Diketopyrrolopyrrole (DPP) derivatives containing sulfonamide (Sulfonamide-DPP), pyridyl (Dipyridyl-DPP) and N-methylpyridyl (MePyridyl-DPP) substituents were assessed as antibacterial photosensitizers. Non-charged DPPs showed an intense absorption band centered at about 480 nm and green fluorescence emission (Φ ~ 0.7) in acetonitrile.
View Article and Find Full Text PDFA novel tricationic Zn(II)phthalocyanine derivative, (NCH)ZnPc, was synthesized by ring expansion reaction of boron(III) [2,9(10),16(17)-trinitrosubphthalocyaninato]chloride. First, the reaction of this subphthalocyanine with 2,3-naphthalenedicarbonitrile and Zn(CHCOO) catalyzed by 8-diazabicyclo[5.4.
View Article and Find Full Text PDFA nanoplatform concept was developed to synthesize accessible photoactive magnetic nanoparticles (MNPs) of FeO coated with silica. This approach was based on the covalent binding of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TPPF) to aminopropyl-grafted MNPs by nucleophilic aromatic substitution reaction (SAr) to obtain conjugate MNP-P1. After modification, the remaining pentafluorophenyl groups of TPPF attached to MNPs were substituted by dimethylaminoethoxy groups to form MNP-P2.
View Article and Find Full Text PDFDifferent experimental conditions can be used to detect the presence of reactive oxygen species (ROS) in the photodynamic inactivation of microorganisms. Here, we describe the effect of the media and the addition of ROS scavengers to obtain insight about the oxidative processes that take place during the photokilling of bacteria. In addition, 9,10-dimethylanthracene was used to sense the generation of singlet molecular oxygen, O(Δ), in microbial cells.
View Article and Find Full Text PDFChromophore-fullerene C60 hybrids possess interesting properties that enable them to act as heavy atom-free photosensitizers and reactive oxygen species (ROS) producers. Here, two new diketopyrrolopyrrole-C60 conjugates were efficiently synthesized and characterized. The conjugates show broadband absorption in the visible spectral region, in which diketopyrrolopyrrole dyes act as light-harvesting antenna with very high capacity to populate excited triplet states.
View Article and Find Full Text PDFA covalently linked BODIPY-fullerene C dyad (BDP-C ) was synthesized as a two-segment structure, which consists of a visible light-harvesting antenna attached to an energy or electron acceptor moiety. This structure was designed to improve the photodynamic action of fullerene C to inactivate bacteria. The absorption spectrum of BDP-C was found to be a superposition of the spectra of its constitutional moieties, whereas the fluorescence emission of the BODIPY unit was strongly quenched by the fullerene C .
View Article and Find Full Text PDFPhotodiagnosis Photodyn Ther
December 2018
New porphyrin derivatives bearing basic aliphatic amino groups were synthesized from the condensation of meso-4-[(3-N,N-dimethylaminopropoxy)phenyl]dipyrromethane, pentafluorobenzaldehyde and 4-(3-N,N-dimethylaminopropoxy)benzaldehyde. The reaction was catalyzed by trifluoroacetic acid in acetonitrile. This approach was used to obtain porphyrins with different patterns of substitution, of which three of them were isolated: 5,15-di(4-pentafluorophenyl)-10,20-di[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (FAPP), 5-(4-pentafluorophenyl)-10,15,20-tris[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (FAPP) and 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (TAPP).
View Article and Find Full Text PDFIn this study, the phytoplankton structure of a freshwater reservoir located in central Argentina (Embalse Río Tercero) was analyzed using Beutler's method (Photosynthesis Research 72: 39-53, 2002), aiming to provide water quality control agencies with a reliable tool for early detection of algae blooms, particularly cyanobacteria. The method estimated the concentration of chlorophyll a (Chl a) contributed by individual algal groups in a real sample by fitting its fluorescence excitation spectrum to a linear combination of norm spectra of relevant algae groups. To this purpose, norm spectra for five algae genera usually found in Embalse Río Tercero, Microcystis, Chlorella, Cyclotella, Ceratium and Porphyridium, were constructed and posteriorly used to analyze samples collected in the reservoir in years 2014-2016.
View Article and Find Full Text PDFA novel chlorin derivative (TPCF -NMe ) has been synthesized as a syn adduct of a pyrrolidine-fused chlorin bearing a C-linked N,N-dimethylaminophenyl residue. The absorption spectrum of TPCF -NMe is essentially identical to that of TPCF in N,N-dimethylformamide, indicating a very weak interaction between the chlorin macrocycle and the amine group in the ground state. However, the fluorescence emission of the chlorin moiety in TPCF -NMe is effectively quenched by the attached amine unit.
View Article and Find Full Text PDFThe photodynamic mechanism sensitized by N,N-dimethyl-2-[4-(3-N,N,N-trimethylammoniopropoxy)phenyl]fulleropyrrolidinium (DPC) was investigated in Staphylococcus aureus cells. Different experimental conditions were used to detect reactive oxygen species (ROS) in S. aureus cell suspensions.
View Article and Find Full Text PDFA porphyrin-fullerene C60 dyad (TCP-C60) substituted by carbazoyl groups was used to obtain electrogenerated polymeric films on optically transparent indium tin oxide (ITO) electrodes. This approach produced stable and reproducible polymers, holding fullerene units. The properties of this film were compared with those formed by layers of TCP/TCP-C60 and TCP/ZnTCP.
View Article and Find Full Text PDFThe effect of divalent cations, EDTA and chitosan (CS) on the uptake and photoinactivation of Escherichia coli produced by 5,10,15,20-tetrakis(4-N,N,N-trimethylammoniumphenyl)porphyrin (TMAP(4+)), 5,10-di(4-methylphenyl)-15,20-di(4-N,N,N-trimethylammoniumphenyl)porphyrin (MPAP(2+)) and 5,10,15,20-tetra(4-sulphonatophenyl)porphyrin (TPPS(4-)) were examined under different conditions. These porphyrins were rapidly bound to E. coli cells (<2.
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