5-Amino-1H-1,2,4-triazol-4-ium-3-carboxyl­ate hemihydrate

The asymmetric unit of the title compound, C3H4N4O2·0.5H2O, comprises two whole mol­ecules of 5-amino-1H-1,2,4-triazole-3-carb­oxy­lic acid in its zwitterionic form (proton transfer occurs from the carb­oxy­lic acid group to the N hetero­atom at position 1), plus one water mol­ecule of crystallization. The organic moieties are disposed into supra­molecular layers linked by N—H⋯O and N—H⋯N hydrogen bonds parallel to the bc plane. Additional O—H⋯O and N—H⋯O hydrogen bonds involving the water mol­ecules and the organic mol­ecules lead to the formation of double-deck supra­molecular arrangements which are inter­connected along the a axis via π–π stacking [centroid–centroid distance = 3.507 (3) Å]

Octatosylaminophthalocyanine: a reusable chromogenic anion chemosensor

Detailed herein is the use of 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine as a chromogenic chemosensor for anions. The host:guest complexes formed during the sensing event can be regenerated by acid treatment without loss of the sensing ability. This allows the phthalocyanine chemosensor to be reused. This system also responds in a colorimetric manner when exposed to the neutral solvent molecules, dimethyl sulfoxide and methanol. A single-crystal X-ray structure of the Pc 1:2 MeOH complex was obtained. It illustrates the main interactions between the host:guest species in the solid state. Fits of the binding curves are consistent with this stoichiometry predominating in the solution state

Spherical and rod shaped mesoporous nanosilicas for cancer- targeted and photosensitizers delivery in photodynamic therapy

Mesoporous silica nanoparticles (MSNPs) have attracted much attention in many biomedical applications. One of the fields in which smart functional nanosystems have found wide application is cancer treatment. Here, we present new silica nanoparticle-based systems which have been explored as efficient vehicles to transport and deliver photosensitizers (PSs) into tumor tissues during photodynamic therapy (PDT). In this work, we report the preparation, characterization, and in vitro studies of distinct shaped MSNPs grafted with S-glycoside porphyrins (Pors). The ensuing nanomaterials were fully characterized, and their properties as third-generation PSs for PDT against two bladder cancer cell lines, HT-1376 and UM-UC-3, were examined. The best uptake results were obtained for MSNP-PS2, while MSNP-PS1 showed the lowest cellular uptake among the nanocarriers tested, but revealed the best phototoxicity in both cancer cells. Overall, the phototoxicity was higher with MSNPs than with mesoporous silica nanorods (MSNRs) and higher uptake and phototoxicity were consistently observed in UM-UC-3 rather than in HT-1376 cancer cellpublishe

Methyl 2-(4,6-dichloro-1,3,5-triazin-2-yl­amino)acetate

The title compound, C6H6Cl2N4O2, was prepared by the nucleophilic substitution of 2,4,6-trichloro-1,3,5-triazine by glycine methyl ester hydro­chloride, and was isolated from the reaction by using flash chromatography. The crystal structure at 150 K reveals the presence two crystallographically independent mol­ecules in the asymmetric unit which differ in the orientation of the pendant methoxy­carbonyl group. Each mol­ecular unit is engaged in strong and highly directional N—H⋯N hydrogen-bonding inter­actions with a symmetry-related mol­ecule, forming supra­molecular dimers which act as the synthons in the crystal packing

Photodynamic inactivation of a RNA-virus model using water-soluble β-octa-Substituted pyridinium-pyrazolyl phthalocyanines

Among the various groups of microorganisms, viruses have generally a greater capacity for mutation, especially RNA viruses, as was demonstrated by SARS-CoV2 virus mutations. This high mutation rate promotes the development of their resistance to traditional antivirals and establishes the resistance behaviour in virus populations, decreasing their susceptibility to these drugs. In this context, the photodynamic treatment appears as a potentially effective method against microorganisms and, considering its mode of action is not likely to lead to the development of resistance. In this work, two newly zinc(II) phthalocyanines (ZnPcs) bearing pyridinium-pyrazolyl groups (2a and 3a) were synthesized, characterized, and applied in photodynamic inactivation (PDI) of bacteriophage Φ6 (or Phage Phi6) as a RNA-virus model. These quaternized dyes were applied at different concentrations (from 5.0 to 20 μM, and under white light irradiation in the irradiance range between 50 and 150 mW/cm2) to test their efficiency for possible clinical or environmental applications. The results showed that the new cationic ZnPcs 2a and 3a efficiently inactivate the RNA-virus model (bacteriophage Φ6), even at the lowest tested irradiance. These compounds are thus promising photosensitizers to be used in various contexts.info:eu-repo/semantics/publishedVersio

Galactodendritic Phthalocyanine Targets Carbohydrate- Binding Proteins Enhancing Photodynamic Therapy

Photosensitizers (PSs) are of crucial importance in the effectiveness of photodynamic therapy (PDT) for cancer. Due to their high reactive oxygen species production and strong absorption in the wavelength range between 650 and 850 nm, where tissue light penetration is rather high, phthalocyanines (Pcs) have been studied as PSs of excellence. In this work, we report the evaluation of a phthalocyanine surrounded by a carbohydrate shell of sixteen galactose units distributed in a dendritic manner (PcGal16) as a new and efficient third generation PSs for PDT against two bladder cancer cell lines, HT-1376 and UMUC- 3. Here, we define the role of galacto-dendritic units in promoting the uptake of a Pc through interaction with GLUT1 and galectin-1. The photoactivation of PcGal16 induces cell death by generating oxidative stress. Although PDT with PcGal16 induces an increase on the activity of antioxidant enzymes immediately after PDT, bladder cancer cells are unable to recover from the PDT-induced damage effects for at least 72 h after treatment. PcGal16 co-localization with galectin-1 and GLUT1 and/or generation of oxidative stress after PcGal16 photoactivation induces changes in the levels of these proteins. Knockdown of galectin-1 and GLUT1, via small interfering RNA (siRNA), in bladder cancer cells decreases intracellular uptake and phototoxicity of PcGal16. The results reported herein show PcGal16 as a promising therapeutic agent for the treatment of bladder cancer, which is the fifth most common type of cancer with the highest rate of recurrence of any cancer

Glycine methyl ester hydro­chloride

The title compound [systematic name: (methoxy­carbonyl­meth­yl)ammonium chloride], crystallizes as a salt, C3H8NO2 +·Cl−, with the charged species inter­acting mutually via strong and highly directional N+—H⋯Cl− hydrogen bonds which lead to the formation of a supra­molecular tape running parallel to the c axis. Tapes close pack in the solid state mediated by multipoint recognition synthons based on weak C—H⋯O inter­actions and van der Waals contacts between adjacent methyl groups

Thiophene- and carbazole-substituted N-Methyl-Fulleropyrrolidine acceptors in PffBT4T-2OD based solar cells

The impact of fullerene side chain functionalization with thiophene and carbazole groups on the device properties of bulk-heterojunction polymer:fullerene solar cells is discussed through a systematic investigation of material blends consisting of the conjugated polymer poly[(5,6-difluoro-2,1,3-benzothiadiazol-4,7-diyl)-alt-(3,3‴-di(2-octyldodecyl)-2,2′;5′,2″;5″,2‴-quaterthiophen-5,5‴-diyl)] (PffBT4T-2OD) as donor and C60 or C70 fulleropyrrolidines as acceptors. The photovoltaic performance clearly depended on the molecular structure of the fulleropyrrolidine substituents although no direct correlation with the surface morphology of the photoactive layer, as determined by atomic force microscopy, could be established. Although some fulleropyrrolidines possess favorable lowest unoccupied molecular orbital levels, when compared to the standard PC71BM, they originated OPV cells with inferior efficiencies than PC71BM-based reference cells. Fulleropyrrolidines based on C60 produced, in general, better devices than those based on C70, and we attribute this observation to the detrimental effect of the structural and energetic disorder that is present in the regioisomer mixtures of C70-based fullerenes, but absent in the C60-based fullerenes. These results provide new additional knowledge on the effect of the fullerene functionalization on the efficiency of organic solar cells.This work was financially supported by: Base Funding — UIDB/00511/2020 of the Laboratory forProcess Engineering, Environment, Biotechnology and Energy — LEPABE — funded by national funds through theFCT/MCTES (PIDDAC). This work was partially funded within the scope of the project i3N, UIDB/50025/2020 & UIDP/50025/2020, financed by national funds through the FCT/MEC. Thanks are also due to FCT/MEC for thefinancial support to QOPNA (FCT UID/QUI/00062/2019), CICECO-Aveiro Institute of Materials (UIDB/50011/2020& UIDP/50011/2020), CQE (FCT UIDB/00100/2020), and CIQUP (FCT UID/QUI/UI0081/2019) research units, throughnational funds and where applicable co-financed by the FEDER, within the PT2020 Partnership Agreement. H.G.thanks Fundação para a Ciência e a Tecnologia (FCT) for his PhD scholarship (SFRH/BD/103009/2014). The researchcontracts of F.F. (REF. -168-89-ARH/2018) is funded by national funds (OE), through FCT—Fundação para aCiência e Tecnologia, I.P., in the scope of the framework contract foreseen in the numbers 4, 5, and 6 of article 23,of the Decree-Law 57/2016, of August 29, changed by Law 57/2017, of July 19. M.M.F. acknowledges also supportfrom FCT under the project IF/00894/2015

5,10,15,20-Tetra­kis(1-methyl­pyridinium-4-yl)porphyrin tetra­iodide tetra­hydrate

The asymmetric unit of the title compound, C44H38N8 2+·4I−·4H2O, comprises two halves of non-equivalent cations of 5,10,15,20-tetra­kis­(1-methyl­pyridinium)porphyrin (with the full mol­ecule of each completed by the application of inversion symmetry), four charge balancing iodide anions and four water mol­ecules of crystallization (two water mol­ecules are fully occupied and four mol­ecules have a site occupancy of 50%). The porphyrin cations are arranged into supramolecular columns parallel to the b axis, mediated by π–π [centroid–centroid distance = 3.762 (4) Å] and C—H⋯π supra­molecular inter­actions [C⋯centroid distance = 3.522 (7) Å, C—H⋯centroid = 128°], leading to the formation of columns parallel to the b axis. The close packing leads to the presence of a one-dimensional channel filled with partially occupied water mol­ecules engaged in O—H⋯O and O—H⋯I hydrogen bond

1,1′-[(5-Hy­droxy­methyl-1,3-phenyl­ene)bis­(methyl­ene)]dipyridin-4(1H)-one monohydrate

The asymmetric unit of the title compound, C19H18N2O3, comprises a whole organic dipyridinone mol­ecule plus a water mol­ecule of crystallization. The planes of the pyridinone rings are approximately perpendicular with the plane of the central aromatic ring [dihedral angles = 80.68 (8) and 83.65 (8)°]. The C—O bond of the hy­droxy group subtends an angle of 31.71 (10)° with the plane through the central aromatic ring. The crystal packing is mediated by the presence of several O—H⋯O hydrogen-bonding inter­actions and while the water mol­ecules form a C 2 1(4) chain parallel to the c axis of the unit cell, the pendant hy­droxy groups are engaged in O—H⋯O=C hydrogen bonds described by a C 1 1(12) graph-set motif which runs parallel to the a axis