Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme Article Swipe
Josipa Matić
,
Tana Tandarić
,
Marijana Raðić Stojković
,
Filip Šupljika
,
Zrinka Karačić
,
Ana Tomašić Paić
,
Lucija Horvat
,
Robert Vianello
,
Lidija‐Marija Tumir
·
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.3762/bjoc.19.40
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.3762/bjoc.19.40
Two novel conjugate molecules were designed: pyrene and phenanthridine-amino acid units with a different linker length between the aromatic fragments. Molecular modelling combined with spectrophotometric experiments revealed that in neutral and acidic buffered water solutions conjugates predominantly exist in intramolecularly stacked conformations because of the π–π stacking interaction between pyrene and phenanthridine moieties. The investigated systems exhibited a pH-dependent excimer formation that is significantly red-shifted relative to the pyrene and phenanthridine fluorescence. While the conjugate with a short linker showed negligible spectrophotometric changes due to the polynucleotide addition, the conjugate with a longer and more flexible linker exhibited a micromolar and submicromolar binding affinity for ds-polynucleotides and inactivated a mutant of dipeptidyl peptidase enzyme E451A. Confocal microscopy revealed that the conjugate with the longer linker entered the HeLa cell membranes and blue fluorescence was visualized as the dye accumulated in the cell membrane.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.3762/bjoc.19.40
- https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-19-40.pdf
- OA Status
- diamond
- Cited By
- 2
- References
- 61
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4375956184
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- OpenAlex ID
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https://openalex.org/W4375956184Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.3762/bjoc.19.40Digital Object Identifier
- Title
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Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzymeWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2023Year of publication
- Publication date
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2023-04-26Full publication date if available
- Authors
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Josipa Matić, Tana Tandarić, Marijana Raðić Stojković, Filip Šupljika, Zrinka Karačić, Ana Tomašić Paić, Lucija Horvat, Robert Vianello, Lidija‐Marija TumirList of authors in order
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https://doi.org/10.3762/bjoc.19.40Publisher landing page
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https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-19-40.pdfDirect link to full text PDF
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YesWhether a free full text is available
- OA status
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diamondOpen access status per OpenAlex
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https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-19-40.pdfDirect OA link when available
- Concepts
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Chemistry, Phenanthridine, Linker, Conjugate, Pyrene, Fluorescence, Polynucleotide, Stereochemistry, Combinatorial chemistry, Biochemistry, Organic chemistry, Quantum mechanics, Computer science, Mathematics, Mathematical analysis, Operating system, PhysicsTop concepts (fields/topics) attached by OpenAlex
- Cited by
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2Total citation count in OpenAlex
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2024: 1, 2023: 1Per-year citation counts (last 5 years)
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61Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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