Interactions of oligonucleotide analogs containing methylphosphonate internucleotide linkages and 2'-O-methylribonucleosides.
Identifieur interne : 002886 ( Ncbi/Merge ); précédent : 002885; suivant : 002887Interactions of oligonucleotide analogs containing methylphosphonate internucleotide linkages and 2'-O-methylribonucleosides.
Auteurs : J M Kean [États-Unis] ; C D Cushman ; H. Kang ; T E Leonard ; P S MillerSource :
- Nucleic acids research [ 0305-1048 ] ; 1994.
Descripteurs français
- KwdFr :
- ADN (), ARN (), Adénosine (), Adénosine (analogues et dérivés), Composés organiques du phosphore (), Données de séquences moléculaires, Guanosine (), Guanosine (analogues et dérivés), Oligonucléotides (), Stabilité de médicament, Structures macromoléculaires, Stéréoisomérie, Séquence nucléotidique, Température.
- MESH :
English descriptors
- KwdEn :
- Adenosine (analogs & derivatives), Adenosine (chemistry), Base Sequence, DNA (chemistry), Drug Stability, Guanosine (analogs & derivatives), Guanosine (chemistry), Macromolecular Substances, Molecular Sequence Data, Oligonucleotides (chemistry), Organophosphorus Compounds (chemistry), RNA (chemistry), Stereoisomerism, Temperature.
- MESH :
- chemical , analogs & derivatives : Adenosine, Guanosine.
- chemical , chemistry : Adenosine, DNA, Guanosine, Oligonucleotides, Organophosphorus Compounds, RNA.
- Base Sequence, Drug Stability, Macromolecular Substances, Molecular Sequence Data, Stereoisomerism, Temperature.
Abstract
The interactions of oligonucleotide analogs, 12-mers, which contain deoxyribo- or 2'-O-methylribose sugars and methylphosphonate internucleotide linkages with complementary 12-mer DNA and RNA targets and the effect of chirality of the methylphosphonate linkage on oligomer-target interactions was studied. Oligomers containing a single Rp or Sp methylphosphonate linkage (type 1) or oligomers containing a single phosphodiester linkage at the 5'-end followed by 10 contiguous methylphosphonate linkages of random chirality (type 2) were prepared. The deoxyribo- and 2'-O-methylribo- type 1 12-mers formed stable duplexes with both the RNA and DNA as determined by UV melting experiments. The melting temperatures, Tms, of the 2'-O-methylribo-12-mer/RNA duplexes (49-53 degrees C) were higher than those of the deoxyribo-12mer/RNA duplexes (31-36 degrees C). The Tms of the duplexes formed by the Rp isomers of these oligomers were approximately 3-5 degrees C higher than those formed by the corresponding Sp isomers. The deoxyribo type 2 12-mer formed a stable duplex, Tm 34 degrees C, with the DNA target and a much less stable duplex with the RNA target, Tm < 5 degrees C. In contrast, the 2'-O-methylribo type 2 12-mer formed a stable duplex with the RNA target, Tm 20 degrees C, and a duplex of lower stability with the DNA target, Tm < 5 degrees C. These results show that the previously observed greater stability of oligo-2'-O-methylribonucleotide/RNA duplexes versus oligodeoxyribonucleotide/RNA duplexes extends to oligomers containing methylphosphonate linkages and that the configuration of the methylphosphonate linkage strongly influences the stability of the duplexes.
DOI: 10.1093/nar/22.21.4497
PubMed: 7526343
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Interactions of oligonucleotide analogs containing methylphosphonate internucleotide linkages and 2'-O-methylribonucleosides.</title><author><name sortKey="Kean, J M" sort="Kean, J M" uniqKey="Kean J" first="J M" last="Kean">J M Kean</name><affiliation wicri:level="2"><nlm:affiliation>Department of Biochemistry, School of Hygiene and Public Health, Johns Hopkins University, Baltimore, MD 21205.</nlm:affiliation><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Biochemistry, School of Hygiene and Public Health, Johns Hopkins University, Baltimore</wicri:cityArea></affiliation></author><author><name sortKey="Cushman, C D" sort="Cushman, C D" uniqKey="Cushman C" first="C D" last="Cushman">C D Cushman</name></author><author><name sortKey="Kang, H" sort="Kang, H" uniqKey="Kang H" first="H" last="Kang">H. Kang</name></author><author><name sortKey="Leonard, T E" sort="Leonard, T E" uniqKey="Leonard T" first="T E" last="Leonard">T E Leonard</name></author><author><name sortKey="Miller, P S" sort="Miller, P S" uniqKey="Miller P" first="P S" last="Miller">P S Miller</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="1994">1994</date><idno type="RBID">pubmed:7526343</idno><idno type="pmid">7526343</idno><idno type="doi">10.1093/nar/22.21.4497</idno><idno type="wicri:Area/PubMed/Corpus">002856</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002856</idno><idno type="wicri:Area/PubMed/Curation">002856</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">002856</idno><idno type="wicri:Area/PubMed/Checkpoint">002728</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">002728</idno><idno type="wicri:Area/Ncbi/Merge">002886</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Interactions of oligonucleotide analogs containing methylphosphonate internucleotide linkages and 2'-O-methylribonucleosides.</title><author><name sortKey="Kean, J M" sort="Kean, J M" uniqKey="Kean J" first="J M" last="Kean">J M Kean</name><affiliation wicri:level="2"><nlm:affiliation>Department of Biochemistry, School of Hygiene and Public Health, Johns Hopkins University, Baltimore, MD 21205.</nlm:affiliation><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Biochemistry, School of Hygiene and Public Health, Johns Hopkins University, Baltimore</wicri:cityArea></affiliation></author><author><name sortKey="Cushman, C D" sort="Cushman, C D" uniqKey="Cushman C" first="C D" last="Cushman">C D Cushman</name></author><author><name sortKey="Kang, H" sort="Kang, H" uniqKey="Kang H" first="H" last="Kang">H. Kang</name></author><author><name sortKey="Leonard, T E" sort="Leonard, T E" uniqKey="Leonard T" first="T E" last="Leonard">T E Leonard</name></author><author><name sortKey="Miller, P S" sort="Miller, P S" uniqKey="Miller P" first="P S" last="Miller">P S Miller</name></author></analytic><series><title level="j">Nucleic acids research</title><idno type="ISSN">0305-1048</idno><imprint><date when="1994" type="published">1994</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Adenosine (analogs & derivatives)</term><term>Adenosine (chemistry)</term><term>Base Sequence</term><term>DNA (chemistry)</term><term>Drug Stability</term><term>Guanosine (analogs & derivatives)</term><term>Guanosine (chemistry)</term><term>Macromolecular Substances</term><term>Molecular Sequence Data</term><term>Oligonucleotides (chemistry)</term><term>Organophosphorus Compounds (chemistry)</term><term>RNA (chemistry)</term><term>Stereoisomerism</term><term>Temperature</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN ()</term><term>ARN ()</term><term>Adénosine ()</term><term>Adénosine (analogues et dérivés)</term><term>Composés organiques du phosphore ()</term><term>Données de séquences moléculaires</term><term>Guanosine ()</term><term>Guanosine (analogues et dérivés)</term><term>Oligonucléotides ()</term><term>Stabilité de médicament</term><term>Structures macromoléculaires</term><term>Stéréoisomérie</term><term>Séquence nucléotidique</term><term>Température</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Adenosine</term><term>Guanosine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Adenosine</term><term>DNA</term><term>Guanosine</term><term>Oligonucleotides</term><term>Organophosphorus Compounds</term><term>RNA</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Adénosine</term><term>Guanosine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Drug Stability</term><term>Macromolecular Substances</term><term>Molecular Sequence Data</term><term>Stereoisomerism</term><term>Temperature</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ADN</term><term>ARN</term><term>Adénosine</term><term>Composés organiques du phosphore</term><term>Données de séquences moléculaires</term><term>Guanosine</term><term>Oligonucléotides</term><term>Stabilité de médicament</term><term>Structures macromoléculaires</term><term>Stéréoisomérie</term><term>Séquence nucléotidique</term><term>Température</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The interactions of oligonucleotide analogs, 12-mers, which contain deoxyribo- or 2'-O-methylribose sugars and methylphosphonate internucleotide linkages with complementary 12-mer DNA and RNA targets and the effect of chirality of the methylphosphonate linkage on oligomer-target interactions was studied. Oligomers containing a single Rp or Sp methylphosphonate linkage (type 1) or oligomers containing a single phosphodiester linkage at the 5'-end followed by 10 contiguous methylphosphonate linkages of random chirality (type 2) were prepared. The deoxyribo- and 2'-O-methylribo- type 1 12-mers formed stable duplexes with both the RNA and DNA as determined by UV melting experiments. The melting temperatures, Tms, of the 2'-O-methylribo-12-mer/RNA duplexes (49-53 degrees C) were higher than those of the deoxyribo-12mer/RNA duplexes (31-36 degrees C). The Tms of the duplexes formed by the Rp isomers of these oligomers were approximately 3-5 degrees C higher than those formed by the corresponding Sp isomers. The deoxyribo type 2 12-mer formed a stable duplex, Tm 34 degrees C, with the DNA target and a much less stable duplex with the RNA target, Tm < 5 degrees C. In contrast, the 2'-O-methylribo type 2 12-mer formed a stable duplex with the RNA target, Tm 20 degrees C, and a duplex of lower stability with the DNA target, Tm < 5 degrees C. These results show that the previously observed greater stability of oligo-2'-O-methylribonucleotide/RNA duplexes versus oligodeoxyribonucleotide/RNA duplexes extends to oligomers containing methylphosphonate linkages and that the configuration of the methylphosphonate linkage strongly influences the stability of the duplexes.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">7526343</PMID><DateCompleted><Year>1994</Year><Month>12</Month><Day>19</Day></DateCompleted><DateRevised><Year>2019</Year><Month>05</Month><Day>01</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0305-1048</ISSN><JournalIssue CitedMedium="Print"><Volume>22</Volume><Issue>21</Issue><PubDate><Year>1994</Year><Month>Oct</Month><Day>25</Day></PubDate></JournalIssue><Title>Nucleic acids research</Title><ISOAbbreviation>Nucleic Acids Res.</ISOAbbreviation></Journal><ArticleTitle>Interactions of oligonucleotide analogs containing methylphosphonate internucleotide linkages and 2'-O-methylribonucleosides.</ArticleTitle><Pagination><MedlinePgn>4497-503</MedlinePgn></Pagination><Abstract><AbstractText>The interactions of oligonucleotide analogs, 12-mers, which contain deoxyribo- or 2'-O-methylribose sugars and methylphosphonate internucleotide linkages with complementary 12-mer DNA and RNA targets and the effect of chirality of the methylphosphonate linkage on oligomer-target interactions was studied. Oligomers containing a single Rp or Sp methylphosphonate linkage (type 1) or oligomers containing a single phosphodiester linkage at the 5'-end followed by 10 contiguous methylphosphonate linkages of random chirality (type 2) were prepared. The deoxyribo- and 2'-O-methylribo- type 1 12-mers formed stable duplexes with both the RNA and DNA as determined by UV melting experiments. The melting temperatures, Tms, of the 2'-O-methylribo-12-mer/RNA duplexes (49-53 degrees C) were higher than those of the deoxyribo-12mer/RNA duplexes (31-36 degrees C). The Tms of the duplexes formed by the Rp isomers of these oligomers were approximately 3-5 degrees C higher than those formed by the corresponding Sp isomers. The deoxyribo type 2 12-mer formed a stable duplex, Tm 34 degrees C, with the DNA target and a much less stable duplex with the RNA target, Tm < 5 degrees C. In contrast, the 2'-O-methylribo type 2 12-mer formed a stable duplex with the RNA target, Tm 20 degrees C, and a duplex of lower stability with the DNA target, Tm < 5 degrees C. These results show that the previously observed greater stability of oligo-2'-O-methylribonucleotide/RNA duplexes versus oligodeoxyribonucleotide/RNA duplexes extends to oligomers containing methylphosphonate linkages and that the configuration of the methylphosphonate linkage strongly influences the stability of the duplexes.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kean</LastName><ForeName>J M</ForeName><Initials>JM</Initials><AffiliationInfo><Affiliation>Department of Biochemistry, School of Hygiene and Public Health, Johns Hopkins University, Baltimore, MD 21205.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cushman</LastName><ForeName>C D</ForeName><Initials>CD</Initials></Author><Author ValidYN="Y"><LastName>Kang</LastName><ForeName>H</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Leonard</LastName><ForeName>T E</ForeName><Initials>TE</Initials></Author><Author ValidYN="Y"><LastName>Miller</LastName><ForeName>P S</ForeName><Initials>PS</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>CA42762</GrantID><Acronym>CA</Acronym><Agency>NCI NIH HHS</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013487">Research Support, U.S. Gov't, P.H.S.</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Nucleic Acids Res</MedlineTA><NlmUniqueID>0411011</NlmUniqueID><ISSNLinking>0305-1048</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D046911">Macromolecular Substances</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009841">Oligonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009943">Organophosphorus Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>02YX82IHZ5</RegistryNumber><NameOfSubstance UI="C024341">2'-O-methyladenosine</NameOfSubstance></Chemical><Chemical><RegistryNumber>12133JR80S</RegistryNumber><NameOfSubstance UI="D006151">Guanosine</NameOfSubstance></Chemical><Chemical><RegistryNumber>329W4YM10Z</RegistryNumber><NameOfSubstance UI="C032627">methylphosphonic acid</NameOfSubstance></Chemical><Chemical><RegistryNumber>63231-63-0</RegistryNumber><NameOfSubstance UI="D012313">RNA</NameOfSubstance></Chemical><Chemical><RegistryNumber>9007-49-2</RegistryNumber><NameOfSubstance UI="D004247">DNA</NameOfSubstance></Chemical><Chemical><RegistryNumber>K72T3FS567</RegistryNumber><NameOfSubstance UI="D000241">Adenosine</NameOfSubstance></Chemical><Chemical><RegistryNumber>W722H4PA1S</RegistryNumber><NameOfSubstance UI="C024900">2'-O-methylguanosine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000241" MajorTopicYN="N">Adenosine</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001483" MajorTopicYN="N">Base Sequence</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004247" MajorTopicYN="N">DNA</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004355" MajorTopicYN="N">Drug Stability</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006151" MajorTopicYN="N">Guanosine</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D046911" MajorTopicYN="N">Macromolecular Substances</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008969" MajorTopicYN="N">Molecular Sequence Data</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009841" MajorTopicYN="N">Oligonucleotides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009943" MajorTopicYN="N">Organophosphorus Compounds</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012313" MajorTopicYN="N">RNA</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013696" MajorTopicYN="N">Temperature</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>1994</Year><Month>10</Month><Day>25</Day></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>1994</Year><Month>10</Month><Day>25</Day><Hour>0</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>1994</Year><Month>10</Month><Day>25</Day><Hour>0</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">7526343</ArticleId><ArticleId IdType="pmc">PMC308485</ArticleId><ArticleId IdType="doi">10.1093/nar/22.21.4497</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>Biochemistry. 1979 Nov 13;18(23):5134-43</Citation><ArticleIdList><ArticleId IdType="pubmed">497173</ArticleId></ArticleIdList></Reference><Reference><Citation>Nucleic Acids Res. 1993 Dec 25;21(25):5957-63</Citation><ArticleIdList><ArticleId 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Kang</name><name sortKey="Leonard, T E" sort="Leonard, T E" uniqKey="Leonard T" first="T E" last="Leonard">T E Leonard</name><name sortKey="Miller, P S" sort="Miller, P S" uniqKey="Miller P" first="P S" last="Miller">P S Miller</name></noCountry><country name="États-Unis"><region name="Maryland"><name sortKey="Kean, J M" sort="Kean, J M" uniqKey="Kean J" first="J M" last="Kean">J M Kean</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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