"Caged" peptide nucleic acids activated by red light in a singlet oxygen mediated process
Common ‘caged’ nucleic acid binders, which can be applied for temporal and spatial control of gene expression, are activated by high energy light (<450nm). The light of this type is damaging to cells and is strongly absorbed by cellular components. Therefore, shifting the triggering light to the...
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| Main Authors: | , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
12 November 2013
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| In: |
Bioorganic & medicinal chemistry letters
Year: 2013, Volume: 23, Issue: 24, Pages: 6544-6548 |
| ISSN: | 1464-3405 |
| DOI: | 10.1016/j.bmcl.2013.11.003 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1016/j.bmcl.2013.11.003 Verlag, lizenzpflichtig, Volltext: https://www.sciencedirect.com/science/article/pii/S0960894X13012821 
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| Author Notes: | Sandra G. König, Andriy Mokhir |
| Summary: | Common ‘caged’ nucleic acid binders, which can be applied for temporal and spatial control of gene expression, are activated by high energy light (<450nm). The light of this type is damaging to cells and is strongly absorbed by cellular components. Therefore, shifting the triggering light to the visible region (>550nm) is highly desirable. Herein we report on a cyclic peptide nucleic acid (PNA), whose backbone contains a 9,10-dialkoxy-substituted anthracene linker. The sequence of this compound was selected to be complementary to a representative microRNA (miR-92). We demonstrated that the cyclic PNA does not bind complementary nucleic acids and is, correspondingly, ‘caged’. Its uncaging can be conducted by its exposure to red light (635nm) in the presence of pyropheophorbide-a. The latter process is mediated by singlet oxygen (1O2), which cleaves the 9,10-dialcoxyanthracene linker within the PNA with formation of a linear PNA, an efficient binder of the complementary ribonucleic acid. This is the first example of a red light-activated, ‘caged’ peptide nucleic acid. |
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| Item Description: | Gesehen am 08.12.2021 |
| Physical Description: | Online Resource |
| ISSN: | 1464-3405 |
| DOI: | 10.1016/j.bmcl.2013.11.003 |