Terminal lipophilization of a unique DNA dodecamer by various nucleolipid headgroups: Their incorporation into artificial lipid bilayers and hydrodynamic properties

DC FieldValueLanguage
dc.contributor.authorWerz, Emma
dc.contributor.authorRosemeyer, Helmut
dc.date.accessioned2021-12-23T16:05:32Z-
dc.date.available2021-12-23T16:05:32Z-
dc.date.issued2015
dc.identifier.issn18605397
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7060-
dc.description.abstractA series of six cyanine-5-labeled oligonucleotides (LONs 10-15), each terminally lipophilized with different nucleolipid head groups, were synthesized using the recently prepared phosphoramidites 4b-9b. The insertion of the LONs within an artificial lipid bilayer, composed of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (POPE), was studied by single molecule fluorescence spectroscopy and microscopy with the help of an optically transparent microfluidic sample carrier with perfusion capabilities. The incorporation of the lipo-oligonucleotides into the bilayer was studied with respect to efficiency (maximal bilayer brightness) as well as stability against perfusion (final stable bilayer brightness). Attempts to correlate these parameters with the log P values of the corresponding nucleolipid head groups failed, a result which clearly demonstrates that not only the lipophilicity but mainly the chemical structure and topology of the head group is of decisive importance for the optimal interaction of a lipo-oligonucleotide with an artificial lipid bilayer. Moreover, fluorescence half-live and diffusion time values were measured to determine the diffusion coefficients of the lipo-oligonucleotides.
dc.language.isoen
dc.publisherBEILSTEIN-INSTITUT
dc.relation.ispartofBEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
dc.subject5-FLUOROURIDINE
dc.subjectBIOMIMETIC LIPOPHILIZATION
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectDEOXYRIBONUCLEIC-ACID
dc.subjectDUPLEX FORMATION
dc.subjectFLUOROPHORES
dc.subjectFUNCTIONALIZATION
dc.subjectlipid bilayer
dc.subjectlipo-oligonucleotides
dc.subjectMEMBRANES
dc.subjectnucleic acids
dc.subjectNUCLEIC-ACIDS
dc.subjectnucleolipids
dc.subjectOLIGONUCLEOTIDES
dc.subjectSPECTROSCOPY
dc.titleTerminal lipophilization of a unique DNA dodecamer by various nucleolipid headgroups: Their incorporation into artificial lipid bilayers and hydrodynamic properties
dc.typejournal article
dc.identifier.doi10.3762/bjoc.11.103
dc.identifier.isiISI:000355504400001
dc.description.volume11
dc.description.startpage913
dc.description.endpage929
dc.publisher.placeTRAKEHNER STRASSE 7-9, FRANKFURT AM MAIN, 60487, GERMANY
dcterms.isPartOf.abbreviationBeilstein J. Org. Chem.
dcterms.oaStatusGreen Published, gold, Green Submitted
crisitem.author.deptInstitut für Chemie neuer Materialien-
crisitem.author.deptidinstitute11-
crisitem.author.parentorgFB 05 - Biologie/Chemie-
crisitem.author.grandparentorgUniversität Osnabrück-
crisitem.author.netidRoHe783-
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