Amphiphilicity-Controlled Localization of Red Emitting Bicationic Fluorophores in Tumor Cells Acting as Bio-Probes and Anticancer Drugs Article Swipe
Alessio Cesaretti
,
Letizia Mencaroni
,
Carmela Bonaccorso
,
Valentina Botti
,
Eleonora Calzoni
,
Benedetta Carlotti
,
Cosimo G. Fortuna
,
Nicolò Montegiove
,
Anna Spalletti
,
Fausto Elisei
·
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.3390/molecules27123713
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.3390/molecules27123713
Small organic molecules arouse lively interest for their plethora of possible biological applications, such as anticancer therapy, for their ability to interact with nucleic acids, or bioimaging, thanks to their fluorescence emission. Here, a panchromatic series of styryl-azinium bicationic dyes, which have already proved to exhibit high water-solubility and significant red fluorescence in water, were investigated through spectrofluorimetric titrations to assess the extent of their association constants with DNA and RNA. Femtosecond-resolved transient absorption spectroscopy was also employed to characterize the changes in the photophysical properties of these fluorophores upon interaction with their biological targets. Finally, in vitro experiments conducted on tumor cell lines revealed that some of the bicationic fluorophores had a peculiar localization within cell nuclei exerting important antiproliferative effects, others were instead found to localize in the cytoplasm without leading to cell death, being useful to mark specific organelles in light of live cell bioimaging. Interestingly, this molecule-dependent behavior matched the different amphiphilicity featured by these bioactive compounds, which are thus expected to be caught in a tug-of-war between lipophilicity, ensured by the presence of aromatic rings and needed to pass cell membranes, and hydrophilicity, granted by charged groups and necessary for stability in aqueous media.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.3390/molecules27123713
- https://www.mdpi.com/1420-3049/27/12/3713/pdf?version=1654773137
- OA Status
- gold
- Cited By
- 6
- References
- 54
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4282826476
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- OpenAlex ID
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https://openalex.org/W4282826476Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.3390/molecules27123713Digital Object Identifier
- Title
-
Amphiphilicity-Controlled Localization of Red Emitting Bicationic Fluorophores in Tumor Cells Acting as Bio-Probes and Anticancer DrugsWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
-
2022Year of publication
- Publication date
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2022-06-09Full publication date if available
- Authors
-
Alessio Cesaretti, Letizia Mencaroni, Carmela Bonaccorso, Valentina Botti, Eleonora Calzoni, Benedetta Carlotti, Cosimo G. Fortuna, Nicolò Montegiove, Anna Spalletti, Fausto EliseiList of authors in order
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https://doi.org/10.3390/molecules27123713Publisher landing page
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https://www.mdpi.com/1420-3049/27/12/3713/pdf?version=1654773137Direct link to full text PDF
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-
YesWhether a free full text is available
- OA status
-
goldOpen access status per OpenAlex
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-
https://www.mdpi.com/1420-3049/27/12/3713/pdf?version=1654773137Direct OA link when available
- Concepts
-
Lipophilicity, Fluorescence, Chemistry, Biophysics, Nucleic acid, Cytoplasm, Organelle, DNA, Nanomedicine, Molecule, Membrane, Combinatorial chemistry, Photochemistry, Nanotechnology, Biochemistry, Organic chemistry, Materials science, Nanoparticle, Biology, Quantum mechanics, PhysicsTop concepts (fields/topics) attached by OpenAlex
- Cited by
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6Total citation count in OpenAlex
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2025: 1, 2024: 2, 2023: 2, 2022: 1Per-year citation counts (last 5 years)
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54Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.interact | 21 |
| abstract_inverted_index.interest | 5 |
| abstract_inverted_index.localize | 127 |
| abstract_inverted_index.peculiar | 113 |
| abstract_inverted_index.plethora | 8 |
| abstract_inverted_index.possible | 10 |
| abstract_inverted_index.presence | 176 |
| abstract_inverted_index.revealed | 104 |
| abstract_inverted_index.specific | 140 |
| abstract_inverted_index.targets. | 94 |
| abstract_inverted_index.therapy, | 16 |
| abstract_inverted_index.bioactive | 159 |
| abstract_inverted_index.conducted | 99 |
| abstract_inverted_index.constants | 66 |
| abstract_inverted_index.cytoplasm | 130 |
| abstract_inverted_index.different | 154 |
| abstract_inverted_index.emission. | 31 |
| abstract_inverted_index.important | 119 |
| abstract_inverted_index.molecules | 2 |
| abstract_inverted_index.necessary | 193 |
| abstract_inverted_index.stability | 195 |
| abstract_inverted_index.transient | 72 |
| abstract_inverted_index.absorption | 73 |
| abstract_inverted_index.anticancer | 15 |
| abstract_inverted_index.bicationic | 38, 109 |
| abstract_inverted_index.biological | 11, 93 |
| abstract_inverted_index.compounds, | 160 |
| abstract_inverted_index.membranes, | 185 |
| abstract_inverted_index.organelles | 141 |
| abstract_inverted_index.properties | 85 |
| abstract_inverted_index.titrations | 58 |
| abstract_inverted_index.tug-of-war | 170 |
| abstract_inverted_index.association | 65 |
| abstract_inverted_index.bioimaging, | 26 |
| abstract_inverted_index.bioimaging. | 147 |
| abstract_inverted_index.experiments | 98 |
| abstract_inverted_index.interaction | 90 |
| abstract_inverted_index.significant | 49 |
| abstract_inverted_index.characterize | 79 |
| abstract_inverted_index.fluorescence | 30, 51 |
| abstract_inverted_index.fluorophores | 88, 110 |
| abstract_inverted_index.investigated | 55 |
| abstract_inverted_index.localization | 114 |
| abstract_inverted_index.panchromatic | 34 |
| abstract_inverted_index.spectroscopy | 74 |
| abstract_inverted_index.applications, | 12 |
| abstract_inverted_index.photophysical | 84 |
| abstract_inverted_index.Interestingly, | 148 |
| abstract_inverted_index.amphiphilicity | 155 |
| abstract_inverted_index.lipophilicity, | 172 |
| abstract_inverted_index.styryl-azinium | 37 |
| abstract_inverted_index.hydrophilicity, | 187 |
| abstract_inverted_index.water-solubility | 47 |
| abstract_inverted_index.antiproliferative | 120 |
| abstract_inverted_index.molecule-dependent | 150 |
| abstract_inverted_index.spectrofluorimetric | 57 |
| abstract_inverted_index.Femtosecond-resolved | 71 |
| cited_by_percentile_year.max | 96 |
| cited_by_percentile_year.min | 89 |
| corresponding_author_ids | https://openalex.org/A5017599983 |
| countries_distinct_count | 1 |
| institutions_distinct_count | 10 |
| corresponding_institution_ids | https://openalex.org/I27483092 |
| sustainable_development_goals[0].id | https://metadata.un.org/sdg/6 |
| sustainable_development_goals[0].score | 0.6200000047683716 |
| sustainable_development_goals[0].display_name | Clean water and sanitation |
| citation_normalized_percentile.value | 0.6405593 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | False |