Biological nitric oxide signalling: chemistry and terminology

Abstract

Biological nitrogen oxide signalling and stress is an area of extreme clinical, pharmacological, toxicological, biochemical and chemical research interest. The utility of nitric oxide and derived species as signalling agents is due to their novel and vast chemical interactions with a variety of biological targets. Herein, the chemistry associated with the interaction of the biologically relevant nitrogen oxide species with fundamental biochemical targets is discussed. Specifically, the chemical interactions of nitrogen oxides with nucleophiles (e.g. thiols), metals (e.g. hemeproteins) and paramagnetic species (e.g. dioxygen and superoxide) are addressed. Importantly, the terms associated with the mechanisms by which NO (and derived species) react with their respective biological targets have been defined by numerous past chemical studies. Thus, in order to assist researchers in referring to chemical processes associated with nitrogen oxide biology, the vernacular associated with these chemical interactions is addressed.

Heteroorganic molecules and bacterial biofilms: Controlling biodeterioration of cultural heritage

“…However, its neutral charge and solubility in water (~1.7 mM) makes NO an ideal chemical signalling molecule. 9,256 Most bioenergetic NO is generated through the nitrogen cycle with nitrifying and denitrifying microorganisms playing a key role in the inter-conversion of nitrogen containing speciesdinitrogen (N 2 ), ammonium ions (NH 4 + ), and nitrate (NO 3 -) -as shown in its essential, minimized version in Scheme 1a. Enzymatic NO, on the other hand is formed from L-arginine by NO synthase (NOS) as seen in Scheme 1b.…”

“…8 Free radical and redox processes within bacterial biofilms are critical to the life cycle of the biofilm because they trigger events that include cell proliferation and survival, enzyme inhibition, cell death and cell transformation. 9 These processes often rely on "redox shuttling" aided by polymers within the biofilm matrix itself. 10 As such, these electron transfer events can be considered to be "chemical signalling processes" that result in changes to the biofilm, including growth and dispersal.…”

“…265 An overview of some of the specific reactions and interactions of NO and RNI with biological targets is given in Scheme 2. For a more detailed review see Fang, 261 and Heinrich et al 9 and references therein.…”

Nitric oxide: Protein tyrosine phosphorylation and protein S-nitrosylation in cancer

“…Lipophilic compartments like the cell membrane will concentrate NO and O 2 , two non-polar species, and facilitate the reaction between them, although these reactions are relatively slow. [23] In aqueous systems, N 2 O 3 in the presence of a nucleophile such as thiolate or an amine group will form a hybrid of covalent and ionic resonance structures NO + -NO 2 -. Nitrosation reactions between NO + and the thiolate or between NO + and the amine form RSNO and nitrosamines, respectively.…”

“…Nitrosation reactions between NO + and the thiolate or between NO + and the amine form RSNO and nitrosamines, respectively. [23] Although RSNOs are broadly classified as NO donors, their actions can also be exerted through trans-nitrosylation, without release of NO.[9] Trans-nitrosylation is the exchange between a thiol group and a nitrosothiol group. Exchange may occur between a low-molecular-weight RSNO and a thiol group belonging to a peptide or protein without release of NO.…”