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The Journal of Organic Chemistry Feb 2024An efficient O-H insertion of hydrogenphosphate derivatives and α-diazo compounds has been developed to construct α-phosphoryloxy scaffolds. Diverse α-phosphoryloxy...
An efficient O-H insertion of hydrogenphosphate derivatives and α-diazo compounds has been developed to construct α-phosphoryloxy scaffolds. Diverse α-phosphoryloxy skeletons could be obtained under mild and catalyst-free conditions in good yields. The control experiments suggest a protonation and nucleophilic addition process of α-diazo compounds via a diazonium ion pair for this transformation.
PubMed: 38270667
DOI: 10.1021/acs.joc.3c02605 -
Organic & Biomolecular Chemistry Jul 2023Herein, a visible light-induced synthesis of polysubstituted oxazoles from diazo compounds is reported. This developed synthetic method differs from traditional routes...
Herein, a visible light-induced synthesis of polysubstituted oxazoles from diazo compounds is reported. This developed synthetic method differs from traditional routes that rely on transition metals and external chemical oxidants. Our method uses readily available and inexpensive diazonium compounds as well as nitrile substrates with a catalytic amount of (i-Pr)SiCl species, delivering the corresponding valuable multi-substituted oxazole products (up to 95% yield). This protocol exhibits a broad substrate scope and is easily carried out under mild reaction conditions. Notably, gram-scale synthesis in a continuous flow fashion has been performed.
PubMed: 37350096
DOI: 10.1039/d3ob00878a -
Biological Trace Element Research Dec 2022Novel three nickel(II) complexes of type [Ni(metf)(o-phen)]Cl (1), [Ni(metf)(opda)]Cl (2), [Ni(metf)(2-2'bipy)]Cl (3), (Metf = metformin,...
Novel three nickel(II) complexes of type [Ni(metf)(o-phen)]Cl (1), [Ni(metf)(opda)]Cl (2), [Ni(metf)(2-2'bipy)]Cl (3), (Metf = metformin, o-phen = ortho-phenanthroline, opda = ortho-phenylenediamine, 2-2' bipy = 2-2' bipyridyl) were synthesized and characterized by various analytical and spectral techniques. Based on these studies, octahedral geometry is assigned to these complexes. The DNA binding properties of these complexes were investigated by absorption, emission, and viscosity studies. From the spectral data, it was concluded that the complexes bind to DNA through groove mode of binding. The intrinsic binding constants (K) from absorption spectroscopy were 1.60 × 10, 3.57 × 10, and 5.70 × 10 M for 1, 2, and 3, respectively, and Stern-Volmer quenching constants (K) from emission spectroscopy were 0.11, 0.87, and 0.24, respectively. Thermal degradation pattern of the compounds was studied and Coats-Redfern method is used to determine kinetic parameters for complexes 1, 2, and 3 from thermal studies. The software Discovery Studio 2.1 was used to assess the binding affinity and interaction pattern of complexes with the B-DNA receptor protein and complex 1 has the highest dock score.
Topics: 2,2'-Dipyridyl; Coordination Complexes; DNA; Diazonium Compounds; Ligands; Metformin; Molecular Docking Simulation; Nickel; Pyridines
PubMed: 34993912
DOI: 10.1007/s12011-022-03100-1 -
Journal of the Mechanical Behavior of... Jan 2020Lack of wet adhesion and biomechanical mismatch at tissue interfaces are the major challenges related to surgical adhesive formulations. Carbene-based bioadhesives seek...
Lack of wet adhesion and biomechanical mismatch at tissue interfaces are the major challenges related to surgical adhesive formulations. Carbene-based bioadhesives seek to address those limitations, due to their ability to covalently bond to wet tissue surfaces. Herein, diazirine-grafted polyamidoamine (PAMAM) dendrimers (PDz) dissolved in various liquid polyethylene glycols (PEG) are reported. Non-aqueous liquid PEG 400 reinforced with high molecular weight PEGs (2 kDa, 6 kDA and 10 kDa) dissolved PDz to form tertiary blends for optimization of viscosity and shear storage modulus. Dynamic photorheometry correlated PEG molar mass and tertiary ratios to adhesion strength, swelling-in-water profile and potential weight loss in aqueous medium. Tertiary blended adhesives demonstrate an improvement in elongation and adhesion strength compared to the binary blends used as control.
Topics: Dendrimers; Diazomethane; Molecular Weight; Polyethylene Glycols; Tissue Adhesives; Water
PubMed: 31539737
DOI: 10.1016/j.jmbbm.2019.103405 -
Molecules (Basel, Switzerland) Dec 2016Nitrogen-containing molecules are key scaffolds that are widely applied in organic synthesis as precursors of highly functionalized materials, and are also investigated...
Nitrogen-containing molecules are key scaffolds that are widely applied in organic synthesis as precursors of highly functionalized materials, and are also investigated for their biological activities. This Special Issue collects seven innovative contributions which expand our knowledge of the chemistry of nitro compounds, amines, diazonium salts, and peptides, and that provide a good overview about their main reactivities.
Topics: Amines; Nitro Compounds; Nitroso Compounds; Peptides; Quaternary Ammonium Compounds
PubMed: 28025551
DOI: 10.3390/molecules22010009 -
Analytical Biochemistry Jun 2018Pyruvate carboxylase (PC) catalyzes the conversion of pyruvate to oxaloacetate (OAA), an important metabolic reaction in a wide range of organisms. Small molecules...
Pyruvate carboxylase (PC) catalyzes the conversion of pyruvate to oxaloacetate (OAA), an important metabolic reaction in a wide range of organisms. Small molecules directed against PC would enable detailed studies on the metabolic role of this enzyme and would have the potential to be developed into pharmacological agents. Currently, specific and potent small molecule regulators of PC are unavailable. To assist in efforts to find, develop, and characterize small molecule effectors of PC, a novel fixed-time assay has been developed based on the reaction of OAA with the diazonium salt, Fast Violet B (FVB), which produces a colored adduct with an absorbance maximum at 530 nm. This fixed time assay is reproducible, sensitive and responsive to known effectors of Rhizobium etli PC, Staphylococcus aureus PC, and Listeria monocytogenes PC, and is highly amenable to high-throughput screening. The assay was validated using a plate uniformity assessment test and a pilot screen of a library of 1280 compounds. The results indicate that the assay is suitable for screening small molecule libraries to find novel small molecule effectors of PC.
Topics: Bacterial Proteins; Enzyme Inhibitors; Listeria monocytogenes; Pyruvate Carboxylase; Rhizobium etli; Staphylococcus aureus
PubMed: 29655770
DOI: 10.1016/j.ab.2018.04.012 -
Biomaterials Mar 2024Impaired angiogenesis, bacterial infection, persistent severe pain, exacerbated inflammation, and oxidative stress injury are intractable problems in the treatment of...
Impaired angiogenesis, bacterial infection, persistent severe pain, exacerbated inflammation, and oxidative stress injury are intractable problems in the treatment of chronic diabetic ulcer wounds. A strategy that effectively targets all these issues has proven challenging. Herein, an in-situ sprayable nanoparticle-gel composite comprising platinum clusters (Pt) loaded-mesoporous polydopamine (MPDA) nanoparticle and QX-314-loaded fibrin gel (Pt@MPDA/QX314@Fibrin) was developed for diabetic wound analgesia and therapy. The composite shows good local analgesic effect of QX-314 mediated by near-infrared light (NIR) activation of transient receptor potential vanilloid 1 (TRPV1) channel, as well as multifunctional therapeutic effects of rapid hemostasis, anti-inflammation, antioxidation, and antibacterial properties that benefit the fast-healing of diabetic wounds. Furthermore, it demonstrates that the composite, with good biodegradability and biosafety, significantly relieved wound pain by inhibiting the expression of c-Fos in the dorsal root ganglion and the activation of glial cells in the spinal cord dorsal horn. Consequently, our designed sprayable Pt@MPDA/QX314@Fibrin composite with good biocompatibility, NIR activation of TRPV1 channel-mediated QX-314 local wound analgesia and comprehensive treatments, is promising for chronic diabetic wound therapy.
Topics: Rats; Animals; Pain; Analgesics; Diabetes Mellitus; Nanocomposites; Fibrin; Anti-Bacterial Agents; Diazonium Compounds; Lidocaine; Pyridines
PubMed: 38224643
DOI: 10.1016/j.biomaterials.2024.122467 -
Journal of the American Chemical Society Mar 2017A critical challenge to translating field effect transistors into biochemical sensor platforms is the requirement of a gate electrode, which imposes restrictions on...
A critical challenge to translating field effect transistors into biochemical sensor platforms is the requirement of a gate electrode, which imposes restrictions on sensor device architectures and results in added expense, poorer scalability, and electrical noise. Here we show that it is possible to eliminate the need of the physical gate electrode and dielectrics altogether using a synthetic tube-in-a-tube (Tube2) semiconductor. Composed of a semiconducting single-walled carbon nanotube nested in a charged, impermeable covalent functional shell, Tube2 allows the semiconducting conduction pathway to be modulated solely by surface functional groups in a chemically gated-all-around configuration. The removal of physical gates significantly simplifies the device architecture and enables photolithography-free, highly scalable fabrication of transistor sensors in nonconventional configurations that are otherwise impossible. We show that concomitant FET sensitivity and single-mismatch selectivity can be achieved with Tube2 even in a two-terminal, thin film transistor device configuration that is as simple as a chemiresistor. Miniaturized two-terminal field effect point sensors can also be fabricated, using a straightforward dice-and-dip procedure, for the detection of tuberculosis biomarkers.
Topics: Biomarkers; Diazonium Compounds; Electric Conductivity; Electrodes; Humans; Microfluidic Analytical Techniques; Nanotubes, Carbon; Oligonucleotides; Semiconductors; Tuberculosis
PubMed: 28169545
DOI: 10.1021/jacs.6b12111 -
Food Additives & Contaminants. Part A,... Jun 2024Ochratoxin A (OTA) is a toxic fungal metabolite that is commonly found in cereals and animal feed. It is economically damaging and potentially hazardous to human health....
Ochratoxin A (OTA) is a toxic fungal metabolite that is commonly found in cereals and animal feed. It is economically damaging and potentially hazardous to human health. Herein, we propose an electrochemical immunosensor for the rapid detection of OTA using anti-OTA antibodies and diazonium-functionalized, screen-printed electrodes. We attached 4-aminobenzoic acid to an electrode surface, activated the carboxyl groups on the surface with carbodiimide, and attached an antibody to the diazo layer. Subsequently, we used bovine serum protein as a blocker to prevent non-specific antigens from binding to the antibody. We evaluated the performance of the sensor by cyclic voltammetry, electrochemical impedance spectroscopy, and differential pulse voltammetry. The sensor is highly specific and sensitive, has good linear responses in the range 20-200 ng/mL, a limit of detection of 0.5 ng/mL, and good recoveries of 90.5%-100.9% in spiked samples. It can be stored at 4 °C for approximately 2 weeks, and is highly stable, with a current response variation of no more than 4.6%.
Topics: Ochratoxins; Food Contamination; Electrochemical Techniques; Electrodes; Immunoassay; Food Analysis; Diazonium Compounds; Biosensing Techniques; Animals
PubMed: 38598095
DOI: 10.1080/19440049.2024.2339322 -
Spectrochimica Acta. Part A, Molecular... Feb 2018Ti6Al4V alloy is the most commonly used in orthopedic industry as an endoprosthesis. Ti6Al4V exhibits good mechanical properties, except the abrasion resistance. Surface...
Ti6Al4V alloy is the most commonly used in orthopedic industry as an endoprosthesis. Ti6Al4V exhibits good mechanical properties, except the abrasion resistance. Surface modification of Ti6Al4V in order to obtain organic layer, and then the attachment of the polymer, can allow for overcoming this problem. The aim of the work was the modification of Ti6Al4V surface by diazonium compounds: salt or cation generated in situ and examine the influence of the reducing agent - ascorbic acid, and the temperature of reaction on modification process. Moreover, the simulated body fluid was used for the assessment of the organic layer stability on Ti6Al4V surface. The evaluation of the modification was carried out using the following methods: Raman microspectroscopy, scanning electron microscopy and energy-dispersive X-ray spectroscopy. Higher temperature of modification by 4-hydroxymethylbenzenediazonium cation, provides the largest amount of organic layer on the Ti6Al4V alloy. In the case of the Ti6Al4V modified by Variamine Blue B salt, the amount of organic layer is not dependent on the reaction condition. Moreover, the ascorbic acid and the presence of TiO does not effect on the modification. The modified surface is completely coated with the organic layer which is stable in simulated body fluid.
Topics: Alloys; Body Fluids; Diazonium Compounds; Image Processing, Computer-Assisted; Oxides; Spectrometry, Fluorescence; Spectrum Analysis, Raman; Surface Properties; Temperature; Titanium
PubMed: 28982066
DOI: 10.1016/j.saa.2017.09.070