Dataset Information

Novel Nanohybrids Based on Supramolecular Assemblies of Meso-tetrakis-(4-sulfonatophenyl) Porphyrin J-aggregates and Amine-Functionalized Carbon Nanotubes.

ABSTRACT: The ability of multiwalled carbon nanotubes (MWCNTs) covalently functionalized with polyamine chains of different length (ethylenediamine, EDA and tetraethylenepentamine, EPA) to induce the J-aggregation of meso-tetrakis(4-sulfonatophenyl)porphyrin (TPPS) was investigated in different experimental conditions. Under mild acidic conditions, protonated amino groups allow for the assembly by electrostatic interaction with the diacid form of TPPS, leading to hybrid nanomaterials. The presence of only one pendant amino group for a chain in EDA does not lead to any aggregation, whereas EPA (with four amine groups for chain) is effective in inducing J-aggregation using different mixing protocols. These nanohybrids have been characterized through UV/Vis extinction, fluorescence emission, resonance light scattering, and circular dichroism spectroscopy. Their morphology and chemical composition have been elucidated through transmission electron microscopy (TEM) and scanning transmission electron microscopy (STEM). TEM and STEM analysis evidence single or bundles of MWCNTs in contact with TPPS J-aggregates nanotubes. The nanohybrids are quite stable for days, even in aqueous solutions mimicking physiological medium (NaCl 0.15 M). This property, together with their peculiar optical features in the therapeutic window of visible spectrum, make them potentially useful for biomedical applications.

SUBMITTER: Trapani M

PROVIDER: S-EPMC7221796 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Novel Nanohybrids Based on Supramolecular Assemblies of Meso-tetrakis-(4-sulfonatophenyl) Porphyrin J-aggregates and Amine-Functionalized Carbon Nanotubes.

Trapani Mariachiara M Mazzaglia Antonino A Piperno Anna A Cordaro Annalaura A Zagami Roberto R Castriciano Maria Angela MA Romeo Andrea A Monsù Scolaro Luigi L

Nanomaterials (Basel, Switzerland) 20200402 4

The ability of multiwalled carbon nanotubes (MWCNTs) covalently functionalized with polyamine chains of different length (ethylenediamine, EDA and tetraethylenepentamine, EPA) to induce the J-aggregation of meso-tetrakis(4-sulfonatophenyl)porphyrin (TPPS) was investigated in different experimental conditions. Under mild acidic conditions, protonated amino groups allow for the assembly by electrostatic interaction with the diacid form of TPPS, leading to hybrid nanomaterials. The presence of only ...[more]

PMID: 32252418

Similar Datasets

Project description:PURPOSE: Sonodynamic therapy is a developing noninvasive modality for cancer treatment, based on the selective activation of a sonosensitizer agent by acoustic cavitation. The activated sonosensitizer agent might generate reactive oxygen species leading to cancer cell death. We investigated the potential poly-methyl methacrylate core-shell nanoparticles (NPs) loaded with meso-tetrakis (4-sulfonatophenyl) porphyrin (TPPS) have to function as an innovative sonosensitizing system, ie, TPPS-NPs. METHODS: Shockwaves (SWs) generated by a piezoelectric device were used to induce acoustic cavitation. The cytotoxic effect of the sonodynamic treatment with TPPS-NPs and SWs was investigated on the human neuroblastoma cell line, SH-SY5Y. Cells were exposed for 12 hours to TPPS-NPs (100 ?g/mL) and then to SWs (0.43 mJ/mm(2) for 500 impulses, 4 impulses/second). Treatment with SWs, TPPS, and NPs alone or in combination was carried out as control. RESULTS: There was a statistically significant decrease in SH-SY5Y cell proliferation after the sonodynamic treatment with TPPS-NPs and SWs. Indeed, there was a significant increase in necrotic (16.91% ± 3.89%) and apoptotic (27.45% ± 3.03%) cells at 48 hours. Moreover, a 15-fold increase in reactive oxygen species production for cells exposed to TPPS-NPs and SWs was observed at 1 hour compared with untreated cells. A statistically significant enhanced mRNA (messenger ribonucleic acid) expression of NRF2 (P<0.001) and a significant downregulation of TIGAR (P<0.05) and MAP3K5 (P<0.05) genes was observed in cells exposed to TPPS-NPs and SWs at 24 hours, along with a statistically significant release of cytochrome c (P<0.01) at 48 hours. Lastly, the sonosensitizing system was also investigated in an in vitro three-dimensional model, and the sonodynamic treatment significantly decreased the neuroblastoma spheroid growth. CONCLUSION: The sonosensitizing properties of TPPS were significantly enhanced once loaded onto NPs, thus enhancing the sonodynamic treatment's efficacy in an in vitro neuroblastoma model.

Project description:A porphyrin cis tautomer, where the two central NH protons are on adjacent pyrrole rings, has long been invoked as an intermediate in porphyrin tautomerism. Only recently, however, has such a species been isolated and structurally characterized. Thus, single-crystal X-ray structure determinations of two highly saddled free-base porphyrins, ?-heptakis(trifluoromethyl)-meso-tetrakis(p-fluorophenyl)porphyrin, H2[(CF3)7TFPP], and ?-octaiodo-5,10,15,20-tetrakis(4'-trifluoromethylphenyl)porphyrin, H2[I8TCF3PP], unambiguously revealed cis tautomeric structures, each stabilized as a termolecular complex with a pair of ROH (R = CH3 or H) molecules that form hydrogen-bonded N-H···O-H···N straps connecting the central NH groups with the antipodal unprotonated nitrogens. The unusual substitution patterns of these two porphyrins, however, have left open the question how readily such supramolecular assemblies might be engineered, which prompted us to examine the much more synthetically accessible ?-octabromo-meso-tetraphenylporphyrins. Herein, single-crystal X-ray structures were obtained for two such compounds, 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(4'-trifluoromethylphenyl)porphyrin, H2[Br8TCF3PP], and 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(4'-fluorophenyl)porphyrin, H2[Br8TFPP], and although the central hydrogens could not all be located unambiguously, the electron density could be convincingly modeled as porphyrin cis tautomers, existing in each case as a bis-methanol adduct. In addition, a perusal of the Cambridge Structural Database suggests that there may well be additional examples of porphyrin cis tautomers that have not been recognized as such. We are therefore increasingly confident that porphyrin cis tautomers are readily accessible via supramolecular engineering, involving the simple stratagem of crystallizing a strongly saddled porphyrin from a solvent system containing an amphiprotic species such as water or an alcohol.

Dataset Information

Novel Nanohybrids Based on Supramolecular Assemblies of Meso-tetrakis-(4-sulfonatophenyl) Porphyrin J-aggregates and Amine-Functionalized Carbon Nanotubes.

Publications

Novel Nanohybrids Based on Supramolecular Assemblies of Meso-tetrakis-(4-sulfonatophenyl) Porphyrin J-aggregates and Amine-Functionalized Carbon Nanotubes.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets