Singlet Molecular Oxygen Generation in the Reaction of Biological Haloamines of Amino Acids and Polyamines with Hydrogen Peroxide
ABSTRACT Leucocytes generate hypohalous acids (HOCl and HOBr) to defend the host against pathogens. In cells, hypohalous acids react with amine‐containing molecules, such as amino acids and polyamines, producing chloramines and bromamines, reservoirs of oxidizing power that can potentially damage ho...
Gespeichert in:
Veröffentlicht in: | Photochemistry and photobiology 2023-03, Vol.99 (2), p.661-671 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 671 |
---|---|
container_issue | 2 |
container_start_page | 661 |
container_title | Photochemistry and photobiology |
container_volume | 99 |
creator | Nascimento, Rafaela Oliveira Prado, Fernanda Manso Medeiros, Marisa Helena Gennari Ronsein, Graziella Eliza Di Mascio, Paolo |
description | ABSTRACT
Leucocytes generate hypohalous acids (HOCl and HOBr) to defend the host against pathogens. In cells, hypohalous acids react with amine‐containing molecules, such as amino acids and polyamines, producing chloramines and bromamines, reservoirs of oxidizing power that can potentially damage host tissues at sites of inflammation. Hypohalous acids also react with H2O2 to produce stoichiometric amounts of singlet molecular oxygen (1O2), but its generation in leucocytes is still under debate. Additionally, it is unclear whether haloamines generate 1O2 following a reaction with H2O2. Herein, we provide evidence of the generation of 1O2 in the reactions between amino acid‐derived (taurine, N‐α‐acetyl‐Lysine and glycine) and polyamine‐derived (spermine and spermidine) haloamines and H2O2 in an aqueous solution. The unequivocal formation of 1O2 was detected by monitoring its characteristic monomol light emission at 1270 nm in the near‐infrared region. For amino acid‐derived haloamines, the presence of 1O2 was further confirmed by chemical trapping with anthracene‐9,10‐divinylsulfonate and HPLC‐MS/MS detection. Altogether, photoemission and chemical trapping studies demonstrated that chloramines were less effective at producing 1O2 than bromamines of amino acids and polyamines. Thus, 1O2 formation via bromamines and H2O2 may be a potential source of 1O2 in nonilluminated biological systems.
Generation of 1O2 in the reactions between amino acid‐derived (taurine, N‐α‐acetyl‐Lysine and glycine) and polyamine‐derived (spermine and spermidine) haloamines and H2O2 in an aqueous solution. 1O2 formation via bromamines and H2O2 may be a potential source of 1O2 in nonilluminated biological systems. |
doi_str_mv | 10.1111/php.13708 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2709017304</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2709017304</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3538-d23e853f855352495550a3a83e2c93442f26fd9161bdba369952f286e669cffe3</originalsourceid><addsrcrecordid>eNp1kc1OGzEURi0EghS64AWQJTbtYsA_Y894maKWVAIR0XY9cjx3EiPHTu0ZwSz75nVIyqIS3tj3fkdHlj6Ezim5ovlcb1abK8orUh-gCa0ELShR1SGaEMJpUUshTtCHlJ4IoaWq6DE64ZKUlaJsgv78sH7poMf3wYEZnI744WVcgse34CHq3gaPrcf9CvAjaPM6hw5_scGFpTXa4Zl2Qa-th7QNpvkV8NTYNmHtWzwPbtynz7Zf4dnYxrD1zyGGF9vCGTrqtEvwcX-fol_fvv68mRV3D7ffb6Z3heGC10XLONSCd7UQXLBSCSGI5rrmwIziZck6JrtWUUkX7UJzqZTIq1qClMp0HfBT9Gnn3cTwe4DUN2ubDDinPYQhNawiitCKkzKjl_-hT2GIPv8uU4rxiiomM_V5R5kYUorQNZto1zqODSXNtpcm99K89pLZi71xWKyhfSP_FZGB6x3wbB2M75ua-Wy-U_4FM_GWuQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2792371926</pqid></control><display><type>article</type><title>Singlet Molecular Oxygen Generation in the Reaction of Biological Haloamines of Amino Acids and Polyamines with Hydrogen Peroxide</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Nascimento, Rafaela Oliveira ; Prado, Fernanda Manso ; Medeiros, Marisa Helena Gennari ; Ronsein, Graziella Eliza ; Di Mascio, Paolo</creator><creatorcontrib>Nascimento, Rafaela Oliveira ; Prado, Fernanda Manso ; Medeiros, Marisa Helena Gennari ; Ronsein, Graziella Eliza ; Di Mascio, Paolo</creatorcontrib><description>ABSTRACT
Leucocytes generate hypohalous acids (HOCl and HOBr) to defend the host against pathogens. In cells, hypohalous acids react with amine‐containing molecules, such as amino acids and polyamines, producing chloramines and bromamines, reservoirs of oxidizing power that can potentially damage host tissues at sites of inflammation. Hypohalous acids also react with H2O2 to produce stoichiometric amounts of singlet molecular oxygen (1O2), but its generation in leucocytes is still under debate. Additionally, it is unclear whether haloamines generate 1O2 following a reaction with H2O2. Herein, we provide evidence of the generation of 1O2 in the reactions between amino acid‐derived (taurine, N‐α‐acetyl‐Lysine and glycine) and polyamine‐derived (spermine and spermidine) haloamines and H2O2 in an aqueous solution. The unequivocal formation of 1O2 was detected by monitoring its characteristic monomol light emission at 1270 nm in the near‐infrared region. For amino acid‐derived haloamines, the presence of 1O2 was further confirmed by chemical trapping with anthracene‐9,10‐divinylsulfonate and HPLC‐MS/MS detection. Altogether, photoemission and chemical trapping studies demonstrated that chloramines were less effective at producing 1O2 than bromamines of amino acids and polyamines. Thus, 1O2 formation via bromamines and H2O2 may be a potential source of 1O2 in nonilluminated biological systems.
Generation of 1O2 in the reactions between amino acid‐derived (taurine, N‐α‐acetyl‐Lysine and glycine) and polyamine‐derived (spermine and spermidine) haloamines and H2O2 in an aqueous solution. 1O2 formation via bromamines and H2O2 may be a potential source of 1O2 in nonilluminated biological systems.</description><identifier>ISSN: 0031-8655</identifier><identifier>EISSN: 1751-1097</identifier><identifier>DOI: 10.1111/php.13708</identifier><identifier>PMID: 36047912</identifier><language>eng</language><publisher>United States: Blackwell Publishing Ltd</publisher><subject>Acids ; Amino Acids ; Anthracene ; Aqueous solutions ; Chloramines ; Glycine ; Hydrogen peroxide ; Hydrogen Peroxide - chemistry ; Leukocytes ; Light emission ; Lysine ; Oxidation ; Oxygen ; Photoelectric emission ; Polyamines ; Singlet Oxygen - chemistry ; Spermidine ; Spermine ; Tandem Mass Spectrometry ; Taurine ; Trapping</subject><ispartof>Photochemistry and photobiology, 2023-03, Vol.99 (2), p.661-671</ispartof><rights>2022 American Society for Photobiology.</rights><rights>Copyright © 2023 American Society for Photobiology</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3538-d23e853f855352495550a3a83e2c93442f26fd9161bdba369952f286e669cffe3</citedby><cites>FETCH-LOGICAL-c3538-d23e853f855352495550a3a83e2c93442f26fd9161bdba369952f286e669cffe3</cites><orcidid>0000-0003-4458-4354 ; 0000-0002-2340-6770 ; 0000-0003-4125-8350 ; 0000-0002-1007-2046 ; 0000-0002-5438-1174</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fphp.13708$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fphp.13708$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36047912$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nascimento, Rafaela Oliveira</creatorcontrib><creatorcontrib>Prado, Fernanda Manso</creatorcontrib><creatorcontrib>Medeiros, Marisa Helena Gennari</creatorcontrib><creatorcontrib>Ronsein, Graziella Eliza</creatorcontrib><creatorcontrib>Di Mascio, Paolo</creatorcontrib><title>Singlet Molecular Oxygen Generation in the Reaction of Biological Haloamines of Amino Acids and Polyamines with Hydrogen Peroxide</title><title>Photochemistry and photobiology</title><addtitle>Photochem Photobiol</addtitle><description>ABSTRACT
Leucocytes generate hypohalous acids (HOCl and HOBr) to defend the host against pathogens. In cells, hypohalous acids react with amine‐containing molecules, such as amino acids and polyamines, producing chloramines and bromamines, reservoirs of oxidizing power that can potentially damage host tissues at sites of inflammation. Hypohalous acids also react with H2O2 to produce stoichiometric amounts of singlet molecular oxygen (1O2), but its generation in leucocytes is still under debate. Additionally, it is unclear whether haloamines generate 1O2 following a reaction with H2O2. Herein, we provide evidence of the generation of 1O2 in the reactions between amino acid‐derived (taurine, N‐α‐acetyl‐Lysine and glycine) and polyamine‐derived (spermine and spermidine) haloamines and H2O2 in an aqueous solution. The unequivocal formation of 1O2 was detected by monitoring its characteristic monomol light emission at 1270 nm in the near‐infrared region. For amino acid‐derived haloamines, the presence of 1O2 was further confirmed by chemical trapping with anthracene‐9,10‐divinylsulfonate and HPLC‐MS/MS detection. Altogether, photoemission and chemical trapping studies demonstrated that chloramines were less effective at producing 1O2 than bromamines of amino acids and polyamines. Thus, 1O2 formation via bromamines and H2O2 may be a potential source of 1O2 in nonilluminated biological systems.
Generation of 1O2 in the reactions between amino acid‐derived (taurine, N‐α‐acetyl‐Lysine and glycine) and polyamine‐derived (spermine and spermidine) haloamines and H2O2 in an aqueous solution. 1O2 formation via bromamines and H2O2 may be a potential source of 1O2 in nonilluminated biological systems.</description><subject>Acids</subject><subject>Amino Acids</subject><subject>Anthracene</subject><subject>Aqueous solutions</subject><subject>Chloramines</subject><subject>Glycine</subject><subject>Hydrogen peroxide</subject><subject>Hydrogen Peroxide - chemistry</subject><subject>Leukocytes</subject><subject>Light emission</subject><subject>Lysine</subject><subject>Oxidation</subject><subject>Oxygen</subject><subject>Photoelectric emission</subject><subject>Polyamines</subject><subject>Singlet Oxygen - chemistry</subject><subject>Spermidine</subject><subject>Spermine</subject><subject>Tandem Mass Spectrometry</subject><subject>Taurine</subject><subject>Trapping</subject><issn>0031-8655</issn><issn>1751-1097</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kc1OGzEURi0EghS64AWQJTbtYsA_Y894maKWVAIR0XY9cjx3EiPHTu0ZwSz75nVIyqIS3tj3fkdHlj6Ezim5ovlcb1abK8orUh-gCa0ELShR1SGaEMJpUUshTtCHlJ4IoaWq6DE64ZKUlaJsgv78sH7poMf3wYEZnI744WVcgse34CHq3gaPrcf9CvAjaPM6hw5_scGFpTXa4Zl2Qa-th7QNpvkV8NTYNmHtWzwPbtynz7Zf4dnYxrD1zyGGF9vCGTrqtEvwcX-fol_fvv68mRV3D7ffb6Z3heGC10XLONSCd7UQXLBSCSGI5rrmwIziZck6JrtWUUkX7UJzqZTIq1qClMp0HfBT9Gnn3cTwe4DUN2ubDDinPYQhNawiitCKkzKjl_-hT2GIPv8uU4rxiiomM_V5R5kYUorQNZto1zqODSXNtpcm99K89pLZi71xWKyhfSP_FZGB6x3wbB2M75ua-Wy-U_4FM_GWuQ</recordid><startdate>202303</startdate><enddate>202303</enddate><creator>Nascimento, Rafaela Oliveira</creator><creator>Prado, Fernanda Manso</creator><creator>Medeiros, Marisa Helena Gennari</creator><creator>Ronsein, Graziella Eliza</creator><creator>Di Mascio, Paolo</creator><general>Blackwell Publishing Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>4T-</scope><scope>7TM</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>K9.</scope><scope>NAPCQ</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4458-4354</orcidid><orcidid>https://orcid.org/0000-0002-2340-6770</orcidid><orcidid>https://orcid.org/0000-0003-4125-8350</orcidid><orcidid>https://orcid.org/0000-0002-1007-2046</orcidid><orcidid>https://orcid.org/0000-0002-5438-1174</orcidid></search><sort><creationdate>202303</creationdate><title>Singlet Molecular Oxygen Generation in the Reaction of Biological Haloamines of Amino Acids and Polyamines with Hydrogen Peroxide</title><author>Nascimento, Rafaela Oliveira ; Prado, Fernanda Manso ; Medeiros, Marisa Helena Gennari ; Ronsein, Graziella Eliza ; Di Mascio, Paolo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3538-d23e853f855352495550a3a83e2c93442f26fd9161bdba369952f286e669cffe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acids</topic><topic>Amino Acids</topic><topic>Anthracene</topic><topic>Aqueous solutions</topic><topic>Chloramines</topic><topic>Glycine</topic><topic>Hydrogen peroxide</topic><topic>Hydrogen Peroxide - chemistry</topic><topic>Leukocytes</topic><topic>Light emission</topic><topic>Lysine</topic><topic>Oxidation</topic><topic>Oxygen</topic><topic>Photoelectric emission</topic><topic>Polyamines</topic><topic>Singlet Oxygen - chemistry</topic><topic>Spermidine</topic><topic>Spermine</topic><topic>Tandem Mass Spectrometry</topic><topic>Taurine</topic><topic>Trapping</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nascimento, Rafaela Oliveira</creatorcontrib><creatorcontrib>Prado, Fernanda Manso</creatorcontrib><creatorcontrib>Medeiros, Marisa Helena Gennari</creatorcontrib><creatorcontrib>Ronsein, Graziella Eliza</creatorcontrib><creatorcontrib>Di Mascio, Paolo</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Docstoc</collection><collection>Nucleic Acids Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Nursing & Allied Health Premium</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Photochemistry and photobiology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nascimento, Rafaela Oliveira</au><au>Prado, Fernanda Manso</au><au>Medeiros, Marisa Helena Gennari</au><au>Ronsein, Graziella Eliza</au><au>Di Mascio, Paolo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Singlet Molecular Oxygen Generation in the Reaction of Biological Haloamines of Amino Acids and Polyamines with Hydrogen Peroxide</atitle><jtitle>Photochemistry and photobiology</jtitle><addtitle>Photochem Photobiol</addtitle><date>2023-03</date><risdate>2023</risdate><volume>99</volume><issue>2</issue><spage>661</spage><epage>671</epage><pages>661-671</pages><issn>0031-8655</issn><eissn>1751-1097</eissn><abstract>ABSTRACT
Leucocytes generate hypohalous acids (HOCl and HOBr) to defend the host against pathogens. In cells, hypohalous acids react with amine‐containing molecules, such as amino acids and polyamines, producing chloramines and bromamines, reservoirs of oxidizing power that can potentially damage host tissues at sites of inflammation. Hypohalous acids also react with H2O2 to produce stoichiometric amounts of singlet molecular oxygen (1O2), but its generation in leucocytes is still under debate. Additionally, it is unclear whether haloamines generate 1O2 following a reaction with H2O2. Herein, we provide evidence of the generation of 1O2 in the reactions between amino acid‐derived (taurine, N‐α‐acetyl‐Lysine and glycine) and polyamine‐derived (spermine and spermidine) haloamines and H2O2 in an aqueous solution. The unequivocal formation of 1O2 was detected by monitoring its characteristic monomol light emission at 1270 nm in the near‐infrared region. For amino acid‐derived haloamines, the presence of 1O2 was further confirmed by chemical trapping with anthracene‐9,10‐divinylsulfonate and HPLC‐MS/MS detection. Altogether, photoemission and chemical trapping studies demonstrated that chloramines were less effective at producing 1O2 than bromamines of amino acids and polyamines. Thus, 1O2 formation via bromamines and H2O2 may be a potential source of 1O2 in nonilluminated biological systems.
Generation of 1O2 in the reactions between amino acid‐derived (taurine, N‐α‐acetyl‐Lysine and glycine) and polyamine‐derived (spermine and spermidine) haloamines and H2O2 in an aqueous solution. 1O2 formation via bromamines and H2O2 may be a potential source of 1O2 in nonilluminated biological systems.</abstract><cop>United States</cop><pub>Blackwell Publishing Ltd</pub><pmid>36047912</pmid><doi>10.1111/php.13708</doi><tpages>671</tpages><orcidid>https://orcid.org/0000-0003-4458-4354</orcidid><orcidid>https://orcid.org/0000-0002-2340-6770</orcidid><orcidid>https://orcid.org/0000-0003-4125-8350</orcidid><orcidid>https://orcid.org/0000-0002-1007-2046</orcidid><orcidid>https://orcid.org/0000-0002-5438-1174</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0031-8655 |
ispartof | Photochemistry and photobiology, 2023-03, Vol.99 (2), p.661-671 |
issn | 0031-8655 1751-1097 |
language | eng |
recordid | cdi_proquest_miscellaneous_2709017304 |
source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
subjects | Acids Amino Acids Anthracene Aqueous solutions Chloramines Glycine Hydrogen peroxide Hydrogen Peroxide - chemistry Leukocytes Light emission Lysine Oxidation Oxygen Photoelectric emission Polyamines Singlet Oxygen - chemistry Spermidine Spermine Tandem Mass Spectrometry Taurine Trapping |
title | Singlet Molecular Oxygen Generation in the Reaction of Biological Haloamines of Amino Acids and Polyamines with Hydrogen Peroxide |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-16T11%3A51%3A16IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Singlet%20Molecular%20Oxygen%20Generation%20in%20the%20Reaction%20of%20Biological%20Haloamines%20of%20Amino%20Acids%20and%20Polyamines%20with%20Hydrogen%20Peroxide&rft.jtitle=Photochemistry%20and%20photobiology&rft.au=Nascimento,%20Rafaela%20Oliveira&rft.date=2023-03&rft.volume=99&rft.issue=2&rft.spage=661&rft.epage=671&rft.pages=661-671&rft.issn=0031-8655&rft.eissn=1751-1097&rft_id=info:doi/10.1111/php.13708&rft_dat=%3Cproquest_cross%3E2709017304%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2792371926&rft_id=info:pmid/36047912&rfr_iscdi=true |