Antimicrobial activity of o-carboranylalanine.
Identifieur interne : 002940 ( Main/Exploration ); précédent : 002939; suivant : 002941Antimicrobial activity of o-carboranylalanine.
Auteurs : G. Oros [Hongrie] ; I. Ujváry ; R J NachmanSource :
- Amino acids [ 0939-4451 ] ; 1999.
Descripteurs français
- KwdFr :
- Anti-infectieux (pharmacologie), Antibactériens (MeSH), Bactéries à Gram négatif (croissance et développement), Bactéries à Gram négatif (effets des médicaments et des substances chimiques), Bactéries à Gram positif (croissance et développement), Bactéries à Gram positif (effets des médicaments et des substances chimiques), Champignons (croissance et développement), Champignons (effets des médicaments et des substances chimiques), Composés du bore (pharmacologie), Phénylalanine (analogues et dérivés), Phénylalanine (pharmacologie), Plantes (effets des médicaments et des substances chimiques), Tests de sensibilité microbienne (MeSH).
- MESH :
- analogues et dérivés : Phénylalanine.
- croissance et développement : Bactéries à Gram négatif, Bactéries à Gram positif, Champignons.
- effets des médicaments et des substances chimiques : Bactéries à Gram négatif, Bactéries à Gram positif, Champignons, Plantes.
- pharmacologie : Anti-infectieux, Composés du bore, Phénylalanine.
- Antibactériens, Tests de sensibilité microbienne.
English descriptors
- KwdEn :
- Anti-Bacterial Agents (MeSH), Anti-Infective Agents (pharmacology), Boron Compounds (pharmacology), Fungi (drug effects), Fungi (growth & development), Gram-Negative Bacteria (drug effects), Gram-Negative Bacteria (growth & development), Gram-Positive Bacteria (drug effects), Gram-Positive Bacteria (growth & development), Microbial Sensitivity Tests (MeSH), Phenylalanine (analogs & derivatives), Phenylalanine (pharmacology), Plants (drug effects).
- MESH :
- chemical , analogs & derivatives : Phenylalanine.
- chemical , pharmacology : Anti-Infective Agents, Boron Compounds, Phenylalanine.
- chemical : Anti-Bacterial Agents.
- drug effects : Fungi, Gram-Negative Bacteria, Gram-Positive Bacteria, Plants.
- growth & development : Fungi, Gram-Negative Bacteria, Gram-Positive Bacteria.
- Microbial Sensitivity Tests.
Abstract
Functionalized polyhedral carboranes, including amino acid analogs, have unique physicochemical properties and are used as experimental anticancer agents. However, our current knowledge on their effect in nonmammalian biological systems is limited. We investigated the activity spectrum in vitro of o-carboranylalanine (o-Cba), considered to be a highly lipophilic analog of phenylalanine, against representative plant pathogenic bacteria and fungi of various taxonomic position. The antibacterial effect of o-Cba against some species was comparable to that of the widely used agricultural antibiotic, streptomycin. The sensitivity of individual bacterial species to o-Cba within the same genus varied to a greater extent than the average sensitivity of various genera. In general, this carborane-containing amino acid was more toxic to Gram positive bacteria (Bacillus, Corynebacterium, Curtobacterium, Micrococcus, Rhodococcus, and Staphylococcus) than to Gram negative ones (Agrobacterium, Erwinia, Escherichia, Pseudomonas, Rhizobium, and Xanthomonas). Compared to the commercial fungicide, prochloraz, o-Cba was weakly toxic against various fungi (Zygo- and Ascomycota). It was also inferior to the commercial fungicide metalaxyl in inhibiting the vegetative growth of oomyceteous plant pathogens (Pythium irregulare, Phytophthora cryptogea and Plasmopara halstedii). Against the asexual spores of P. halstedii, o-Cba, however, was over a thousandfold more active than tridemorph, a selective zoospore inhibitor fungicide. For all taxonomic groups, the observed antimicrobial effect of o-Cba could be diminished with histidine, but not with phenylalanine. In studies on healthy and mildew-infected sunflower and tobacco plants o-Cba showed neither fungicidal nor phytotoxic effects at 500 ppm. This is the first report on the biological activity spectrum of a carborane-containing amino acid.
DOI: 10.1007/BF01361661
PubMed: 10707765
Affiliations:
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Ujváry</name></author><author><name sortKey="Nachman, R J" sort="Nachman, R J" uniqKey="Nachman R" first="R J" last="Nachman">R J Nachman</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="1999">1999</date><idno type="RBID">pubmed:10707765</idno><idno type="pmid">10707765</idno><idno type="doi">10.1007/BF01361661</idno><idno type="wicri:Area/Main/Corpus">002895</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Corpus" wicri:corpus="PubMed">002895</idno><idno type="wicri:Area/Main/Curation">002895</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Curation">002895</idno><idno type="wicri:Area/Main/Exploration">002895</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Antimicrobial activity of o-carboranylalanine.</title><author><name sortKey="Oros, G" sort="Oros, G" uniqKey="Oros G" first="G" last="Oros">G. 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However, our current knowledge on their effect in nonmammalian biological systems is limited. We investigated the activity spectrum in vitro of o-carboranylalanine (o-Cba), considered to be a highly lipophilic analog of phenylalanine, against representative plant pathogenic bacteria and fungi of various taxonomic position. The antibacterial effect of o-Cba against some species was comparable to that of the widely used agricultural antibiotic, streptomycin. The sensitivity of individual bacterial species to o-Cba within the same genus varied to a greater extent than the average sensitivity of various genera. In general, this carborane-containing amino acid was more toxic to Gram positive bacteria (Bacillus, Corynebacterium, Curtobacterium, Micrococcus, Rhodococcus, and Staphylococcus) than to Gram negative ones (Agrobacterium, Erwinia, Escherichia, Pseudomonas, Rhizobium, and Xanthomonas). Compared to the commercial fungicide, prochloraz, o-Cba was weakly toxic against various fungi (Zygo- and Ascomycota). It was also inferior to the commercial fungicide metalaxyl in inhibiting the vegetative growth of oomyceteous plant pathogens (Pythium irregulare, Phytophthora cryptogea and Plasmopara halstedii). Against the asexual spores of P. halstedii, o-Cba, however, was over a thousandfold more active than tridemorph, a selective zoospore inhibitor fungicide. For all taxonomic groups, the observed antimicrobial effect of o-Cba could be diminished with histidine, but not with phenylalanine. In studies on healthy and mildew-infected sunflower and tobacco plants o-Cba showed neither fungicidal nor phytotoxic effects at 500 ppm. This is the first report on the biological activity spectrum of a carborane-containing amino acid.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">10707765</PMID><DateCompleted><Year>2000</Year><Month>03</Month><Day>24</Day></DateCompleted><DateRevised><Year>2019</Year><Month>11</Month><Day>03</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0939-4451</ISSN><JournalIssue CitedMedium="Print"><Volume>17</Volume><Issue>4</Issue><PubDate><Year>1999</Year></PubDate></JournalIssue><Title>Amino acids</Title><ISOAbbreviation>Amino Acids</ISOAbbreviation></Journal><ArticleTitle>Antimicrobial activity of o-carboranylalanine.</ArticleTitle><Pagination><MedlinePgn>357-68</MedlinePgn></Pagination><Abstract><AbstractText>Functionalized polyhedral carboranes, including amino acid analogs, have unique physicochemical properties and are used as experimental anticancer agents. However, our current knowledge on their effect in nonmammalian biological systems is limited. We investigated the activity spectrum in vitro of o-carboranylalanine (o-Cba), considered to be a highly lipophilic analog of phenylalanine, against representative plant pathogenic bacteria and fungi of various taxonomic position. The antibacterial effect of o-Cba against some species was comparable to that of the widely used agricultural antibiotic, streptomycin. The sensitivity of individual bacterial species to o-Cba within the same genus varied to a greater extent than the average sensitivity of various genera. In general, this carborane-containing amino acid was more toxic to Gram positive bacteria (Bacillus, Corynebacterium, Curtobacterium, Micrococcus, Rhodococcus, and Staphylococcus) than to Gram negative ones (Agrobacterium, Erwinia, Escherichia, Pseudomonas, Rhizobium, and Xanthomonas). Compared to the commercial fungicide, prochloraz, o-Cba was weakly toxic against various fungi (Zygo- and Ascomycota). It was also inferior to the commercial fungicide metalaxyl in inhibiting the vegetative growth of oomyceteous plant pathogens (Pythium irregulare, Phytophthora cryptogea and Plasmopara halstedii). Against the asexual spores of P. halstedii, o-Cba, however, was over a thousandfold more active than tridemorph, a selective zoospore inhibitor fungicide. For all taxonomic groups, the observed antimicrobial effect of o-Cba could be diminished with histidine, but not with phenylalanine. In studies on healthy and mildew-infected sunflower and tobacco plants o-Cba showed neither fungicidal nor phytotoxic effects at 500 ppm. This is the first report on the biological activity spectrum of a carborane-containing amino acid.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Oros</LastName><ForeName>G</ForeName><Initials>G</Initials><AffiliationInfo><Affiliation>Plant Protection Institute, Hungarian Academy of Sciences, Budapest, Hungary. H10452ORO@helka.iif.hu</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ujváry</LastName><ForeName>I</ForeName><Initials>I</Initials></Author><Author ValidYN="Y"><LastName>Nachman</LastName><ForeName>R J</ForeName><Initials>RJ</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType><PublicationType UI="D013486">Research Support, U.S. Gov't, Non-P.H.S.</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>Austria</Country><MedlineTA>Amino Acids</MedlineTA><NlmUniqueID>9200312</NlmUniqueID><ISSNLinking>0939-4451</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000900">Anti-Bacterial Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000890">Anti-Infective Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001896">Boron Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>47E5O17Y3R</RegistryNumber><NameOfSubstance UI="D010649">Phenylalanine</NameOfSubstance></Chemical><Chemical><RegistryNumber>61216-60-2</RegistryNumber><NameOfSubstance UI="C014388">carboranylalanine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000900" MajorTopicYN="N">Anti-Bacterial Agents</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000890" MajorTopicYN="N">Anti-Infective Agents</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001896" MajorTopicYN="N">Boron Compounds</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005658" MajorTopicYN="N">Fungi</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006090" MajorTopicYN="N">Gram-Negative Bacteria</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006094" MajorTopicYN="N">Gram-Positive Bacteria</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010649" MajorTopicYN="N">Phenylalanine</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010944" MajorTopicYN="N">Plants</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2000</Year><Month>3</Month><Day>9</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2000</Year><Month>4</Month><Day>1</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2000</Year><Month>3</Month><Day>9</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">10707765</ArticleId><ArticleId IdType="doi">10.1007/BF01361661</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Hongrie</li></country><region><li>Hongrie centrale</li></region><settlement><li>Budapest</li></settlement></list><tree><noCountry><name sortKey="Nachman, R J" sort="Nachman, R J" uniqKey="Nachman R" first="R J" last="Nachman">R J Nachman</name><name sortKey="Ujvary, I" sort="Ujvary, I" uniqKey="Ujvary I" first="I" last="Ujváry">I. Ujváry</name></noCountry><country name="Hongrie"><region name="Hongrie centrale"><name sortKey="Oros, G" sort="Oros, G" uniqKey="Oros G" first="G" last="Oros">G. Oros</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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