Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA
Efficient protocols based on Cu(I)-catalyzed azide–alkyne cycloaddition were developed for the synthesis of conjugates of pyrrole–imidazole polyamide minor groove binders (MGB) with fluorophores and with triplex-forming oligonucleotides (TFOs). Diverse bifunctional linkers were synthesized and used...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2016-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.12.128 |
| _version_ | 1818941125879136256 |
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| author | Svetlana V. Vasilyeva Vyacheslav V. Filichev Alexandre S. Boutorine |
| author_facet | Svetlana V. Vasilyeva Vyacheslav V. Filichev Alexandre S. Boutorine |
| author_sort | Svetlana V. Vasilyeva |
| collection | DOAJ |
| description | Efficient protocols based on Cu(I)-catalyzed azide–alkyne cycloaddition were developed for the synthesis of conjugates of pyrrole–imidazole polyamide minor groove binders (MGB) with fluorophores and with triplex-forming oligonucleotides (TFOs). Diverse bifunctional linkers were synthesized and used for the insertion of terminal azides or alkynes into TFOs and MGBs. The formation of stable triple helices by TFO-MGB conjugates was evaluated by gel-shift experiments. The presence of MGB in these conjugates did not affect the binding parameters (affinity and triplex stability) of the parent TFOs. |
| first_indexed | 2024-12-20T06:50:34Z |
| format | Article |
| id | doaj.art-a19f47fd4162467babbf58432d0c792f |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T06:50:34Z |
| publishDate | 2016-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-a19f47fd4162467babbf58432d0c792f2022-12-21T19:49:32ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-06-011211348136010.3762/bjoc.12.1281860-5397-12-128Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNASvetlana V. Vasilyeva0Vyacheslav V. Filichev1Alexandre S. Boutorine2Institute of Chemical Biology & Fundamental Medicine, SB of RAS, pr. Lavrent’eva 8, 630090 Novosibirsk, RussiaInstitute of Fundamental Sciences, Massey University, Private Bag 11-222, 4442 Palmerston North, New ZealandStructure and Instability of Genomes, Sorbonne Universités, Muséum National d'Histoire Naturelle, INSERM U 1154, CNRS UMR 7196, 57 rue Cuvier, C.P. 26, 75231 Paris cedex 05, FranceEfficient protocols based on Cu(I)-catalyzed azide–alkyne cycloaddition were developed for the synthesis of conjugates of pyrrole–imidazole polyamide minor groove binders (MGB) with fluorophores and with triplex-forming oligonucleotides (TFOs). Diverse bifunctional linkers were synthesized and used for the insertion of terminal azides or alkynes into TFOs and MGBs. The formation of stable triple helices by TFO-MGB conjugates was evaluated by gel-shift experiments. The presence of MGB in these conjugates did not affect the binding parameters (affinity and triplex stability) of the parent TFOs.https://doi.org/10.3762/bjoc.12.128binding affinityclick chemistryCu(I)-catalyzed azide–alkyne cycloadditionpyrrole–imidazole polyamidessequence specificity: DNAtriplex-forming oligonucleotides |
| spellingShingle | Svetlana V. Vasilyeva Vyacheslav V. Filichev Alexandre S. Boutorine Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA Beilstein Journal of Organic Chemistry binding affinity click chemistry Cu(I)-catalyzed azide–alkyne cycloaddition pyrrole–imidazole polyamides sequence specificity: DNA triplex-forming oligonucleotides |
| title | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
| title_full | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
| title_fullStr | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
| title_full_unstemmed | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
| title_short | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
| title_sort | application of cu i catalyzed azide alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double stranded dna |
| topic | binding affinity click chemistry Cu(I)-catalyzed azide–alkyne cycloaddition pyrrole–imidazole polyamides sequence specificity: DNA triplex-forming oligonucleotides |
| url | https://doi.org/10.3762/bjoc.12.128 |
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