Arylboronate Ester Based Diazeniumdiolates (BORO/NO), a Class of Hydrogen Peroxide Inducible Nitric Oxide (NO) Donors

Abstract

Here, we report the design, synthesis, and evaluation of arylboronate ester based diazeniumdiolates (BORO/NO), a class of nitric oxide (NO) donors activated by hydrogen peroxide (H2O2), a reactive oxygen species (ROS), to generate NO. We provide evidence for the NO donors' ability to permeate bacteria to produce NO when exposed to H2O2 supporting possible applications for BORO/NO to study molecular mechanisms of NO generation in response to elevated ROS.

Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates

“…We have long taken this absence of relevant prior literature as a tacit suggestion that attempts to diazeniumdiolate an amide by directly reacting it with NO would probably be fruitless, until now continuing our focus on the amine /NO adducts that have proven so useful as biomedical research tools and potential clinical entities. 3 − 9 …”

Small molecule generators of biologically reactive sulfur species

“…In the past three decades, reactive nitrogen species such as nitric oxide (NO), 151 nitroxyl 5,142 and peroxynitrite 152,153 have been systematically studied and this is, in part, due to the ready availability of small molecules that dissociate to generate these species. [154][155][156][157][158] Scheme 10 Sulfinate based SO 2 donors. Reactive oxygen species (ROS) are another major redox regulator that have been found to be involved in many pathophysiological processes and regulating them has enormous implications in disease biology.…”

FLUORO/NO: A Nitric Oxide Donor with a Fluorescence Reporter

“…Nitric oxide detection from 1 : Stock solutions of 1 (1 m m ) were prepared in DMSO and of porcine liver esterase (1 U mL −1 ; Sigma–Aldrich) in phosphate buffer (pH 7.4). A typical reaction mixture consisted of 1 (25 μ m ) and esterase (0.5 U mL −1 ) prepared by mixing 1 (12.5 μL of stock) and esterase (250 μL of stock) with phosphate buffer (237.5 μL, 10 m m, pH 7.4) at 37 °C.…”