RESUMO
From the array of small molecule organic fluorophores available as functional materials and in biology, synthetic procedures that allow for a simpler and rapid synthesis of organic fluorophores with desirable photophysical properties are in high demand. In addition, fluorophores with good brightness and tuneability in both solid and solution states are only available in certain numbers. Herein, we introduce a new family of pyrrolo[2,1-a]isoindolylidene-malononitrile (PIYM) fluorophores that exhibit pronounced emission in the visible region in solution and red-NIR emission in the solid state, with tuneability, efficient brightness and stability. PIYM fluorophores were efficiently synthesized via two simple MCR reaction pathways from commercially available, as well as newly synthesized, building blocks. Furthermore, the observed photophysical nature is rationalized from both electrochemical and theoretical calculations (DFT and TD-DFT). In the future, we anticipate that these PIYM fluorophores, with their excellent stability and lower molecular weight, will open ways to enhance the development of NIR-emitting fluorophores with more significant applications in both materials and biological fields.
Assuntos
Corantes Fluorescentes , Nitrilas , Corantes Fluorescentes/química , IonóforosRESUMO
Bioconjugation is the chemical strategy of covalent modification of biomolecules, using either an external reagent or other biomolecules. Since its inception in the twentieth century, the technique has grown by leaps and bounds, and has a variety of applications in chemical biology. However, it is yet to reach its full potential in the study of biochemical processes in live cells, mainly because the bioconjugation strategies conflict with cellular processes. This has mostly been overcome by using transition metal catalysts, but the presence of metal centers limit them to in vitro use, or to the cell surface. These hurdles can potentially be circumvented by using metal-free strategies. However, the very modifications that are necessary to make such metal-free reactions proceed effectively may impact their biocompatibility. This is because biological processes are easily perturbed and greatly depend on the prevailing inter- and intracellular environment. With this taken into consideration, this review analyzes the applicability of the transition-metal-free strategies reported in this decade to the study of biochemical processes in vivo.
Assuntos
Química Click/métodos , Reação de Cicloadição/métodos , Coloração e Rotulagem/métodos , Alcinos/síntese química , Alcinos/química , Animais , Azidas/síntese química , Azidas/química , Catálise , Humanos , Indicadores e Reagentes , Metais/química , Proteínas/análiseRESUMO
Skeletally diverse and complex aza-cyclopenta(cd)diindene, pyrrolo(3,4-d)pyridine-13-carboxamide, and furo-pyrrolo(1,2-a)imidazole-4-carboxamide fused polyheterocyclic hybrid scaffolds and a furo(2,3-b)furan core have been accessed via one-pot three-component reaction by exploiting the build/couple/pair strategy of diversity oriented synthesis (DOS). This protocol is metal free, has a good substrate scope and affords products with good to excellent yields and regio- and chemo-selectivity. The heterocyclic skeletons obtained in this study mimic natural products such as eupolauramine, gracilamine and presilphiperfolanol.
RESUMO
A library of 4H-chromene derivatives with heterocyclic substituent's at the 3 and 4-positions was synthesized in a convenient DBU catalysed three component synthesis between salicylaldehyde, acetonitrile derivatives and thiazolidinedione to afford 2-amino-3-benzothiazole-4-heterocycle-4H-chromenes and 2-amino-3-thiophenoyl-4-heterocycle-4H-chromenes derivatives in ethanol and a mixture of ethanol and water (1 : 1) at room temperature. The significance of this protocol is the feasibility of incorporating substituents simultaneously at the 3 and 4 positions of 4H-chromenes in an efficient three component reaction.
RESUMO
Antimicrobial therapy against extensively drug-resistant (XDR) P. aeruginosa biofilms is less efficient compared to the treatment of equal bacterial counts of free-floating planktonic cells, which has become a serious threat in hospital environment. P. aeruginosa regulate their cooperative activities and physiological processes through a cell to cell chemical communication process called Quorum sensing (QS). This attracted our interest to synthesize, and to chemically characterize two anti-QS compounds, N-(4-{4-fluoroanilno} butanoyl) -l-homoserine lactone (FABHL) and N-(4-{4-chlororoanilno} butanoyl) -l-homoserine lactone (CABHL) to inhibit biofilm formation via disabling the QS circuits. Structural and morphological properties of these compounds were characterized by 1H Nuclear Magnetic Resonance (NMR), 13C NMR and High-resolution mass spectrometry (HRMS). Two biofilm forming XDR P. aeruginosa isolates were included in this study. Anti-biofilm property of FABHL or CABHL was confirmed by biofilm formation assay and it was shown to occur without affecting the bacterial growth. Anti-QS property of FABHL or CABHL was determined by evaluating the expression levels of QS genes (lasR and rhlR) by quantitative real time PCR (qRT-PCR). Although, FABHL and CABHL downregulates the expression levels of QS genes, lasR expression was significantly reduced. Molecular modeling studies revealed that the binding energy of FABHL and CABHL with LasR protein was -4.27 and -4.51, respectively. Hence, the synthesized compounds have the potential to serve as a potent anti-biofilm agent via disabling the QS systems. Lethality of FABHL and CABHL against PBMCs was assessed by 3-(4, 5- dimethylthiazol-2-yl)-2, 5-diphynyl tetrazolium bromide (MTT) assay. Cell viability was observed for both the compounds.