Visible‐Light‐Induced Annihilation of Tumor Cells with Platinum–Porphyrin Conjugates

Naik, Anu; Rubbiani, Riccardo; Gasser, Gilles; Spingler, Bernhard

doi:10.1002/anie.201400533

Cited by 199 publications

(157 citation statements)

References 44 publications

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“…This investigation will complement the well-known photochemistry of tetra(4-methylpyridinium)porphyrin com-plexes, [18] which have a charge of 4 + , as well as other PDT systems that we have recently reported. [19] Interestingly, James and co-workers have shown that tricationic porphyrins are taken up ten times better than tetracationic porphyrins by HT-29 cells. [20] In this study, we present the synthesis, characterisation and (photo)toxicity of novel porphyrins 2-4 against two human cancer cell lines (Scheme 1).…”

Section: Introductionmentioning

confidence: 98%

(Metallo)porphyrins as Potent Phototoxic Anti‐Cancer Agents after Irradiation with Red Light

Antoni

Naik

Albert

et al. 2014

Chemistry A European J

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Novel photoactive (metallo)porphyrins were synthesised and characterised. When irradiated with light at a wavelength greater than 600 nm, these porphyrins act as photosensitisers and show high cytotoxicity towards two different human cancer cell lines with IC50 values down to 0.4 μM. A paramagnetic copper(II) porphyrin is the first photosensitiser to display excellent phototoxicity, explained by the electron paramagnetic resonance (EPR) spin trapping of hydroxy radicals and experimentally confirmed by the discovery of elevated levels of reactive oxygen species (ROS) inside A2780 cells after irradiation with red light. This finding indicates that paramagnetic compounds should be considered for photodynamic therapy (PDT). Furthermore, an additive effect of cisplatin and a zinc porphyrin, both at subtherapeutic concentrations of 0.22 μM, was observed.

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Section: Introductionmentioning

confidence: 98%

(Metallo)porphyrins as Potent Phototoxic Anti‐Cancer Agents after Irradiation with Red Light

Antoni

Naik

Albert

et al. 2014

Chemistry A European J

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“…26 In this work, we designed and synthesized fluorescent BODIPY-Pt conjugate (BODIPY-Pt), then studied its cellular uptake and cytotoxicities in human cervical carcinoma (HeLa) and human breast cancer (MCF-7) cell lines. The 1,3,5,7-tetramethyl-8-(4-pyridyl)-4,4′-difluorobora-diazaindacene (BODIPY) was synthesized according to the literature, 27 and BODIPY-Pt was prepared by using the reported method (Scheme 1) in 48% yield, 1,28 but using BODIPY as the imaging reporter. The structure of BODIPY-Pt was confirmed by proton nuclear magnetic resonance ( 1 H NMR) ( Figure S1) and matrix-assisted laser desorption/ ionization time-of-flight mass spectrometry (MALDI-TOF MS) ( Figure S2).…”

mentioning

confidence: 99%

Mitochondria-Localized Fluorescent BODIPY-Platinum Conjugate

Sun

Guan

Zheng

et al. 2015

ACS Med. Chem. Lett.

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A convenient synthesis of a BODIPY (1,3,5,7-tetramethyl-8-(4-pyridyl)-4,4′-difluoroboradiazaindacene) labeled platinum compound (BODIPY-Pt) was developed by direct conjugation of cisplatin with the pyridine group of BODIPY. The membrane permeability and selective uptake of BODIPY-Pt in the mitochondria was studied using confocal laser scanning microscopy (CLSM). The fluorescent BODIPYPt conjugate showed high cellular proliferation inhibition against human cervical carcinoma (HeLa) and human breast cancer (MCF-7) cells, with half maximal inhibitory concentrations (IC 50 ) of 27.37 and 12.14 μM, respectively. This work highlights the potential of using BODIPY labeled Pt compounds to realize the visualization of Pt distribution in living cells.

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“…8 To mimic the coordination interactions between PhenPt and DNA, several control experiments were performed. Guanosine triphosphate (GTP) was utilized as a competitive ligand to study the disassembly of the metallacycle M via fluorescence spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

Antitumor Activity of a Unique Polymer That Incorporates a Fluorescent Self-Assembled Metallacycle

et al. 2017

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Despite the well-known anticancer activity of mono- and multi-nuclear platinum complexes, studies of the antitumor performances of platinum-based supramolecular coordination complexes are rare. Herein, we report on the synthesis of a four-armed amphiphilic copolymer Pt-PAZMB-b-POEGMA containing a theranostic metallacycle M, in which the tetraphenylethene derivative acts as an aggregation-induced emissive fluorescent probe for live cell imaging and the 3,6-bis[trans-Pt(PEt3)2]phenanthrene (PhenPt) is an anticancer drug. This copolymer was further self-assembled into nanoparticles of different sizes and vesicles depending upon the experimental conditions. The impact of the morphology and size of the assemblies on their endocytic pathways, uptake rates, internalization amounts and cytotoxicities were fully investigated. The self-assemblies were further employed to encapsulate doxorubicin (DOX) to achieve a synergistic anticancer effect. Controlled drug release was also realized via amphiphilicity changes and was driven by a glutathione-induced cascade elimination reaction. The DOX-loaded nanoparticles of around 50 nm in size exhibited an excellent antitumor performance as well as a low systemic toxicity, due to an enhanced permeability and retention effect.

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Visible‐Light‐Induced Annihilation of Tumor Cells with Platinum–Porphyrin Conjugates

Cited by 199 publications

References 44 publications

(Metallo)porphyrins as Potent Phototoxic Anti‐Cancer Agents after Irradiation with Red Light

(Metallo)porphyrins as Potent Phototoxic Anti‐Cancer Agents after Irradiation with Red Light

Mitochondria-Localized Fluorescent BODIPY-Platinum Conjugate

Antitumor Activity of a Unique Polymer That Incorporates a Fluorescent Self-Assembled Metallacycle

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