Possible molecular basis of the biochemical effects of cysteine-derived persulfides

Autores
Cuevasanta, Ernesto; Benchoam, Dayana; Semelak, Jonathan Alexis; Möller, Matías N.; Zeida, Ari; Trujillo, Madia; Alvarez, Beatriz; Estrin, Dario Ariel
Año de publicación
2022
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Persulfides (RSSH/RSS−) are species closely related to thiols (RSH/RS−) and hydrogen sulfide (H2S/HS−), and can be formed in biological systems in both low and high molecular weight cysteine-containing compounds. They are key intermediates in catabolic and biosynthetic processes, and have been proposed to participate in the transduction of hydrogen sulfide effects. Persulfides are acidic, more acidic than thiols, and the persulfide anions are expected to be the predominant species at neutral pH. The persulfide anion has high nucleophilicity, due in part to the alpha effect, i.e., the increased reactivity of a nucleophile when the neighboring atom has high electron density. In addition, persulfides have electrophilic character, a property that is absent in both thiols and hydrogen sulfide. In this article, the biochemistry of persulfides is described, and the possible ways in which the formation of a persulfide could impact on the properties of the biomolecule involved are discussed.
Fil: Cuevasanta, Ernesto. Universidad de la Republica; Uruguay
Fil: Benchoam, Dayana. Universidad de la Republica; Uruguay
Fil: Semelak, Jonathan Alexis. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Möller, Matías N.. Universidad de la Republica; Uruguay
Fil: Zeida, Ari. Universidad de la Republica; Uruguay
Fil: Trujillo, Madia. Universidad de la Republica; Uruguay
Fil: Alvarez, Beatriz. Universidad de la Republica; Uruguay
Fil: Estrin, Dario Ariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Materia
ALPHA EFFECT
CYSTEINE
HYDROGEN SULFIDE
PERSULFIDE
SULFHYDRYL
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/210129
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/210129
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Possible molecular basis of the biochemical effects of cysteine-derived persulfidesCuevasanta, ErnestoBenchoam, DayanaSemelak, Jonathan AlexisMöller, Matías N.Zeida, AriTrujillo, MadiaAlvarez, BeatrizEstrin, Dario ArielALPHA EFFECTCYSTEINEHYDROGEN SULFIDEPERSULFIDESULFHYDRYLhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Persulfides (RSSH/RSS−) are species closely related to thiols (RSH/RS−) and hydrogen sulfide (H2S/HS−), and can be formed in biological systems in both low and high molecular weight cysteine-containing compounds. They are key intermediates in catabolic and biosynthetic processes, and have been proposed to participate in the transduction of hydrogen sulfide effects. Persulfides are acidic, more acidic than thiols, and the persulfide anions are expected to be the predominant species at neutral pH. The persulfide anion has high nucleophilicity, due in part to the alpha effect, i.e., the increased reactivity of a nucleophile when the neighboring atom has high electron density. In addition, persulfides have electrophilic character, a property that is absent in both thiols and hydrogen sulfide. In this article, the biochemistry of persulfides is described, and the possible ways in which the formation of a persulfide could impact on the properties of the biomolecule involved are discussed.Fil: Cuevasanta, Ernesto. Universidad de la Republica; UruguayFil: Benchoam, Dayana. Universidad de la Republica; UruguayFil: Semelak, Jonathan Alexis. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; ArgentinaFil: Möller, Matías N.. Universidad de la Republica; UruguayFil: Zeida, Ari. Universidad de la Republica; UruguayFil: Trujillo, Madia. Universidad de la Republica; UruguayFil: Alvarez, Beatriz. Universidad de la Republica; UruguayFil: Estrin, Dario Ariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; ArgentinaFrontiers Media2022-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/210129Cuevasanta, Ernesto; Benchoam, Dayana; Semelak, Jonathan Alexis; Möller, Matías N.; Zeida, Ari; et al.; Possible molecular basis of the biochemical effects of cysteine-derived persulfides; Frontiers Media; Frontiers in Molecular Biosciences; 9; 9-2022; 1-92296-889XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.frontiersin.org/articles/10.3389/fmolb.2022.975988/fullinfo:eu-repo/semantics/altIdentifier/doi/10.3389/fmolb.2022.975988info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:57:40Zoai:ri.conicet.gov.ar:11336/210129instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:57:40.977CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Possible molecular basis of the biochemical effects of cysteine-derived persulfides
title Possible molecular basis of the biochemical effects of cysteine-derived persulfides
spellingShingle Possible molecular basis of the biochemical effects of cysteine-derived persulfides
Cuevasanta, Ernesto
ALPHA EFFECT
CYSTEINE
HYDROGEN SULFIDE
PERSULFIDE
SULFHYDRYL
title_short Possible molecular basis of the biochemical effects of cysteine-derived persulfides
title_full Possible molecular basis of the biochemical effects of cysteine-derived persulfides
title_fullStr Possible molecular basis of the biochemical effects of cysteine-derived persulfides
title_full_unstemmed Possible molecular basis of the biochemical effects of cysteine-derived persulfides
title_sort Possible molecular basis of the biochemical effects of cysteine-derived persulfides
dc.creator.none.fl_str_mv Cuevasanta, Ernesto
Benchoam, Dayana
Semelak, Jonathan Alexis
Möller, Matías N.
Zeida, Ari
Trujillo, Madia
Alvarez, Beatriz
Estrin, Dario Ariel
author Cuevasanta, Ernesto
author_facet Cuevasanta, Ernesto
Benchoam, Dayana
Semelak, Jonathan Alexis
Möller, Matías N.
Zeida, Ari
Trujillo, Madia
Alvarez, Beatriz
Estrin, Dario Ariel
author_role author
author2 Benchoam, Dayana
Semelak, Jonathan Alexis
Möller, Matías N.
Zeida, Ari
Trujillo, Madia
Alvarez, Beatriz
Estrin, Dario Ariel
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ALPHA EFFECT
CYSTEINE
HYDROGEN SULFIDE
PERSULFIDE
SULFHYDRYL
topic ALPHA EFFECT
CYSTEINE
HYDROGEN SULFIDE
PERSULFIDE
SULFHYDRYL
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Persulfides (RSSH/RSS−) are species closely related to thiols (RSH/RS−) and hydrogen sulfide (H2S/HS−), and can be formed in biological systems in both low and high molecular weight cysteine-containing compounds. They are key intermediates in catabolic and biosynthetic processes, and have been proposed to participate in the transduction of hydrogen sulfide effects. Persulfides are acidic, more acidic than thiols, and the persulfide anions are expected to be the predominant species at neutral pH. The persulfide anion has high nucleophilicity, due in part to the alpha effect, i.e., the increased reactivity of a nucleophile when the neighboring atom has high electron density. In addition, persulfides have electrophilic character, a property that is absent in both thiols and hydrogen sulfide. In this article, the biochemistry of persulfides is described, and the possible ways in which the formation of a persulfide could impact on the properties of the biomolecule involved are discussed.
Fil: Cuevasanta, Ernesto. Universidad de la Republica; Uruguay
Fil: Benchoam, Dayana. Universidad de la Republica; Uruguay
Fil: Semelak, Jonathan Alexis. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Möller, Matías N.. Universidad de la Republica; Uruguay
Fil: Zeida, Ari. Universidad de la Republica; Uruguay
Fil: Trujillo, Madia. Universidad de la Republica; Uruguay
Fil: Alvarez, Beatriz. Universidad de la Republica; Uruguay
Fil: Estrin, Dario Ariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
description Persulfides (RSSH/RSS−) are species closely related to thiols (RSH/RS−) and hydrogen sulfide (H2S/HS−), and can be formed in biological systems in both low and high molecular weight cysteine-containing compounds. They are key intermediates in catabolic and biosynthetic processes, and have been proposed to participate in the transduction of hydrogen sulfide effects. Persulfides are acidic, more acidic than thiols, and the persulfide anions are expected to be the predominant species at neutral pH. The persulfide anion has high nucleophilicity, due in part to the alpha effect, i.e., the increased reactivity of a nucleophile when the neighboring atom has high electron density. In addition, persulfides have electrophilic character, a property that is absent in both thiols and hydrogen sulfide. In this article, the biochemistry of persulfides is described, and the possible ways in which the formation of a persulfide could impact on the properties of the biomolecule involved are discussed.
publishDate 2022
dc.date.none.fl_str_mv 2022-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/210129
Cuevasanta, Ernesto; Benchoam, Dayana; Semelak, Jonathan Alexis; Möller, Matías N.; Zeida, Ari; et al.; Possible molecular basis of the biochemical effects of cysteine-derived persulfides; Frontiers Media; Frontiers in Molecular Biosciences; 9; 9-2022; 1-9
2296-889X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/210129
identifier_str_mv Cuevasanta, Ernesto; Benchoam, Dayana; Semelak, Jonathan Alexis; Möller, Matías N.; Zeida, Ari; et al.; Possible molecular basis of the biochemical effects of cysteine-derived persulfides; Frontiers Media; Frontiers in Molecular Biosciences; 9; 9-2022; 1-9
2296-889X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.frontiersin.org/articles/10.3389/fmolb.2022.975988/full
info:eu-repo/semantics/altIdentifier/doi/10.3389/fmolb.2022.975988
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Frontiers Media
publisher.none.fl_str_mv Frontiers Media
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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