Ferrocenyl-modified DNA: synthesis, characterization and integration with semiconductor electrodes.
Identifieur interne : 002356 ( PubMed/Curation ); précédent : 002355; suivant : 002357Ferrocenyl-modified DNA: synthesis, characterization and integration with semiconductor electrodes.
Auteurs : Andrew R. Pike [Royaume-Uni] ; Lyndsey C. Ryder ; Benjamin R. Horrocks ; William Clegg ; Bernard A. Connolly ; Andrew HoultonSource :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 0947-6539 ] ; 2004.
Descripteurs français
- KwdFr :
- MESH :
- analogues et dérivés : Cytidine.
- synthèse chimique : ADN, Oligodésoxyribonucléotides.
- ADN, Composés du fer II, Modèles moléculaires, Oligodésoxyribonucléotides, Silice, Électricité statique, Électrochimie.
English descriptors
- KwdEn :
- MESH :
- chemical , analogs & derivatives : Cytidine.
- chemical , chemical synthesis : DNA, Oligodeoxyribonucleotides.
- chemical , chemistry : DNA, Oligodeoxyribonucleotides.
- Electrochemistry, Ferrous Compounds, Metallocenes, Models, Molecular, Silicon Dioxide, Static Electricity.
Abstract
The ferrocenyl-nucleoside, 5-ethynylferrocenyl-2'-deoxycytidine (1) has been prepared by Pd-catalyzed cross-coupling between ethynylferrocene and 5-iodo-2'-deoxycytidine and incorporated into oligonucleotides by using automated solid-phase synthesis at both silica supports (CPG) and modified single-crystal silicon electrodes. Analysis of DNA oligonucleotides prepared and cleaved from conventional solid supports confirms that the ferrocenyl-nucleoside remains intact during synthesis and deprotection and that the resulting strands may be oxidised and reduced in a chemically reversible manner. Melting curve data show that the ferrocenyl-modified oligonucleotides form duplex structures with native complementary strands. The redox potential of fully solvated ferrocenyl 12-mers, 350 mV versus SCE, was shifted by +40 mV to a more positive potential upon treatment with the complement contrary to the anticipated negative shift based on a simple electrostatic basis. Automated solid-phase methods were also used to synthesise 12-mer ferrocenyl-containing oligonucleotides directly at chemically modified silicon <111> electrodes. Hybridisation to the surface-bound ferrocenyl-DNA caused a shift in the reduction potential of +34 mV to more positive values, indicating that, even when a ferrocenyl nucleoside is contained in a film, the increased density of anions from the phosphate backbone of the complement is still dominated by other factors, for example, the hydrophobic environment of the ferrocene moiety in the duplex or changes in the ferrocene-phosphate distances. The reduction potential is shifted >100 mV after hybridisation when the aqueous electrolyte is replaced by THF/LiClO(4), a solvent of much lower dielectric constant; this is consistent with an explanation based on conformation-induced changes in ferrocene-phosphate distances.
DOI: 10.1002/chem.200400632
PubMed: 15551318
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Ryder</name></author><author><name sortKey="Horrocks, Benjamin R" sort="Horrocks, Benjamin R" uniqKey="Horrocks B" first="Benjamin R" last="Horrocks">Benjamin R. Horrocks</name></author><author><name sortKey="Clegg, William" sort="Clegg, William" uniqKey="Clegg W" first="William" last="Clegg">William Clegg</name></author><author><name sortKey="Connolly, Bernard A" sort="Connolly, Bernard A" uniqKey="Connolly B" first="Bernard A" last="Connolly">Bernard A. Connolly</name></author><author><name sortKey="Houlton, Andrew" sort="Houlton, Andrew" uniqKey="Houlton A" first="Andrew" last="Houlton">Andrew Houlton</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2004">2004</date><idno type="RBID">pubmed:15551318</idno><idno type="pmid">15551318</idno><idno type="doi">10.1002/chem.200400632</idno><idno type="wicri:Area/PubMed/Corpus">002356</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002356</idno><idno type="wicri:Area/PubMed/Curation">002356</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">002356</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Ferrocenyl-modified DNA: synthesis, characterization and integration with semiconductor electrodes.</title><author><name sortKey="Pike, Andrew R" sort="Pike, Andrew R" uniqKey="Pike A" first="Andrew R" last="Pike">Andrew R. Pike</name><affiliation wicri:level="1"><nlm:affiliation>Chemistry Laboratories, School of Natural Sciences Bedson Building, University of Newcastle upon Tyne, Newcastle upon Tyne, NE1 7RU, UK.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Chemistry Laboratories, School of Natural Sciences Bedson Building, University of Newcastle upon Tyne, Newcastle upon Tyne, NE1 7RU</wicri:regionArea></affiliation></author><author><name sortKey="Ryder, Lyndsey C" sort="Ryder, Lyndsey C" uniqKey="Ryder L" first="Lyndsey C" last="Ryder">Lyndsey C. Ryder</name></author><author><name sortKey="Horrocks, Benjamin R" sort="Horrocks, Benjamin R" uniqKey="Horrocks B" first="Benjamin R" last="Horrocks">Benjamin R. Horrocks</name></author><author><name sortKey="Clegg, William" sort="Clegg, William" uniqKey="Clegg W" first="William" last="Clegg">William Clegg</name></author><author><name sortKey="Connolly, Bernard A" sort="Connolly, Bernard A" uniqKey="Connolly B" first="Bernard A" last="Connolly">Bernard A. Connolly</name></author><author><name sortKey="Houlton, Andrew" sort="Houlton, Andrew" uniqKey="Houlton A" first="Andrew" last="Houlton">Andrew Houlton</name></author></analytic><series><title level="j">Chemistry (Weinheim an der Bergstrasse, Germany)</title><idno type="ISSN">0947-6539</idno><imprint><date when="2004" type="published">2004</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Cytidine (analogs & derivatives)</term><term>DNA (chemical synthesis)</term><term>DNA (chemistry)</term><term>Electrochemistry</term><term>Ferrous Compounds</term><term>Metallocenes</term><term>Models, Molecular</term><term>Oligodeoxyribonucleotides (chemical synthesis)</term><term>Oligodeoxyribonucleotides (chemistry)</term><term>Silicon Dioxide</term><term>Static Electricity</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN ()</term><term>ADN (synthèse chimique)</term><term>Composés du fer II</term><term>Cytidine (analogues et dérivés)</term><term>Modèles moléculaires</term><term>Oligodésoxyribonucléotides ()</term><term>Oligodésoxyribonucléotides (synthèse chimique)</term><term>Silice</term><term>Électricité statique</term><term>Électrochimie</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Cytidine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>DNA</term><term>Oligodeoxyribonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>DNA</term><term>Oligodeoxyribonucleotides</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Cytidine</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>ADN</term><term>Oligodésoxyribonucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Electrochemistry</term><term>Ferrous Compounds</term><term>Metallocenes</term><term>Models, Molecular</term><term>Silicon Dioxide</term><term>Static Electricity</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ADN</term><term>Composés du fer II</term><term>Modèles moléculaires</term><term>Oligodésoxyribonucléotides</term><term>Silice</term><term>Électricité statique</term><term>Électrochimie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The ferrocenyl-nucleoside, 5-ethynylferrocenyl-2'-deoxycytidine (1) has been prepared by Pd-catalyzed cross-coupling between ethynylferrocene and 5-iodo-2'-deoxycytidine and incorporated into oligonucleotides by using automated solid-phase synthesis at both silica supports (CPG) and modified single-crystal silicon electrodes. Analysis of DNA oligonucleotides prepared and cleaved from conventional solid supports confirms that the ferrocenyl-nucleoside remains intact during synthesis and deprotection and that the resulting strands may be oxidised and reduced in a chemically reversible manner. Melting curve data show that the ferrocenyl-modified oligonucleotides form duplex structures with native complementary strands. The redox potential of fully solvated ferrocenyl 12-mers, 350 mV versus SCE, was shifted by +40 mV to a more positive potential upon treatment with the complement contrary to the anticipated negative shift based on a simple electrostatic basis. Automated solid-phase methods were also used to synthesise 12-mer ferrocenyl-containing oligonucleotides directly at chemically modified silicon <111> electrodes. Hybridisation to the surface-bound ferrocenyl-DNA caused a shift in the reduction potential of +34 mV to more positive values, indicating that, even when a ferrocenyl nucleoside is contained in a film, the increased density of anions from the phosphate backbone of the complement is still dominated by other factors, for example, the hydrophobic environment of the ferrocene moiety in the duplex or changes in the ferrocene-phosphate distances. The reduction potential is shifted >100 mV after hybridisation when the aqueous electrolyte is replaced by THF/LiClO(4), a solvent of much lower dielectric constant; this is consistent with an explanation based on conformation-induced changes in ferrocene-phosphate distances.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">15551318</PMID><DateCompleted><Year>2006</Year><Month>07</Month><Day>19</Day></DateCompleted><DateRevised><Year>2017</Year><Month>11</Month><Day>16</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0947-6539</ISSN><JournalIssue CitedMedium="Print"><Volume>11</Volume><Issue>1</Issue><PubDate><Year>2004</Year><Month>Dec</Month><Day>17</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Ferrocenyl-modified DNA: synthesis, characterization and integration with semiconductor electrodes.</ArticleTitle><Pagination><MedlinePgn>344-53</MedlinePgn></Pagination><Abstract><AbstractText>The ferrocenyl-nucleoside, 5-ethynylferrocenyl-2'-deoxycytidine (1) has been prepared by Pd-catalyzed cross-coupling between ethynylferrocene and 5-iodo-2'-deoxycytidine and incorporated into oligonucleotides by using automated solid-phase synthesis at both silica supports (CPG) and modified single-crystal silicon electrodes. Analysis of DNA oligonucleotides prepared and cleaved from conventional solid supports confirms that the ferrocenyl-nucleoside remains intact during synthesis and deprotection and that the resulting strands may be oxidised and reduced in a chemically reversible manner. Melting curve data show that the ferrocenyl-modified oligonucleotides form duplex structures with native complementary strands. The redox potential of fully solvated ferrocenyl 12-mers, 350 mV versus SCE, was shifted by +40 mV to a more positive potential upon treatment with the complement contrary to the anticipated negative shift based on a simple electrostatic basis. Automated solid-phase methods were also used to synthesise 12-mer ferrocenyl-containing oligonucleotides directly at chemically modified silicon <111> electrodes. Hybridisation to the surface-bound ferrocenyl-DNA caused a shift in the reduction potential of +34 mV to more positive values, indicating that, even when a ferrocenyl nucleoside is contained in a film, the increased density of anions from the phosphate backbone of the complement is still dominated by other factors, for example, the hydrophobic environment of the ferrocene moiety in the duplex or changes in the ferrocene-phosphate distances. The reduction potential is shifted >100 mV after hybridisation when the aqueous electrolyte is replaced by THF/LiClO(4), a solvent of much lower dielectric constant; this is consistent with an explanation based on conformation-induced changes in ferrocene-phosphate distances.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Pike</LastName><ForeName>Andrew R</ForeName><Initials>AR</Initials><AffiliationInfo><Affiliation>Chemistry Laboratories, School of Natural Sciences Bedson Building, University of Newcastle upon Tyne, Newcastle upon Tyne, NE1 7RU, UK.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ryder</LastName><ForeName>Lyndsey C</ForeName><Initials>LC</Initials></Author><Author ValidYN="Y"><LastName>Horrocks</LastName><ForeName>Benjamin R</ForeName><Initials>BR</Initials></Author><Author ValidYN="Y"><LastName>Clegg</LastName><ForeName>William</ForeName><Initials>W</Initials></Author><Author ValidYN="Y"><LastName>Connolly</LastName><ForeName>Bernard A</ForeName><Initials>BA</Initials></Author><Author ValidYN="Y"><LastName>Houlton</LastName><ForeName>Andrew</ForeName><Initials>A</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005296">Ferrous Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000075163">Metallocenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009838">Oligodeoxyribonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>5CSZ8459RP</RegistryNumber><NameOfSubstance UI="D003562">Cytidine</NameOfSubstance></Chemical><Chemical><RegistryNumber>7631-86-9</RegistryNumber><NameOfSubstance UI="D012822">Silicon Dioxide</NameOfSubstance></Chemical><Chemical><RegistryNumber>9007-49-2</RegistryNumber><NameOfSubstance UI="D004247">DNA</NameOfSubstance></Chemical><Chemical><RegistryNumber>U96PKG90JQ</RegistryNumber><NameOfSubstance UI="C004998">ferrocene</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D003562" MajorTopicYN="N">Cytidine</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="N">analogs & derivatives</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004247" MajorTopicYN="N">DNA</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004563" MajorTopicYN="N">Electrochemistry</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005296" MajorTopicYN="Y">Ferrous Compounds</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000075163" MajorTopicYN="N">Metallocenes</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009838" MajorTopicYN="N">Oligodeoxyribonucleotides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012822" MajorTopicYN="N">Silicon Dioxide</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D055672" MajorTopicYN="N">Static Electricity</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2004</Year><Month>11</Month><Day>20</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2006</Year><Month>7</Month><Day>20</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2004</Year><Month>11</Month><Day>20</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">15551318</ArticleId><ArticleId IdType="doi">10.1002/chem.200400632</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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