Synthesis and cellular uptake of porphyrin decorated iron oxide nanoparticles—a potential candidate for bimodal anticancer therapy

Gu, Hongwei; Xu, Keming; Yang, Zhimou; Chang, C. K.; Xu, Bing

doi:10.1039/b507779f

Cited by 180 publications

(124 citation statements)

References 25 publications

(11 reference statements)

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“…However, recent studies link magnetic resonance imaging (MRI) and PDT [66,172] for example for the imaging and treatment of brain tumors [175]. Another example is the combined use of PDT and magnetohypothermia using magnetic nanoparticles [176,177]. This is related to a hyperthermia approach that combines PDT and photothermal therapy (PTT) [178], in which photothermal agents can selectively heat the local environment [179].…”

Section: Additional Applicationsmentioning

confidence: 99%

Nanodrug applications in photodynamic therapy

Paszko

Ehrhardt

Senge

et al. 2011

Photodiagnosis and Photodynamic Therapy

322

215

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SummaryPhotodynamic therapy (PDT) has developed over last century and is now becoming a more widely used medical tool having gained regulatory approval for the treatment of various diseases such as cancer and macular degeneration. It is a two-step technique in which delivery of a photosensitizing drug is followed by irradiation of light. Activated photosensitizers transfer energy to molecular oxygen which results in generation of reactive oxygen species which in turn cause cells apoptosis or necrosis. Although this modality has significantly improved quality of life and survival time for many cancer patients it still offers significant potential for further improvement. In addition to the development of new PDT drugs, the use of nanosized carriers for photosensitizers is a promising approach which might improve the efficiency of photodynamic activity and which can overcome many side effects associated with classic photodynamic therapy. This review aims at highlighting the different types of nanomedical approaches currently used in PDT and outlines future trends and limitations of nanodelivery of photosensitizers. PDT -photodynamic therapy; PGA -poly(glycolic acid); PGLA -poly(D,L-lactide-coglycolide); PLA -poly(lactic acid); PS -photosensitizer; PEG -polyethylene glycol; ALA  aminolevulinic acid; m-THPC  5,10,15,20-tetra-(m-hydroxyphenyl)chlorine; m-THPP  meso-tetra(p-hydroxyphenyl); PpIX  protoporphyrin; Hp  hematoporphyrin; Pc4  silicon phthalocyanine; Ig  immunoglobulin; Tf  transferrin; TfR  transferrin receptor; VEGF  vascular endothelial growth factor; EPR  enhanced permeability and retention effect; FRET  fluorescence resonance energy transfer; MRI  magnetic resonance imaging; RES  reticuloendothelial system; ROS  reactive oxygen species; NP  nanoparticle; ND -nanodiamonds; SNP  silica nanoparticle; AMD  age-related macular degeneration; CNV  choroidal neovascularization; PTT  photothermal therapy;

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Section: Additional Applicationsmentioning

confidence: 99%

Nanodrug applications in photodynamic therapy

Paszko

Ehrhardt

Senge

et al. 2011

Photodiagnosis and Photodynamic Therapy

322

215

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“…Porphyrins possess characteristic structural and photophysical properties that make them well suited for adaptation into artificial designs, not only for solar energy conversion but also for applications in photodynamic therapy (24)(25)(26)(27)(28)(29), enzyme mimics (30)(31)(32), catalysis (33)(34)(35)(36)(37), and molecular electronic devices (38,39). In the context of solar energy, many multiporphyrin light-harvesting designs have been developed ranging from organic polymers, metalorganic frameworks, and supramolecular ensembles.…”

mentioning

confidence: 99%

Synthesis and photophysical studies of self-assembled multicomponent supramolecular coordination prisms bearing porphyrin faces

Shi

Sánchez‐Molina

Cao

et al. 2014

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

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Multicomponent self-assembly, wherein two unique donor precursors are combined with a single metal acceptor instead of the more common two-component assembly, can be achieved by selecting Lewis-basic sites and metal nodes that select for heteroligated coordination spheres. Platinum(II) ions show a thermodynamic preference for mixed pyridyl/carboxylate coordination environments and are thus suitable for such designs. The use of three or more unique building blocks increases the structural complexity of supramolecules. Herein, we describe the synthesis and characterization of rectangular prismatic supramolecular coordination complexes (SCCs) with two faces occupied by porphyrin molecules, motivated by the search for new multichromophore complexes with promising light-harvesting properties. These prisms are obtained from the self-assembly of a 90°Pt(II) acceptor with a meso-substituted tetrapyridylporphyrin (TPyP) and dicarboxylate ligands. The generality of this self-assembly reaction is demonstrated using five dicarboxylate ligands, two based on a rigid central phenyl ring and three alkyl-spaced variants, to form a total of five free-base and five Zn-metallated porphyrin prisms. All 10 SCCs are characterized by 31 P and 1 H multinuclear NMR spectroscopy and electrospray ionization mass spectrometry, confirming the structure of each self-assembly and the stoichiometry of formation. The photophysical properties of the resulting SCCs were investigated revealing that the absorption and emission properties of the free-base and metallated porphyrin prisms preserve the spectral features associated with free TPyP. supramolecular chemistry | metallacages T he use of sunlight is ubiquitous as the input for carbonneutral, renewable energy schemes (1). Every strategy that relies on solar energy conversion, ranging from direct conversion to electricity in photovoltaics (2) to the generation of fuels via electrocatalysis (3), photoanode (4, 5), or photocathode devices (6), or photocatalysis (7) requires that photons be absorbed by a molecule or material as the first step in providing the driving force for subsequent transformation. Natural systems have evolved light-harvesting complexes, comprising multiprotein ensembles embedded with pigment molecules to enhance photon absorption for photosynthesis (8). These pigment-rich sites are arranged such that excitation of a distal chromophore will ultimately result in energy transfer to a reaction center via a series of migration and transfer processes (9). Strategies to replicate natural light-harvesting complexes necessarily demand the organization of multiple chromophores (10), a requirement that makes self-assembly and supramolecular chemistry particularly well suited for such efforts (11-13). As such, a variety of approaches have been applied toward the development of new materials that exhibit broadband absorption and efficient energy transfer (14-16). The subsequent studies of such materials span investigations of the fundamental science behind energy migration and transfer, t...

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“…Upon excitation with various concentrations of polymers, the very sharp B-band strictly followed the Lambert-Beer law, suggesting that aggregation was not significant for those polymers (Fig. 6B) [28,29].…”

Section: Self-assembly Behavior Of Spplgamentioning

confidence: 90%

Synthesis and Characterization of Star-Shaped Porphyrin-cored Poly(Glutamic Acid) Conjugates as Highly Efficient Photosensitizers

Dai

Yang

et al. 2016

J. Photopol. Sci. Technol.

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Photodynamic therapy (PDT) has drawn wide attention in intensive preclinical and clinical cancer therapy due to its noninvasive nature. A simple and facile synthesis of highly efficient delivery system for photosensitizers (PS) with visualized tumor environment is hence critical. Herein, a simple, safe and promising fluorescent probe, star-shaped poly(glutamic acid) with a porphyrin core (SPPLGA) was synthesized via ring-opening polymerization of β-benzyl-L-glutamate N-carboxyanhydride monomer with 5, 10, 15, 20-tetrakis-(4-aminophenyl)-21H, 23H-porphyrine (TAPP) as the initator, followed by the deprotection of benzyl groups on poly(benzyl-L-glutamate). The structure of this novel polymer was thoroughly studied by Nuclear magnetic resonance spectroscopy(NMR), Gel permeation chromatography (GPC) and Fourier transform infrared spectroscopy (FT-IR). Such star-shaped poly(glutamic acid) with porphyrin core could self-assemble into micelles in aqueous solution and exhibit pH-sensitive critical micelle concentration. It was observed that with the decrease in pH, the fluorescence intensity of the SPPLGA increased. On the other hand, the incorporation of poly(glutamic acid) not only improved solubility of porphyrin in water, but also enhanced the production efficiency of the singlet oxygen (about double that of porphyrin). Those results suggest that these polymer, as promising pH-responsive and tumor-selective photosensitizers, are very promising for PDT and can potentially be used as "theranostics" for future cancer prognosis and therapeutic planning.

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Synthesis and cellular uptake of porphyrin decorated iron oxide nanoparticles—a potential candidate for bimodal anticancer therapy

Abstract: This paper reports the synthesis, characterization, and cellular uptake of the conjugate of porphyrin and iron oxide nanoparticles, which may lead to a bimodal anticancer agent that can be used in the combinational treatment of photodynamic therapy (PDT) and hyperthermia therapy (HT).

Cited by 180 publications

References 25 publications

Nanodrug applications in photodynamic therapy

Nanodrug applications in photodynamic therapy

Synthesis and photophysical studies of self-assembled multicomponent supramolecular coordination prisms bearing porphyrin faces

Synthesis and Characterization of Star-Shaped Porphyrin-cored Poly(Glutamic Acid) Conjugates as Highly Efficient Photosensitizers

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