A prochelator with a modular masking group featuring hydrogen peroxide activation with concurrent fluorescent reporting

Abstract

Metal chelators masked with protecting groups for targeted release have the potential to conditionally modulate cellular metals. We report a new route to prepare cis-cinnamate protecting groups that enabled development of a prochelator with chemical stimulus response, fluorescent reporting and active compound release in a single structure.

Activity‐Based Sensing: A Synthetic Methods Approach for Selective Molecular Imaging and Beyond

“…[290] ation boronate-based prochelators for iron provided significant cytoprotection against oxidative damage, [297] prevented metal-dependent amyloid aggregation, [298] and captured metals in ap eroxide-dependent manner with concomitant fluorescent reporting. [299] More recently,F ranz, Thiele,a nd co-workers reported aH 2 O 2 -responsive prochelator that unmasks upon the generation of ROSi na ctivated macrophages,and then complexes copper to elicit fungal killing. [300] In addition to chelators,caged enzyme inhibitors can also be developed using ABS approaches (Figure 8, blue Prodrugs section).…”

Reactive Oxygen Species (ROS) Responsive Polymers for Biomedical Applications

“…They are susceptibility toward H 2 O 2 , but cannot be oxidized by other ROS . They are important building blocks for constructing organic compounds and functional polymers . In a study by Frechet and co‐workers, oxidation‐sensitive dextran (Oxi‐DEX) microparticles with ≈ 100 nm in diameter were prepared by conjugating arylboronic esters to the hydroxyls of dextran .…”

“…[ 16 ] They are important building blocks for constructing organic compounds and functional polymers. [41][42][43] In a study by Frechet and co-workers, oxidation-sensitive dextran (Oxi-DEX) Macromolecular Bioscience www.mbs-journal.de microparticles with ≈ 100 nm in diameter were prepared by conjugating arylboronic esters to the hydroxyls of dextran. [ 44 ] The microparticles showed a markedly accelerated degradation rate by the addition of 1 × 10 −3 M H 2 O 2 .…”

“…Poly(propylene sulfi de) [19][20][21][22] Selenium-containing polymers [26,28,29] [ 25,30] Telluriumcontaining polymers [35][36][37] Poly(thioketal) [38][39][40]46] [ [41][42][43][44][45]55] Phenylboronic acid/ ester containing polymers Poly(L-methionine) [49] Poly(L-proline) [53,54] Macromolecular Bioscience www.mbs-journal.de and SN38 resulted in enhanced proliferation inhibition of tumor cells via inducing cell apoptosis. In addition to drug carrier, the thioether-containing particles themselves can also show inherent therapeutic properties against oxidative stress.…”

Visualization of Endogenous and Exogenous Hydrogen Peroxide Using A Lysosome-Targetable Fluorescent Probe

“…Therefore, p -dihydroxyborylbenzyloxycarbonyl moiety has become one of the most efficient reactive groups with H 2 O 2 . In recent decade, fluorescent probes have been widely employed with different fluorophores, which were successfully applied in various living cells and tissues for monitoring the H 2 O 2 -induced biological process 14 15 16 17 18 19 20 21 . However, detecting H 2 O 2 in some special organelles such as in lysosome is still very challenging.…”