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Phthalocyanines: from Dyes to Photosensitizers in Diagnostics and Treatment of Cancer

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Phthalocyanines: from Dyes to Photosensitizers in Diagnostics and Treatment of Cancer Phthalocyanines: From Dyes to Photosensitizers in Diagnostics and Treatment of Cancer. Spectroscopy and Raman Imaging Studies of Phthalocyanines in Human Breast Tissues Beata Brozek-Pluska1 Marek Orlikowski2 Halina Abramczyk1* 1Lodz University of Technology, Faculty of Chemistry, Institute of Applied Radiation Chemistry, Laboratory of Laser Molecular Spectroscopy, Wroblewskiego 15, 93-590 Lodz, Poland. 2Lodz University of Technology, Faculty of Electrical, Electronic, Computer and Control Engineering, Institute of Electrical Power Engeneering, Instrument Transformers and EMC Division, Stefanowskiego 18/22, 90-924 Lodz, Poland. *Corresponding Author: Halina Abramczyk e-mail: [email protected] Table of contents List of abbreviations ............................................................................................................................ 2 I. Introduction ................................................................................................................................. 3 II. Synthesis, Materials and Experimental Methods ............................................................................ 6 A. Synthesis .................................................................................................................................. 6 B. Patients and Samples ............................................................................................................... 8 C. Raman spectroscopy and imaging ........................................................................................... 8 D. Pump-probe transient absorption spectroscopy ..................................................................... 12 III. UV-vis Absorption Spectroscopy of Phthalocyanines ................................................................ 13 IV. IR spectroscopy of phthalocyanines films .................................................................................. 20 V. Raman Spectroscopy of Phthalocyanines ..................................................................................... 26 VI. Raman Imaging of Phthalocyanines in Human Breast Tissue .................................................... 33 VII. Femtosecond Spectroscopy of Phthalocyanines ........................................................................ 47 VIII. Concluding Remarks ................................................................................................................ 57 IX. References ................................................................................................................................... 58 1 List of abbreviations RI - Raman imaging PDD - Photodynamic diagnostics PDT - Photodynamic therapy PS – photosensitizer ISC - intersystem crossing ZnPcS4 - zinc tetrasulfonated phthalocyanine tetrasodium salt AlPcS4 (salt)– aluminum tetrasulfonated phthalocyanine tetrasodium salt AlPcS4 (acid)– aluminum phthalocyanine chloride tetrasulphonic acid NA - numerical aperture UHTS - Ultra High Throughput Spectrometer VB - vibronic band ZnPc - zinc phthalocyanine AlPc - aluminum phthalocyanine TERS – tip enhanced Raman spectroscopy STED microscopy – stimulated emission depletion microscopy SERS – surface enhanced Raman spectroscopy [AlPcN(4)] - tetra-substituted cationic aluminum phthalocyanine PCR– polymerase chain reaction Her2 – human epidermal growth factor receptor 2 FPPTAS – femtosecond pump-probe transient absorption spectroscopy ESA - excited state absorption 2 I. Introduction Cancer has become a major cause of mortality. In 2012 there were an estimated 14.1 million new cases of cancer in the world1, and for this reason there is a considerable interest in the development of new techniques allowing noninvasive diagnosis and tracking of the progress of therapies used to treat a cancer. Cancer is a multi-factorial disease that demonstrates various mechanisms and phases of pathogenesis. Therefore, selection of diagnostics and treatment methods, and selection of markers informing about the development of cancer diseases must be reliable to improve patient survival rates. The World Health Organization estimates that around 30% of all cancers can be cured if identified earlier and more precisely.1 Presently a histological analysis, being the standard procedure for cancer diagnostics including human breast cancer, is highly invasive, sometimes can be inconvenient, time consuming, and in a number of cases can lead to ambiguous results prone to human interpretation. This evidently demonstrates a need to develop new methods that would enable an unequivocal diagnosis within a short time and with high precision. Current diagnostic and imaging methods are often limited by inadequate sensitivity, specificity and spatial resolution.2 Spectroscopic methods are ideally suited to study abnormalities in biological tissues, including cancer, and their use can be enhanced by photosensitizers. Optical methods offer several significant advantages over the routine clinical imaging methods, including: a) non-invasiveness through the use of safe, non-ionizing radiation, b) display of contrast between soft tissues based on optical properties of the tissue, c) high spatial resolution (less than 0.5 micron lateral resolution in the visible range). Among spectroscopic methods Raman imaging (RI) based on Raman scattering due to molecular vibrations, is an emerging field that has generated a lot of interest both for the label free Raman methods and the biofunctionalized and targeted methods using unique properties 3 of phthalocyanines.3-6 RI has reached now a level of sophistication in terms of sensitivity, selectivity and specificity that makes it competitive with more classical methods for example confocal fluorescence microscopy.5-15 RI provides direct biochemical information because vibrational fingerprint features reflect chemical composition of cells, their organelles and tissues. The structural fingerprinting is very effective owing to narrow and highly resolved Raman bands (0.1 nm compared with a typical bandwidth of 10–50 nm for fluorescence). Resonance Raman effect and Surface Enhanced Raman Scattering are able to amplify the signal of the probe to the point that it can be detected in crowded biological structures. RI combined with contrast enhancing probes active in Raman spectroscopy and able to cross cell membranes may identify specific gene products, DNA sequences, metabolic products and intracellular processes.5,16 In biomedical applications one requires: high spatial resolution far below the diffraction limit, strong signal enhancement and high temporal resolution enabling monitoring dynamics of photosensitizers in biological systems. The most promising method to study evolution in time is the femtosecond pump-probe transient absorption spectroscopy.17,18 Phthalocyanines are important photosensitizers in medical photodiagnostics and therapy (PDD and PDT).The unique physical and chemical properties of phthalocyanines such as the similarity in structure to the biological molecules (chlorophyll, haemoglobin), their diversity regarding the central metal, substituents, and intrinsic capability to self-assemble have activated the interest in this group of chemical compounds for many years and are important for applications in optics and medicine.19-40 Photodynamic therapy (PDT) is a promising cancer treatment that involves the combination of visible light and a photosensitizer. Each factor of this therapy (photosensitizer, light) is harmless by itself, but when combined with oxygen, can produce lethal cytotoxic agents that can destroy cancer cells. The most important factor in PDT is selectivity towards 4 diseased tissue as only those cells that are simultaneously exposed to the photosensitizer, light and oxygen are subject to the cytotoxic effect. The selectivity of PDT is produced also by a preferential uptake of the photosensitizer by the diseased tissue and the ability to confine activation of the photosensitizer to this diseased tissue by restricting the illumination to that specific region. Therefore, PDT allows the selective destruction of cancers leaving normal tissue intact.41 The detailed mechanism of photodynamic reactions in the tissues is not yet completely understood; however, three mechanisms can take place, Type I, II and III, and the predominance of one of these mechanisms depends on the concentration of oxygen in tissues. In the Type II of PDT, the excited triplet state of the photosensitizer (3PS*) is reached through the intersystem crossing (ISC) from the first excited singlet state (1PS*), derived from the ground state (1PS), by the absorption of laser light. Due to the sufficiently long lifetime of the triplet state (3PS*), a photosensitizer can interact efficiently with the environment of the tissue. The 3PS* state of the photosensitizer reacts directly with the triplet state oxygen 3 1 molecule ( O2), generating highly toxic singlet oxygen ( O2*) and effectively destroying tumor tissue. This process competes with the radiant (fluorescence, phosphorescence) and radiationless (internal conversion) deactivation of the 3PS* state of the photosensitizer. Phthalocyanines have been studied by various spectroscopic and theoretical methods for many decades.20-38 Although the studies provide extensive information about these systems, a number of problems still remain to be resolved: the mechanisms of communication between different states such as metal-centered, ligand-centered, charge-transfer states as well as the reactions induced by light, the early intermediates upon photon
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