6277-67-4Relevant articles and documents
Nanofiltration-Enabled In Situ Solvent and Reagent Recycle for Sustainable Continuous-Flow Synthesis
Fodi, Tamas,Didaskalou, Christos,Kupai, Jozsef,Balogh, Gyorgy T.,Huszthy, Peter,Szekely, Gyorgy
, p. 3435 - 3444 (2017)
Solvent usage in the pharmaceutical sector accounts for as much as 90 % of the overall mass during manufacturing processes. Consequently, solvent consumption poses significant costs and environmental burdens. Continuous processing, in particular continuou
Exploring the copper binding ability of Mets7 hCtr-1 protein domain and His7 derivative: An insight in Michael addition catalysis
Rimoldi, Isabella,Bucci, Raffaella,Feni, Lucia,Santagostini, Laura,Facchetti, Giorgio,Pellegrino, Sara
, (2020/10/26)
Mets7 is a methionine-rich motif present in hCtr-1 transporter that is involved in copper cellular trafficking. Its ability to bind Cu(I) was recently exploited to develop metallopeptide catalysts for Henry condensation. Here, the catalytic activity of Me
Deep-Red-Fluorescent Zinc Probe with a Membrane-Targeting Cholesterol Unit
Hong, Jayeon,Kim, Jin Ju,You, Youngmin,Yu, Seungyeon
, p. 11562 - 11576 (2020/09/09)
Organelle-targeting fluorescence probes are valuable because they can provide spatiotemporal information about the trafficking of analytes of interest. The spatiotemporal resolution can be improved by using low-energy emission signals because they are barely contaminated by autofluorescence noises. In this study, we designed and synthesized a deep-red-fluorescent zinc probe (JJ) with a membrane-targeting cholesterol unit. This zinc probe consists of a boron-azadipyrromethene (aza-BODIPY) fluorophore and a zinc receptor that is tethered to a tri(ethylene glycol)-cholesterol chain. In aqueous solutions buffered to pH 7.4, JJ exhibits weak fluorescence with a peak wavelength of 663 nm upon excitation at 622 nm. The addition of ZnCl2 elicits an approximately 5-fold enhancement of the fluorescence emission with a fluorescence dynamic range of 141000. Our electrochemical and picosecond transient photoluminescence investigations indicate that the fluorescence turn-on response is due to the zinc-induced abrogation of the formation of a nonemissive intramolecularly charge-separated species, which occurs with a driving force of 0.98 eV. The fluorescence zinc response was found to be fully reversible and to be unaffected by pH changes or the presence of biological metal ions. These properties are due to tight zinc binding with a dissociation constant of 4 pM. JJ was found to be nontoxic to HeLa cells up to submicromolar concentrations, which enables cellular imaging. Colocalization experiments were performed with organelle-specific stains and revealed that JJ is rapidly internalized into intracellular organelles, including lysosomes and endoplasmic reticula. Unexpectedly, probe internalization was found to permeabilize the cell membrane, which facilitates the influx of exogens such as zinc ions. Such permeabilization does not arise for a control probe without the tri(ethylene glycol)-cholesterol chain (JJC). Our results show that the membrane-targeting cholesterol unit can disrupt membrane integrity.
Synthesis, properties and reactivity of BCl2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold
Burke, Luke,Diaz-Rodriguez, Roberto M.,Robertson, Katherine N.,Thompson, Alison
, p. 2139 - 2147 (2020/03/27)
The synthesis and characterisation of the BCl2-chelated complexes of both archetypal aza-dipyrrin sub-Types are presented. A stepwise halogen exchange, leading to a mixed-halide Cl-B-F intermediate, is implicated in the conversion of F-Aza-BODIPYs to Cl-Aza-BODIPYs upon treatment with BCl3. The utility of the Cl-Aza-BODIPY scaffold to facilitate substitutions at boron is demonstrated under mild conditions through treatment with aryl Grignard reagents. Additionally, the lability of the B-Cl bond enables facile removal of the BCl2 group, i.e. deprotection of F-Aza-BODIPYs, under aqueous conditions. Three aza-dipyrrin HX salts were also synthesised and characterised. The pKa of the protonated aza-dipyrrin was determined to be 4, thereby providing insight regarding the storage and stability of such species.