Asymmetric Monomethine Cyanine Dyes with Hydrophobic Functionalities for Fluorescent Intercalator Displacement Assay
A new green procedure has been applied for the synthesis and purification of asymmetric monomethine cyanine dyes. The photophysical properties of the newly synthesized compounds have been examined by combined application of spectroscopic and theoretical methods. The structural characteristics of the...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/1/114 |
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| author | Sonia Ilieva Nadezhda Bozova Miroslav Rangelov Nadezhda Todorova Aleksey Vasilev Diana Cheshmedzhieva |
| author_facet | Sonia Ilieva Nadezhda Bozova Miroslav Rangelov Nadezhda Todorova Aleksey Vasilev Diana Cheshmedzhieva |
| author_sort | Sonia Ilieva |
| collection | DOAJ |
| description | A new green procedure has been applied for the synthesis and purification of asymmetric monomethine cyanine dyes. The photophysical properties of the newly synthesized compounds have been examined by combined application of spectroscopic and theoretical methods. The structural characteristics of the molecules and dimer formation were characterized by quantum chemical computation and juxtaposed to the aggregachromism in UV/Vis spectra. The applicability of the dyes as fluorogenic nucleic acid probes has been proven by fluorescence titration, and their binding constants have been calculated. The mode of ligand–dsDNA/RNA interaction was rationalized by means of CD spectroscopy, molecular docking analysis, and fluorescent intercalator displacement experiments. |
| first_indexed | 2024-03-08T15:01:03Z |
| format | Article |
| id | doaj.art-14044423ffd142ee80e77afaaeded5f7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-08T15:01:03Z |
| publishDate | 2023-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-14044423ffd142ee80e77afaaeded5f72024-01-10T15:04:11ZengMDPI AGMolecules1420-30492023-12-0129111410.3390/molecules29010114Asymmetric Monomethine Cyanine Dyes with Hydrophobic Functionalities for Fluorescent Intercalator Displacement AssaySonia Ilieva0Nadezhda Bozova1Miroslav Rangelov2Nadezhda Todorova3Aleksey Vasilev4Diana Cheshmedzhieva5Faculty of Chemistry and Pharmacy, Sofia University “St. Kliment Ohridski”, 1 J. Bourchier Ave., 1164 Sofia, BulgariaFaculty of Chemistry and Pharmacy, Sofia University “St. Kliment Ohridski”, 1 J. Bourchier Ave., 1164 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 1113 Sofia, BulgariaInstitute of Biodiversity and Ecosystem Research, Bulgarian Academy of Sciences, 1113 Sofia, BulgariaFaculty of Chemistry and Pharmacy, Sofia University “St. Kliment Ohridski”, 1 J. Bourchier Ave., 1164 Sofia, BulgariaFaculty of Chemistry and Pharmacy, Sofia University “St. Kliment Ohridski”, 1 J. Bourchier Ave., 1164 Sofia, BulgariaA new green procedure has been applied for the synthesis and purification of asymmetric monomethine cyanine dyes. The photophysical properties of the newly synthesized compounds have been examined by combined application of spectroscopic and theoretical methods. The structural characteristics of the molecules and dimer formation were characterized by quantum chemical computation and juxtaposed to the aggregachromism in UV/Vis spectra. The applicability of the dyes as fluorogenic nucleic acid probes has been proven by fluorescence titration, and their binding constants have been calculated. The mode of ligand–dsDNA/RNA interaction was rationalized by means of CD spectroscopy, molecular docking analysis, and fluorescent intercalator displacement experiments.https://www.mdpi.com/1420-3049/29/1/114asymmetric monomethine cyanine dyesRNADNAfluorescence titrationbiomolecular probesDFT |
| spellingShingle | Sonia Ilieva Nadezhda Bozova Miroslav Rangelov Nadezhda Todorova Aleksey Vasilev Diana Cheshmedzhieva Asymmetric Monomethine Cyanine Dyes with Hydrophobic Functionalities for Fluorescent Intercalator Displacement Assay Molecules asymmetric monomethine cyanine dyes RNA DNA fluorescence titration biomolecular probes DFT |
| title | Asymmetric Monomethine Cyanine Dyes with Hydrophobic Functionalities for Fluorescent Intercalator Displacement Assay |
| title_full | Asymmetric Monomethine Cyanine Dyes with Hydrophobic Functionalities for Fluorescent Intercalator Displacement Assay |
| title_fullStr | Asymmetric Monomethine Cyanine Dyes with Hydrophobic Functionalities for Fluorescent Intercalator Displacement Assay |
| title_full_unstemmed | Asymmetric Monomethine Cyanine Dyes with Hydrophobic Functionalities for Fluorescent Intercalator Displacement Assay |
| title_short | Asymmetric Monomethine Cyanine Dyes with Hydrophobic Functionalities for Fluorescent Intercalator Displacement Assay |
| title_sort | asymmetric monomethine cyanine dyes with hydrophobic functionalities for fluorescent intercalator displacement assay |
| topic | asymmetric monomethine cyanine dyes RNA DNA fluorescence titration biomolecular probes DFT |
| url | https://www.mdpi.com/1420-3049/29/1/114 |
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