Recent Advances in Hydrogen Peroxide Responsive Organoborons for Biological and Biomedical Applications

Abstract

Hydrogen peroxide is the most stable reactive oxygen species generated endogenously, participating in numerous physiological processes and abnormal pathological conditions. Mounting evidence suggests that a higher level of H2O2 exists in various disease conditions. Thus, H2O2 functions as an ideal target for site‐specific bioimaging and therapeutic targeting. The unique reactivity of organoborons with H2O2 provides a method for developing chemoselective molecules for biological and biomedical applications. This review highlights the design and application of boron‐derived molecules for H2O2 detection, and the utility of boron moieties toward masking reactive compounds leading to the development of metal prochelators and prodrugs for selectively delivering an active species at the target sites with elevated H2O2 levels. Additionally, the emergence of H2O2‐responsive theranostic agents consisting of both therapeutic and diagnostic moieties in one integrated system are discussed. The purpose of this review is to provide a better understanding of the role of boron‐derived molecules toward biological and pharmacological applications.

Flucytosine‐based prodrug activation by cold physical plasma

“…The activation mechanism of arylboronate ester prodrugs is depicted in Scheme 1 (bottom). [44,45] The boron atom in arylboronate esters is characterized by an empty p-orbital and can thus be attacked by H 2 O 2 . The resulting species suffer a 1,2 rearrangement: an oxygen atom is inserted within the carbon−boron bond, causing migration of the phenyl ring from the boron to the adjacent oxygen atom yielding a phenyl borate.…”

Recent Studies on Hydrogels Based on H2O2-Responsive Moieties: Mechanism, Preparation and Application

“…Until now, different types of H 2 O 2 -responsive materials have been explored, including MRI contrast agents, fluorescent sensors, transistors, drug delivery systems, mitochondria-directed tools, etc. [ 20 , 21 ]. Gu et al published a review paper on the topic of H 2 O 2 -responsive materials, in which the biomedical applications were emphasized [ 17 ].…”

Boron- and phosphorus-containing molecular/nano platforms: exploiting pathological redox imbalance to fight cancer

“…To this end, carbon-based homocyclic agents offer a relatively limited degree of tuneability due the intrinsic electronic properties of the carbon element. In contrast, boron [21][22][23][24][25][26] and phosphorus [27][28][29][30][31] heterocycles captivate due to their unique and wide regioselective chemistry (vide infra). This results in major advantages for rational drug design, which can selectively be attributed to either boron or phosphorus atom.…”

“…This results in major advantages for rational drug design, which can selectively be attributed to either boron or phosphorus atom. In short, high degree of tuneability of B- [21][22][23][24][25][26] and P-containing [27][28][29][30][31] heterocycles in combination with chemical stability allow for precise molecular engineering. Thus, physicochemical traits (e.g., stability, lipophilicity and solubility) as well as pharmacological characteristics (e.g., bioavailability and pharmacological activity) may be tailored to suit highly specific demandsa truly desirable feature for rational drug design and development.…”

“…Thus, physicochemical traits (e.g., stability, lipophilicity and solubility) as well as pharmacological characteristics (e.g., bioavailability and pharmacological activity) may be tailored to suit highly specific demandsa truly desirable feature for rational drug design and development. 23 Whilst there are several reviews outlining the value of boron- [21][22][23]25,32,33 or phosphorus-containing 28,30,[34][35][36][37][38] compounds as small-molecule anti-cancer agents, very few highlight their importance in platform-based rational molecular/nano engineering. 31,39 Thus, in this mini-review we highlight striking advances from organoboron 24,25,[39][40][41][42][43] and phosphorus compounds [44][45][46][47][48][49][50][51] as intriguing platforms to directly or indirectly exploit pathological levels of ROS towards the treatment of cancer.…”