Ferredoxin-mediated reduction of 2-nitrothiophene inhibits photosynthesis: mechanism and herbicidal potential.
Identifieur interne : 000125 ( Main/Exploration ); précédent : 000124; suivant : 000126Ferredoxin-mediated reduction of 2-nitrothiophene inhibits photosynthesis: mechanism and herbicidal potential.
Auteurs : Yehouda Marcus [Israël] ; Michael Gurevitz [Israël]Source :
- The Biochemical journal [ 1470-8728 ] ; 2020.
Descripteurs français
- KwdFr :
- Anabaena (effets des médicaments et des substances chimiques), Anabaena (métabolisme), Ferrédoxines (métabolisme), Ferrédoxines (pharmacologie), Herbicides (métabolisme), Herbicides (pharmacologie), Photosynthèse (effets des médicaments et des substances chimiques), Photosynthèse (physiologie), Structure tertiaire des protéines (MeSH), Thiophènes (composition chimique), Thiophènes (métabolisme).
- MESH :
- composition chimique : Thiophènes.
- effets des médicaments et des substances chimiques : Anabaena, Photosynthèse.
- métabolisme : Anabaena, Ferrédoxines, Herbicides, Thiophènes.
- pharmacologie : Ferrédoxines, Herbicides.
- physiologie : Photosynthèse.
- Structure tertiaire des protéines.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Thiophenes.
- chemical , metabolism : Ferredoxins, Herbicides, Thiophenes.
- drug effects : Anabaena, Photosynthesis.
- metabolism : Anabaena.
- chemical , pharmacology : Ferredoxins, Herbicides.
- physiology : Photosynthesis.
- Protein Structure, Tertiary.
Abstract
Searching for compounds that inhibit the growth of photosynthetic organisms highlighted a prominent effect at micromolar concentrations of the nitroheteroaromatic thioether, 2-nitrothiophene, applied in the light. Since similar effects were reminiscent to those obtained also by radicals produced under excessive illumination or by herbicides, and in light of its redox potential, we suspected that 2-nitrothiophene was reduced by ferredoxin, a major reducing compound in the light. In silico examination using docking and tunneling computing algorithms of the putative interaction between 2-nitrothiophene and cyanobacterial ferredoxin has suggested a site of interaction enabling robust electron transfer from the iron-sulfur cluster of ferredoxin to the nitro group of 2-nitrothiophene. ESR and oximetry analyses of cyanobacterial cells (Anabaena PCC7120) treated with 50 μM 2-nitrothiophene under illumination revealed accumulation of oxygen radicals and peroxides. Gas chromatography mass spectrometry analysis of 2-nitrothiophene-treated cells identified cytotoxic nitroso and non-toxic amino derivatives. These products of the degradation pathway of 2-nitrohiophene, which initializes with a single electron transfer that forms a short-live anion radical, are then decomposed to nitrate and thiophene, and may be further reduced to a nitroso hydroxylamine and amino derivatives. This mechanism of toxicity is similar to that of nitroimidazoles (e.g. ornidazole and metronidazole) reduced by ferredoxin in anaerobic bacteria and protozoa, but differs from that of ornidazole in planta.
DOI: 10.1042/BCJ20190830
PubMed: 32150261
Affiliations:
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Wise Faculty of Life Sciences, Tel Aviv University, Ramat Aviv, Tel Aviv 69978</wicri:regionArea><wicri:noRegion>Tel Aviv 69978</wicri:noRegion></affiliation></author><author><name sortKey="Gurevitz, Michael" sort="Gurevitz, Michael" uniqKey="Gurevitz M" first="Michael" last="Gurevitz">Michael Gurevitz</name><affiliation wicri:level="1"><nlm:affiliation>Department of Plant Molecular Biology and Ecology, George S. Wise Faculty of Life Sciences, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel.</nlm:affiliation><country xml:lang="fr">Israël</country><wicri:regionArea>Department of Plant Molecular Biology and Ecology, George S. 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Since similar effects were reminiscent to those obtained also by radicals produced under excessive illumination or by herbicides, and in light of its redox potential, we suspected that 2-nitrothiophene was reduced by ferredoxin, a major reducing compound in the light. In silico examination using docking and tunneling computing algorithms of the putative interaction between 2-nitrothiophene and cyanobacterial ferredoxin has suggested a site of interaction enabling robust electron transfer from the iron-sulfur cluster of ferredoxin to the nitro group of 2-nitrothiophene. ESR and oximetry analyses of cyanobacterial cells (Anabaena PCC7120) treated with 50 μM 2-nitrothiophene under illumination revealed accumulation of oxygen radicals and peroxides. Gas chromatography mass spectrometry analysis of 2-nitrothiophene-treated cells identified cytotoxic nitroso and non-toxic amino derivatives. These products of the degradation pathway of 2-nitrohiophene, which initializes with a single electron transfer that forms a short-live anion radical, are then decomposed to nitrate and thiophene, and may be further reduced to a nitroso hydroxylamine and amino derivatives. This mechanism of toxicity is similar to that of nitroimidazoles (e.g. ornidazole and metronidazole) reduced by ferredoxin in anaerobic bacteria and protozoa, but differs from that of ornidazole in planta.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">32150261</PMID><DateCompleted><Year>2020</Year><Month>10</Month><Day>21</Day></DateCompleted><DateRevised><Year>2020</Year><Month>10</Month><Day>21</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1470-8728</ISSN><JournalIssue CitedMedium="Internet"><Volume>477</Volume><Issue>6</Issue><PubDate><Year>2020</Year><Month>03</Month><Day>27</Day></PubDate></JournalIssue><Title>The Biochemical journal</Title><ISOAbbreviation>Biochem J</ISOAbbreviation></Journal><ArticleTitle>Ferredoxin-mediated reduction of 2-nitrothiophene inhibits photosynthesis: mechanism and herbicidal potential.</ArticleTitle><Pagination><MedlinePgn>1149-1158</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1042/BCJ20190830</ELocationID><Abstract><AbstractText>Searching for compounds that inhibit the growth of photosynthetic organisms highlighted a prominent effect at micromolar concentrations of the nitroheteroaromatic thioether, 2-nitrothiophene, applied in the light. Since similar effects were reminiscent to those obtained also by radicals produced under excessive illumination or by herbicides, and in light of its redox potential, we suspected that 2-nitrothiophene was reduced by ferredoxin, a major reducing compound in the light. In silico examination using docking and tunneling computing algorithms of the putative interaction between 2-nitrothiophene and cyanobacterial ferredoxin has suggested a site of interaction enabling robust electron transfer from the iron-sulfur cluster of ferredoxin to the nitro group of 2-nitrothiophene. ESR and oximetry analyses of cyanobacterial cells (Anabaena PCC7120) treated with 50 μM 2-nitrothiophene under illumination revealed accumulation of oxygen radicals and peroxides. Gas chromatography mass spectrometry analysis of 2-nitrothiophene-treated cells identified cytotoxic nitroso and non-toxic amino derivatives. These products of the degradation pathway of 2-nitrohiophene, which initializes with a single electron transfer that forms a short-live anion radical, are then decomposed to nitrate and thiophene, and may be further reduced to a nitroso hydroxylamine and amino derivatives. This mechanism of toxicity is similar to that of nitroimidazoles (e.g. ornidazole and metronidazole) reduced by ferredoxin in anaerobic bacteria and protozoa, but differs from that of ornidazole in planta.</AbstractText><CopyrightInformation>© 2020 The Author(s). Published by Portland Press Limited on behalf of the Biochemical Society.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Marcus</LastName><ForeName>Yehouda</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>Department of Plant Molecular Biology and Ecology, George S. Wise Faculty of Life Sciences, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gurevitz</LastName><ForeName>Michael</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Department of Plant Molecular Biology and Ecology, George S. Wise Faculty of Life Sciences, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Biochem J</MedlineTA><NlmUniqueID>2984726R</NlmUniqueID><ISSNLinking>0264-6021</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005288">Ferredoxins</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D006540">Herbicides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D013876">Thiophenes</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D017033" MajorTopicYN="N">Anabaena</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005288" MajorTopicYN="N">Ferredoxins</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006540" MajorTopicYN="N">Herbicides</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010788" MajorTopicYN="N">Photosynthesis</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000502" MajorTopicYN="Y">physiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D017434" MajorTopicYN="N">Protein Structure, Tertiary</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013876" MajorTopicYN="N">Thiophenes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">ferredoxin</Keyword><Keyword MajorTopicYN="Y">herbicidal potential</Keyword><Keyword MajorTopicYN="Y">nitroheteroaromatic</Keyword><Keyword MajorTopicYN="Y">photosynthesis</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2019</Year><Month>11</Month><Day>12</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2020</Year><Month>02</Month><Day>19</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2020</Year><Month>03</Month><Day>09</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>3</Month><Day>10</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>10</Month><Day>22</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>3</Month><Day>10</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32150261</ArticleId><ArticleId IdType="pii">222321</ArticleId><ArticleId IdType="doi">10.1042/BCJ20190830</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Israël</li></country></list><tree><country name="Israël"><noRegion><name sortKey="Marcus, Yehouda" sort="Marcus, Yehouda" uniqKey="Marcus Y" first="Yehouda" last="Marcus">Yehouda Marcus</name></noRegion><name sortKey="Gurevitz, Michael" sort="Gurevitz, Michael" uniqKey="Gurevitz M" first="Michael" last="Gurevitz">Michael Gurevitz</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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