ΦΔ Values Research Articles

Tuning Fluorescence and Singlet Oxygen Quantum Yields of Subporphyrazines by Axial Functionalization.

The axial functionalization of Subporphyrazines (SubPzs) with unreported alkoxy groups, carboxy and carboperoxy rests, as well as sulfanyl, aryl and amino groups, forming B-O, B-S, B-C, and B-N bonds, respectively, has been investigated. The studied oxygen nucleophiles include aromatic and sterically demanding aliphatic alcohols, along with carboxylic acids and peracids. In general, direct substitution of the chloro-SubPz by oxygen nucleophiles of diverse nature proceeds smoothly, with yields of the isolated alkoxy and carboxy-substituted SubPzs ranging from 49 to 100 %. Conversely, direct substitution with sulphur, carbon and nitrogen nucleophiles do not afford the corresponding substituted SubPzs. In these cases, a stepwise procedure involving an axial triflate-SubPz intermediate was employed, affording only the phenyl-SubPz in 8 % yield. The major compound under these conditions was the unreported SubPz μ-oxo dimer, presumably arising from substitution of the triflate-SubPz by the in situ generated hydroxy-SubPz. This result indicates a quite low reactivity of the TfO-SubPz intermediate with carbon, sulphur and nitrogen nucleophiles. All SubPzs prepared in this work exhibited fluorescence at 510-515 nm with quantum yields ranging from 0.1 to 0.24. Additionally, all SubPzs generated singlet oxygen, with ΦΔ values ranging from 0.15 to 0.57, which show no apparent correlation with the axial substituents.

Singlet Oxygen Quantum Yields of Pyrogenic Dissolved Organic Matter from Lab-Prepared and Wildfire Chars.

Wildfires or prescribed fires release pyrogenic dissolved organic matter (pyDOM) into the environment, which can photochemically produce singlet oxygen (1O2) in sun-lit surface waters. 1O2 quantum yields (ΦΔ) are well-studied for non-pyrogenic DOM, but little is understood about the 1O2 generation from pyDOM, especially the ΦΔ values from real wildfire samples and their wavelength dependence. In this study, time-resolved 1O2 phosphorescence was used to determine the wavelength-dependent ΦΔ values for pyDOM generated from wildfire char and a series of lab-prepared chars produced by combusting oak and pine wood. Wildfire and most lab-prepared pyDOM generally had similar ΦΔ values (2.1-2.7%) at 365 nm compared to the reference Suwannee River Natural Organic Matter (SRNOM) isolate (2.4%). Interestingly, pyDOM from the highest combustion temperature char was found to possess extremely low ΦΔ values compared to SRNOM and other pyDOM at all excitation wavelengths. In addition, it was revealed that the predicted steady-state concentration of 1O2 from pyDOM was similar to that from SRNOM, indicating that the addition of pyDOM from wood chars may not strongly impact surface water photochemistry.

Photodynamic Anticancer and Antibacterial Activities of Sn(IV) N-Confused Meso-tetra(methylthiophenyl)porphyrin

A Sn(IV) meso-tetra(4-methylthiolphenyl) N-confused porphyrin (4-Sn) complex was prepared to facilitate a comparison of the photophysicochemical and singlet oxygen photosensitiser properties of a series of Sn(IV) complexes of meso-4-methylthiolphenyl-substituted porphyrin, corrole, chlorin, and N-confused porphyrin. 4-Sn has an unusually high singlet oxygen quantum (ΦΔ) yield of 0.88, markedly higher than the ΦΔ values of the other complexes in this series. A Thorlabs M660L4 LED (280 mW · cm−2) was used to study the photodynamic activity of Sn-4 against the MCF-7 cancer cell line through irradiation at 660 nm for 30 min. The IC50 value was calculated to be 1.4 (± 0.8) µM, markedly lower than the previously reported values for the rest of the series. Photodynamic antimicrobial activity was also determined against Staphylococcus aureus and Escherichia coli, and 4-Sn was found to deactivate both Gram-(+) and Gram-(−) bacteria despite the absence of cationic charges on the ligand structure.

Combination of Light and Ultrasound: Exploring Sono–Photochemical Activities of Phthalocyanine-Based Sensitizers

Recently, there has been increasing interest in photodynamic therapy (PDT) compared to traditional methods (immunotherapy, surgery, chemotherapy, or radiotherapy) in the treatment of cancer. Also, sonodynamic therapy (SDT) is a non-invasive therapeutic modality that enables high tissue penetration by triggered ultrasound (US). Phthalocyanines (Pcs) are known as one of the most important classes of sensitizers used in PDT and SDT. Motivated by these facts, in this study, to assess potentials for sono-PDT (SPDT), the preparation of peripherally substituted metal-free (2), zinc (3), and indium (4) Pcs was completed by 3-methoxybenzyloxy substituents. The resulting compounds were characterized by applying spectroscopic techniques including 1H NMR, FT-IR, UV–vis, and MS. In sono–photochemical studies, the calculated singlet oxygen quantum yield (ΦΔ) values were 0.68 for ZnPc (3) and 0.83 for InPc (4) after light irradiation; these values increased to 0.81 for 3 and 0.94 for 4 after combination US and light irradiation. The obtained data proved that the singlet oxygen production increased considerably by changing the method from light irradiation to US/light. This research will enrich the literature on increasing singlet oxygen production by the SPDT method. Theoretical calculations based on density functional theory (DFT) give further explanations of the optical and (photo)chemical processes behind the singlet oxygen generation. Our calculations are able to provide the energy of the excited states with excellent agreement with the experimental results, and they also allow us to understand and predict the activity of these Pcs based on their excited states and a clear enhancement of the spin–orbit coupling (SOC) when a metal center is included in the Pcs. This work thus exploits new insights into the advanced sono-photodynamic properties of potential sensitizers for efficient SPDT applications.

Novel Graphene Oxide/Zinc Phthalocyanine Composites Bearing 3‐Chloro‐4‐Fluorophenoxy: Potential Usage for Sono/Photochemical Applications

AbstractThe aim of this paper is to explore the therapeutic contribution of graphene oxide (GO) to new sono/photosensitizers through sono/photochemical studies for the first time. For this purpose, new zinc (II) phthalocyanine bearing 3‐chloro‐4‐fluorophenoxy 2 was synthesized and then its GO‐based composites were prepared by non‐covalently coating ZnPc 2 on the graphene oxide surface. The photoactivity of these materials was compared and discussed in terms of their potential ability to be used in photosensitizer in photodynamic therapy (PDT) and sono‐photodynamic therapy (SPDT). In these application areas, GO can serve as photosensitizer carrier, while ZnPc 2 can be acting as PDT/SPDT agent. Therefore, phthalocyanine composites containing different percentages of graphene oxide by weight (wt.% GO) were prepared. SEM (scanning electron microscopy) results supported the interaction between GO and ZnPc 2. In the sono‐photochemical study, both ZnPc 2 and its composites gave very higher ΦΔ values than the photochemical study. The sono‐photochemical ΦΔ values were found to be 0.928 for 0 wt.% GO, 0.869 for 0.25 wt.% GO, 0.891 for 0.50 wt.% GO, 0.868 for 1 wt.% GO, 0.908 for 3 wt.% GO, 0.845 for 5 wt.% GO and 0.851 for 10 wt.% GO, respectively. According to obtained results, these materials could be promise as good photosensitizers for both the photochemical study and the sono‐photochemical study due to their very high singlet oxygen generation.

Photoantimicrobial activity of Schiff-base morpholino phthalocyanines against drug resistant micro-organisms in their planktonic and biofilm forms

Antimicrobial photodynamic inactivation (aPDI) is a treatment for the eradication of drug-resistant micro-organisms. One of the advantages of this technique, is that there is minimal possibility of microbial resistance. Hence, herein, the preparation and characterization of novel neutral and cationic morpholine containing Schiff base phthalocyanines are reported. The cationic complexes gave moderate singlet oxygen quantum yields (ΦΔ) of ∼0.2 in aqueous media. Conversely, the neutral complexes generated very low ΦΔ values making them very poor candidates for antimicrobial studies. The cationic phthalocyanines showed excellent photodynamic activity against planktonic cells of all micro-organisms (Candida albicans, Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, Salmonella enterica subspecies enterica serovar Choleraesuis, vancomycin-resistant Enterococcus faecium, and methicillin-resistant Staphylococcus aureus). The efficiency of aPDI was shown to be both concentration and light-dose-dependent. Mono biofilms were susceptible when treated with 200 µM of cationic Pcs at 108 J/cm2. However, ∼10% of the mixed biofilm survived after treatment.

Comparing Singlet Oxygen Generation of Schiff Base Substituted Novel Silicon Phthalocyanines by Sonophotochemical and Photochemical Applications.

Although the sonophotodynamic method has an effective therapeutic outcome for anticancer treatment compared with the photodynamic method, there are not enough related studies in the literature and this study aims to contribute to the development of sonophotodynamic studies. For this purpose, the Schiff base substituted silicon phthalocyanines were designed and synthesized as effective sensitizer candidates and the photophysicochemical and sonophotochemical features of the phthalocyanines were examined to increase singlet oxygen efficiency. The calculated ΦΔ values indicate that the contribution of substituent groups improved the production of singlet oxygen compared with silicon (IV) phthalocyanine dichloride (SiPcCI2 ) and also the sonophotochemical applications increased the singlet oxygen yields. The ΦΔ values (ΦΔ =0.76 for axially bis-{4-[(E)-(pyridin-3-ylimino)methyl]phenol} substituted silicon (IV) phthalocyanine (2a), 0.68 for axially bis-4-[(E)-{[(pyridin-3-yl)methyl]imino}methyl]phenol substituted silicon (IV) phthalocyanine (2b) in photochemical study) reached to ΦΔ =0.98 for 2a, 0.94 for 2b in sonophotochemical study. This article will enrich the literature on increasing singlet oxygen yield.

First Planar Binuclear Phthalocyanines Sharing a Common Carbazole Linkage: Synthesis, Optical and Photochemical Properties

Abstract The first examples of planar binuclear phthalocyanines sharing a common carbazole unit were obtained using indirect and direct mixed cyclization approaches. The synthetic route to the starting 9-benzylcarbazole-2,3,6,7-tetranitrile was reconsidered and literature conditions were successfully optimized. In addition to the binuclear complex, a low-symmetry A3B phthalocyanine with free cyano groups was isolated and identified. Accurate assignment of absorption bands in the UV-Vis spectra was performed using magnetic circular dichroism and simplified TD-DFT calculations. The target binuclear complexes demonstrate the ability of singlet oxygen generation, with ΦΔ values reaching 0.15 for the tert-butyl-substituted compound. The products of photodegradation were studied using mass spectrometry and UV-Vis spectroscopy. Electrochemical and spectroelectrochemical studies showed a gradual oxidation of the macrocycle, accompanied by the interruption of an extended binuclear π-system.

Novel silicon phthalocyanines with improved singlet oxygen generation by Sono-photochemical applications

Although it has been proven, that the SPDT method, which improves the low penetration disadvantage of PDT, significantly increases the singlet oxygen yield, the number of relevant studies in the literature is limited. Therefore, this study aimed to show the improved singlet oxygen generation using newly synthesized silicon (IV) phthalocyanines containing terminal fluoro, chloro, bromo-phenoxy moiety by sono-photochemical applications. While the calculated ΦΔ values were 0.41 for compound 1, 0.39 for compound 2, and 0.29 for compound 3 after photochemical applications, these values increased to 0.77 for compound 1, 0.74 for compound 2, and 0.65 for compound 3 after sono-photochemical applications. The results proved that the contribution of the substituents increased the therapeutic efficacy of silicon (IV) phthalocyanine dichloride (SiPcCl2), and the applied irradiation method also increased the singlet oxygen yield approximately-two times. This article will enrich the literature on increasing singlet oxygen yield.

Carbohydrate-based block copolymer nanoparticles: Novel nanocarrier for delivery of chlorine-aluminum phthalocyanine for use in photodynamic therapy

The development of third-generation photosensitizers for use in photodynamic therapy (PDT) is one of the most promising directions in current cancer therapy. Nanoparticles based on the block copolymer maltoheptaose-b-poly (methyl methacrylate) (MH-b-PMMA) containing the photosensitizer chlorine-aluminum phthalocyanine (ClAlPc) were developed for application in PDT. The MH-b-PMMA@ClAlPc nanoparticles showed a hydrodynamic radius of 41 nm, low polydispersity index, negative zeta potential, high encapsulation efficiency, and optimal stability. Furthermore, MH-b-PMMA@ClAlPc nanoparticles were able to generate cytotoxic singlet oxygen (1O2), showing singlet oxygen quantum yields (ΦΔ) values close to free ClAlPc. The drug release profile from MH-b-PMMA@ClAlPc was described by a biphasic model, consisting of fast release at early time, followed by a sustained release profile. The nanoparticles were mainly located in the intestinal surrounding cells and did not induce lethality to Caenorhabditis elegans at low concentrations. Our findings highlight that glyconanoparticles have potential to be employed as novel nanocarriers for hydrophobic photosensitizers in PDT.

Light-driven antimicrobial therapy of palladium porphyrins and their chitosan immobilization derivatives and their photophysical-chemical properties

The emergence of antimicrobial resistance has made the development of photodynamic therapy (PDT) related applications essential, since microorganisms can not form resistance to this method. Porphyrins are well-known photosensitizers for PDT related applications. Thus, the present study outlines the synthesis, characterization and evaluation of the utility of palladium porphyrins and their chitosan inclusion complexes as photosensitizer dye in photodynamic antimicrobial therapy (PACT). Before in vitro cell studies, the photophysical-chemical studies of all obtained structures were performed in solution. It was observed that the immobilization of the porphyrins into the chitosan influenced the photophysical-chemical and PACT activity properties. The determined fluorescence quantum yield was very low, in the range of 0.007–0.028 for all samples indicating the efficient triplet state population to cause high singlet oxygen quantum yield (ΦΔ). The measured ΦΔ values were in the range of 0.51–0.61 for the porphyrins and 0.53–0.66 for porphyrin chitosan immobilization complexes. Our results demonstrate that the PACT activity of cationic porphyrin (P3) and its chitosan immobilization form (P3-Ct) were more efficient in decreasing the number of viable cells up to 100% in vitro.

Subphthalocyanines as Efficient Photosensitizers with Nanomolar Photodynamic Activity against Cancer Cells.

Because cancer is the second leading cause of death globally, investigation of new photosensitizers for photodynamic therapy is highly desirable. In this work, different peripherally substituted subphthalocyanines (SubPcs) with either a benzocrown moiety (CE-) or a tyrosine methyl ester (Tyr-) as the axial ligand have been prepared. Target SubPcs showed high ΦΔ values, >0.50 in EtOH. Both CE- and Tyr- moieties increased substantially the hydrophilicity of the compounds (log P = 1.79-2.63, n-octanol/PBS). Uptake to cells, subcellular localization, and monitoring of the progression of cell death over time are described. Improved spectroscopic behavior of the CE- series in cell culture medium resulted in higher photodynamic activity versus that of the Tyr- series. In particular, the peripherally triethylsulfanyl SubPc-CE exhibited extraordinarily low EC50 values of 2.3 and 4.4 nM after light activation and high TC50 values of 14.49 and 5.25 μM (i.e., dark toxicity without activation) on SK-MEL-28 and HeLa cells, respectively, which rank it among the best photosensitizers ever.

Perylene Diimide-Based Multicomponent Metallacages as Photosensitizers for Visible Light-Driven Photocatalytic Oxidation Reaction

Perylene Diimide-Based Multicomponent Metallacages as Photosensitizers for Visible Light-Driven Photocatalytic Oxidation Reaction

BODIPY-Ruthenium(II) Bis-Terpyridine Complexes for Cellular Imaging and Type-I/-II Photodynamic Therapy.

A series of multichromophoric ruthenium(II) complexes with the formulation [Ru(tpy-BODIPY)(tpy-R)]Cl2 (1-4), having a heteroleptic Ru(II)-bis-tpy (tpy = 4'-phenyl-2,2':6',2″-terpyridine) moiety covalently linked to a boron-dipyrromethene (BODIPY) pendant, have been prepared and characterized and their application as a phototherapeutic and photodetection agent in cancer therapy has been explored. Ligand L1 with a terpyridine-BODIPY moiety and complex 1 as its PF6 salt (1a) have been structurally characterized by a single-crystal X-ray diffraction study. Complex 1a has a distorted-octahedral RuN6 core with a Ru(II)-bis-terpyridine unit that is covalently linked to one photoactive BODIPY unit. The complexes exhibit strong absorbance near 502 nm (ε ≈ (3.7-7.8) × 104 M-1 cm-1) and high singlet oxygen sensitization ability, giving singlet oxygen quantum yield (ΦΔ) values ranging from 0.57 to 0.75 in DMSO. An emission-based study using complex 4 and Singlet Oxygen Sensor Green (SOSG) displays the formation of singlet oxygen inside the cells and also in the buffer medium upon light irradiation. DNA (pUC19) photocleavage experiments using ROS scavengers/stabilizers reveal photoinduced generation of singlet oxygen by a type-II process and of the superoxide anion radical by a type-I process. Complex 4 having a pendant biotin moiety as a cancer cell targeting group shows high photocytotoxicity with a remarkable phototherapeutic index (PI) value of >1400 in HeLa cancer cells with a low light dose activation (400-700 nm, 2.2 J cm-2). The complexes display reduced activity in noncancerous HPL1D cells. The emission property of the complexes is used for cellular imaging, thus making them suitable as next-generation theranostic PDT agents.

Unveiling the photophysical, biomolecule binding and photo-oxidative capacity of novel Ru(II)-polypyridyl corroles: A multipronged approach

Two fluorinated corrole derivatives, namely H3MebpyCor and RuMebpyCor, were synthesized and characterized in terms of their photophysical, electrochemical, and photooxidation behavior. Their biomolecular binding capacity toward Human Serum Albumin (HSA) and calf thymus DNA (CT-DNA) was also evaluated. The experimental data were correlated with theoretical analysis via Time Dependent Density Functional Theory (TDDFT) and Molecular Docking calculations. We found an extremely low fluorescence quantum yield for both corroles dissolved in acetonitrile (CH3CN) and dimethyl sulfoxide (DMSO), which suggests a relaxation pathway through nonradiative processes, such as internal conversion. However, the internal conversion channel in RuMebpyCor competes with the energy transfer to the Ru(II) moiety, placing triplet state formation as a second mechanism of relaxation for this structure. Both corroles showed no aggregation and good photostability. The singlet oxygen (1O2) quantum yield (ΦΔ) values also highlight their potential application in photoinactivation approaches. Theoretical analysis suggests that the introduction of Ru(II) ion coordinated in the bipyridyl unit significantly alters the optically induced electronic transitions, and that the solvents play an important role in defining the optical spectra of the two corroles. Additionally, they interact spontaneously and moderate to strong via ground-state association (static process) with HSA and CT-DNA. However, for the HSA binding assays the dynamic fluorescence quenching mechanism can also occur at high corrole concentrations. Finally, in silico calculations suggest that the main binding region into CT-DNA is the minor groove, while subdomain IIA (site I) is the main binding region for HSA:H3MebpyCor (experimental proportion 1:1) and both subdomains IIA and IB (sites I and III, respectively) for HSA:RuMebpyCor (experimental proportion 1:2).

Quantitative Structure-Property Relationship Modelling for the Prediction of Singlet Oxygen Generation by Heavy-Atom-Free BODIPY Photosensitizers*.

Heavy‐atom‐free sensitizers forming long‐living triplet excited states via the spin‐orbit charge transfer intersystem crossing (SOCT‐ISC) process have recently attracted attention due to their potential to replace costly transition metal complexes in photonic applications. The efficiency of SOCT‐ISC in BODIPY donor‐acceptor dyads, so far the most thoroughly investigated class of such sensitizers, can be finely tuned by structural modification. However, predicting the triplet state yields and reactive oxygen species (ROS) generation quantum yields for such compounds in a particular solvent is still very challenging due to a lack of established quantitative structure‐property relationship (QSPR) models. In this work, the available data on singlet oxygen generation quantum yields (ΦΔ) for a dataset containing >70 heavy‐atom‐free BODIPY in three different solvents (toluene, acetonitrile, and tetrahydrofuran) were analyzed. In order to build reliable QSPR model, a series of new BODIPYs were synthesized that bear different electron donating aryl groups in the meso position, their optical and structural properties were studied along with the solvent dependence of singlet oxygen generation, which confirmed the formation of triplet states via the SOCT‐ISC mechanism. For the combined dataset of BODIPY structures, a total of more than 5000 quantum‐chemical descriptors was calculated including quantum‐chemical descriptors using density functional theory (DFT), namely M06‐2X functional. QSPR models predicting ΦΔ values were developed using multiple linear regression (MLR), which perform significantly better than other machine learning methods and show sufficient statistical parameters (R=0.88–0.91 and q2=0.62–0.69) for all three solvents. A small root mean squared error of 8.2 % was obtained for ΦΔ values predicted using MLR model in toluene. As a result, we proved that QSPR and machine learning techniques can be useful for predicting ΦΔ values in different media and virtual screening of new heavy‐atom‐free BODIPYs with improved photosensitizing ability.

Singlet Oxygen Quantum Yields in Environmental Waters.

Singlet oxygen (1O2) is a reactive oxygen species produced in sunlit waters via energy transfer from the triplet states of natural sensitizers. There has been an increasing interest in measuring apparent 1O2 quantum yields (ΦΔ) of aquatic and atmospheric organic matter samples, driven in part by the fact that this parameter can be used for environmental fate modeling of organic contaminants and to advance our understanding of dissolved organic matter photophysics. However, the lack of reproducibility across research groups and publications remains a challenge that significantly limits the usability of literature data. In the first part of this review, we critically evaluate the experimental techniques that have been used to determine ΦΔ values of natural organic matter, we identify and quantify sources of errors that potentially explain the large variability in the literature, and we provide general experimental recommendations for future studies. In the second part, we provide a qualitative overview of known ΦΔ trends as a function of organic matter type, isolation and extraction procedures, bulk water chemistry parameters, molecular and spectroscopic organic matter features, chemical treatments, wavelength, season, and location. This review is supplemented with a comprehensive database of ΦΔ values of environmental samples.

Photophysicochemical behaviour of phenoxy propanoic acid functionalised zinc phthalocyanines when grafted onto iron oxide and silica nanoparticles: Effects in photodynamic antimicrobial chemotherapy

This work reports on the covalent linkage of (3-aminopropyl)triethoxysilane (APTES) functionalised iron oxide (IONPs–APTES) and silica (SiNPs–APTES) nanoparticles with zinc(II) tetra–([3–(4–phenoxy) propanoic acid) phthalocyanine] (1) and zinc(II) mono–([3–(4–phenoxy) propanoic acid) phthalocyanine (2) via an amide bond to form the conjugates, 1–IONPs-APTES, 1–SiNPs–APTES, 2-IONPs-APTES and 2-SiNPs-APTES). The photophysicochemical behaviour of the conjugates was investigated. These were characterized by a decrease in the fluorescence quantum yields and lifetimes, and an increase in the triplet quantum yield and singlet oxygen quantum yield when compared to complex 1 and 2 alone. The conjugates to IONPs-APTES displayed higher ΦT than those of SiNPs-APTES probably due to the heavy atom effect of iron compared to silica and the high loading capacity of the relatively smaller iron oxide NPs, however, there was no significant difference in the ΦΔ values of 2-IONPs-APTES (ΦΔ=0.59) and 2-SiNPs-APTES (ΦΔ=0.58), suggesting that the energy transfer process between the excited triplet state of 2-IONPs-APTES and ground state molecular oxygen was not effective. Photodynamic antimicrobial chemotherapy (PACT) studies showed that linkage of Pcs to NPs improves their photoinactivation capability against Staphylococcus aureus and Escherichia coli. IONPs-APTES and its conjugates generally displayed the highest log reductions than SiNPs-APTES and its conjugates except for studies after 75 min of irradiation for S. Aureus where the log reductions are the same. 2-IONP-APTES was recovered using a magnet after each photodegradation cycle and its stability after 3 cycles confirmed re-usability.

BODIPY-Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect.

Boron-dipyrromethene derivatives, including cationic and iodinated analogs, were obtained and subjected to physicochemical and in vitro photodynamic activity studies. Iodinated derivatives revealed a substantial heavy atom effect manifested by a bathochromic shift of the absorption band by about 30 nm and fluorescence intensity reduced by about 30-35 times, compared to that obtained for non-iodinated ones. In consequence, singlet oxygen generation significantly increased with ΦΔ values in the range 0.69-0.97. The in vitro photodynamic activity was evaluated on Gram-positive Staphylococcus aureus, Gram-negative Escherichia coli, and on human androgen-sensitive prostate adenocarcinoma cells (LNCaP). The novel cationic, iodinated BODIPY, demonstrated the highest activity toward all studied cells. An excellent cytotoxic effect was found against LNCaP cells with an IC50 value of 19.3 nM, whereas the viability of S. aureus was reduced by >5.6 log10 at 0.25 μM concentration and by >5.3 log10 in the case of E. coli at 5 μM. Thus, this analog seems to be a very promising candidate for the application in both anticancer and antimicrobial photodynamic therapy.

Measurement of singlet oxygen generation of 9(Hydroxymethyl)anthracene substituted silicon phthalocyanine by sono-photochemical and photochemical studies

Sono-photochemical study which combines photochemical and sonochemical studies is a favorable alternative modality to produce high singlet oxygen. However, though there are many articles about the calculation of singlet oxygen quantum yield for Photodynamic therapy (PDT) studies in the literature, there is no study to measure the efficiency of singlet oxygen for Sono-photodynamic therapy (SPDT) method. Therefore, this study aimed to synthesis a complex with improved photochemical properties and then calculates the efficiency of singlet oxygen by both of photochemical and sono-photochemical studies in DMSO and DMF. The designed complex showed remarkably high singlet oxygen quantum yields. The ΦΔ values (0.74 in DMSO, 0.72 in DMF for photochemical study) reached to 0.96 in DMSO, 0.88 in DMF for sono-photochemical study and these results prove that SPDT improves the therapeutic activity due to the sono-photochemical effect. This article will lead to the studies that seek to obtain highly efficient singlet oxygen.