Synthesis and Cellular Studies of Nonaggregated Water-Soluble Phthalocyanines

Liu, Wei; Jensen, Timothy J.; Fronczek, Frank R.; Hammer, Robert P.; Smith, Kevin M.; Vicente, M. Graça H.

doi:10.1021/jm049375b

Cited by 146 publications

(66 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…On the other hand, it is also possible that the localization of Si(sol) 2 Pc in lipid droplets is not the prime reason for its high phototoxicity, because redistribution of this compound over the cytosol was observed upon illumination (Figure 5c). Similar behavior has been found by Liu et al 51 who observed that PSs, that is, ZnPc derivatives containing carboxylate groups accumulated in lysosomes and redistributed upon brief light exposure. Redistribution of Si(sol) 2 Pc may be due to the destruction of the lipid droplets by ROS.…”

Section: Discussionsupporting

confidence: 87%

Peripheral and Axial Substitution of Phthalocyanines with Solketal Groups: Synthesis and In Vitro Evaluation for Photodynamic Therapy

et al. 2007

View full text Add to dashboard Cite

Phthalocyanines (Pcs) are a class of photosensitizers (PSs) with a strong tendency to aggregate in aqueous environment, which has a negative influence on their photosensitizing ability in photodynamic therapy. Pcs with either peripheral or axial solketal substituents, that is, ZnPc(sol) 8 and Si(sol) 2 Pc, respectively, were synthesized and their tendency to aggregate as well as their photodynamic properties in 14C and B16F10 cell lines were evaluated. The results were compared to more hydrophilic silicon Pcs, that is, Si(PEG750) 2 Pc and Pc4. The order of cellular uptake was Pc4 > ZnPc(sol) 8 > Si(PEG750) 2 Pc > Si(sol 2 )Pc. In contrast, Si(sol 2 )Pc showed the highest photocytotoxicity, while ZnPc(sol) 8 did not show any photocytotoxicity up to a concentration of 10 µM in both cell types. UV/vis spectroscopy showed that Si(sol) 2 Pc is less prone to aggregation than ZnPc(sol) 8 , which can explain the lack of photoactivity of the latter. Si(sol) 2 Pc was predominantly located in lipid droplets, whereas Si(PEG750) 2 Pc was homogeneously distributed in the cytosol, which is probably the main cause of their difference in photoactivity. The very high photodynamic efficacy of Si(sol) 2 Pc makes this PS an interesting candidate for future studies.

show abstract

Section: Discussionsupporting

confidence: 87%

Peripheral and Axial Substitution of Phthalocyanines with Solketal Groups: Synthesis and In Vitro Evaluation for Photodynamic Therapy

et al. 2007

View full text Add to dashboard Cite

show abstract

“…Compared to the traditional synthetic route using 4-nitrophthalonitrile, a higher yield was obtained by the substitution reaction of the hydroxyl compound with 4-chlorophthalonitrile. Substitution reactions are a common synthetic route for the water-soluble zinc phthalocyanines [38]. In our prior study, water-soluble glucose conjugated zinc phthalocyanines were prepared in high yield by this route [32].…”

Section: Resultsmentioning

confidence: 99%

Zinc Phthalocyanine Labelled Polyethylene Glycol: Preparation, Characterization, Interaction with Bovine Serum Albumin and Near Infrared Fluorescence Imaging in Vivo

Cao

Cui

et al. 2012

Molecules

View full text Add to dashboard Cite

Zinc phthalocyanine labelled polyethylene glycol was prepared to track and monitor the in vivo fate of polyethylene glycol. The chemical structures were characterized by nuclear magnetic resonance and infrared spectroscopy. Their light stability and fluorescence quantum yield were evaluated by UV-Visible and fluorescence spectroscopy methods. The interaction of zinc phthalocyanine labelled polyethylene glycol with bovine serum albumin was evaluated by fluorescence titration and isothermal titration calorimetry methods. Optical imaging in vivo, organ aggregation as well as distribution of fluorescence experiments for tracking polyethylene glycol were performed with zinc phthalocyanine labelled polyethylene glycol as fluorescent agent. Results show that zinc phthalocyanine labelled polyethylene glycol has good optical stability and high emission ability in the near infrared region. Imaging results demonstrate that zinc phthalocyanine labelled polyethylene glycol can track and monitor the in vivo process by near infrared fluorescence imaging, which implies its potential in biomaterials evaluation in vivo by a real-time noninvasive method.

show abstract

“…It is worth noting that the inclusion of the NLS signal in the peptide did not direct the ZnPc into the nucleus, as observed also for other PSs studied by the same group. However it was hypothesized a possible release of the conjugates from the lysosomes during irradiation and subsequent relocalization in cellular sites more sensitive to light induced oxidative stress like the nucleus [83][84][85].…”

Section: Photosensitizers Conjugated To Peptidesmentioning

confidence: 99%

Strategies for optimizing the delivery to tumors of macrocyclic photosensitizers used in photodynamic therapy (PDT)

Moret

Reddi

2017

J. Porphyrins Phthalocyanines

View full text Add to dashboard Cite

This review briefly summaries the principles and mechanisms of action of photodynamic therapy (PDT) as concerns its application in the oncological field, highlighting its drawbacks and some of the strategies that have been or are being explored to overcome them. The major aim is to increase the efficiency and selectivity of the photosensitizer (PS) uptake in the cancer cells for optimizing the PDT effects on tumors while sparing normal cells. Some attempts to achieve this are based on the conjugation of the PS to biomolecules (small ligands, peptides) functioning as carriers with the ability to efficiently penetrate cells and/or specifically recognize and bind proteins/receptors overexpressed on the surface of cancer cells. Alternatively, the PS can be entrapped in nanocarriers derived from various types of materials that can target the tumor by exploiting the enhanced permeability and retention (EPR) effects. The use of nanocarriers is particularly attractive because it allows the simultaneous delivery of more than one drug with the possibility of combining PDT with other therapeutic modalities.

show abstract

Synthesis and Cellular Studies of Nonaggregated Water-Soluble Phthalocyanines

Cited by 146 publications

References 58 publications

Peripheral and Axial Substitution of Phthalocyanines with Solketal Groups: Synthesis and In Vitro Evaluation for Photodynamic Therapy

Peripheral and Axial Substitution of Phthalocyanines with Solketal Groups: Synthesis and In Vitro Evaluation for Photodynamic Therapy

Zinc Phthalocyanine Labelled Polyethylene Glycol: Preparation, Characterization, Interaction with Bovine Serum Albumin and Near Infrared Fluorescence Imaging in Vivo

Strategies for optimizing the delivery to tumors of macrocyclic photosensitizers used in photodynamic therapy (PDT)

Contact Info

Product

Resources

About