title: A comparison of the chemistry associated with the biological signaling and actions of nitroxyl (HNO) and nitric oxide (NO).
abstract: Nitric oxide (NO) and nitroxyl (HNO) are reported to have numerous biological activities with significant therapeutic potential. Many of these activities are overlapping. The chemistry by which these two species act is likely to be distinct in spite of their apparent close structural similarities. Discussed in this review is the chemistry of NO and HNO with their likely biological targets - thiolproteins, metalloproteins (more specifically iron heme proteins) and free radical processes. Based on the chemistry discussed, it can be concluded that the biological actions of NO are likely due primarily to its interactions with metal centers and reaction with radical species. The likely biological targets for HNO are, similarly, metal centers and radical species (albeit with different chemistry compared to NO). HNO is also particularly good at directly modifying thiols while NO-mediated thiol modification requires other reactants to be present and is not as facile. Thus, a fundamental difference between NO and HNO that likely distinguishes them with regards to their biological activity is the greater propensity for HNO to react with thiols compared to NO.
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA 94928, USA. jon.fukuto@sonoma.edu
authors.forename: Jon M
authors.initials: JM
authors.lastname: Fukuto
authors.forename: Cinthya J
authors.initials: CJ
authors.lastname: Cisneros
authors.forename: Renee L
authors.initials: RL
authors.lastname: Kinkade
mesh_terms: D000818:Animals; D005609:Free Radicals / Q000737:chemistry / Q000378:metabolism; D006418:Heme / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D007501:Iron / Q000737:chemistry / Q000378:metabolism; D008667:Metalloproteins / Q000737:chemistry / Q000378:metabolism; D009569:Nitric Oxide / Q000737:chemistry / Q000502:physiology*; D009589:Nitrogen Oxides / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction; D011485:Protein Binding; D026403:S-Nitrosothiols / Q000737:chemistry / Q000378:metabolism; D015398:Signal Transduction
chemical_list: D005609:Free Radicals; D008667:Metalloproteins; D009589:Nitrogen Oxides; D026403:S-Nitrosothiols; D009569:Nitric Oxide; D006418:Heme; D007501:Iron; C039900:nitroxyl