Bilirubin ditaurate (taurobilirubin) proved to be very suitable for estimation of efficiency of different photosensitizers and for determination of the activity of singlet oxygen. The degree of its bleaching was measured at 450 nm, the excitation light was over 600 nm. Halogen lamps were used as light sources. The decoloration of bilirubin ditaurate was related to the intensity of the light source in the presence of the photosensitizer meso-tetra (4-sulfonatophenyl)-porphine (TPPS4). From photosensitizers conventionally used in photodynamic therapy (photosan 3, TPPS4, and Zn and Al chelates of phthalocyanine) chloroaluminium phthalocyanine was most effective. From synthetic dyes of nonporphyrin type thiazine dyes were most active. The presumption is expressed that the efficiency of noncoherent light is comparable to the laser radiation when photosensitizers with large absorption band 600-700 nm are used for photodynamic therapy.

• MeSH
• bilirubin analogy a deriváty   chemie   MeSH
• fotochemie MeSH
• fotochemoterapie MeSH
• fotosenzibilizující látky chemie   MeSH
• taurin analogy a deriváty   chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• bilirubin MeSH
• fotosenzibilizující látky MeSH
• taurin MeSH
• taurobilirubin MeSH Prohlížeč

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.

• MeSH
• fotochemoterapie * MeSH
• fotosenzibilizující látky chemie   farmakologie   MeSH
• isoindoly chemie   farmakologie   MeSH
• lidé MeSH
• nádorové buněčné linie MeSH
• vztahy mezi strukturou a aktivitou MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• fotosenzibilizující látky MeSH
• isoindoly MeSH
• phthalocyanine MeSH Prohlížeč

Six common water-soluble singlet oxygen ((1)O2) photosensitizers - 5,10,15,20-tetrakis(1-methyl-4-pyridinio) porphine (TMPyP), meso-tetrakis(4-sulfonathophenyl)porphine (TPPS4), Al(III) phthalocyanine chloride tetrasulfonic acid (AlPcS4), eosin Y, rose bengal, and methylene blue - were investigated in terms of their ability to produce delayed fluorescence (DF) in solutions at room temperature. All the photosensitizers dissolved in air-saturated phosphate buffered saline (PBS, pH 7.4) exhibit easily detectable DF, which can be nearly completely quenched by 10 mM NaN3, a specific (1)O2 quencher. The DF kinetics has a biexponential rise-decay character in a microsecond time domain. Therefore, we propose that singlet oxygen-sensitized delayed fluorescence (SOSDF), where the triplet state of a photosensitizer reacts with (1)O2 giving rise to an excited singlet state of the photosensitizer, is the prevailing mechanism. It was confirmed by additional evidence, such as a monoexponential decay of triplet-triplet transient absorption kinetics, dependence of SOSDF kinetics on oxygen concentration, absence of SOSDF in a nitrogen-saturated sample, or the effect of isotopic exchange H2O-D2O. Eosin Y and AlPcS4 show the largest SOSDF quantum yield among the selected photosensitizers, whereas rose bengal possesses the highest ratio of SOSDF intensity to prompt fluorescence intensity. The rate constant for the reaction of triplet state with (1)O2 giving rise to the excited singlet state of photosensitizer was estimated to be ~/>1 × 10(9) M(-1) s(-1). SOSDF kinetics contains information about both triplet and (1)O2 lifetimes and concentrations, which makes it a very useful alternative tool for monitoring photosensitizing and (1)O2 quenching processes, allowing its detection in the visible spectral region, utilizing the photosensitizer itself as a (1)O2 probe. Under our experimental conditions, SOSDF was up to three orders of magnitude more intense than the infrared (1)O2 phosphorescence and by far the most important pathway of DF. SOSDF was also detected in a suspension of 3T3 mouse fibroblast cells, which underlines the importance of SOSDF and its relevance for biological systems.

• MeSH
• buňky 3T3 MeSH
• fluorescenční spektrometrie MeSH
• fotosenzibilizující látky chemie   MeSH
• kinetika MeSH
• koncentrace vodíkových iontů MeSH
• kvantová teorie MeSH
• myši MeSH
• singletový kyslík chemie   MeSH
• teplota MeSH
• voda chemie   MeSH
• zvířata MeSH
• Check Tag
• myši MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• fotosenzibilizující látky MeSH
• singletový kyslík MeSH
• voda MeSH

Halogenated and alkylated BODIPY derivatives are reported as suitable candidates for their use as photosensitizers in photodynamic therapy due to their efficient intersystem crossing (ISC) between states of different spin multiplicities. Spin-orbit couplings (SOCs) are evaluated using an effective one-electron spin-orbit Hamiltonian for brominated and alkylated BODIPY derivatives to investigate the quantitative effect of alkyl and bromine substituents on ISC. BODIPY derivatives containing bromine atoms have been found to have significantly stronger SOCs than alkylated BODIPY derivatives outside the Frank-Condon region while they are nearly the same at local minima. Based on calculated time-dependent density functional theory (TD-DFT) vertical excitation energies and SOCs, excited-state dynamics of three BODIPY derivatives were further explored with TD-DFT surface hopping molecular dynamics employing a simple accelerated approach. Derivatives containing bromine atoms have been found to have very similar lifetimes, which are much shorter than those of the derivatives possessing just the alkyl moieties. However, both bromine atoms and alkyl moieties reduce the HOMO/LUMO gap, thus assisting the derivatives to behave as efficient photosensitizers.

• MeSH
• alkylace MeSH
• fotosenzibilizující látky * MeSH
• halogenace * MeSH
• sloučeniny boru MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene MeSH Prohlížeč
• fotosenzibilizující látky * MeSH
• sloučeniny boru MeSH

Six water-soluble macrocyclic photosensitizers, the members of two groups of expanded porphyrins (metallotexaphyrins and free-base sapphyrins) containing hydrophilic substituents and meso-tetra(4-sulfonatophenyl)-porphyrin, were tested by UV-Vis absorption and resonance Raman spectroscopy in the in vitro binding experiments with intact mitochondria isolated from swine liver. Studied macrocycles showed markedly different affinity to mitochondria. The highest uptake was observed for sapphyrin-sugar conjugate and metallotexaphyrins. Sapphyrin-polyamine conjugates exhibit something less affinity to mitochondria, while the porphyrin of anionic character showed very low mitochondrial uptake. Obtained spectroscopic results confirm that the binding process altered the self-aggregation degree of expanded porphyrins.

• MeSH
• algoritmy MeSH
• fotochemoterapie MeSH
• fotosenzibilizující látky chemická syntéza   chemie   MeSH
• jaterní mitochondrie chemie   MeSH
• molekulární struktura MeSH
• porfyriny chemická syntéza   chemie   MeSH
• prasata MeSH
• Ramanova spektroskopie MeSH
• spektrofotometrie MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• srovnávací studie MeSH
• Názvy látek
• fotosenzibilizující látky MeSH
• porfyriny MeSH

Polymeric polyurethane nanofabrics doped by zinc tetraphenylporphyrin (ZnTPP) and/or zinc phthalocyanine (ZnPc) photosensitizers were prepared by the electrospinning method and characterized by microscopic methods, steady-state and time-resolved fluorescence, and absorption spectroscopy. Nanofabrics doped by both ZnTPP and ZnPc efficiently harvest visible light to generate triplet states and singlet oxygen O2(1Delta(g)) with a lifetime of about 15 micros in air atmosphere. The energy transfer between the excited singlet states of ZnTPP and ground states of ZnPc is described in details. All nanofabrics have bactericidal surfaces and photooxidize inorganic and organic substrates. ZnTPP and ZnPc in the polyurethane nanofabrics are less photostable than incorporated free-base tetraphenylporphyrin (TPP).

• MeSH
• časové faktory MeSH
• fluorescenční spektrometrie MeSH
• fotochemie MeSH
• fotosenzibilizující látky chemie   MeSH
• indoly chemie   MeSH
• isoindoly MeSH
• kyslík chemie   MeSH
• metaloporfyriny chemie   MeSH
• molekulární struktura MeSH
• nanostruktury chemie   MeSH
• organokovové sloučeniny chemie   MeSH
• oxidace-redukce MeSH
• polyurethany chemická syntéza   chemie   MeSH
• povrchové vlastnosti MeSH
• sloučeniny zinku MeSH
• spektrofotometrie ultrafialová MeSH
• velikost částic MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• fotosenzibilizující látky MeSH
• indoly MeSH
• isoindoly MeSH
• kyslík MeSH
• metaloporfyriny MeSH
• organokovové sloučeniny MeSH
• polyurethany MeSH
• sloučeniny zinku MeSH
• zinc tetraphenylporphyrin MeSH Prohlížeč
• Zn(II)-phthalocyanine MeSH Prohlížeč

Photodynamic therapy (PDT) is a clinically-approved cancer treatment that is based on production of cytotoxic reactive oxygen species to induce cell death. However, its efficiency depends on distribution of photosensitizer (PS) and depth of light penetration through the tissues. Tendency of pathological cancer tissues to exhibit lower pH than healthy tissues inspired us to explore dual-targeted pH-activatable photosensitizers based on tunable near-infrared (NIR) boron-dipyrromethene (BODIPY) dyes. Our BODIPY PSs were designed to carry three main attributes: (i) biotin or cRGD peptide as an effective cancer cell targeting unit, (ii) amino moiety that is protonated in acidic (pH <6.5) conditions for pH-activation of the PS based on photoinduced electron transfer (PET) and (iii) hydrophilic groups enhancing the water solubility of very hydrophobic BODIPY dyes. Illumination of such compounds with suitable light (>640nm) allowed for high phototoxicity against HeLa (αvβ3 integrin and biotin receptor positive) and A549 (biotin receptor positive) cells compared to healthy MRC-5 (biotin negative) cells. Moreover, no dark toxicity was observed on selected cell lines (>10 μM) providing promising photosensitizers for tumour-targeted photodynamic therapy.

• Klíčová slova
• Activatable, BODIPY, Biotin, Integrin, Near-infrared, Photodynamic, Photosensitizer, cRGD peptide,
• MeSH
• biotin * chemie   MeSH
• buňky A549 MeSH
• cyklické peptidy chemie   farmakologie   MeSH
• fotochemoterapie * MeSH
• fotosenzibilizující látky * chemie   farmakologie   MeSH
• HeLa buňky MeSH
• infračervené záření MeSH
• koncentrace vodíkových iontů MeSH
• lidé MeSH
• sloučeniny boru * chemie   farmakologie   MeSH
• viabilita buněk účinky léků   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene MeSH Prohlížeč
• biotin * MeSH
• cyclic arginine-glycine-aspartic acid peptide MeSH Prohlížeč
• cyklické peptidy MeSH
• fotosenzibilizující látky * MeSH
• sloučeniny boru * MeSH

Novel multifunctional photosensitizers (MFPSs), 5,10,15-tris(4-N-methylpyridinium)-20-(4-phenylthio)-[21H,23H]-porphine trichloride (PORTH) and 5,10,15-tris(4-N-methylpyridinium)-20-(4-(butyramido-methylcysteinyl)-hydroxyphenyl)-[21H,23H]-porphine trichloride (PORTHE), derived from 5,10,15-Tris(4-methylpyridinium)-20-phenyl-[21H,23H]-porphine trichloride (Sylsens B) and designed for treatment of onychomycosis were characterized and their functionality evaluated. MFPSs should function as nail penetration enhancer and as photosensitizer for photodynamic treatment (PDT) of onychomycosis. Spectrophotometry was used to characterize MFPSs with and without 532 nm continuous-wave 5 mW cm(-2) laser light (± argon/mannitol/NaN3 ). Nail penetration enhancement was screened (pH 5, pH 8) using water uptake in nails and fluorescence microscopy. PDT efficacy was tested (pH 5, ± argon/mannitol/NaN3 ) in vitro with Trichophyton mentagrophytus microconida (532 nm, 5 mW cm(-2) ). A light-dependent absorbance decrease and fluorescence increase were found, PORTH being less photostable. Argon and mannitol increased PORTH and PORTHE photostability; NaN3 had no effect. PDT (0.6 J cm(-2) , 2 μm) showed 4.6 log kill for PORTH, 4.4 for Sylsens B and 3.2 for PORTHE (4.1 for 10 μm). Argon increased PORTHE, but decreased PORTH PDT efficacy; NaN3 increased PDT effect of both MFPSs whereas mannitol increased PDT effect of PORTHE only. Similar penetration enhancement effects were observed for PORTH (pH 5 and 8) and PORTHE (pH 8). PORTHE is more photostable, effective under low oxygen conditions and thus realistic candidate for onychomycosis PDT.

• MeSH
• fluorescence MeSH
• fotochemoterapie MeSH
• fotosenzibilizující látky farmakologie   terapeutické užití   MeSH
• koncentrace vodíkových iontů MeSH
• lidé MeSH
• nehty účinky léků   metabolismus   MeSH
• onychomykóza farmakoterapie   terapie   MeSH
• světlo * MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• fotosenzibilizující látky MeSH

Electrospun nanofibers possess large surface to volume ratios, high porosity, and good mechanical properties that are necessary for biological applications. We prepared different types of photoactive polymeric nanofiber materials with encapsulated or externally bound porphyrin photosensitizers. The kinetics of formation and the decay of both singlet oxygen O2((1)Δg) and porphyrin triplet states that are generated by irradiation of nanofiber materials in an air atmosphere or in an air-saturated aqueous solution were measured and evaluated by luminescence and transient absorption spectroscopy in the temperature range between 5 and 60 °C. We found shortening of the O2((1)Δg) lifetime and a significant increase in singlet oxygen-sensitized delayed fluorescence at higher temperatures. These photophysical data show an increase in the diffusion coefficient for O2((1)Δg) with temperature, and they are consistent with a stronger antibacterial effect of the nanofiber material on Escherichia coli at higher temperature.

• MeSH
• antibakteriální látky chemie   MeSH
• difuze MeSH
• Escherichia coli MeSH
• fotosenzibilizující látky chemie   MeSH
• kinetika MeSH
• mikroskopie elektronová rastrovací MeSH
• nanovlákna chemie   MeSH
• polymery chemie   MeSH
• porfyriny chemie   MeSH
• singletový kyslík chemie   MeSH
• spektrální analýza MeSH
• světlo MeSH
• teplota * MeSH
• voda chemie   MeSH
• vzduch MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• antibakteriální látky MeSH
• fotosenzibilizující látky MeSH
• polymery MeSH
• porfyriny MeSH
• singletový kyslík MeSH
• voda MeSH

Photodynamic therapy (PDT) is one of the treatments for cancer. This therapy uses a combination of a photosensitizer (PS), light irradiation, and oxygen O2, which is converted to cytotoxic 1O2 and other forms of reactive oxygen species (ROS), causing selective damage to the target tissue. In this work, we studied effect of two porphyrin photosensitizers TMPyP and ZnTPPS4 at three different concentrations (0.25, 0.5, 5μM) after two irradiation doses (5 and 25 J/cm2). Photodynamic efect of TMPyP and ZnTPPS4 were confirmed by a battery of in vitro tests including MTT, reactive oxygen species (ROS) production and mitochondrial membrane potential test (MMP). Morphological changes of the cells before and after treatment were imaged by atomic force microscopy (AFM). The most effective combination of irradiation dose and concentration for both PSs showed a concentration of 5 μM and a irradiation dose of 25 J/cm2 in both cell cultures.

• Klíčová slova
• Cancer cells, PDT, Photodynamic therapy, Porphyrine photosensitizer, TMPyP, ZnTPPS(4),
• MeSH
• fotochemoterapie * metody   MeSH
• fotosenzibilizující látky farmakologie   terapeutické užití   MeSH
• metaloporfyriny * MeSH
• nádory * farmakoterapie   MeSH
• porfyriny * farmakologie   MeSH
• reaktivní formy kyslíku MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• fotosenzibilizující látky MeSH
• metaloporfyriny * MeSH
• porfyriny * MeSH
• reaktivní formy kyslíku MeSH
• zinc-tetrakis(p-sulfonatophenyl)porphyrin MeSH Prohlížeč