Synthesis and photodynamic potential of tetra- and octa-triethyleneoxysulfonyl substituted zinc phthalocyanines

Atílla, Devrim; Saydan, Nil; Durmuş, Mahmut; Gürek, Ayşe Gül; Khan, Tania; Rück, Angelika; Walt, Heinrich; Nyokong, Tebello; Ahsen, Vefa

doi:10.1016/j.jphotochem.2006.08.022

Cited by 72 publications

(35 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…7,8 The biggest hurdle for most photosensitizers, including ZnPc, for PDT is the low physiological acceptance level owing to their high hydrophobic characteristics responsible for the poor solubility in a bodily fluid. To overcome this problem, ZnPc derivatives, such as tetrasulfonated ZnPc (ZnPcS 4 ), 9 [1,2,3,4-tetrakis(a/b-Dgalactopyranos-6-yl)-phthalocyaninato]zinc, 10 tetra-and octatriethyleneoxysulfonyl substituted ZnPc, 11 have been designed to increase the water solubility. Various delivery vehicles including liposome, 12 emulsion 13 and nanoparticles 14 have also been developed to transport water-insoluble photosensitizers to targets.…”

Section: Introductionmentioning

confidence: 99%

Significant increase in the water dispersibility of zinc phthalocyanine nanowires and applications in cancer phototherapy

et al. 2012

View full text Add to dashboard Cite

The phototherapy is one of the widely accepted noninvasive clinical methodologies to eradicate cancer cells owing to its minimal side effects and high selectivity to the light of specific wavelength. As represented by photodynamic (PD) and photothermal (PT) therapy, the phototherapy requires light and photosensitizer to generate reactive oxygen species and heat, respectively. Zinc phthalocyanine (ZnPc) is one of the promising photosensitizers as it has a strong absorption cross-section in the spectral range of 650-900 nm that guarantees maximum tissue penetration. One critical issue in using Pc molecule, including ZnPc as a biocompatible sensitizer is the poor water solubility. To increase water solubility, various chemical modifications inducing hydrophilicity have been widely attempted to introduce various functional groups in the ZnPc backbone. We report that ZnPc nanowires (NWs) directly grown from ZnPc powder by vaporization-condensation-recrystallization process show surprisingly increased water dispersibility without any functionalization. The ZnPc NW solution exhibits highly efficient dual PD and PT effects upon the irradiation of near infrared (808 nm) laser. The dual phototherapeutic effect of ZnPc NW is proven to enhance cytotoxic efficiency according to both in vitro and in vivo experimental results. NPG Asia Materials (2012) 4, e12; doi:10.1038/am.2012.22; published online 13 April 2012Keywords: nanowire; photosensitizer; phototherapy; Zinc phthalocyanine INTRODUCTION Phototherapy, represented by photodynamic therapy (PDT) and photothermal therapy (PTT), is an advanced modality for the treatment of malignant tumors as it is widely used for clinical cancer treatments. PDT selectively destroys neoplastic lesions using cytotoxic reactive oxygen species (ROS) generated by light activation of the photosensitizer. 1,2 One of the crucial factors determining the PDT efficacy is the photochemical and photophysical properties of the photosensitizer. 3,4 Currently, four main classes of photosensitizer, such as porphyrin derivatives, chlorins, porphycenes, and phthalocyanines (Pcs), have been approved by the U.S. Food and Drug Administration (FDA) for clinical applications against cancer. 5,6 Among these, metallo-phthalocyanine has attracted considerable interest, having a photodynamic (PD) property that can be readily tuned by the type of central metal ion and the functional groups introduced as a Pc ring substituent. Zinc phthalocyanine (ZnPc) is known to exhibit a high PD effect as it possesses a diamagnetic Zn(II) central metal ion whose d shell is fully occupied, by which the yield of triplet excited state with long lifetime essential for the generation of ROS becomes high. 7 Moreover, ZnPc has

show abstract

Section: Introductionmentioning

confidence: 99%

Significant increase in the water dispersibility of zinc phthalocyanine nanowires and applications in cancer phototherapy

et al. 2012

View full text Add to dashboard Cite

show abstract

“…Our previous studies have already reported synthesis, photophysical and photochemical properties of various substituted phthalocyanines [21][22][23][24][25]. These phthalocyanine complexes show interesting photophysical and photochemical properties especially high singlet oxygen quantum yields which are very important for PDT of cancer.…”

Section: Introductionmentioning

confidence: 99%

Photophysical, photochemical and aggregation behavior of novel peripherally tetra-substituted phthalocyanine derivatives

Saka

Göl

Durmuş

et al. 2012

Journal of Photochemistry and Photobiology A: Chemistry

Self Cite

View full text Add to dashboard Cite

“…Design of the effective PS with a poor aggregation ability is the other important factor for increasing efficacy of treatment 10 . In the last few years many efforts are made in respect to the synthesis of Pcs with adequate to PDT aplication properties 11,12,13 . The Aeromonas hydrophilia species are ubiquitous in nature and can cause diseases in fish, reptiles, amphibians, and humans.…”

Section: Introductionmentioning

confidence: 99%

Improved antimicrobial therapy with cationic tetra- and octa-substituted phthalocyanines

et al. 2008

View full text Add to dashboard Cite

Photodynamic therapy (PDT) today is an innovative and not yet widespread light-drug initiated treatment that is based on the photoactive compound irradiated with proper light to produce oxygen species that are toxic to the pathogenic biological objects-bacteria, viruses, tumor cells. The obstacles that limited the efficacy of PDT concern to the selectivity and multi-drug resistance prolong time for cellular release and side effects of skin photosensitivity for commercial porphyrin originated photosensitizers (PS). Now there are very intensive investigations for introducing in practice a new, with a least side effects PSs for PDT. The usefulness of the more extended macromolecules structured with proper substituents refers not only to the improved optical properties like far-red and with intensive absorption and emission capacity, but mainly to the ability for selective delivery and adhesion to the target cells, such as bacteria or other pathogens. The present study focuses on the charge effect of photodynamic agent on the uptake capacity toward gram-negative bacteria cells and their further photoinactivation. The multi-drug resistant microorganism Aeromanas hydrophilla, which is causing diseases to fishes and humans, is treated. The new octa-cationic phthalocyanines are designed to compare PDT efficacy to the efficacy of tetra-substituted derivatives with the same functional peripheral substituents. The higher cellular accumulation to the bacteria cells as a result of the high number of positive charges of photosensitizer, leading to the better adhesion to the cellular membranes and improved photoinactivation of bacteria causing superficial and intraorgan infections. These results set a base of a rationale design of covalently octa-substituted phthalocyanines with positive charge for a successful treatment of microorganisms.

show abstract

Synthesis and photodynamic potential of tetra- and octa-triethyleneoxysulfonyl substituted zinc phthalocyanines

Cited by 72 publications

References 35 publications

Significant increase in the water dispersibility of zinc phthalocyanine nanowires and applications in cancer phototherapy

Significant increase in the water dispersibility of zinc phthalocyanine nanowires and applications in cancer phototherapy

Photophysical, photochemical and aggregation behavior of novel peripherally tetra-substituted phthalocyanine derivatives

Improved antimicrobial therapy with cationic tetra- and octa-substituted phthalocyanines

Contact Info

Product

Resources

About