sources. Even though they possess high photosensitizing efficiency, their practical use is still limited, mostly because of insufficient absorption of visible and/or near-infrared light. This limitation can be overcome by introducing organic chromophores that absorb longer-wavelength light, either by covalent attachment to C60 or by its encapsulation in a polymeric matrix. In this work, we investigated the photosensitizing properties of the C60 molecule functionalized with organic units comprising thiophene or selenophene rings. The chemical structures of the synthesized dyads were characterized by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. The influence of the S/Se atoms and vinyl linkage between the organic unit and C60 on the absorptive and emissive properties of the dyads was investigated and correlated with their photosensitizing activity. For the latter, we used a standard chemical singlet oxygen trap. A selected dyad C60ThSe2 was also applied as a source of singlet oxygen in a model photocatalyzed synthesis of the fine chemical juglone from 1,5-dihydroxynapthalene.

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“…Fullerene derivatives have been reported as photosensitizers owing to their intersystem crossing aptitude which enables efficient production of ROS, good biocompatibility, total body clearance and facile multiple surface modification. [24][25][26][27][28][29] Especially the ease of surface modification obviates the hinders of fullerene derivatives in PDT such as limited penetration depth of UV to Vis irradiation, hydrophobicity and lack of vehicles for targeting. [30][31][32][33] In order to overcome the proper (NIR) light absorption, solubility and target specificity limitations, many fullerene chromophore dyad/triad systems have been developed.…”

Section: Introductionmentioning

confidence: 99%

“…[30][31][32][33] In order to overcome the proper (NIR) light absorption, solubility and target specificity limitations, many fullerene chromophore dyad/triad systems have been developed. [25,[34][35][36] These nanocarriers can be developed tailormade through knocking together right pieces, whereas the balance between hydrophilic and hydrophobic parts is controlled and grafted with targeting units such as carbohydrates. [37][38][39][40] Therefore, we have decided to apply the approach based on facile Bingel reaction for the efficient functionalization of fullerene with BODIPY and click chemistry to bind carbohydrate moieties.…”

Section: Introductionmentioning

confidence: 99%

Amphiphilic Fullerene‐BODIPY Photosensitizers for Targeted Photodynamic Therapy

2021

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Nanotheranostic tailor‐made carriers are potent platforms for the treatment of cancer that propound a number of advantages over conventional agents for photodynamic therapy (PDT). Herein, four new heavy atom free amphiphilic glucose‐BODIPY‐fullerene dyads (14–17) endowed with carbohydrate units in the styryl units, which can also form nanomicelles (14–17NM) with Tween 80 for PDT are reported. Glucose‐BODIPY‐fullerene systems (14–17) and related nanomicelles (14‐17NM) have been prepared to emcee efficient singlet oxygen generation upon light irradiation. In vitro anti‐tumor effects of the compounds 14–17 and 14–17NM in the presence of light and in darkness have been investigated with K562 human chronic myelogenous leukemia suspension cells. Anti‐tumor toxicity upon light irradiation was due to the formation of singlet oxygen and reactive oxygen species (ROS). This study may provide an accomplished example of efficient PDT applications based on nanovehicles fabricated with universal spin converter, fullerene, light harvesting unit, BODIPY dyes conjugated with targeting units to fight against cancer.

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Perylenebisimide-fullerene dyads as heavy atom free triplet photosensitizers with unique singlet oxygen generation efficiencies

Cited by 14 publications

References 51 publications

Photosensitizing Antivirals

Photosensitizing Antivirals

S/Se-Terchalcogenophene-C60 Dyads: Synthesis and Characterization of Optical and Photosensitizing Properties

Amphiphilic Fullerene‐BODIPY Photosensitizers for Targeted Photodynamic Therapy

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