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Article ; Online: Examining the reaction of NO and H2S and the possible cross-talk between the two signaling pathways.

Bianco, Christopher L / Fukuto, Jon M

Proceedings of the National Academy of Sciences of the United States of America

2015 Volume 112, Issue 34, Page(s) 10573–10574

MeSH term(s)	Animals ; Hydrogen Sulfide/metabolism ; Male ; Nitric Oxide/metabolism ; Nitrogen Oxides/metabolism ; Sulfides/metabolism
Chemical Substances	Nitrogen Oxides ; Sulfides ; Nitric Oxide (31C4KY9ESH) ; Hydrogen Sulfide (YY9FVM7NSN)
Language	English
Publishing date	2015-08-25
Publishing country	United States
Document type	Comment ; Journal Article
ZDB-ID	209104-5
ISSN	1091-6490 ; 0027-8424
ISSN (online)	1091-6490
ISSN	0027-8424
DOI	10.1073/pnas.1513510112
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Article ; Online: Investigations on the role of hemoglobin in sulfide metabolism by intact human red blood cells.

Bianco, Christopher L / Savitsky, Anton / Feelisch, Martin / Cortese-Krott, Miriam M

Biochemical pharmacology

2018 Volume 149, Page(s) 163–173

Abstract: In addition to their role as oxygen transporters, red blood cells (RBCs) contribute to cardiovascular homeostasis by regulating nitric oxide (NO) metabolism via interaction of hemoglobin (Hb) with nitrite and NO itself. RBCs were proposed to also ... ...

Abstract	In addition to their role as oxygen transporters, red blood cells (RBCs) contribute to cardiovascular homeostasis by regulating nitric oxide (NO) metabolism via interaction of hemoglobin (Hb) with nitrite and NO itself. RBCs were proposed to also participate in sulfide metabolism. Although Hb is known to react with sulfide, sulfide metabolism by intact RBCs has not been characterized so far. Therefore we explored the role of Hb in sulfide metabolism in intact human RBCs. We find that upon exposure of washed RBCs to sulfide, no changes in oxy/deoxyhemoglobin (oxy/deoxyHb) are observed by UV-vis and EPR spectroscopy. However, sulfide reacts with methemoglobin (metHb), forming a methemoglobin-sulfide (metHb-SH) complex. Moreover, while metHb-SH is stable in cell-free systems even in the presence of biologically relevant thiols, it gradually decomposes to produce oxyHb, inorganic polysulfides and thiosulfate in intact cells, as detected by EPR and mass spectrometry. Taken together, our results demonstrate that under physiological conditions RBCs are able to metabolize sulfide via intermediate formation of a metHb-SH complex, which subsequently decomposes to oxyHb. We speculate that decomposition of metHb-SH is preceded by an inner-sphere electron transfer, forming reduced Hb (which binds oxygen to form oxyHb) and thiyl radical (a process we here define as "reductive sulfhydration"), which upon release, gives rise to the oxidized products, thiosulfate and polysulfides. Thus, not only is metHb an efficient scavenger and regulator of sulfide in blood, intracellular sulfide itself may play a role in keeping Hb in the reduced oxygen-binding form and, therefore, be involved in RBC physiology and function.
MeSH term(s)	Cells, Cultured ; Erythrocytes/metabolism ; Hemoglobins/metabolism ; Humans ; Hydrogen Sulfide/metabolism ; Methemoglobin/metabolism ; Thiosulfates/metabolism
Chemical Substances	Hemoglobins ; Thiosulfates ; Methemoglobin (9008-37-1) ; Hydrogen Sulfide (YY9FVM7NSN)
Language	English
Publishing date	2018-01-31
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	208787-x
ISSN	1873-2968 ; 0006-2952
ISSN (online)	1873-2968
ISSN	0006-2952
DOI	10.1016/j.bcp.2018.01.045
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Article ; Online: Interaction of Quinone-Related Electron Acceptors with Hydropersulfide Na

Abiko, Yumi / Nakai, Yumi / Luong, Nho C / Bianco, Christopher L / Fukuto, Jon M / Kumagai, Yoshito

Chemical research in toxicology

2019 Volume 32, Issue 4, Page(s) 551–556

Abstract: We previously reported that 9,10-phenanthraquinone (9,10-PQ), an atmospheric electron acceptor, undergoes redox cycling with dithiols as electron donors, resulting in the formation of semiquinone radicals and monothiyl radicals; however, monothiols have ... ...

Abstract	We previously reported that 9,10-phenanthraquinone (9,10-PQ), an atmospheric electron acceptor, undergoes redox cycling with dithiols as electron donors, resulting in the formation of semiquinone radicals and monothiyl radicals; however, monothiols have little reactivity. Because persulfide and polysulfide species are highly reducing, we speculate that 9,10-PQ might undergo one-electron reduction with these reactive sulfides. In the present study, we explored the redox cycling capability of a variety of quinone-related electron acceptors, including 9,10-PQ, during interactions with the hydropersulfide Na
MeSH term(s)	Electrons ; Humans ; Molecular Structure ; Oxidation-Reduction ; Phenanthrenes/chemistry ; Phenanthrenes/metabolism ; Sulfides/chemistry ; Sulfides/metabolism ; Tumor Cells, Cultured
Chemical Substances	Phenanthrenes ; Sulfides ; 9,10-phenanthrenequinone (42L7BZ8H74) ; sodium sulfide (YGR27ZW0Y7)
Language	English
Publishing date	2019-02-15
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	639353-6
ISSN	1520-5010 ; 0893-228X
ISSN (online)	1520-5010
ISSN	0893-228X
DOI	10.1021/acs.chemrestox.8b00158
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Article ; Online: The chemical biology of HNO signaling.

Bianco, Christopher L / Toscano, John P / Bartberger, Michael D / Fukuto, Jon M

Archives of biochemistry and biophysics

2017 Volume 617, Page(s) 129–136

Abstract: Nitroxyl (HNO) is a simple molecule with significant potential as a pharmacological agent. For example, its use in the possible treatment of heart failure has received recent attention due to its unique therapeutic properties. Recent progress has been ... ...

Abstract	Nitroxyl (HNO) is a simple molecule with significant potential as a pharmacological agent. For example, its use in the possible treatment of heart failure has received recent attention due to its unique therapeutic properties. Recent progress has been made on the elucidation of the mechanisms associated with its biological signaling. Importantly, the biochemical mechanisms described for HNO bioactivity are consistent with its unique and novel chemical properties/reactivity. To date, much of the biology of HNO can be associated with interactions and modification of important regulatory thiol proteins. Herein will be provided a description of HNO chemistry and how this chemistry translates to some of its reported biological effects.
MeSH term(s)	Aldehyde Dehydrogenase/chemistry ; Animals ; Antioxidants/chemistry ; Heart Failure/therapy ; Humans ; Nitric Oxide/metabolism ; Nitrogen Oxides/chemistry ; Protein Binding ; Selenoproteins/chemistry ; Signal Transduction ; Sulfhydryl Compounds/chemistry
Chemical Substances	Antioxidants ; Nitrogen Oxides ; Selenoproteins ; Sulfhydryl Compounds ; Nitric Oxide (31C4KY9ESH) ; Aldehyde Dehydrogenase (EC 1.2.1.3) ; nitroxyl (GFQ4MMS07W)
Language	English
Publishing date	2017-03-01
Publishing country	United States
Document type	Journal Article ; Review
ZDB-ID	523-x
ISSN	1096-0384 ; 0003-9861
ISSN (online)	1096-0384
ISSN	0003-9861
DOI	10.1016/j.abb.2016.08.014
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Article ; Online: Selenols are resistant to irreversible modification by HNO.

Bianco, Christopher L / Moore, Cathy D / Fukuto, Jon M / Toscano, John P

Free radical biology & medicine

2016 Volume 99, Page(s) 71–78

Abstract: The discovery of nitric oxide (NO) as an endogenously generated signaling species in mammalian cells has spawned a vast interest in the study of the chemical biology of nitrogen oxides. Of these, nitroxyl (azanone, HNO) has gained much attention for its ... ...

Abstract	The discovery of nitric oxide (NO) as an endogenously generated signaling species in mammalian cells has spawned a vast interest in the study of the chemical biology of nitrogen oxides. Of these, nitroxyl (azanone, HNO) has gained much attention for its potential role as a therapeutic for cardiovascular disease. Known targets of HNO include hemes/heme proteins and thiols/thiol-containing proteins. Recently, due to their roles in redox signaling and cellular defense, selenols and selenoproteins have also been speculated to be additional potential targets of HNO. Indeed, as determined in the current work, selenols are targeted by HNO. Such reactions appear to result only in formation of diselenide products, which can be easily reverted back to the free selenol. This characteristic is distinct from the reaction of HNO with thiols/thiolproteins. These findings suggest that, unlike thiolproteins, selenoproteins are resistant to irreversible oxidative modification, support that Nature may have chosen to use selenium instead of sulfur in certain biological systems for its enhanced resistance to electrophilic and oxidative modification.
Language	English
Publishing date	2016-10
Publishing country	United States
Document type	Journal Article
ZDB-ID	807032-5
ISSN	1873-4596 ; 0891-5849
ISSN (online)	1873-4596
ISSN	0891-5849
DOI	10.1016/j.freeradbiomed.2016.07.008
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Article: The chemical biology of HNO signaling

Bianco, Christopher L / John P. Toscano / Jon M. Fukuto / Michael D. Bartberger

Archives of biochemistry and biophysics. 2017 Mar. 01, v. 617

2017

Abstract	Nitroxyl (HNO) is a simple molecule with significant potential as a pharmacological agent. For example, its use in the possible treatment of heart failure has received recent attention due to its unique therapeutic properties. Recent progress has been made on the elucidation of the mechanisms associated with its biological signaling. Importantly, the biochemical mechanisms described for HNO bioactivity are consistent with its unique and novel chemical properties/reactivity. To date, much of the biology of HNO can be associated with interactions and modification of important regulatory thiol proteins. Herein will be provided a description of HNO chemistry and how this chemistry translates to some of its reported biological effects.
Keywords	biochemical mechanisms ; heart failure ; medicinal properties ; physicochemical properties ; proteins ; thiols
Language	English
Dates of publication	2017-0301
Size	p. 129-136.
Publishing place	Elsevier Inc.
Document type	Article
ZDB-ID	523-x
ISSN	1096-0384 ; 0003-9861
ISSN (online)	1096-0384
ISSN	0003-9861
DOI	10.1016/j.abb.2016.08.014
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Chemical Biology of Hydropersulfides and Related Species: Possible Roles in Cellular Protection and Redox Signaling.

Álvarez, Lucía / Bianco, Christopher L / Toscano, John P / Lin, Joseph / Akaike, Takaaki / Fukuto, Jon M

Antioxidants & redox signaling

2017 Volume 27, Issue 10, Page(s) 622–633

Abstract: Significance: For >20 years, physiological signaling associated with the endogenous generation of hydrogen sulfide (H: Critical issues: The fact that H: Future directions: Currently, it is known that persulfides possess unique and novel chemical ... ...

Abstract	Significance: For >20 years, physiological signaling associated with the endogenous generation of hydrogen sulfide (H Critical issues: The fact that H Future directions: Currently, it is known that persulfides possess unique and novel chemical properties that may explain their biological prevalence. However, significantly more work will be required to establish the possible physiological roles of these species. Moreover, an understanding of the regulation of their biosynthesis and degradation will become important topics in piecing together their biology. Antioxid. Redox Signal. 00, 000-000.
Language	English
Publishing date	2017-10-01
Publishing country	United States
Document type	Journal Article
ZDB-ID	1483836-9
ISSN	1557-7716 ; 1523-0864
ISSN (online)	1557-7716
ISSN	1523-0864
DOI	10.1089/ars.2017.7081
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Article ; Online: Nitroxyl (HNO) signaling.

Fukuto, Jon M / Bianco, Christopher L / Chavez, Tyler A

Free radical biology & medicine

2009 Volume 47, Issue 9, Page(s) 1318–1324

Abstract: Nitroxyl (HNO) has become a nitrogen oxide of significant interest due to its reported biological activity. The actions of HNO in the cardiovascular system appear to make it a good candidate for therapeutic applications for cardiovascular disorders and ... ...

Abstract	Nitroxyl (HNO) has become a nitrogen oxide of significant interest due to its reported biological activity. The actions of HNO in the cardiovascular system appear to make it a good candidate for therapeutic applications for cardiovascular disorders and other potentially important effects have been noted as well. Although the chemistry associated with this activity has not been firmly established, the propensity for HNO to react with thiols and metals are likely mechanisms. Herein, are described the biological activity of HNO and some of the chemistry of HNO that may be responsible for its biological effects.
MeSH term(s)	Animals ; Humans ; Nitrogen Oxides/chemistry ; Nitrogen Oxides/metabolism ; Signal Transduction/physiology
Chemical Substances	Nitrogen Oxides ; nitroxyl (GFQ4MMS07W)
Language	English
Publishing date	2009-11-01
Publishing country	United States
Document type	Journal Article ; Review
ZDB-ID	807032-5
ISSN	1873-4596 ; 0891-5849
ISSN (online)	1873-4596
ISSN	0891-5849
DOI	10.1016/j.freeradbiomed.2009.06.014
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Article ; Online: The reaction of hydrogen sulfide with disulfides: formation of a stable trisulfide and implications for biological systems.

Bianco, Christopher L / Akaike, Takaaki / Ida, Tomoaki / Nagy, Peter / Bogdandi, Virag / Toscano, John P / Kumagai, Yoshito / Henderson, Catherine F / Goddu, Robert N / Lin, Joseph / Fukuto, Jon M

British journal of pharmacology

2018 Volume 176, Issue 4, Page(s) 671–683

Abstract: Background and purpose: The signalling associated with hydrogen sulfide (H: Experimental approach: Using standard analytical techniques (: Key results: H: Conclusions and implications: In aqueous systems, the reaction between H: Linked ... ...

Abstract	Background and purpose: The signalling associated with hydrogen sulfide (H Experimental approach: Using standard analytical techniques ( Key results: H Conclusions and implications: In aqueous systems, the reaction between H Linked articles: This article is part of a themed section on Chemical Biology of Reactive Sulfur Species. To view the other articles in this section visit http://onlinelibrary.wiley.com/doi/10.1111/bph.v176.4/issuetoc.
MeSH term(s)	Cell Survival/drug effects ; HEK293 Cells ; Humans ; Sulfides/chemistry ; Sulfides/pharmacology
Chemical Substances	Sulfides
Language	English
Publishing date	2018-06-28
Publishing country	England
Document type	Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	80081-8
ISSN	1476-5381 ; 0007-1188
ISSN (online)	1476-5381
ISSN	0007-1188
DOI	10.1111/bph.14372
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Article ; Online: Biological hydropersulfides and related polysulfides - a new concept and perspective in redox biology.

Fukuto, Jon M / Ignarro, Louis J / Nagy, Peter / Wink, David A / Kevil, Christopher G / Feelisch, Martin / Cortese-Krott, Miriam M / Bianco, Christopher L / Kumagai, Yoshito / Hobbs, Adrian J / Lin, Joseph / Ida, Tomoaki / Akaike, Takaaki

FEBS letters

2018 Volume 592, Issue 12, Page(s) 2140–2152

Abstract: The chemical biology of thiols (RSH, e.g., cysteine and cysteine-containing proteins/peptides) has been a topic of extreme interest for many decades due to their reported roles in protein structure/folding, redox signaling, metal ligation, cellular ... ...

Abstract	The chemical biology of thiols (RSH, e.g., cysteine and cysteine-containing proteins/peptides) has been a topic of extreme interest for many decades due to their reported roles in protein structure/folding, redox signaling, metal ligation, cellular protection, and enzymology. While many of the studies on thiol/sulfur biochemistry have focused on thiols, relatively ignored have been hydropersulfides (RSSH) and higher order polysulfur species (RSS
MeSH term(s)	Animals ; Cysteine/chemistry ; Humans ; Hydrogen Sulfide/chemistry ; Hydrogen Sulfide/metabolism ; Oxidation-Reduction ; Signal Transduction ; Sulfhydryl Compounds ; Sulfides/chemistry ; Sulfides/metabolism
Chemical Substances	Sulfhydryl Compounds ; Sulfides ; persulfides ; Cysteine (K848JZ4886) ; Hydrogen Sulfide (YY9FVM7NSN)
Language	English
Publishing date	2018-05-24
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	212746-5
ISSN	1873-3468 ; 0014-5793
ISSN (online)	1873-3468
ISSN	0014-5793
DOI	10.1002/1873-3468.13090
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