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WIREs Nanomed Nanobiotechnol
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Recent applications of phthalocyanines and naphthalocyanines for imaging and therapy

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With high extinction coefficients and long absorption wavelengths in the near infrared region, phthalocyanines (Pcs) and naphthalocyanines (Ncs) are well‐suited for optical imaging and phototherapies in biological tissues. Pcs and Ncs have been used in a range of theranostic applications. Peripheral and axial substituents can be introduced to Pcs and Ncs for chemical modification. Seamless metal chelation of Pcs or Ncs can expand their possibilities as medical therapeutic and imaging agents. Nanoparticulate approaches enable unique ways to deliver Pcs and Ncs to target tissues and improve their solubility, biocompatibility, biodistribution and stability. Herein, we highlight some recent Pc or Nc nanoscale systems for theranostic applications. WIREs Nanomed Nanobiotechnol 2017, 9:e1420. doi: 10.1002/wnan.1420 This article is categorized under: Therapeutic Approaches and Drug Discovery > Emerging Technologies Diagnostic Tools > In Vivo Nanodiagnostics and Imaging Nanotechnology Approaches to Biology > Nanoscale Systems in Biology
Chemical structure of (a) porphyrins (b) phthalocyanines, and (c) naphthalocyanines. (d) Simplified Jablonski diagram showing some possible activated singlet oxygen deactivation pathways. PS and ROS represent photosensitizers and reactive oxygen species, respectively. Green and red indicate ground and excited state photosensitizers, respectively.
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(a) Schematic illustration of axial conjugation of CD to SiPc, (b) Tumor growth delay after PDT treatment with conjugates. Illumination with laser light (30 J/cm2) was applied for the PDT. (Reprinted with permission from Ref Copyright 2011 Royal Society of Chemistry)
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Tumor treatment using dendrimer Pc encapsulated micelles. (a) Chemical structure of anionic dendrimer phthalocyanine (DPc). (b) DPc encapsulated polyion complex micelle (DPC/m) was formed by mixing DPc and PEG‐PLL. (c) Growth curves of subcutaneous A549 tumors in control mice and mice administered with 0.37 µmol/kg DPc, 0.37 µmol/kg DPc/m, and 2.7 µmol/kg PHE (n = 6). (d) DPc/m is safe to skin (top left) and liver (bottom left) whereas PHE‐induced phototoxicity to skin (top right) and liver (bottom right). 24 hours after administration of photosensitizing agents, the tumors were photoirradiated using a diode laser (fluence: 100 J/cm2). (Reprinted with permission from Ref Copyright 2009 Elsevier)
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Phototherapy of Pc encapsulated hollow silica nanoparticles. (a) Representative photos showing tumor treatment outcome of different groups, treated with saline, laser, [email protected] alone and [email protected] + laser, respectively. Scale bar: 2 cm. (b) Relative tumor volumes of four different groups. (c) Survival curves of four different groups treated as indicated. (Reprinted with permission from Ref Copyright 2013 Elsevier)
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Optical imaging (a) in vivo and (b) fluorescence dissected of dissected organs with lactose substituted Zinc Pc. Liver cancer bearing mice injected with 200 μL of 2 × 10−4 mol/L: excitation 625 nm, emission 700 nm. (Reprinted with permission from Ref Copyright 2013 ScienceDirect)
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In vivo photoacoustic images showing transverse slices of tumor‐bearing mice (a) oxygenated hemoglobin (HbO2) and deoxygenated hemoglobin (Hb) signals were acquired before injection of PcS4, showing the endogenous contrast between the different organs, the red signal represents HbO2 while the blue signals represent Hb in the color bar which is normalized within individual deoxygenated and oxygenated hemoglobin signals to give 0–100% scale. Phthalocyanine PA signals at various time points after tail‐vein administration of (b) PcS4 (c) ZnPcS4 and (d) AlPcS4. Background PA signal from the tissues were acquired at 900 nm laser wavelength with the dashed red lines delineating tumor tissue. (Reprinted with permission from Ref Copyright 2015 The Optical Society)
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Photoacoustic images of a mouse bearing a HT29 tumor before and after intravascular injection of SiNc. Greyscale background is overlaid with the signal from SiNc (hot scale). (a) Pre‐injection image, indicating tumor (dashed white circle) and surrounding blood vessels (BV, dotted red circles), overlaid with deoxygenated (blue scale) and oxygenated (red scale) hemoglobin signal. (b–f) Images acquired after 5 (B), 15 (C), 30 (D), 45 (E), 60 (F) minutes after intravenous injection of SiNc in a tumor‐bearing animal. (Reprinted with permission from Ref Copyright 2015 Society of Nuclear Medicine and Molecular Imaging)
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Noninvasive and multimodal imaging using surfactant‐stripped nanoformulated naphthalocyanines (nanonaps). (a) Schematic illustration of nanonaps. PEO, PPO, Nc dyes are in blue, black and red, respectively. (b) Normalized absorbance of nanonaps formed from BPc (blue), ZnBNc (dark green), BNc (light green), or ONc (bronze). (c) Photographs of nanonaps in water, from left to right: BPc, ZnBNc, BNc, ONc. (d) Depth encoded PA MIP (maximum intensity of projection) of the intestine visualizing ZnBNc nanonaps. (e) Nanonaps labeling using 64Cu, Pluronic F127 PEO blocks, PPO blocks and Nc dye are in blue, black, and red, respectively and 64Cu is shown as the radioactive yellow circle. (f) Representative PET imaging of nanonaps delineating stomach and intestine. BPc, 2,9,16,23‐tetra‐tert‐butyl‐29H, 31H‐phthalocyanine; ZnBNc, Zinc‐2,11,20,29‐tetra‐tert buyl‐2,3, naphthalocyanine; BNc, 2,11,20,29‐tetra‐tert buyl‐2,3, naphthalocyanine and ONc, 5,9,14,18,23,27,32,36‐octabutoxy‐2,3,‐naphthalocyanine. (Reprinted with permission from Ref Copyright 2014 Nature Publishing Group).
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Chemical structures of some polymers used as Pc and Nc carriers. (a) Poly (ethylene glycol)‐block‐poly caprolactone (PEG‐PCL). (b) 1,2 distearoyl‐sn‐glycero‐3‐phosphoethanolamine‐N‐[methoxy(polyethylene glycol)‐2000]. (DSPE‐PEG2000). (c) Poly [2‐methoxy‐5‐(2‐ethylhexyloxy)‐1,4‐phenylenevinylene] (MEH‐PPV). (d) Carboxyl polystyrene‐graft‐ethylene oxide, PS‐PEG‐COOH. (e) Pluronic block copolymer, m = 100, n = 65 for Pluronic F127.
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