Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA
Two novel unnatural amino acids, prepared by linking a dicationic purple-coloured and fluorescent naphthalene diimide (NDI) at core position to amino acid side chains of variable length, strongly interacted with ds-DNA/RNA by threading intercalation. Different from a reference NDI dye with identical...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2020-08-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.16.170 |
| _version_ | 1819330877069459456 |
|---|---|
| author | Annike Weißenstein Myroslav O. Vysotsky Ivo Piantanida Frank Würthner |
| author_facet | Annike Weißenstein Myroslav O. Vysotsky Ivo Piantanida Frank Würthner |
| author_sort | Annike Weißenstein |
| collection | DOAJ |
| description | Two novel unnatural amino acids, prepared by linking a dicationic purple-coloured and fluorescent naphthalene diimide (NDI) at core position to amino acid side chains of variable length, strongly interacted with ds-DNA/RNA by threading intercalation. Different from a reference NDI dye with identical visible range absorbance (520–540 nm) and Stokes shifts in emission (+60 nm, quantum yield > 0.2), only these amino acid–NDI conjugates showed selective fluorimetric response for GC-DNA in respect to AT(U)-polynucleotides. The DNA/RNA binding-induced circular dichroism (ICD) response of NDI at 450–550 nm strongly depended on the length and rigidity of the linker to the amino acid unit, which controls the orientation of the NDI unit inside within the intercalative binding site. The ICD selectivity also depends on the type of polynucleotide, thus the studied NDI dyes act as dual fluorimetric/ICD probes for sensing the difference between here used GC-DNA, AT-DNA and AU-RNA. |
| first_indexed | 2024-12-24T14:05:30Z |
| format | Article |
| id | doaj.art-0710311186774f94ae50fd03c94047ca |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-24T14:05:30Z |
| publishDate | 2020-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-0710311186774f94ae50fd03c94047ca2022-12-21T16:52:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-08-011612032204510.3762/bjoc.16.1701860-5397-16-170Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNAAnnike Weißenstein0Myroslav O. Vysotsky1Ivo Piantanida2Frank Würthner3Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, GermanyInstitut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, GermanyDivision of Organic Chemistry & Biochemistry, Ruđer Bošković Institute, PO Box 180, 10002 Zagreb, Croatia,Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, GermanyTwo novel unnatural amino acids, prepared by linking a dicationic purple-coloured and fluorescent naphthalene diimide (NDI) at core position to amino acid side chains of variable length, strongly interacted with ds-DNA/RNA by threading intercalation. Different from a reference NDI dye with identical visible range absorbance (520–540 nm) and Stokes shifts in emission (+60 nm, quantum yield > 0.2), only these amino acid–NDI conjugates showed selective fluorimetric response for GC-DNA in respect to AT(U)-polynucleotides. The DNA/RNA binding-induced circular dichroism (ICD) response of NDI at 450–550 nm strongly depended on the length and rigidity of the linker to the amino acid unit, which controls the orientation of the NDI unit inside within the intercalative binding site. The ICD selectivity also depends on the type of polynucleotide, thus the studied NDI dyes act as dual fluorimetric/ICD probes for sensing the difference between here used GC-DNA, AT-DNA and AU-RNA.https://doi.org/10.3762/bjoc.16.170amino acid–fluorophore conjugatecircular dichroismdna/rna recognitionfluorescenceintercalationnaphthalene diimide |
| spellingShingle | Annike Weißenstein Myroslav O. Vysotsky Ivo Piantanida Frank Würthner Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA Beilstein Journal of Organic Chemistry amino acid–fluorophore conjugate circular dichroism dna/rna recognition fluorescence intercalation naphthalene diimide |
| title | Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA |
| title_full | Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA |
| title_fullStr | Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA |
| title_full_unstemmed | Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA |
| title_short | Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA |
| title_sort | naphthalene diimide amino acid conjugates as novel fluorimetric and cd probes for differentiation between ds dna and ds rna |
| topic | amino acid–fluorophore conjugate circular dichroism dna/rna recognition fluorescence intercalation naphthalene diimide |
| url | https://doi.org/10.3762/bjoc.16.170 |
| work_keys_str_mv | AT annikeweißenstein naphthalenediimideaminoacidconjugatesasnovelfluorimetricandcdprobesfordifferentiationbetweendsdnaanddsrna AT myroslavovysotsky naphthalenediimideaminoacidconjugatesasnovelfluorimetricandcdprobesfordifferentiationbetweendsdnaanddsrna AT ivopiantanida naphthalenediimideaminoacidconjugatesasnovelfluorimetricandcdprobesfordifferentiationbetweendsdnaanddsrna AT frankwurthner naphthalenediimideaminoacidconjugatesasnovelfluorimetricandcdprobesfordifferentiationbetweendsdnaanddsrna |