607383-59-5Relevant academic research and scientific papers
Design, synthesis and evaluation of enzyme-responsive fluorogenic probes based on pyridine-flanked diketopyrrolopyrrole dyes
Jenni, Sébastien,Ponsot, Flavien,Baroux, Pierre,Collard, Lucile,Ikeno, Takayuki,Hanaoka, Kenjiro,Quesneau, Valentin,Renault, Kévin,Romieu, Anthony
supporting information, (2020/12/02)
The ever-growing demand for fluorogenic dyes usable in the rapid construction of analyte-responsive fluorescent probes, has recently contributed to a revival of interest in the chemistry of diketopyrrolopyrrole (DPP) pigments. In this context, we have explored the potential of symmetrical and unsymmetrical DPP derivatives bearing two or one 4-pyridyl substituents acting as optically tunable group(s). The unique fluorogenic behavior of these molecules, closely linked to N-substitution/charge state of their pyridine unit (i.e., neutral pyridine or cationic pyridinium), has been used to design DPP-based fluorescent probes for detection of hypoxia-related redox enzymes and penicillin G acylase (PGA). In this paper, we describe synthesis, spectral characterization and bioanalytical validations of these probes. Dramatic differences in terms of aqueous stability and enzymatic fluorescence activation were observed. This systematic study enables to delineate the scope of application of pyridine-flanked DPP fluorophores in the field of enzyme biosensing.
Protected pyrimidine nucleosides for cell-specific metabolic labeling of RNA
Beasley, Samantha,Nguyen, Kim,Fazio, Michael,Spitale, Robert C.
supporting information, p. 3912 - 3915 (2018/09/27)
RNA molecules can perform a myriad of functions, from the regulation of gene expression to providing the genetic blueprint for protein synthesis. Characterizing RNA expression dynamics, in a cell-specific manner, still remains a great challenge in biology. Herein we present a new set of protected alkynyl nucleosides for cell-specific metabolic labeling of RNA. We anticipate these analogs will find wide spread utility toward the goal of understanding RNA expression in complex cellular and tissue environments, even within living animals.
BODIPY-based high-sensitivity fluorescent probe and synthesis method and application thereof
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, (2018/03/24)
The invention relates to a BODIPY-based high-sensitivity fluorescent probe and a synthesis method and application thereof. A structural general formula of the probe is shown as (I), wherein Trigger is stimulant triggering groups, R1 and R2 are groups for regulating and controlling fluorescent transmission wavelength of the probe and introducing organelle targeting, and R1 and R2 are defined in the description. By the probe, detection of different substrates can be realized without changing mother nucleus structure of the probe by only changing different Trigger groups. In addition, according to different needs on wavelength and targeting, the mother nucleus structure of the probe can be quickly modified. By changing R1 and R2, maximum fluorescent emission wavelength of the probe can be changed, and the probe can target mitochondrion to realize detection of active substances in the mitochondrion. The probe has good biocompatibility, thereby being applicable to detecting biological systems. Application value of the fluorescent probe in the aspect of detecting bioactive molecules and protease over-expressed in inflammatory or tumor tissue has potential social benefit and economic benefit.
Enzyme-Responsive Polymeric Vesicles for Bacterial-Strain-Selective Delivery of Antimicrobial Agents
Li, Yamin,Liu, Guhuan,Wang, Xiaorui,Hu, Jinming,Liu, Shiyong
, p. 1760 - 1764 (2016/02/03)
Antimicrobial resistance poses serious public health concerns and antibiotic misuse/abuse further complicates the situation; thus, it remains a considerable challenge to optimize/improve the usage of currently available drugs. We report a general strategy
Dual enzyme-responsive "turn-on" fluorescence sensing systems based on in situ formation of 7-hydroxy-2-iminocoumarin scaffolds
Debieu, Sylvain,Romieu, Anthony
supporting information, p. 10348 - 10361 (2015/10/28)
A new strategy for the simultaneous fluorogenic detection of two distinct enzyme activities namely hydrolase (amidase or esterase) and reductase is described. This innovative biosensing method is based on the powerful "covalent-assembly" principle that in
Design, Synthesis, and Functional Evaluation of CO-Releasing Molecules Triggered by Penicillin G Amidase as a Model Protease
Sitnikov, Nikolay S.,Li, Yingchun,Zhang, Danfeng,Yard, Benito,Schmalz, Hans-Günther
, p. 12314 - 12318 (2015/10/12)
Protease-triggered CO-releasing molecules (CORMs) were developed. The viability of the approach was demonstrated through the synthesis of compounds consisting of an η4-oxydiene-Fe(CO)3 moiety connected to a penicillin G amidase (PGA)-cleavable unit through a self-immolative linker. The rate of PGA-induced hydrolysis was investigated by HPLC analysis and the subsequent CO release was quantitatively assessed through headspace gas chromatography. In an in vitro assay with human endothelial cells, typical biological effects of CO, that is, inhibition of the inflammatory response and the induction of heme oxygenase-1 expression, were observed only upon co-administration of the CORM and PGA. This work forms a promising basis for the future development of protease-specific CORMs for potential medicinal applications.
A structurally simple self-immolative reagent that provides three distinct, simultaneous responses per detection event
Nunez, Sean A.,Yeung, Kimy,Fox, Nicole S.,Phillips, Scott T.
experimental part, p. 10099 - 10113 (2012/02/05)
A general design is presented for a stimulus-responsive small molecule that is capable of responding to a specific applied chemical or physical signal by releasing two different types of pendant small molecules and a colorimetric indicator simultaneously. A key aspect of this design is the ease with which these reagents are prepared: typically, only four synthetic steps are required. Moreover, the modular construction strategy provides access to stimuli-responsive reagents that are capable of (i) responding to a variety of applied signals and (ii) releasing a number of different small molecules that contain primary alcohols, secondary alcohols, or phenols. These stimuli-responsive reagents are stable under physiological conditions (neither hydrolysis nor thermal degradation of the reagent occurs in significant quantity), and when they are exposed to the appropriate applied signal, they release both pendant small molecules and the colorimetric indicator completely within hours. Finally, unlike other functional groups, such as carbonates, that are used to connect alcohol-bearing molecules to controlled-release reagents, the linkage described in this article increases in hydrolytic stability (rather than decreases) as the pKa of the pendant alcohol decreases (Figure presented).
Self-cleavable chemiluminescent probes suitable for protease sensing
Richard, Jean-Alexandre,Jean, Ludovic,Schenkels, Caroline,Massonneau, Marc,Romieu, Anthony,Renard, Pierre-Yves
scheme or table, p. 2941 - 2957 (2011/02/26)
A new generation of dioxetane-based chemiluminescent substrates suitable for detecting protease activities is described. Our strategy involves the use of a self-cleavable spacer as the key molecular component of these protease-sensitive chemiluminescent p
Bioactivation of carbamate-based 20(S)-camptothecin prodrugs
Pessah, Neta,Reznik, Mika,Shamis, Marina,Yantiri, Ferda,Xin, Hong,Bowdish, Katherine,Shomron, Noam,Ast, Gil,Shabat, Doron
, p. 1859 - 1866 (2007/10/03)
Two new prodrugs of CPT were synthesized, based on carbamate linkages between the 20-hydroxy group of CPT and a linker designed to be enzymatically removed by either Penicillin-G-Amidase or catalytic antibody 38C2. Cell growth inhibition assays showed an
Composition and method for dyeing dye-susceptible material
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Page/Page column 11, (2008/06/13)
Composition for colouring dye-susceptible material (preferably keratinous material), containing at least one pro-dye (especially a glutaramide) and at least one enzyme capable of reacting, cleaving, or modifying the enzymatically-labile functionality in the pro-dye to form a dye substance or a direct dye; as well as a 2-component-kit.
