The synthesis path of metallated phthalocyanine photosensitizers used in this paper are. Metal phthalocyanine as photosensitizer for photodynamic therapy pdt preparation, characterization and anticancer activities of an amphiphilic phthalocyanine znpcs 2 p 2 authors. Photodynamic therapy pdt has emerged as an effective and minimally invasive cancer treatment modality. Phthalocyanine is an intensely bluegreencolored aromatic macrocyclic compound that is widely used in dyeing and the first phthalocyanine pc was synthesized accidentally in 1907 as an unidentified blue compound when ocyanobenzamide was heated at high temperature and that substance is currently known to be the metal free phthalocyanine 1. Phthalocyanine h 2 pc is a large, aromatic, macrocyclic, organic compound with the formula c 8 h 4 n 2 4 h 2 and is of theoretical or specialized interest. In this study, a combination of pdt mediated by a metal substituted phthalocyaninegallium phthalocyanine chloride gapc and metformin was used against melanoma. It is a tetrapyrrole fundamental parent and a member of phthalocyanines. Porphyrins and phthalocyanines as photosensitizers. The use of pdt against cl is a technology with potential application, safe and accessible montanari et al 2010, and is an attractive alternative to traditional antimicrobial therapy, since it does not induce resistance montanari et al 2010. A series of sulfonated s phthalimidomethyl p zinc phthalocyanines pc was synthesized in a reaction, in which both kinds of substituents were introduc. A smart copperphthalocyanine framework nanoparticle for.
Phthalocyanine h2pc is a large, aromatic, macrocyclic, organic compound with the formula c 8 h 4 n 2 4 h 2 and is of theoretical or specialized interest. Further metal phthalocyanines were characterized by uvvisible spectroscopy and the observed data matches with the data reported in the. Synthesis, characterization, electrochemistry, and. An efficient twostep synthesis of metalfree phthalocyanines. In the present study, two novel phthalocyanines, tetra.
The use of phthalocyanines in cancer therapy aip publishing. Metal phthalocyanine pdf presentation photoshop cs4 tetrasulfonic acids, pdflib page size metal phthalocyanine. Luedtkea a institute of organic chemistry, university of zurich, winterthurerstrasse 190, ch8057. Materials science organic and printed electronics photonic and optical materials phthalocyanine and porphyrin dyes phthalocyanines. Galliumiiiphthalocyanine chloride dye content 97 %. Indiumiii phthalocyanine chloride dye content 90 %. The hydrophilic mpc, tetrasulfonic acid tetrasodium salt copper phthalocyanine tscupc, is coated on the surface of swnhs via noncovalent. Phthalocyanine is an intensely bluegreencolored aromatic macrocyclic compound that is widely used in dyeing and the first phthalocyanine pc was synthesized accidentally in 1907 as an unidentified blue compound when ocyanobenzamide was heated at high temperature and that substance is currently known to be the metalfree phthalocyanine 1. Watersoluble aluminium phthalocyaninepolymer conjugates. Pc 4 is absorbed into the epidermis in as little as 1 hour and the absorption increased with increasing time and dose. The very important blue pigment copper phthalocyanine is a tetraazatetrabenzoporphin and the basic polyene chromogen of the molecule is as in 119, which has an azaannulene type ring. The potential use of unsubstituted aluminium phthalocyanine alclpc as a sensitizer for photodynamic therapy pdt of cancer has not been fully exploited in spite of its higher efficiency as compared to the sulphonated derivatives. Synthesis and spectral and thermal characterization of new.
Photodynamic therapy with the phthalocyanine photosensitizer pc 4. The results show that one of the five separating parts with formula of znpcs 2 p 2 exhibited rather good pdt activity. In a typical treatment of pdt, the patient receives an injection of the photosensitizer and waits for a short. The pdt thera peutic procedure is based on activating photoactive reagents, i. Combined regimen of photodynamic therapy mediated by. This chapter will focus on macrocycles porphyrins and phthalocyanines as potential photosensitizers for the treatment of melanoma by photodynamic therapy. Advances in technology are opening novel avenues for discovery of compounds that will mitigate the everincreasing drugresistant microbes. The biomedical applications of carbon nanomaterials, especially integrating noninvasive photothermal therapy ptt and photodynamic therapy pdt, into a single system have enormous potential in cancer therapy.
Upon testing, inpc has shown a relatively high singlet oxygen quantum yield within the cells subjected to pdt 0. Metal free phthalocyanine has at least four polymorphs. The compound was further characterized by nmr, ms and thermal analysis. Pdf studies about phthalocyanine photosensitizers to be used in. Biotinylatedcationic zincii phthalocyanine towards. The q band of the metalfree phthalocyanine 2 was observed as 2 split bands at max 668 and 705 nm as expected due to d2h symmetry. The high photodynamic inactivation was shown with the complexes of znii, gaiii and siiv towards most model pathogenic strains, which suggested the efficiency in. Synthesis, characterization and photocatalytic studies of. Antimicrobial photodynamic activity of phthalocyanine. Phthalocyanines as sensitizers for photodynamic therapy of cancer. Other macrocycles for pdt of melanoma and concluding remarks. Toxicological and efficacy assessment of posttransition.
Phthalocyanines as photosensitizers in the photodynamic therapy. Photodynamic therapy pdt of neoplasms using photosensitizers and red light. Combined regimen of photodynamic therapy mediated by gallium. The interest for glycosylated metal phthalocyanines was stimulated by comparing the extensive work on glycosylated porphyrins with the almost unknown phthalocyanine counterparts and their application in pdt. Consequently, there has been extensive research focusing mainly on the design of pss with optimized pharmaceutical properties and. The fluorination of ptype metal phthalocyanines produces ntype semiconductors, allowing the design of organic electronic circuits that contain.
Metalorganic molecules have been explored for their applications in optoelectronics 1,2 and spintronics 3,4,5,6,7,8. Sep 30, 2019 phthalocyanine plural phthalocyanines organic chemistry any of a family of macrocyclic compounds having a structure similar to that of porphyrin. Porphyrin and phthalocyanine photosensitizers as pdt agents. Scientific research and development supplier details. This treatment involves either local or systemic administration of a. A short description of the photodynamic therapy as an alternative cancer. Dec 12, 2016 metal organic molecules have been explored for their applications in optoelectronics 1,2 and spintronics 3,4,5,6,7,8. Atp in the above complex could be destroyed by a copper.
Soluble metalfree and metal copper ii, iron iii, and cobalt ii phthalocyanine tetracarboxylic acids 58 were synthesized using a novel method consisting of improved hydrolysis based on the diazo reaction. Journal of porphyrins and phthalocyanines vol 17, no 06n07. In case of phthalocyanines, the role of central metal in determining austin biomol open access 12. The reaction was removed from the heat, and 10 ml of h2o was used to transfer the hot mixture. Metal phthalocyanine as photosensitizer for photodynamic therapy.
For the metal phthalocyanine, electronic transition to the s 1 state 1 a 1u e g gives rise to a single q band where the a 1u and e g orbitals denote the homo. Douglas p, harriman a, porter g, richoux mc 1982 metal phthalocyanines. Carboxylation is a promising way to prepare watersoluble metal phthalocyanines mpccs and facilitates the cellular uptake of mpccs for pdt improvement. The present work is focussed on the principles of photodynamic therapy pdt, emphasizing the. Photoirradiation of the silicon phthalocyanine 4 photosensitizer with red light generates singlet oxygen and other reactive oxygen species to induce cell death. Synthesis and characterization of novel derivatives of. Pdf a short description of the photodynamic therapy as an alternative cancer. Pdf the present work is focussed on the principles of photodynamic. The obtained compounds 58 were characterized by xray diffraction, uvvis spectrometry, and ftir spectrometry and then utilized as catalysts for the epoxidation of. Antimicrobial photodynamic activity of phthalocyanine derivatives. Ruthenium phthalocyanines novel water soluble agents for photodynamic cancer therapy by m.
The porphyrins functionalized with ptii were the first metalporphyrin. An updated overview on the development of new photosensitizers. Our study focuses on the dark toxicity testing of a chloroindiumphthalocyanine photosensitizer inpc upon shsy5y neuroblastoma cell line and its experimental in vitro pdt. Photodynamic therapy, based on the photoactivation of photosensitizers ps, has. Phthalocyanines have several polymorphic forms, and the crystal structures of metalfree and various metal derivatives are different. Mpc complexes have been proved as highly promising photosensitizers for pdt due to their intense absorption in the red region of the visible. Synthesis and photodynamic activity of novel asymmetrically. In phthalocyanine ring system and part of the atom numbering system, the 2,3,9,10,16,17,23,24 positions are referred to as the peripheral sites. In terms of structure, phthalocyanines are similar to natural porphyrins as hemoglobin, chlorophyll and vitamin b12. Herein, we present a novel and facile onestep method for the preparation of watersoluble singlewalled carbon nanohorns swnhs and metal phthalocyanines mpc hybrid for ptt and pdt.
Phthalocyanine is a tetrapyrrole fundamental parent that consists of four isoindole type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen. Photodynamic therapy pdt might represent an adjuvant treatment, because of its bimodal action. The newly prepared metal free phthalocyanine and its zincii counterpart are soluble in most organic solvents. Microbial pathogens have increasingly shown multidrug resistance posing a serious threat to the public health. The separation of regioisomers of metal phthalocyanines.
Sublimation at low pressures on to substrates maintained at room temperature generally yields the metastable. Phthalocyanine definition is a bright greenishblue crystalline compound c32h18n8. Onestep preparation of a watersoluble carbon nanohorn. It has been shown to induce favorable responses in the treatment of cutaneous squamous cell and basal cell carcinomas, as well as cancers of the head, neck, lung, esophagus, and bladder 3, 4. Journal of coordination chemistry 2008, 61 10, 15031512. Pdt using zinc phthalocyanine znpc in liposomes pre. Phthalocyanines containing one or two metal ions are called metal phthalocyanines. Design, synthesis and photophysicochemical properties ayoub i. Spin doping using transition metal phthalocyanine molecules. A spectroscopic study of the interaction of octacarboxylic metal phthalocyanine with bovine serum albumin. The present invention is the dividing an application of chinese patent application 02821738. Photodynamic therapy pdt is emerging as a promising noninvasive treatment for cancers 1, 2.
The q band of the metal free phthalocyanine 2 was observed as 2 split bands at max 668 and 705 nm as expected due to d2h symmetry. Watersoluble aluminium phthalocyaninepolymer conjugates for. Phthalocyanines have several polymorphic forms, and the crystal structures of metal free and various metal derivatives are different. Metalfree phthalocyanine has at least four polymorphs. The series of metal phthalocyanine complexes of znii, aliii, gaiii, iniii, siiv, geiv were synthesized and investigated as antimicrobial photodynamic agents. The synthesis of single and doubledecked anthracenyl functionalized rutheniumii phthalocyanine complexes has been achieved through a controlled electrophilic aromatic substitution reaction of the free unsubstituted rutheniumii phthalocyanine with preformed 9bromo102,3dimethylacrylic acidanthracene andor 9bromo102,3dimethylacrylic aciddianthracene using 1,8diazabicyclo5. It is composed of four isoindole units linked by nitrogen atoms.
In situ monitoring of the complexation of metalfree phthalocyanine via uvvis and fluorescence techniques in this study, the complexation reaction taking place between metalfree phthalocyanine nhth 2 pc and mnoac 2 could easily be monitored by uvvis spectrophotometer. Synthesis, characterization and photocatalytic studies of some metal. Silicon phthalocyanine 4, also known as pc4, is a drug potentially for the treatment of cutaneous neoplasms. Several structural factors influenced on the pdt activities were discussed. Pdf metallophthalocyanines due to their photophysical characteristics as high yield of triplet state and long lifetimes, appear to be good candidates. Phthalocyanine is of course closely related to the highly coloured porphyrins which are classed as polyene chromogens, and contain no donor or acceptor groups. Improved synthesis of soluble metalfreemetal phthalocyanine. Porphyrin and phthalocyanine photosensitizers as pdt. Akc261 26 name product identifier % ghsus classification copperii phthalocyanine cas no 147148 95 100 not classified 3. Copperii phthalocyanine safety data sheet 06142016 en english us sds id. Alraqa 1, 1 department of chemistry, taibah university, almadinah al munawrah, p. Sublimation at low pressures on to substrates maintained at room temperature generally.
H 2 pc has a twodimensional geometry and a ring system consisting of 18. Metal phthalocyanine mpc complexes in particular assume a prominent. Phthalocyanine definition of phthalocyanine by merriam. Use of photodynamic photosensitizer is one of the promising alternative approaches since they offer low risk of bacteria resistance as they use. Photodynamic therapy pdt has been clinically approved for the use as a minimally invasive therapeutic modality relevant to its selective destruction of cancer cells with little or no dark toxicity 1. Dec 19, 2014 the fluorination of ptype metal phthalocyanines produces ntype semiconductors, allowing the design of organic electronic circuits that contain inexpensive heterojunctions made from chemically.
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