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 gradually becoming an alternative method in the treatment of several diseases. Here, we investigated the role of oxygen in photodynamically treated cervical cancer cells (HeLa). The effect of PDT on HeLa cells was assessed by exposing cultured cells to disulphonated zinc phthalocyanine (ZnPcS2) and tetrasulphonated zinc tetraphenylporphyrin (ZnTPPS4). Fluorescence microscopy revealed their different localizations within the cells. ZnTPPS4 seems to be mostly limited to the cytosol and lysosomes, whereas ZnPcS2 is most likely predominantly attached to membrane structures, including plasmalemma and the mitochondrial membrane. Phototoxicity assays of PDT-treated cells carried out under different partial pressures of oxygen showed dose-dependent responses. Interestingly, ZnPcS2 was also photodynamically effective at a minimal level of oxygen, under a nitrogen atmosphere. On the other hand, hyperbaric oxygenation did not lead to a higher PDT efficiency of either photosensitizer. Although both photosensitizers can induce a significant drop in mitochondrial membrane potential, ZnPcS2 has a markedly higher effect on mitochondrial respiration that was completely blocked after two short light cycles. In conclusion, our observations suggest that PDT can be effective even in hypoxic conditions if a suitable sensitizer is chosen, such as ZnPcS2, which can inhibit mitochondrial respiration.

• Klíčová slova
• Hyperbaria, Photodynamic therapy, Photosensitizers,
• MeSH
• fotochemoterapie metody   MeSH
• fotosenzibilizující látky farmakologie   MeSH
• HeLa buňky MeSH
• indoly aplikace a dávkování   farmakologie   MeSH
• kyslík aplikace a dávkování   farmakologie   MeSH
• lidé MeSH
• membránový potenciál mitochondrií účinky léků   MeSH
• metaloporfyriny aplikace a dávkování   farmakologie   MeSH
• mitochondrie účinky léků   MeSH
• organokovové sloučeniny aplikace a dávkování   farmakologie   MeSH
• parciální tlak MeSH
• singletový kyslík analýza   MeSH
• viabilita buněk účinky léků   MeSH
• vztah mezi dávkou a účinkem léčiva MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• fotosenzibilizující látky MeSH
• indoly MeSH
• kyslík MeSH
• metaloporfyriny MeSH
• organokovové sloučeniny MeSH
• singletový kyslík MeSH
• zinc phthalocyanine disulfonate MeSH Prohlížeč
• zinc tetraphenylporphyrin MeSH Prohlížeč

This work presents results on the efficiency of newly designed zinc phthalocyanine-mediated photodynamic therapy of both tumoral and nontumoral cell models using the MTT assay. Further detailed examinations of mechanistic and cell biological effects were focused on the HELA cervical cancer cell model. Here, ROS production, changes in the mitochondrial membrane potential, the determination of genotoxicity, and protein changes determined by capillary chromatography and tandem mass spectrometry with ESI were analyzed. The results showed that, in vitro, 5 Jcm-2 ZnPc PDT caused a significant increase in reactive oxygen species. Still, except for superoxide dismutase, the levels of proteins involved in cell response to oxidative stress did not increase significantly. Furthermore, this therapy damaged mitochondrial membranes, which was proven by a more than 70% voltage-dependent channel protein 1 level decrease and by a 65% mitochondrial membrane potential change 24 h post-therapy. DNA impairment was assessed by an increased level of DNA fragmentation, which might be related to the decreased level of DDB1 (decrease in levels of more than 20% 24 h post-therapy), a protein responsible for maintaining genomic integrity and triggering the DNA repair pathways. Considering these results and the low effective concentration (LC50 = 30 nM), the therapy used is a potentially very promising antitumoral treatment.

• Klíčová slova
• DNA, liposome, mitochondria, oxidative stress, photodynamic therapy, proteins, reactive oxygen species,
• MeSH
• fotochemoterapie * metody   MeSH
• fotosenzibilizující látky * farmakologie   chemie   MeSH
• HeLa buňky MeSH
• indoly * farmakologie   chemie   MeSH
• isoindoly * MeSH
• lidé MeSH
• membránový potenciál mitochondrií * účinky léků   MeSH
• organokovové sloučeniny * farmakologie   chemie   MeSH
• oxidační stres účinky léků   MeSH
• poškození DNA účinky léků   MeSH
• reaktivní formy kyslíku * metabolismus   MeSH
• sloučeniny zinku * farmakologie   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• fotosenzibilizující látky * MeSH
• indoly * MeSH
• isoindoly * MeSH
• organokovové sloučeniny * MeSH
• reaktivní formy kyslíku * MeSH
• sloučeniny zinku * MeSH
• Zn(II)-phthalocyanine MeSH Prohlížeč

The distribution study of zinc phthalocyanine disulfonate (ZnPcS2) in nude mice bearing mammary carcinoma (T50/80) revealed a rapid uptake of the dye by tumor. In experimental photodynamic therapy (PDT), the tumors were exposed to laser radiation (670 nm, 100 mW/cm2, 150 J/ /cm2) after intravenous administration of ZnPcS2 in saline. The results showed the maximum tumor destruction to be achieved for the time interval between injection of the drug (2 mg/kg) and exposure to laser light of 5 min, while a significantly less damage was observed when the time interval was 24 h (p < 0.0001). The degree of damage produced by the treatment was monitored in vivo by means of noninvasive NMR-imaging and subsequently confirmed histologically.

• MeSH
• experimentální nádory mléčných žláz farmakoterapie   metabolismus   MeSH
• fotochemoterapie MeSH
• fotosenzibilizující látky farmakokinetika   MeSH
• indoly farmakokinetika   farmakologie   MeSH
• magnetická rezonanční tomografie MeSH
• myši inbrední BALB C MeSH
• myši nahé MeSH
• myši MeSH
• nekróza MeSH
• organokovové sloučeniny farmakokinetika   farmakologie   MeSH
• tkáňová distribuce MeSH
• zvířata MeSH
• Check Tag
• myši MeSH
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• fotosenzibilizující látky MeSH
• indoly MeSH
• organokovové sloučeniny MeSH
• zinc phthalocyanine disulfonate MeSH Prohlížeč

This study deals with the use of cationic far-red absorbing photosensitizers (λ(max) ~740 nm) from the group of the phthalocyanines, in photodynamic therapy. The photosensitizers differed in their central atom, bearing either hydrogen, zinc or magnesium. These photosensitizers were tested in vitro on the tumour cell line HeLa (cervical cancer) and non-tumour cell line NIH3T3 (mouse fibroblast). The following tests were performed: measurement of reactive oxygen species production, viability testing, Comet assay and cell type detection (apoptotic, necrotic and living cells). The best results were achieved with zinc derivative at relatively low half-maximum inhibitory concentration (0.04 μM) and a total radiation dose of 15 J cm(-2).

• Klíčová slova
• Photosensitizer, Phthalocyanine, cellular damage, oxidative stress, photodynamic treatment, phototoxicity, tumour cells,
• MeSH
• buněčné linie MeSH
• buňky NIH 3T3 MeSH
• fotochemoterapie metody   MeSH
• fotosenzibilizující látky farmakologie   MeSH
• HeLa buňky MeSH
• hořčík farmakologie   MeSH
• indoly farmakologie   MeSH
• isoindoly MeSH
• lidé MeSH
• myši MeSH
• nádorové buněčné linie MeSH
• nádory farmakoterapie   metabolismus   MeSH
• reaktivní formy kyslíku metabolismus   MeSH
• zinek farmakologie   MeSH
• zvířata MeSH
• Check Tag
• lidé MeSH
• myši MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• fotosenzibilizující látky MeSH
• hořčík MeSH
• indoly MeSH
• isoindoly MeSH
• phthalocyanine MeSH Prohlížeč
• reaktivní formy kyslíku MeSH
• zinek MeSH

The formation of self-assemblies between CdSe quantum dots (QDs) and Zn phthalocyanines (Pc) and azaphthalocyanines (AzaPc) bearing alkylsulfanyl substituents and the photophysical properties of these assemblies were studied using both steady-state and time-resolved luminescence/absorption spectroscopy. The formation of the self-assemblies was accompanied by a blue shift of the Q band of the dyes and by a quenching of the CdSe QDs luminescence. The largest spectral shift of the Q-band was approximately 7 nm and was observed for pentan-3-ylsulfanyl-functionalised phthalocyanine (). Assuming a 1 : 1 stoichiometry, the calculated binding constant was 4 × 10(4) M(-1). Pc substituted with the bulky tert-butylsulfanyl groups (1) exhibited a smaller shift of the Q band. The quenching of the CdSe QDs luminescence by 1 was more effective than that observed for 3. The results indicated that the luminescence quenching may be due to a photoinduced charge transfer between 1 or 3 and the CdSe QDs. In contrast, the AzaPc (2) with the same substituents as 1 had little effect on the QDs luminescence. For all cases, we found an inefficient resonance energy transfer between the attached dyes and the CdSe QD. The formation of the self-assemblies had negligible effects on the photogeneration of the singlet oxygen, O2((1)Δg), that was fully controlled only by the absorption of the light by the macrocycles.

• MeSH
• fluorescenční spektrometrie MeSH
• indoly chemie   MeSH
• isoindoly MeSH
• kvantová teorie MeSH
• kvantové tečky * MeSH
• organokovové sloučeniny chemie   MeSH
• rozpouštědla chemie   MeSH
• sloučeniny kadmia chemie   MeSH
• sloučeniny selenu chemie   MeSH
• sloučeniny zinku MeSH
• velikost částic MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• cadmium selenide MeSH Prohlížeč
• indoly MeSH
• isoindoly MeSH
• organokovové sloučeniny MeSH
• phthalocyanine MeSH Prohlížeč
• rozpouštědla MeSH
• sloučeniny kadmia MeSH
• sloučeniny selenu MeSH
• sloučeniny zinku MeSH
• Zn(II)-phthalocyanine MeSH Prohlížeč

BACKGROUND/AIM: Colorectal cancer (CRC) is one of the most widespread malignancies. One of the alternative therapeutic methods appears to be photodynamic therapy (PDT). MATERIALS AND METHODS: This study investigated the efficiency of 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin zinc (ZnTPPS4) and chloro-aluminum phthalocyanine disulfonate (ClAlPcS2) with two commercial photosensitive compounds 5,10,15,20-tetrakis(1-methylpyridinium-4-yl)porphyrin (TMPyP) and tetramethylthionine chloride (methylene blue, MB) in PDT for CRC in vitro. In addition to the study of the photodynamic effect on the viability of the colorectal carcinoma cell line HT29, cellular uptake, ROS production, and DNA damage were investigated. RESULTS: All photosensitizers showed good accumulation within HT29 cells, high efficiency in killing the cells, and a concentration-dependent increase in the production of ROS. CONCLUSION: PDT using ZnTPPS4 and ClAlPcS2 may be effective in the treatment of CRC, achieving a similar photocytotoxic effect at much lower concentrations compared to MB.

• Klíčová slova
• Colorectal adenocarcinoma, DNA fragmentation, photodynamic therapy, phthalocyanines, porphyrins, reactive oxygen species,
• MeSH
• adenokarcinom * farmakoterapie   metabolismus   patologie   MeSH
• buňky HT-29 MeSH
• fotochemoterapie * metody   MeSH
• fotosenzibilizující látky * farmakologie   MeSH
• indoly * farmakologie   MeSH
• kolorektální nádory * farmakoterapie   patologie   metabolismus   MeSH
• lidé MeSH
• metaloporfyriny * farmakologie   MeSH
• organokovové sloučeniny * farmakologie   MeSH
• poškození DNA účinky léků   MeSH
• reaktivní formy kyslíku * metabolismus   MeSH
• viabilita buněk účinky léků   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• fotosenzibilizující látky * MeSH
• indoly * MeSH
• metaloporfyriny * MeSH
• organokovové sloučeniny * MeSH
• reaktivní formy kyslíku * MeSH
• zinc-tetrakis(p-sulfonatophenyl)porphyrin MeSH Prohlížeč

The intramolecular charge transfer (ICT), which is a pathway for excited state relaxation, was studied on the newly synthesized zinc(ii) complexes of tetrapyrazinoporphyrazines bearing one fixed donor (i.e., a dialkylamino substituent). The rest of the peripheral substituents on the core was designed with respect to their different electronic effects (OBu, neopentyl, StBu, COOBu). The photophysical (singlet oxygen and fluorescence quantum yields) and electrochemical (reduction potentials) properties were determined and compared within the series and with compounds that did not contain a donor moiety. The ICT efficiency correlated well with both the electron-deficient character of the core and the Hammett substituent constants σp. The most efficient ICT was observed for the core with the most electron-accepting substituent (COOBu), and the lowest ICT efficiency was detected for the least electron-deficient core (substituted by OBu). Titration of DMSO solutions of target compounds with H2SO4 indicated that basicity of the azomethine bridges was largely influenced by the character of the peripheral substituents while the dialkylamino donor center remained nearly unaffected. Furthermore, protonation of the donor nitrogen caused partial restoration of the fluorescence quantum yield (increase up to 90 times) due to blocking of ICT. The results implied that the ICT efficiency was strongly dependent on the electron-accepting properties of the core whose properties can be readily affected by suitable selection of peripheral substituents.

• MeSH
• elektrochemie MeSH
• elektrony MeSH
• fluorescence MeSH
• indoly chemie   MeSH
• isoindoly MeSH
• organokovové sloučeniny chemie   MeSH
• singletový kyslík chemie   MeSH
• sloučeniny zinku MeSH
• spektrofotometrie ultrafialová MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• indoly MeSH
• isoindoly MeSH
• organokovové sloučeniny MeSH
• singletový kyslík MeSH
• sloučeniny zinku MeSH
• Zn(II)-phthalocyanine MeSH Prohlížeč

Intramolecular charge transfer (ICT) was studied on a series of magnesium, metal-free and zinc complexes of unsymmetrical tetrapyrazinoporphyrazines and tribenzopyrazinoporphyrazines bearing two dialkylamino substituents (donors) and six alkylsulfanyl or aryloxy substituents (non-donors). The dialkylamino substituents were responsible for ICT that deactivated excited states and led to considerable decrease of fluorescence and singlet oxygen quantum yields. Photophysical and photochemical properties were compared to corresponding macrocycles that do not bear any donor centers. The data showed high feasibility of ICT in the tetrapyrazinoporphyrazine macrocycle and significantly lower efficiency of this deactivation process in the tribenzopyrazinoporphyrazine type molecules. Considerable effect of non-donor peripheral substituents on ICT was also described. The results imply that tetrapyrazinoporphyrazines may be more suitable for development of new molecules investigated in applications based on ICT.

• MeSH
• fluorescenční spektrometrie MeSH
• hořčík chemie   MeSH
• indoly chemie   MeSH
• isoindoly MeSH
• komplexní sloučeniny chemie   MeSH
• kvantová teorie MeSH
• singletový kyslík chemie   metabolismus   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• hořčík MeSH
• indoly MeSH
• isoindoly MeSH
• komplexní sloučeniny MeSH
• phthalocyanine MeSH Prohlížeč
• singletový kyslík MeSH

A series of zinc complexes of phthalocyanine, naphthalocyanine and their aza-analogues with alkylsulfanyl substituents was synthesized and characterized by UV-vis and MCD spectroscopy, and their redox properties were investigated using CV, DPV, and SWV approaches as well as spectroelectrochemical methods. Aggregation, photostability, singlet oxygen production, and fluorescence quantum yields of the target complexes were studied as a function of the stepwise substitution of the aromatic C-H fragments by nitrogen atoms. The electronic structure and vertical excitation energies of the target compounds were probed by DFT-PCM and TDDFT-PCM approaches. Introduction of additional nitrogens into the structure leads to a hypsochromic shift of the Q-band and makes the macrocycle strongly electron deficient and more photostable. The impact on the photophysics is limited. The relationships between the type of macrocycle and the studied properties were defined.

• MeSH
• aza sloučeniny chemie   MeSH
• elektrony MeSH
• indoly chemie   MeSH
• isoindoly MeSH
• komplexní sloučeniny chemie   MeSH
• kvantová teorie MeSH
• molekulární modely MeSH
• organokovové sloučeniny chemie   MeSH
• singletový kyslík chemie   MeSH
• zinek chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• aza sloučeniny MeSH
• indoly MeSH
• isoindoly MeSH
• komplexní sloučeniny MeSH
• organokovové sloučeniny MeSH
• phthalocyanine MeSH Prohlížeč
• singletový kyslík MeSH
• zinc naphthalocyanine MeSH Prohlížeč
• zinek MeSH