60444-78-2Relevant articles and documents
FRET-based cyanine probes for monitoring ligation reactions and their applications to mechanistic studies and catalyst screening
Herbst,Shabat
, p. 3715 - 3728 (2016)
There is an ever-increasing need to design better methods to selectively connect two molecules under mild aqueous conditions on a small scale. The process of finding such methods significantly relies on the employment of an appropriate assay. We report here a modular FRET-based assay to monitor such reactions and illustrate how the assay is used to monitor two particular reactions: native chemical ligation (NCL) and oxime ligation. For both reactions we show that by employing appropriately designed probes FRET measurements could be used to monitor the reaction's progress. We additionally demonstrate the usefulness of the developed probe system to study the mechanisms of the ligation reactions, for example, in monitoring the formation of a trimeric intermediate in the NCL reaction. Finally, we demonstrate that FRET measurements conducted in our system allow the quantification of the reaction yield and we show the application of our FRET-based assay to catalyst screening for the oxime ligation.
Reactivity-dependent PCR: Direct, solution-phase in vitro selection for bond formation
Gorin, David J.,Kamlet, Adam S.,Liu, David R.
, p. 9189 - 9191 (2009)
(Figure Presented) In vitro selection is a key component of efforts to discover functional nucleic acids and small molecules from libraries of DNA, RNA, and DNA-encoded small molecules. Such selections have been widely used to evolve RNA and DNA catalysts
Clicking porphyrins to magnetic nanoparticles for photodynamic therapy
Thandu, Merlyn,Rapozzi, Valentina,Xodo, Luigi,Albericio, Fernando,Comuzzi, Clara,Cavalli, Silvia
, p. 90 - 98 (2014)
A method for the preparation of superparamagnetic iron oxide nanoparticle-porphyrin (SPION-TPP) conjugates through click chemistry, which can be used as novel theranostic nanoagents for photodynamic therapy is developed. The synthesis, characterisation, and evaluation of the photocytotoxicity profiles of the nanoconjugates prepared is reported. Upon light irradiation, SPION-TPP nanoconstructs promote a photodynamic effect in vitro in murine amelanotic melanoma B78-H1 cells, with IC50 values in the region of 800 nm, similarly to unbound TPP, whereas they remain non-cytotoxic in the dark. However, these nanoconstructs show poor cellular uptake, which influences a linear dose-response effect. Therefore, the improvement of delivery to cells has also been studied by conjugating a well-known cell-penetrating peptide (TAT peptide) to the SPION-TPP nanoparticles. The new nanoconstructs show lower IC50 values (in the region of 500 nm) and a clear dose-response effect. Our results suggest that TAT-conjugated SPION-TPP nanoparticles are efficient nanodevices both for tracking drugs by means of magnetic resonance imaging (MRI)-based techniques and for treating cancer cells through photodynamic therapy, thus functioning as promising theranostic nanoagents.
Efficient γ-amino-proline-derived cell penetrating peptide-superparamagnetic iron oxide nanoparticle conjugates via aniline-catalyzed oxime chemistry as bimodal imaging nanoagents
Cavalli, Silvia,Carbajo, Daniel,Acosta, Milena,Lope-Piedrafita,Candiota, Ana Paula,Arus, Carles,Royo, Miriam,Albericio, Fernando
, p. 5322 - 5324 (2012)
Aniline-catalyzed oxime chemistry was employed to conjugate a γ-amino-proline-derived cell penetrating peptide to superparamagnetic iron oxide nanoparticles (SPIONs). Internalization of the novel nanoconjugate into HeLa cells was found to be remarkably higher compared to the analogous TAT-SPION conjugate.
Radical Decarboxylative Carbometalation of Benzoic Acids: A Solution to Aromatic Decarboxylative Fluorination
Xu, Peng,López-Rojas, Priscila,Ritter, Tobias
supporting information, p. 5349 - 5354 (2021/05/05)
Abundant aromatic carboxylic acids exist in great structural diversity from nature and synthesis. To date, the synthetically valuable decarboxylative functionalization of benzoic acids is realized mainly by transition-metal-catalyzed decarboxylative cross couplings. However, the high activation barrier for thermal decarboxylative carbometalation that often requires 140 °C reaction temperature limits both the substrate scope as well as the scope of suitable reactions that can sustain such conditions. Numerous reactions, for example, decarboxylative fluorination that is well developed for aliphatic carboxylic acids, are out of reach for the aromatic counterparts with current reaction chemistry. Here, we report a conceptually different approach through a low-barrier photoinduced ligand to metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation strategy, which generates a putative high-valent arylcopper(III) complex, from which versatile facile reductive eliminations can occur. We demonstrate the suitability of our new approach to address previously unrealized general decarboxylative fluorination of benzoic acids.
