Format:
5
ISSN:
1464-3405
Content:
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.
Note:
Gesehen am 08.12.2021
In:
Bioorganic & medicinal chemistry letters, Amsterdam [u.a.] : Elsevier Science, 1991, 23(2013), 24, Seite 6544-6548, 1464-3405
In:
volume:23
In:
year:2013
In:
number:24
In:
pages:6544-6548
In:
extent:5
Language:
English
DOI:
10.1016/j.bmcl.2013.11.003
URL:
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