Construction of Porphyrin-Containing Metallacycle with Improved Stability and Activity within Mesoporous Carbon

Chen, Lijun; Chen, Shangjun; Qin, Yi; Xu, Lin; Yin, Guang‐Qiang; Zhu, Jianxun; Zhu, Fan-Fan; Zheng, Wei; Li, Xiaopeng; Yang, Hai‐Bo

doi:10.1021/jacs.8b02386

Cited by 115 publications

(51 citation statements)

References 66 publications

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“…By judicious selection of the molecular building blocks, the shapes, geometries, and biological properties of the SCCs can be precisely modulated to promote biomedical applications, such as anticancer activity (38)(39)(40)(41)(42), drug delivery (43)(44)(45)(46), bioimaging (47,48), and biorecognition (49)(50)(51). Self-assembled metallacycles have shown potential as photosensitizers for catalysis as well as PDT for cancer therapy and bacterial inactivation (39,40,(52)(53)(54). We envisioned that SCCs with a high level of structural complexity, such as metallacages, could provide favorable photophysical and biological properties over their 2D counterparts due to their 3D structure and high number of functional moieties within the same ensemble.…”

Section: Significancementioning

confidence: 99%

A self-assembled Ru–Pt metallacage as a lysosome-targeting photosensitizer for 2-photon photodynamic therapy

Zhou

Liu

Huang³

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

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118

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Photodynamic therapy (PDT) is a treatment procedure that relies on cytotoxic reactive oxygen species (ROS) generated by the light activation of a photosensitizer. The photophysical and biological properties of photosensitizers are vital for the therapeutic outcome of PDT. In this work a 2D rhomboidal metallacycle and a 3D octahedral metallacage were designed and synthesized via the coordination-driven self-assembly of a Ru(II)-based photosensitizer and complementary Pt(II)-based building blocks. The metallacage showed deep-red luminescence, a large 2-photon absorption cross-section, and highly efficient ROS generation. The metallacage was encapsulated into an amphiphilic block copolymer to form nanoparticles to encourage cell uptake and localization. Upon internalization into cells, the nanoparticles selectively accumulate in the lysosomes, a favorable location for PDT. The nanoparticles are almost nontoxic in the dark, and can efficiently destroy tumor cells via the generation of ROS in the lysosomes under 2-photon near-infrared light irradiation. The superb PDT efficacy of the metallacage-containing nanoparticles was further validated by studies on 3D multicellular spheroids (MCS) and in vivo studies on A549 tumor-bearing mice.

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Section: Significancementioning

confidence: 99%

A self-assembled Ru–Pt metallacage as a lysosome-targeting photosensitizer for 2-photon photodynamic therapy

Zhou

Liu

Huang³

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

118

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“…On the other hand, aggregation-induced quenching may significantly compromise the photophysical functionality of some fluorophores such as porphyrins. In a recent paper, an alternative way to produce porphyrin functionalized hexagonal metallacycle has been reported (Chen et al, 2018). To avoid self-aggregation of the porphyrin rings, the metallacycle depicted in Figure 5 has been produced in the confined cavity of mesoporous carbon FDU-16.…”

Section: Metallacyclesmentioning

confidence: 99%

Section: Metallacyclesmentioning

confidence: 99%

Biomedical Applications of Metallosupramolecular Assemblies—Structural Aspects of the Anticancer Activity

Ahmedova

2018

Front. Chem.

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The design and development of metallosupramolecular systems has resulted in construction of a myriad of fascinating structures with highly diverse properties and potential applications. Assessment of the biomedical applications of metallosupramolecular assemblies is an emerging field of research that stems from the recently demonstrated promising results on such systems. After the pioneering works of Therrien and coworkers on organometallic Ru-cages with promising anticancer properties, this topic has evolved to the more recent studies on bioactivity of supramolecular coordination complexes built from different metal ions and various multidentate ligands. Sufficient amount of data on the anticancer activity of metallosupramolecules has already been reported and allows outlining some general tendencies in the structural aspects of the biological activity. The main structural properties of the complexes that can be readily modified to enhance their activity are the size, the shape and charge of the formed complexes. Moreover, the intrinsic properties of the building components could predetermine some of the main characteristics of the overall supramolecular complex, such as its optical properties, chemical reactivity, solubility, etc., and could, thereby, define the areas of its biomedical applications. The unique structural property of most of the metallosupramolecular assemblies, however, is the presence of a discrete cavity that renders a whole range of additional applications resulting from specific host-guest interactions. The encapsulations of small bioactive or fluorescent molecules have been employed for delivery or recognition purposes in many examples. On the other hand, metallosupramolecules have been imbedded into target-specific polymeric nanoparticles that resulted in a successful combination of their therapeutic and diagnostic properties, making them promising for theranostic application in cancer treatment. The aim of this review paper is to mark out some key tendencies in the reported metallosupramolecular structures in relation with their biological activity and potential areas of biomedical application. In this way, a useful set of guidelines can be delineated to help synthetic chemists broaden the application areas of their supramolecular systems by few structural changes.

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“…Discretem olecular architectures [1][2] hold the attention of researchers for aw ide range of applications in gas storage,m olecular recognition,c atalysis, and drug delivery.O ver the past three decades, numerousm olecular architectures [3] have been developed by alterings uitableo rganic spacers and metal counterparts. However,a nalogous organic molecular assemblies are hard to achieve by using traditional multistep organic synthesis, which generally leads to low yield of the final products.…”

Section: Introductionmentioning

confidence: 99%

Nucleation of Tiny Silver Nanoparticles by Using a Tetrafacial Organic Molecular Barrel: Potential Use in Visible‐Light‐Triggered Photocatalysis

Mondal

Bhandari

Mukherjee

2020

Chemistry A European J

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Coordination-driven self-assembly of discrete molecular architectures of diverses hapesa nd sizes has been well studied in the last three decades. Use of dynamic imine bonds ford esigning analogous metal-free architectures has become ag rowing challenge recently.T his article reports an organic molecular barrel (OB4 R)a sapotential templatef or nucleation and stabilization of very tiny (< 1.5 nm) Ag nanoparticles (AgNPs). Imine bond condensation of ar igid tetraaldehyde with af lexible diamine followed by imine-bond reduction yielded the discrete tetragonal organic barrel (OB4 R). The presence of am olecular pocket ornamented with eight diamine moieties gives the potential for encapsulation of silver(I). The organic barrelw as finally used as amolecular vesself or the controlled nucleation of silver nanopar-ticles (AgNPs) with fine size tuning through bindingo fA g I ions in the confined space of the barrel followed by reduction. Transmission electronm icroscopy (TEM) analysiso ft he Ag 0 @OB4 R composite revealed that the mean particles ize is 1.44 AE 0.16 nm. The composite materialh as approximately 52 wt %s ilver loading.T he barrel-supported ultrafine AgNPs [Ag 0 @OB4 R ]a re found to be an efficient photocatalystf or facile Ullmann-type aryl-amination coupling of haloarenes at ambient temperature without using anya dditives. The catalyst was stable fors everal cycles of reuse without any agglomeration. The new composite Ag 0 @OB4 R represents the first example of discrete organic barrel-supported AgNPs employed as ap hotocatalyst in Ullmann-typec oupling reactions at room temperature.

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Construction of Porphyrin-Containing Metallacycle with Improved Stability and Activity within Mesoporous Carbon

Cited by 115 publications

References 66 publications

A self-assembled Ru–Pt metallacage as a lysosome-targeting photosensitizer for 2-photon photodynamic therapy

A self-assembled Ru–Pt metallacage as a lysosome-targeting photosensitizer for 2-photon photodynamic therapy

Biomedical Applications of Metallosupramolecular Assemblies—Structural Aspects of the Anticancer Activity

Nucleation of Tiny Silver Nanoparticles by Using a Tetrafacial Organic Molecular Barrel: Potential Use in Visible‐Light‐Triggered Photocatalysis

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