title: The chemical biology of hydropersulfides (RSSH): Chemical stability, reactivity and redox roles.
abstract: Recent reports indicate the ubiquitous prevalence of hydropersulfides (RSSH) in mammalian systems. The biological utility of these and related species is currently a matter of significant speculation. The function, lifetime and fate of hydropersulfides will be assuredly based on their chemical properties and reactivity. Thus, to serve as the basis for further mechanistic studies regarding hydropersulfide biology, some of the basic chemical properties/reactivity of hydropersulfides was studied. The nucleophilicity, electrophilicity and redox properties of hydropersulfides were examined under biological conditions. These studies indicate that hydropersulfides can be nucleophilic or electrophilic, depending on the pH (i.e. the protonation state) and can act as good one- and two-electron reductants. These diverse chemical properties in a single species make hydropersulfides chemically distinct from other, well-known sulfur containing biological species, giving them unique and potentially important biological function.
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA, 94928, USA.
authors.forename: Simran S
authors.initials: SS
authors.lastname: Saund
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA, 94928, USA.
authors.forename: Victor
authors.initials: V
authors.lastname: Sosa
authors.affiliation: Department of Biology, Sonoma State University, Rohnert Park, CA, 94928, USA.
authors.forename: Stephanie
authors.initials: S
authors.lastname: Henriquez
authors.affiliation: Department of Chemistry, University of California, Davis, One Shield Ave., Davis, CA, 95616, USA.
authors.forename: Q Nhu N
authors.initials: QN
authors.lastname: Nguyen
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA, 94928, USA.
authors.forename: Christopher L
authors.initials: CL
authors.lastname: Bianco
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA, 94928, USA.
authors.forename: Shuhei
authors.initials: S
authors.lastname: Soeda
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA, 94928, USA.
authors.forename: Robert
authors.initials: R
authors.lastname: Millikin
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA, 94928, USA.
authors.forename: Corey
authors.initials: C
authors.lastname: White
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA, 94928, USA.
authors.forename: Henry
authors.initials: H
authors.lastname: Le
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA, 94928, USA.
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Ono
authors.affiliation: Department of Chemistry, University of California, Davis, One Shield Ave., Davis, CA, 95616, USA.
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo
authors.affiliation: Environmental Biology Section, Faculty of Medicine, University of Tsukuba, Tsukuba, Ibaraki, 305-8575, Japan.
authors.forename: Yoshito
authors.initials: Y
authors.lastname: Kumagai
authors.affiliation: Department of Environmental Health Sciences and Molecular Toxicology, Tohoku University Graduate School of Medicine, Sendai, 980-8575, Japan.
authors.forename: Takaaki
authors.initials: T
authors.lastname: Akaike
authors.affiliation: Department of Biology, Sonoma State University, Rohnert Park, CA, 94928, USA. Electronic address: linj@sonoma.edu.
authors.forename: Joseph
authors.initials: J
authors.lastname: Lin
authors.affiliation: Department of Chemistry, Sonoma State University, Rohnert Park, CA, 94928, USA. Electronic address: fukuto@sonoma.edu.
authors.forename: Jon M
authors.initials: JM
authors.lastname: Fukuto
mesh_terms: D000818:Animals; D003486:Cyanides / Q000737:chemistry / Q000378:metabolism; D003542:Cystathionine gamma-Lyase / Q000378:metabolism; D005978:Glutathione / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010446:Peptide Fragments / Q000378:metabolism; D051381:Rats; D054631:Receptor-Like Protein Tyrosine Phosphatases, Class 3 / Q000378:metabolism; D011994:Recombinant Proteins / Q000378:metabolism; D015398:Signal Transduction; D013440:Sulfides / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D003486:Cyanides; D010446:Peptide Fragments; D011994:Recombinant Proteins; D013440:Sulfides; C051552:persulfides; C486288:PTPRJ protein, human; D054631:Receptor-Like Protein Tyrosine Phosphatases, Class 3; D003542:Cystathionine gamma-Lyase; D005978:Glutathione
keywords: Electrophilicity; Hydropersulfide; Nucleophilicity; Redox regulation; Thiols