{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Dumas A"],"funding":["Swiss National Science Foundation"],"pagination":["6825-34"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC3159459"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["39(15)"],"pubmed_abstract":["Guanosines with substituents at the 8-position can provide useful fluorescent probes that effectively mimic guanine residues even in highly demanding model systems such as polymorphic G-quadruplexes and duplex DNA. Here, we report the synthesis and photophysical properties of a small family of 8-substituted-2'-deoxyguanosines that have been incorporated into the human telomeric repeat sequence using phosphoramidite chemistry. These include 8-(2-pyridyl)-2'-deoxyguanosine (2PyG), 8-(2-phenylethenyl)-2'-deoxyguanosine (StG) and 8-[2-(pyrid-4-yl)-ethenyl]-2'-deoxyguanosine (4PVG). On DNA folding and stability, 8-substituted guanosines can exhibit context-dependent effects but were better tolerated by G-quadruplex and duplex structures than pyrimidine mismatches. In contrast to previously reported fluorescent guanine analogs, 8-substituted guanosines exhibit similar or even higher quantum yields upon their incorporation into nucleic acids (Φ = 0.02-0.45). We have used these highly emissive probes to quantify energy transfer efficiencies from unmodified DNA nucleobases to 8-substituted guanosines. The resulting DNA-to-probe energy transfer efficiencies (η(t)) are highly structure selective, with η(t)(duplex) < η(t)(single-strand) < η(t)(G-quadruplex). These trends were independent of the exact structural features and thermal stabilities of the G-quadruplexes or duplexes containing them. The combination of efficient energy transfer, high probe quantum yield, and high molar extinction coefficient of the DNA provides a highly sensitive and reliable readout of G-quadruplex formation even in highly diluted sample solutions of 0.25 nM."],"journal":["Nucleic acids research"],"pubmed_title":["Highly fluorescent guanosine mimics for folding and energy transfer studies."],"pmcid":["PMC3159459"],"funding_grant_id":["130074"],"pubmed_authors":["Dumas A","Luedtke NW"],"additional_accession":[]},"is_claimable":false,"name":"Highly fluorescent guanosine mimics for folding and energy transfer studies.","description":"Guanosines with substituents at the 8-position can provide useful fluorescent probes that effectively mimic guanine residues even in highly demanding model systems such as polymorphic G-quadruplexes and duplex DNA. Here, we report the synthesis and photophysical properties of a small family of 8-substituted-2'-deoxyguanosines that have been incorporated into the human telomeric repeat sequence using phosphoramidite chemistry. These include 8-(2-pyridyl)-2'-deoxyguanosine (2PyG), 8-(2-phenylethenyl)-2'-deoxyguanosine (StG) and 8-[2-(pyrid-4-yl)-ethenyl]-2'-deoxyguanosine (4PVG). On DNA folding and stability, 8-substituted guanosines can exhibit context-dependent effects but were better tolerated by G-quadruplex and duplex structures than pyrimidine mismatches. In contrast to previously reported fluorescent guanine analogs, 8-substituted guanosines exhibit similar or even higher quantum yields upon their incorporation into nucleic acids (Φ = 0.02-0.45). We have used these highly emissive probes to quantify energy transfer efficiencies from unmodified DNA nucleobases to 8-substituted guanosines. The resulting DNA-to-probe energy transfer efficiencies (η(t)) are highly structure selective, with η(t)(duplex) < η(t)(single-strand) < η(t)(G-quadruplex). These trends were independent of the exact structural features and thermal stabilities of the G-quadruplexes or duplexes containing them. The combination of efficient energy transfer, high probe quantum yield, and high molar extinction coefficient of the DNA provides a highly sensitive and reliable readout of G-quadruplex formation even in highly diluted sample solutions of 0.25 nM.","dates":{"release":"2011-01-01T00:00:00Z","publication":"2011 Aug","modification":"2024-11-15T16:08:10.463Z","creation":"2019-03-27T00:43:11Z"},"accession":"S-EPMC3159459","cross_references":{"pubmed":["21551219"],"doi":["10.1093/nar/gkr281"]}}