Spectrochim Acta A Mol Biomol Spectrosc
December 2024
This work describes the successful design and synthesis of a new fluorescence resonance energy transfer (FRET)-based sensor, denoted as RD1. This sensor incorporates a robust dual-fluorophore design, which combines a rhodamine and a dansyl derivative, functionalized with a thiosemicarbazide group that acts as Hg(II) specific recognition site. A synthetic pathway was developed that allowed the efficient synthesis of RD1 with a remarkable overall yield of 44% over four steps, through microwave-assisted protocols.
View Article and Find Full Text PDFTo unveil and shape the molecular connectivity in (metallo)porphyrin-carbon nanotube hybrids are of main relevance for the multiple medicinal, photoelectronic, catalytic, and photocatalytic applications of these materials. Multi-walled carbon nanotubes (MWCNTs) were modified through 1,3-dipolar cycloaddition reactions with azomethine ylides generated in situ and carrying pentafluorophenyl groups, followed by immobilization of the β-amino-tetraphenylporphyrinate Zn(II). The functionalities were confirmed via XPS and FTIR, whereas Raman spectroscopy showed disruptions on the graphitic carbon nanotube surface upon both steps.
View Article and Find Full Text PDFIn this work we pursued research involving the microwave-assisted -alkylation of a NH pyrrolidine-fused chlorin with methyl 4-(bromomethyl) benzoate and subsequent ester hydrolysis as a straightforward strategy to obtain carboxylic acid functionality in the pyrrolidine-fused chlorin, as a single reaction product. We studied the reaction's scope by extending the -alkylation of the free-base chlorin and its corresponding Zn(II) complex to other alkyl halides, including 1,4-diiodobutane, -(2-bromoethyl)phthalimide, and 2-bromoethanaminium bromide. In addition, two new chlorin-dansyl dyads were synthesized by reacting dansyl chloride with the 2-aminoethyl pyrrolidine-fused chlorin (dyad ) and NH pyrrolidine-fused chlorin (dyad ).
View Article and Find Full Text PDFWe report the use of a carboxylated pyrrolidine-fused chlorin (TCPC) as a fluorescent probe for the determination of glutathione (GSH) in 7.4 pH phosphate buffer. TCPC is a very stable, highly emissive molecule that has been easily obtained from meso-tetrakis(4-methoxycarbonylphenyl) porphyrin (TCPP) through a 1,3-dipolar cycloaddition approach.
View Article and Find Full Text PDFIn this work new rosamine-silica composites were prepared and their sensing ability towards different amines was assessed. Rice husk wastes were used as a biogenic silica source. Silica was extracted by thermal treatment, before rice husk ash and after acid leaching with citric acid-treated rice husk ash.
View Article and Find Full Text PDFThe search for accurate and sensitive methods to detect chemical substances, namely cations and anions, is urgent and widely sought due to the enormous impact that some of these chemical species have on human health and on the environment. Here, we present a new platform for the efficient sensing of Cu and Li cations. For this purpose, two novel photoactive diketopyrrolopyrrole-rhodamine conjugates were synthesized through the condensation of a diketopyrrolopyrrole dicarbaldehyde with rhodamine B hydrazide.
View Article and Find Full Text PDFBiomimetic models are valuable platforms to improve our knowledge on the molecular mechanisms governing membrane-driven processes in (patho)physiological conditions, including membrane permeability, transport, and fusion. However, current membrane models are over simplistic and do not include the membrane's lipid remodelling in response to extracellular stimuli. Our study describes the synthesis of glycated dimyristoyl-phosphatidylethanolamine (DMPE-glyc), which was structurally characterised by mass spectrometry (ESI-MS) and quantified by NMR spectroscopy to be further incorporated in a complex phospholipid (PL) membrane model enriched in cholesterol (Chol) and (glyco)sphingolipids (GSL) designed to mimic epithelial membranes (PL/Chol/GSL) under hyperglycaemia conditions.
View Article and Find Full Text PDFFunctionalization of xanthene fluorophores with specific receptor units is an important topic of research aiming for the development of new analytical tools for biological sciences, clinical diagnosis, food and environmental monitoring. Herein, we report a new dihydrorosamine containing two active amino groups, which was functionalized with 3-benzyloxy-1-(3'-carboxypropyl)-2-methyl-4-pyridinone through an amide coupling strategy. Benzylated mono- and di-functionalized dihydrorosamine derivatives (H in position 9 of the xanthene) were obtained, but with modest reaction yields, requiring long and laborious purification procedures.
View Article and Find Full Text PDFChlorins are highly interesting compounds due to their spectroscopic properties in both UV-Vis and NIR regions. Upon coordination to a metal ion, the corresponding metallochlorins exhibit more valuable physicochemical properties that enable a broader range of applications, such as in photodynamic therapy (PDT), water splitting catalysis, optical sensor devices and dye-sensitized solar cells. Synthetic chemistry has been in a continuous quest to fulfil most green chemistry requirements through the development of efficient reactions.
View Article and Find Full Text PDFFunctional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines ( and , respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine , which also showed the most interesting photophysical properties, specially toward biogenic amines (BAs).
View Article and Find Full Text PDFIndomethacin is a potent non-steroidal anti-inflammatory drug (NSAID) with a strong selective inhibitor activity towards cyclooxygenase-2 (COX-2), an enzyme that is highly overexpressed in various tumour cells, being involved in tumourigenesis. Concomitantly, porphyrins have gained much attention as promising photosensitizers (PSs) for the non-invasive photodynamic therapy (PDT) of cancer. Herein, we report the design, and determine the singlet oxygen generation capacity and in vitro cellular toxicity of porphyrin- and chlorin-indomethacin conjugates (P2-Ind and C2-Ind).
View Article and Find Full Text PDFThe development of straightforward reproducible methods for the preparation of new photoluminescent coordination polymers (CPs) is an important goal in luminescence and chemical sensing fields. Isophthalic acid derivatives have been reported for a wide range of applications, and in addition to their relatively low cost, have encouraged its use in the preparation of novel lanthanide-based coordination polymers (LnCPs). Considering that the photoluminescent properties of these CPs are highly dependent on the existence of water molecules in the crystal structure, our research efforts are now focused on the preparation of CP with the lowest water content possible, while considering a green chemistry approach.
View Article and Find Full Text PDFParasitol Int
February 2021
Quantification of parasites in the context of Chagas disease is required to monitor the treatment with benznidazole, disease-associated cardiomyopathies and graft rejection after heart transplantation. As parasitological exams lack sensitivity, Real Time Polymerase Chain Reaction (rt-PCR) has emerged to evaluate the parasite load in blood samples and cardiac biopsies. However, despite its higher sensitivity, rt-PCR does not provide information on the location and distribution of amastigote nests within infected tissues, the characterization of inflammatory infiltrates or changes to tissue architecture.
View Article and Find Full Text PDFA series of metal-organic coordination complexes based on alkaline-earth metal centers [Mg(II), Ca(II), and Ba(II)] and the ligand 5-aminoisophthalate (aip) revealed notable structural diversity, both in the materials' dimensionality and in their hydrogen bonding networks: [Mg(HO)]∙[Mg(Haip)(HO)]∙(Haip)∙3(aip)∙10(HO) () and [Mg(aip)(phen)(HO)]∙(HO) () were isolated as discrete complexes (0D); [Ca(aip)(HO)]∙(HO) (), [Ca(aip)(phen)(HO)]∙(phen)∙(HO) (), and [Ba(aip)(phen)(HO)]∙2(phen)∙2(HO) () revealed metal-organic chain (1D) structures, while the [Ba(aip)(HO)] () showed a metal-organic layered (2D) arrangement. Furthermore, most of these metal-organic coordination materials revealed interesting thermal stability properties, being stable at temperatures up to 450 °C.
View Article and Find Full Text PDFLuminescent metal-organic frameworks (LMOFs) are promising materials for lighting and sensing applications. Herein, exposure of the highly luminescent Zn(bpdc)(bpee) MOF (Hbpdc = 4,4'-biphenyldicarboxylic acid and bpee = 1,2-bipyridylethene) to subppm amine contents turns on a new absorption band unambiguously ascribed to free bpee molecules concomitant with the gradual appearance of a new photoluminescence band at shorter wavelengths. These findings combined with Fourier-transform infrared spectra, powder X-ray diffraction and thermogravimetric analysis of exposed LMOF powders confirm that bpee ligands are exchanged by amines and released inside the LMOF, triggering absorption and luminescence features which can be exploited for highly sensitive amine recognition.
View Article and Find Full Text PDFLeptospirosis is considered a neglected disease with an estimated more than one million cases every year. Since rodents are at the same time the main reservoir and generally asymptomatic to infection, understanding why some animal species are resistant and others are susceptible to this infection would shed some light in how to control this important zoonosis. The innate immune response against is mainly dependent on phagocytosis and activation of the Complement System.
View Article and Find Full Text PDFA series of pyridyl analogues of rosamines was prepared by employing two methodologies: (i) the conventional-heating condensation of a pyridinecarboxaldehyde with 3-(diethylamino)phenol in propionic acid, and (ii) the novel ohmic-heating assisted condensation under "on water" conditions, followed by oxidation. The 4-pyridyl substituted rosamine was further converted into the N-methylpyridinium derivative through N-alkylation using methyl iodide. The influence of the position and cationization of the nitrogen atom of the pyridyl ring in the physicochemical properties of fluorophores was investigated by H, C, N NMR spectral analysis, UV/Vis and fluorescence spectroscopy, single-crystal X-ray diffraction (4-pyridyl and N-methylpyridinium derivatives) and thermal-behavior analysis.
View Article and Find Full Text PDFIn this work, we report the synthesis and characterization of three novel copper(II) complexes of naphthyl derived 3-hydroxy-4-pyridinone chelators. Their antibacterial activity against several Gram-positive and Gram-negative reference strains and multidrug-resistant clinical isolates was assessed through determination of the minimum inhibitory concentration (MIC). The complex Cu(naph1pp) shows the highest antibacterial activity, including against multidrug-resistant isolates, nonetheless, being more active against Gram-positive than Gram-negative bacteria.
View Article and Find Full Text PDFRev Inst Med Trop Sao Paulo
June 2018
Leptospirosis is an acute bacterial septicemic febrile disease caused by pathogenic leptospires, which affect humans and animals in all parts of the world. Transmission can occur by direct contact with infected animals or, more commonly, through indirect contact with water or soil contaminated with urine from infected animals. Leptospires enter the body by penetrating mucous membranes or skin abrasions and disseminate through the hematogenic route.
View Article and Find Full Text PDFThe restricted number of antibiotics to treat infections caused by common multidrug resistant bacterial pathogens in the clinical setting demands a continuous search for new molecules with antibacterial properties. Bacterial iron deprivation represents a promising alternative, being iron chelators an attractive class for drug design in which particular compounds seem to have antibacterial effect. In this work, we report the synthesis and characterization of a new fluorescent 3-hydroxy-4-pyridinone (3,4-HPO) iron chelator functionalized with a carboxyrosamine fluorophore (MRB20).
View Article and Find Full Text PDFFront Cell Infect Microbiol
March 2019
Leptospirosis is considered one of the most important zoonosis worldwide. The activation of the Complement System is important to control dissemination of several pathogens in the host. Only a few studies have employed murine models to investigate leptospiral infection and our aim in this work was to investigate the role of murine C5 during infection, comparing wild type C57BL/6 (B6 C5) and congenic C57BL/6 (B6 C5, C5 deficient) mice during the first days of infection.
View Article and Find Full Text PDF[This corrects the article DOI: 10.1371/journal.pone.
View Article and Find Full Text PDFA novel technique for the creation of metal-organic framework (MOF) films based on soft-imprinting and their use as gas sensors was developed. The microporous MOF material [Zn₂(bpdc)₂(bpee)] (bpdc = 4,4'-biphenyldicarboxylate; bpee = 1,2-bipyridylethene) was synthesized solvothermally and activated by removing the occluded solvent molecules from its inner channels. MOF particles were characterized by powder X-ray diffraction and fluorescence spectroscopy, showing high crystallinity and intense photoluminescence.
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