Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine
A water-soluble 2,2′-biphen[4]arene (2,2’-CBP4) containing eight carboxylato moieties was synthesized and characterized. Its complexation behavior towards two alkaloids, palmatine (P) and berberine (B), was investigated by means of fluorescence and 1H NMR spectroscopy in aqueous phosphate buffer sol...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2018-08-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.198 |
| _version_ | 1819283391363678208 |
|---|---|
| author | Xiayang Huang Xinghua Zhang Tianxin Qian Junwei Ma Lei Cui Chunju Li |
| author_facet | Xiayang Huang Xinghua Zhang Tianxin Qian Junwei Ma Lei Cui Chunju Li |
| author_sort | Xiayang Huang |
| collection | DOAJ |
| description | A water-soluble 2,2′-biphen[4]arene (2,2’-CBP4) containing eight carboxylato moieties was synthesized and characterized. Its complexation behavior towards two alkaloids, palmatine (P) and berberine (B), was investigated by means of fluorescence and 1H NMR spectroscopy in aqueous phosphate buffer solution (pH 7.4). In the presence of 2,2’-CBP4, 1H NMR signals of P and B displayed very large upfield shifts, indicating the formation of inclusion complexes with strong binding affinities. Fluorescence titration experiments showed that P and B exhibited dramatic fluorescence enhancement of more than 600 times upon complexation with 2,2’-CBP4. Particularly, the fluorescence intensity is strong enough to be readily distinguished by the naked eye. Although the two guests have similar structures, the association constant of B with 2,2’-CBP4 (Ka = (2.29 ± 0.27) × 106 M−1) is 3.9 times larger than that of P (Ka = (5.87 ± 0.24) × 105 M−1). |
| first_indexed | 2024-12-24T01:30:44Z |
| format | Article |
| id | doaj.art-15f885811cf24cfeb9cad816ee9ab917 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-24T01:30:44Z |
| publishDate | 2018-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-15f885811cf24cfeb9cad816ee9ab9172022-12-21T17:22:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-08-011412236224110.3762/bjoc.14.1981860-5397-14-198Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberineXiayang Huang0Xinghua Zhang1Tianxin Qian2Junwei Ma3Lei Cui4Chunju Li5School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Hai-Quan Road, Shanghai 201418, P. R. ChinaSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Hai-Quan Road, Shanghai 201418, P. R. ChinaDepartment of Chemistry, Center for Supramolecular Chemistry and Catalysis, Shanghai University, Shanghai 200444, P. R. ChinaDepartment of Chemistry, Center for Supramolecular Chemistry and Catalysis, Shanghai University, Shanghai 200444, P. R. ChinaDepartment of Chemistry, Center for Supramolecular Chemistry and Catalysis, Shanghai University, Shanghai 200444, P. R. ChinaSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Hai-Quan Road, Shanghai 201418, P. R. ChinaA water-soluble 2,2′-biphen[4]arene (2,2’-CBP4) containing eight carboxylato moieties was synthesized and characterized. Its complexation behavior towards two alkaloids, palmatine (P) and berberine (B), was investigated by means of fluorescence and 1H NMR spectroscopy in aqueous phosphate buffer solution (pH 7.4). In the presence of 2,2’-CBP4, 1H NMR signals of P and B displayed very large upfield shifts, indicating the formation of inclusion complexes with strong binding affinities. Fluorescence titration experiments showed that P and B exhibited dramatic fluorescence enhancement of more than 600 times upon complexation with 2,2’-CBP4. Particularly, the fluorescence intensity is strong enough to be readily distinguished by the naked eye. Although the two guests have similar structures, the association constant of B with 2,2’-CBP4 (Ka = (2.29 ± 0.27) × 106 M−1) is 3.9 times larger than that of P (Ka = (5.87 ± 0.24) × 105 M−1).https://doi.org/10.3762/bjoc.14.198berberinebiphenareneshost–guest complexesmolecular recognitionpalmatine |
| spellingShingle | Xiayang Huang Xinghua Zhang Tianxin Qian Junwei Ma Lei Cui Chunju Li Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine Beilstein Journal of Organic Chemistry berberine biphenarenes host–guest complexes molecular recognition palmatine |
| title | Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine |
| title_full | Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine |
| title_fullStr | Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine |
| title_full_unstemmed | Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine |
| title_short | Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine |
| title_sort | synthesis of a water soluble 2 2 biphen 4 arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine |
| topic | berberine biphenarenes host–guest complexes molecular recognition palmatine |
| url | https://doi.org/10.3762/bjoc.14.198 |
| work_keys_str_mv | AT xiayanghuang synthesisofawatersoluble22biphen4areneanditsefficientcomplexationandsensitivefluorescenceenhancementtowardspalmatineandberberine AT xinghuazhang synthesisofawatersoluble22biphen4areneanditsefficientcomplexationandsensitivefluorescenceenhancementtowardspalmatineandberberine AT tianxinqian synthesisofawatersoluble22biphen4areneanditsefficientcomplexationandsensitivefluorescenceenhancementtowardspalmatineandberberine AT junweima synthesisofawatersoluble22biphen4areneanditsefficientcomplexationandsensitivefluorescenceenhancementtowardspalmatineandberberine AT leicui synthesisofawatersoluble22biphen4areneanditsefficientcomplexationandsensitivefluorescenceenhancementtowardspalmatineandberberine AT chunjuli synthesisofawatersoluble22biphen4areneanditsefficientcomplexationandsensitivefluorescenceenhancementtowardspalmatineandberberine |