7-Deazapurine and 8-Aza-7-deazapurine Nucleoside and Oligonucleotide Pyrene ``Click'' Conjugates: Synthesis, Nucleobase Controlled Fluorescence Quenching, and Duplex Stability
DC Element | Wert | Sprache |
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dc.contributor.author | Ingale, Sachin A. | |
dc.contributor.author | Pujari, Suresh S. | |
dc.contributor.author | Sirivolu, Venkata Ramana | |
dc.contributor.author | Ding, Ping | |
dc.contributor.author | Xiong, Hai | |
dc.contributor.author | Mei, Hui | |
dc.contributor.author | Seela, Frank | |
dc.date.accessioned | 2021-12-23T16:06:20Z | - |
dc.date.available | 2021-12-23T16:06:20Z | - |
dc.date.issued | 2012 | |
dc.identifier.issn | 00223263 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7365 | - |
dc.description.abstract | 7-Deazapurine and 8-aza-7-deazapurine nucleosides related to dA and dG bearing 7-octadiynyl or 7-tripropargylamine side chains as well as corresponding oligonucleotides were synthesized. ``Click'' conjugation with 1-azidomethyl pyrene (10) resulted in fluorescent derivatives. Octadiynyl conjugates show only monomer fluorescence, while the proximal alignment of pyrene residues in the tripropargylamine derivatives causes excimer emission. 8-Aza-7-deazapurine pyrene `click'' conjugates exhibit fluorescence emission much higher than that of 7-deazapurine derivatives. They are quenched by intramolecular charge transfer between the nucleobase and the dye. Oligonucleotide single strands decorated with two ``double clicked'' pyrenes show weak or no excimer fluorescence. However, when duplexes carry proximal pyrenes in complementary strands, strong excimer fluorescence is observed. A single replacement of a canonical nucleoside by a pyrene conjugate stabilizes the duplex substantially, most likely by stacking interactions: 6-12 degrees C for duplexes with a modified ``adenine'' base and 2-6 degrees C for a modified ``guanine'' base. The favorable photophysical properties of 8-aza-7-deazapurine pyrene conjugates improve the utility of pyrene fluorescence reporters in oligonucleotide sensing as these nucleoside conjugates are not affected by nucleobase induced quenching. | |
dc.description.sponsorship | ChemBiotech, Munster, Germany; We thank Mr. N. Q Tran for the oligonucleotide synthesis and Dr. R. Thiele from Roche Diagnostics, Penzberg for the measurement of the MALDI spectra. We thank Dr. S. Budow for her continuous support throughout the preparation of the manuscript and appreciate critical reading of the manuscript by Dr. P. Leonard. Financial support by ChemBiotech, Munster, Germany is gratefully acknowledged. | |
dc.language.iso | en | |
dc.publisher | AMER CHEMICAL SOC | |
dc.relation.ispartof | JOURNAL OF ORGANIC CHEMISTRY | |
dc.subject | AZIDE | |
dc.subject | BASE | |
dc.subject | BRANCHED SIDE-CHAINS | |
dc.subject | CHARGE-TRANSFER | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Organic | |
dc.subject | DNA OLIGOMERS | |
dc.subject | ELECTRON-TRANSFER | |
dc.subject | EXCIMER FLUORESCENCE | |
dc.subject | HYBRIDIZATION | |
dc.subject | INTERCALATING NUCLEIC-ACIDS | |
dc.subject | TERMINAL TRIPLE BONDS | |
dc.title | 7-Deazapurine and 8-Aza-7-deazapurine Nucleoside and Oligonucleotide Pyrene ``Click'' Conjugates: Synthesis, Nucleobase Controlled Fluorescence Quenching, and Duplex Stability | |
dc.type | journal article | |
dc.identifier.doi | 10.1021/jo202103q | |
dc.identifier.isi | ISI:000298827600015 | |
dc.description.volume | 77 | |
dc.description.issue | 1 | |
dc.description.startpage | 188 | |
dc.description.endpage | 199 | |
dc.contributor.orcid | 0000-0001-7350-0688 | |
dc.contributor.orcid | 0000-0002-8290-4729 | |
dc.contributor.orcid | 0000-0001-9065-4355 | |
dc.contributor.orcid | 0000-0002-5016-4041 | |
dc.contributor.orcid | 0000-0002-0246-3362 | |
dc.contributor.researcherid | AAL-1705-2020 | |
dc.contributor.researcherid | N-3854-2014 | |
dc.contributor.researcherid | N-9429-2015 | |
dc.identifier.eissn | 15206904 | |
dc.publisher.place | 1155 16TH ST, NW, WASHINGTON, DC 20036 USA | |
dcterms.isPartOf.abbreviation | J. Org. Chem. |
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geprüft am 03.06.2024