Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor Applications
Hydroxy-substituted tetrachlorodibenzo[<i>b,e</i>][1,4]dioxin and tetrachlorodibenzo[<i>b,d</i>]furans have been synthesized using 3,4-dichloroanisole, 2,3,6-trichlorophenol and 4,5-dichlorocatechol as starting materials and electrophilic and/or nucleophilic aromatic substitu...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-08-01
|
| Series: | Materials |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1996-1944/14/16/4727 |
| _version_ | 1797523064033902592 |
|---|---|
| author | Stefania Kalantzi Sofia Leonardi Eleanna Vachlioti Eleni G. Kaliatsi Κοnstantina Papachristopoulou Constantinos Stathopoulos Nikolaos Vainos Dionissios Papaioannou |
| author_facet | Stefania Kalantzi Sofia Leonardi Eleanna Vachlioti Eleni G. Kaliatsi Κοnstantina Papachristopoulou Constantinos Stathopoulos Nikolaos Vainos Dionissios Papaioannou |
| author_sort | Stefania Kalantzi |
| collection | DOAJ |
| description | Hydroxy-substituted tetrachlorodibenzo[<i>b,e</i>][1,4]dioxin and tetrachlorodibenzo[<i>b,d</i>]furans have been synthesized using 3,4-dichloroanisole, 2,3,6-trichlorophenol and 4,5-dichlorocatechol as starting materials and electrophilic and/or nucleophilic aromatic substitution reactions for the assembly of the dibenzo[<i>b,e</i>][1,4]dioxin and dibenzo[<i>b,d</i>]furan systems. The thus-obtained phenolic compounds were then alkylated with N-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde)-protected 3-bromopropan-1-amine to give the corresponding N-Dde protected 3-aminopropoxy-substituted tetrachlorodibenzo[<i>b,e</i>][1,4]dioxin and tetrachlorodibenzo[<i>b,d</i>]furans, respectively. Hydrazinolysis-mediated Dde removal from the former compound provided the corresponding amino-substituted dioxin, which was coupled to carboxy-substituted magnetic beads affording magnetic beads coated by the amino-substituted dioxin. The latter is an attractive intermediate for the development of selective single-standard DNA (ssDNA) aptamers, which constitute molecular recognition elements in photonic biosensors with potential application to the monitoring of the dangerous environmental pollutants, dioxins having serious implications in human health. |
| first_indexed | 2024-03-10T08:38:08Z |
| format | Article |
| id | doaj.art-785487f8005e4429bac58dcc19ee308e |
| institution | Directory Open Access Journal |
| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-10T08:38:08Z |
| publishDate | 2021-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Materials |
| spelling | doaj.art-785487f8005e4429bac58dcc19ee308e2023-11-22T08:31:58ZengMDPI AGMaterials1996-19442021-08-011416472710.3390/ma14164727Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor ApplicationsStefania Kalantzi0Sofia Leonardi1Eleanna Vachlioti2Eleni G. Kaliatsi3Κοnstantina Papachristopoulou4Constantinos Stathopoulos5Nikolaos Vainos6Dionissios Papaioannou7Laboratory of Synthetic Organic Chemistry, Department of Chemistry, University of Patras, GR-26504 Patras, GreeceLaboratory of Synthetic Organic Chemistry, Department of Chemistry, University of Patras, GR-26504 Patras, GreeceLaboratory of Synthetic Organic Chemistry, Department of Chemistry, University of Patras, GR-26504 Patras, GreeceDepartment of Biochemistry, School of Medicine, University of Patras, GR-26504 Patras, GreecePhotonics Nanotechnology Research Laboratory, Department of Materials Science, University of Patras, GR-26504 Patras, GreeceDepartment of Biochemistry, School of Medicine, University of Patras, GR-26504 Patras, GreecePhotonics Nanotechnology Research Laboratory, Department of Materials Science, University of Patras, GR-26504 Patras, GreeceLaboratory of Synthetic Organic Chemistry, Department of Chemistry, University of Patras, GR-26504 Patras, GreeceHydroxy-substituted tetrachlorodibenzo[<i>b,e</i>][1,4]dioxin and tetrachlorodibenzo[<i>b,d</i>]furans have been synthesized using 3,4-dichloroanisole, 2,3,6-trichlorophenol and 4,5-dichlorocatechol as starting materials and electrophilic and/or nucleophilic aromatic substitution reactions for the assembly of the dibenzo[<i>b,e</i>][1,4]dioxin and dibenzo[<i>b,d</i>]furan systems. The thus-obtained phenolic compounds were then alkylated with N-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde)-protected 3-bromopropan-1-amine to give the corresponding N-Dde protected 3-aminopropoxy-substituted tetrachlorodibenzo[<i>b,e</i>][1,4]dioxin and tetrachlorodibenzo[<i>b,d</i>]furans, respectively. Hydrazinolysis-mediated Dde removal from the former compound provided the corresponding amino-substituted dioxin, which was coupled to carboxy-substituted magnetic beads affording magnetic beads coated by the amino-substituted dioxin. The latter is an attractive intermediate for the development of selective single-standard DNA (ssDNA) aptamers, which constitute molecular recognition elements in photonic biosensors with potential application to the monitoring of the dangerous environmental pollutants, dioxins having serious implications in human health.https://www.mdpi.com/1996-1944/14/16/4727dioxinstetrachlorodibenzodioxinstetrachlorodibenzofuranshydroxyl-substituted dioxinsamino-substituted dioxinscarboxy-substituted magnetic beads |
| spellingShingle | Stefania Kalantzi Sofia Leonardi Eleanna Vachlioti Eleni G. Kaliatsi Κοnstantina Papachristopoulou Constantinos Stathopoulos Nikolaos Vainos Dionissios Papaioannou Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor Applications Materials dioxins tetrachlorodibenzodioxins tetrachlorodibenzofurans hydroxyl-substituted dioxins amino-substituted dioxins carboxy-substituted magnetic beads |
| title | Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor Applications |
| title_full | Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor Applications |
| title_fullStr | Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor Applications |
| title_full_unstemmed | Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor Applications |
| title_short | Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor Applications |
| title_sort | studies towards the synthesis of novel 3 aminopropoxy substituted dioxins suitable for the development of aptamers for photonic biosensor applications |
| topic | dioxins tetrachlorodibenzodioxins tetrachlorodibenzofurans hydroxyl-substituted dioxins amino-substituted dioxins carboxy-substituted magnetic beads |
| url | https://www.mdpi.com/1996-1944/14/16/4727 |
| work_keys_str_mv | AT stefaniakalantzi studiestowardsthesynthesisofnovel3aminopropoxysubstituteddioxinssuitableforthedevelopmentofaptamersforphotonicbiosensorapplications AT sofialeonardi studiestowardsthesynthesisofnovel3aminopropoxysubstituteddioxinssuitableforthedevelopmentofaptamersforphotonicbiosensorapplications AT eleannavachlioti studiestowardsthesynthesisofnovel3aminopropoxysubstituteddioxinssuitableforthedevelopmentofaptamersforphotonicbiosensorapplications AT elenigkaliatsi studiestowardsthesynthesisofnovel3aminopropoxysubstituteddioxinssuitableforthedevelopmentofaptamersforphotonicbiosensorapplications AT konstantinapapachristopoulou studiestowardsthesynthesisofnovel3aminopropoxysubstituteddioxinssuitableforthedevelopmentofaptamersforphotonicbiosensorapplications AT constantinosstathopoulos studiestowardsthesynthesisofnovel3aminopropoxysubstituteddioxinssuitableforthedevelopmentofaptamersforphotonicbiosensorapplications AT nikolaosvainos studiestowardsthesynthesisofnovel3aminopropoxysubstituteddioxinssuitableforthedevelopmentofaptamersforphotonicbiosensorapplications AT dionissiospapaioannou studiestowardsthesynthesisofnovel3aminopropoxysubstituteddioxinssuitableforthedevelopmentofaptamersforphotonicbiosensorapplications |