Dendrimer porphyrin-based self-assembled nano-devices for biomedical applications

Jeong, Young Hwan; Yoon, Hee Jae; Jang, Woo Dong

doi:10.1038/pj.2012.20

Cited by 21 publications

(17 citation statements)

References 69 publications

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“…We first focus on P3 , which comprises porphyrin units that can generate singlet oxygen upon irradiation with light. 6f The use of SCPNs to prevent porphyrin aggregation may pose advantages compared to previously applied approaches (such as dendrimers or polymer micelles) 28 because they combine easy accessibility with high stability. Figure 4 A shows the delivery of SCPNs based on P3 via endocytosis at different concentrations.…”

Section: Results and Discussionmentioning

confidence: 99%

Catalytically Active Single-Chain Polymeric Nanoparticles: Exploring Their Functions in Complex Biological Media

et al. 2018

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Dynamic single-chain polymeric nanoparticles (SCPNs) are intriguing, bioinspired architectures that result from the collapse or folding of an individual polymer chain into a nanometer-sized particle. Here we present a detailed biophysical study on the behavior of dynamic SCPNs in living cells and an evaluation of their catalytic functionality in such a complex medium. We first developed a number of delivery strategies that allowed the selective localization of SCPNs in different cellular compartments. Live/dead tests showed that the SCPNs were not toxic to cells while spectral imaging revealed that SCPNs provide a structural shielding and reduced the influence from the outer biological media. The ability of SCPNs to act as catalysts in biological media was first assessed by investigating their potential for reactive oxygen species generation. With porphyrins covalently attached to the SCPNs, singlet oxygen was generated upon irradiation with light, inducing spatially controlled cell death. In addition, Cu(I)- and Pd(II)-based SCPNs were prepared and these catalysts were screened in vitro and studied in cellular environments for the carbamate cleavage reaction of rhodamine-based substrates. This is a model reaction for the uncaging of bioactive compounds such as cytotoxic drugs for catalysis-based cancer therapy. We observed that the rate of the deprotection depends on both the organometallic catalysts and the nature of the protective group. The rate reduces from in vitro to the biological environment, indicating a strong influence of biomolecules on catalyst performance. The Cu(I)-based SCPNs in combination with the dimethylpropargyloxycarbonyl protective group showed the best performances both in vitro and in biological environment, making this group promising in biomedical applications.

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Section: Results and Discussionmentioning

confidence: 99%

Catalytically Active Single-Chain Polymeric Nanoparticles: Exploring Their Functions in Complex Biological Media

et al. 2018

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“…[2][3][4][5][6][7] An umber of differentf unctionalg roups were attached to the porphyrin core, including hydrophilico ligoethylene glycols, dendrons, and mono-o rp olysaccharidest oa lter the solubility and photophysical properties and to make use of these compounds for various applications( e.g.,p hotocatalysis, light harvesting, sensing, photodynamic therapies, etc.). [8][9][10][11][12][13][14] There are also examples in which cucurbit[n]urils (CBs) are attached to the porphyrinc ore throughn oncovalenti nteractions; [15,16] however,t hose studiesd on ot involvet he conjugation of functionalized CBs directly to the porphyrin core and enablingthe CBs to be utilized as receptors. CBs are highly versatile macrocyclesp ossessing ah ydrophobicc avity along with carbonyld ecorated hydrophilic portals.…”

Section: Introductionmentioning

confidence: 99%

“Clicked” Porphyrin‐Cucurbituril Conjugate: A New Multifunctional Supramolecular Assembly Based on Triglycosylated Porphyrin and Monopropargyloxycucurbit[7]uril

Koç

Khan

Tuncel

2018

Chemistry A European J

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The design, synthesis, and characterization of a new multifunctional supramolecular assembly based on a photoactive glycosylated porphyrin and covalently attached monofunctionalized cucurbit[7]uril (CB7) are reported. To obtain the target supramolecular assembly, azido-functionalized tetraphenylporphyrin (TPP) was used as a building block. TPP was first glycosylated by copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, then a monopropargyloxy-functionalized-CB7 unit was conjugated to glycosylated TPP with a second CuAAC reaction. The host-guest chemistry of the assembly was investigated by H NMR experiments to establish the availability of the CB7 as a host. The imidazole-based guest, which is known to have high affinity toward CB7, was observed to form inclusion complex with CB7. It was also demonstrated that this supramolecular assembly can serve as an efficient photosensitizer for the generation of singlet oxygen.

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“…Rath and co‐workers synthesized two planar‐fused heterocyclic macrocycles with NIR absorption in free‐base form (Q‐bands in the range of 692–1088 nm) and protonation‐induced enhanced NIR emission (1089 and 1068 nm) . Recently, dendric tetrapyrrole structures containing functional groups, that can be integrated into protein scaffolds, have been studied for biological activities and imaging . The versatility of novel porphyrin and phthalocyanine derivatives with eligible photophysical properties renders them as potential candidates for both biological imaging and PDT in clinical trials.…”

Section: Current Organic Dyes For Nanomedicinementioning

confidence: 99%

Organic Dye Based Nanoparticles for Cancer Phototheranostics

Cai

Huang

et al. 2018

Small

243

157

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Phototheranostics, which simultaneously combines photodynamic and/or photothermal therapy with deep-tissue diagnostic imaging, is a promising strategy for the diagnosis and treatment of cancers. Organic dyes with the merits of strong near-infrared absorbance, high photo-to-radical and/or photothermal conversion efficiency, great biocompatibility, ready chemical structure fine-tuning capability, and easy metabolism, have been demonstrated as attractive candidates for clinical phototheranostics. These organic dyes can be further designed and fabricated into nanoparticles (NPs) using various strategies. Compared to free molecules, these NPs can be equipped with multiple synergistic functions and show longer lifetime in blood circulation and passive tumor-targeting property via the enhanced permeability and retention effect. In this article, the recent progress of organic dye-based NPs for cancer phototheranostic applications is summarized, which extends the anticancer arsenal and holds promise for clinical uses in the near future.

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Dendrimer porphyrin-based self-assembled nano-devices for biomedical applications

Cited by 21 publications

References 69 publications

Catalytically Active Single-Chain Polymeric Nanoparticles: Exploring Their Functions in Complex Biological Media

Catalytically Active Single-Chain Polymeric Nanoparticles: Exploring Their Functions in Complex Biological Media

“Clicked” Porphyrin‐Cucurbituril Conjugate: A New Multifunctional Supramolecular Assembly Based on Triglycosylated Porphyrin and Monopropargyloxycucurbit[7]uril

Organic Dye Based Nanoparticles for Cancer Phototheranostics

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