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Biological chemistry of hydrogen sulfide and persulfides.
Arch Biochem Biophys. 2017 Mar 01; 617:9-25.AB

Abstract

Hydrogen sulfide (H2S) has been traditionally considered to be a toxic molecule for mammals. However, it can be formed endogenously and exert physiological effects with potential health benefits. H2S can partition two-fold in biological membranes and traverse them rapidly, diffusing between compartments. H2S reactivity has similarities to that of thiols, although it is less nucleophilic than thiols and it can form different products. H2S can react with oxidants derived from the partial reduction of oxygen, but direct scavenging is unlikely to explain H2S protective actions. Important effects are exerted on mitochondria including the stimulation or the inhibition of the electron transport chain. Possible mechanisms for unleashing biological consequences are the reactions with metal centers and with thiol oxidation products. The reactions of H2S with disulfides (RSSR) and sulfenic acids (RSOH) lead to the formation of persulfides (RSSH). Persulfides have enhanced nucleophilicity with respect to the corresponding thiol, consistent with the alpha effect. Besides, the inner and outer sulfurs can both act as electrophiles. In this review, we describe the reactions of H2S with oxidized thiol products and the properties of the persulfides formed in the context of the chemical biology of H2S.

Authors+Show Affiliations

Laboratorio de Enzimología, Facultad de Ciencias, Universidad de la República, Montevideo, Uruguay; Center for Free Radical and Biomedical Research, Universidad de la República, Uruguay.Center for Free Radical and Biomedical Research, Universidad de la República, Uruguay; Laboratorio de Fisicoquímica Biológica, Facultad de Ciencias, Universidad de la República, Montevideo, Uruguay.Laboratorio de Enzimología, Facultad de Ciencias, Universidad de la República, Montevideo, Uruguay; Center for Free Radical and Biomedical Research, Universidad de la República, Uruguay. Electronic address: beatriz.alvarez@fcien.edu.uy.

Pub Type(s)

Journal Article
Review

Language

eng

PubMed ID

27697462

Citation

Cuevasanta, Ernesto, et al. "Biological Chemistry of Hydrogen Sulfide and Persulfides." Archives of Biochemistry and Biophysics, vol. 617, 2017, pp. 9-25.
Cuevasanta E, Möller MN, Alvarez B. Biological chemistry of hydrogen sulfide and persulfides. Arch Biochem Biophys. 2017;617:9-25.
Cuevasanta, E., Möller, M. N., & Alvarez, B. (2017). Biological chemistry of hydrogen sulfide and persulfides. Archives of Biochemistry and Biophysics, 617, 9-25. https://doi.org/10.1016/j.abb.2016.09.018
Cuevasanta E, Möller MN, Alvarez B. Biological Chemistry of Hydrogen Sulfide and Persulfides. Arch Biochem Biophys. 2017 Mar 1;617:9-25. PubMed PMID: 27697462.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Biological chemistry of hydrogen sulfide and persulfides. AU - Cuevasanta,Ernesto, AU - Möller,Matías N, AU - Alvarez,Beatriz, Y1 - 2016/09/30/ PY - 2016/07/28/received PY - 2016/09/28/revised PY - 2016/09/29/accepted PY - 2016/10/5/pubmed PY - 2017/5/16/medline PY - 2016/10/5/entrez KW - Disulfide KW - Hydridodisulfide KW - Hydrogen sulfide KW - Persulfide KW - Sulfenic acid KW - Thiol SP - 9 EP - 25 JF - Archives of biochemistry and biophysics JO - Arch Biochem Biophys VL - 617 N2 - Hydrogen sulfide (H2S) has been traditionally considered to be a toxic molecule for mammals. However, it can be formed endogenously and exert physiological effects with potential health benefits. H2S can partition two-fold in biological membranes and traverse them rapidly, diffusing between compartments. H2S reactivity has similarities to that of thiols, although it is less nucleophilic than thiols and it can form different products. H2S can react with oxidants derived from the partial reduction of oxygen, but direct scavenging is unlikely to explain H2S protective actions. Important effects are exerted on mitochondria including the stimulation or the inhibition of the electron transport chain. Possible mechanisms for unleashing biological consequences are the reactions with metal centers and with thiol oxidation products. The reactions of H2S with disulfides (RSSR) and sulfenic acids (RSOH) lead to the formation of persulfides (RSSH). Persulfides have enhanced nucleophilicity with respect to the corresponding thiol, consistent with the alpha effect. Besides, the inner and outer sulfurs can both act as electrophiles. In this review, we describe the reactions of H2S with oxidized thiol products and the properties of the persulfides formed in the context of the chemical biology of H2S. SN - 1096-0384 UR - https://www.unboundmedicine.com/medline/citation/27697462/Biological_chemistry_of_hydrogen_sulfide_and_persulfides_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0003-9861(16)30368-X DB - PRIME DP - Unbound Medicine ER -