Synthesis and Anticancer and Antiviral Activities of C-2′-Branched Arabinonucleosides Article Swipe
Miklós Bege
,
Alexandra Kiss
,
Ilona Bereczki
,
Jan Hodek
,
Lenke Polyák
,
Gábor Szemán-Nagy
,
Lieve Naesens
,
Jan Weber
,
Anikó Borbás
·
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.3390/ijms232012566
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.3390/ijms232012566
d-Arabinofuranosyl-pyrimidine and -purine nucleoside analogues containing alkylthio-, acetylthio- or 1-thiosugar substituents at the C2’ position were prepared from the corresponding 3’,5’-O-silylene acetal-protected nucleoside 2’-exomethylenes by photoinitiated, radical-mediated hydrothiolation reactions. Although the stereochemical outcome of the hydrothiolation depended on the structure of both the thiol and the furanoside aglycone, in general, high d-arabino selectivity was obtained. The cytotoxic effect of the arabinonucleosides was studied on tumorous SCC (mouse squamous cell) and immortalized control HaCaT (human keratinocyte) cell lines by MTT assay. Three pyrimidine nucleosides containing C2’-butylsulfanylmethyl or -acetylthiomethyl groups showed promising cytotoxicity at low micromolar concentrations with good selectivity towards tumor cells. SAR analysis using a methyl β-d-arabinofuranoside reference compound showed that the silyl-protecting group, the nucleobase and the corresponding C2’ substituent are crucial for the cell growth inhibitory activity. The effects of the three most active nucleoside analogues on parameters indicative of cytotoxicity, such as cell size, division time and cell generation time, were investigated by near-infrared live cell imaging, which showed that the 2’-acetylthiomethyluridine derivative induced the most significant functional and morphological changes. Some nucleoside analogues also exerted anti-SARS-CoV-2 and/or anti-HCoV-229E activity with low micromolar EC50 values; however, the antiviral activity was always accompanied by significant cytotoxicity.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.3390/ijms232012566
- https://www.mdpi.com/1422-0067/23/20/12566/pdf?version=1666248241
- OA Status
- gold
- Cited By
- 7
- References
- 49
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4306835874
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4306835874Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.3390/ijms232012566Digital Object Identifier
- Title
-
Synthesis and Anticancer and Antiviral Activities of C-2′-Branched ArabinonucleosidesWork title
- Type
-
articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2022Year of publication
- Publication date
-
2022-10-19Full publication date if available
- Authors
-
Miklós Bege, Alexandra Kiss, Ilona Bereczki, Jan Hodek, Lenke Polyák, Gábor Szemán-Nagy, Lieve Naesens, Jan Weber, Anikó BorbásList of authors in order
- Landing page
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https://doi.org/10.3390/ijms232012566Publisher landing page
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https://www.mdpi.com/1422-0067/23/20/12566/pdf?version=1666248241Direct link to full text PDF
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YesWhether a free full text is available
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goldOpen access status per OpenAlex
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https://www.mdpi.com/1422-0067/23/20/12566/pdf?version=1666248241Direct OA link when available
- Concepts
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HaCaT, Cytotoxicity, Chemistry, Nucleoside, Stereochemistry, Pyrimidine, Cell growth, MTT assay, Uracil, Cell culture, Biochemistry, In vitro, Biology, DNA, GeneticsTop concepts (fields/topics) attached by OpenAlex
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7Total citation count in OpenAlex
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2025: 3, 2024: 3, 2023: 1Per-year citation counts (last 5 years)
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49Number of works referenced by this work
- Related works (count)
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10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.both | 41 |
| abstract_inverted_index.cell | 75, 125, 145, 150, 158 |
| abstract_inverted_index.from | 17 |
| abstract_inverted_index.good | 96 |
| abstract_inverted_index.high | 50 |
| abstract_inverted_index.live | 157 |
| abstract_inverted_index.most | 134, 168 |
| abstract_inverted_index.such | 143 |
| abstract_inverted_index.that | 110, 162 |
| abstract_inverted_index.time | 148 |
| abstract_inverted_index.were | 15, 153 |
| abstract_inverted_index.with | 95, 183 |
| abstract_inverted_index.C2’ | 13, 119 |
| abstract_inverted_index.HaCaT | 72 |
| abstract_inverted_index.Three | 80 |
| abstract_inverted_index.cell) | 68 |
| abstract_inverted_index.lines | 76 |
| abstract_inverted_index.size, | 146 |
| abstract_inverted_index.thiol | 43 |
| abstract_inverted_index.three | 133 |
| abstract_inverted_index.time, | 152 |
| abstract_inverted_index.tumor | 99 |
| abstract_inverted_index.using | 103 |
| abstract_inverted_index.which | 160 |
| abstract_inverted_index.(human | 73 |
| abstract_inverted_index.(mouse | 66 |
| abstract_inverted_index.active | 135 |
| abstract_inverted_index.always | 193 |
| abstract_inverted_index.and/or | 180 |
| abstract_inverted_index.assay. | 79 |
| abstract_inverted_index.cells. | 100 |
| abstract_inverted_index.effect | 57 |
| abstract_inverted_index.group, | 113 |
| abstract_inverted_index.groups | 87 |
| abstract_inverted_index.growth | 126 |
| abstract_inverted_index.methyl | 105 |
| abstract_inverted_index.showed | 88, 109, 161 |
| abstract_inverted_index.-purine | 2 |
| abstract_inverted_index.control | 71 |
| abstract_inverted_index.crucial | 122 |
| abstract_inverted_index.effects | 130 |
| abstract_inverted_index.exerted | 178 |
| abstract_inverted_index.induced | 166 |
| abstract_inverted_index.outcome | 32 |
| abstract_inverted_index.studied | 62 |
| abstract_inverted_index.towards | 98 |
| abstract_inverted_index.values; | 187 |
| abstract_inverted_index.Although | 29 |
| abstract_inverted_index.activity | 182, 191 |
| abstract_inverted_index.analysis | 102 |
| abstract_inverted_index.changes. | 173 |
| abstract_inverted_index.compound | 108 |
| abstract_inverted_index.depended | 36 |
| abstract_inverted_index.division | 147 |
| abstract_inverted_index.general, | 49 |
| abstract_inverted_index.however, | 188 |
| abstract_inverted_index.imaging, | 159 |
| abstract_inverted_index.position | 14 |
| abstract_inverted_index.prepared | 16 |
| abstract_inverted_index.squamous | 67 |
| abstract_inverted_index.tumorous | 64 |
| abstract_inverted_index.activity. | 128 |
| abstract_inverted_index.aglycone, | 47 |
| abstract_inverted_index.analogues | 4, 137, 176 |
| abstract_inverted_index.antiviral | 190 |
| abstract_inverted_index.cytotoxic | 56 |
| abstract_inverted_index.d-arabino | 51 |
| abstract_inverted_index.obtained. | 54 |
| abstract_inverted_index.promising | 89 |
| abstract_inverted_index.reference | 107 |
| abstract_inverted_index.structure | 39 |
| abstract_inverted_index.containing | 5, 83 |
| abstract_inverted_index.derivative | 165 |
| abstract_inverted_index.functional | 170 |
| abstract_inverted_index.furanoside | 46 |
| abstract_inverted_index.generation | 151 |
| abstract_inverted_index.indicative | 140 |
| abstract_inverted_index.inhibitory | 127 |
| abstract_inverted_index.micromolar | 93, 185 |
| abstract_inverted_index.nucleobase | 115 |
| abstract_inverted_index.nucleoside | 3, 22, 136, 175 |
| abstract_inverted_index.parameters | 139 |
| abstract_inverted_index.pyrimidine | 81 |
| abstract_inverted_index.reactions. | 28 |
| abstract_inverted_index.1-thiosugar | 9 |
| abstract_inverted_index.accompanied | 194 |
| abstract_inverted_index.acetylthio- | 7 |
| abstract_inverted_index.alkylthio-, | 6 |
| abstract_inverted_index.nucleosides | 82 |
| abstract_inverted_index.selectivity | 52, 97 |
| abstract_inverted_index.significant | 169, 196 |
| abstract_inverted_index.substituent | 120 |
| abstract_inverted_index.cytotoxicity | 90 |
| abstract_inverted_index.immortalized | 70 |
| abstract_inverted_index.investigated | 154 |
| abstract_inverted_index.substituents | 10 |
| abstract_inverted_index.corresponding | 19, 118 |
| abstract_inverted_index.cytotoxicity, | 142 |
| abstract_inverted_index.cytotoxicity. | 197 |
| abstract_inverted_index.keratinocyte) | 74 |
| abstract_inverted_index.morphological | 172 |
| abstract_inverted_index.near-infrared | 156 |
| abstract_inverted_index.anti-HCoV-229E | 181 |
| abstract_inverted_index.concentrations | 94 |
| abstract_inverted_index.stereochemical | 31 |
| abstract_inverted_index.anti-SARS-CoV-2 | 179 |
| abstract_inverted_index.hydrothiolation | 27, 35 |
| abstract_inverted_index.photoinitiated, | 25 |
| abstract_inverted_index.acetal-protected | 21 |
| abstract_inverted_index.radical-mediated | 26 |
| abstract_inverted_index.silyl-protecting | 112 |
| abstract_inverted_index.-acetylthiomethyl | 86 |
| abstract_inverted_index.2’-exomethylenes | 23 |
| abstract_inverted_index.arabinonucleosides | 60 |
| abstract_inverted_index.3’,5’-O-silylene | 20 |
| abstract_inverted_index.β-d-arabinofuranoside | 106 |
| abstract_inverted_index.C2’-butylsulfanylmethyl | 84 |
| abstract_inverted_index.2’-acetylthiomethyluridine | 164 |
| abstract_inverted_index.d-Arabinofuranosyl-pyrimidine | 0 |
| cited_by_percentile_year.max | 97 |
| cited_by_percentile_year.min | 89 |
| corresponding_author_ids | https://openalex.org/A5010542075 |
| countries_distinct_count | 3 |
| institutions_distinct_count | 9 |
| corresponding_institution_ids | https://openalex.org/I132735039, https://openalex.org/I79741316 |
| citation_normalized_percentile.value | 0.67438308 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | False |