Guest-Host Chemistry with Dendrimers—Binding of Carboxylates in Aqueous Solution.
Recognition and binding of anions in water is difficult due to the ability of water molecules to form strong hydrogen bonds and to solvate the anions. The complexation of two different carboxylates with 1-(4-carbomethoxypyrrolidone)-terminated PAMAM dendrimers was studied in aqueous solution using N...
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Public Library of Science (PLoS)
2015-01-01
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| Series: | PLoS ONE |
| Online Access: | https://journals.plos.org/plosone/article/file?id=10.1371/journal.pone.0138706&type=printable |
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| author | Mario Ficker Johannes F Petersen Jon S Hansen Jørn B Christensen |
| author_facet | Mario Ficker Johannes F Petersen Jon S Hansen Jørn B Christensen |
| author_sort | Mario Ficker |
| collection | DOAJ |
| description | Recognition and binding of anions in water is difficult due to the ability of water molecules to form strong hydrogen bonds and to solvate the anions. The complexation of two different carboxylates with 1-(4-carbomethoxypyrrolidone)-terminated PAMAM dendrimers was studied in aqueous solution using NMR and ITC binding models. Sodium 2-naphthoate and sodium 3-hydroxy-2-naphthoate were chosen as carboxylate model compounds, since they carry structural similarities to many non-steroidal anti-inflammatory drugs and they possess only a limited number of functional groups, making them ideal to study the carboxylate-dendrimer interaction selectively. The binding stoichiometry for 3-hydroxy-2-naphthoate was found to be two strongly bound guest molecules per dendrimer and an additional 40 molecules with weak binding affinity. The NOESY NMR showed a clear binding correlation of sodium 3-hydroxy-2-naphthoate with the lyophilic dendrimer core, possibly with the two high affinity guest molecules. In comparison, sodium 2-naphthoate showed a weaker binding strength and had a stoichiometry of two guests per dendrimer with no additional weakly bound guests. This stronger dendrimer interaction with sodium 3-hydroxy-2-naphthoate is possibly a result of the additional interactions of the dendrimer with the extra hydroxyl group and an internal stabilization of the negative charge due to the hydroxyl group. These findings illustrate the potential of the G4 1-(4-carbomethoxy) pyrrolidone dendrimer to complex carboxylate guests in water and act as a possible carrier of such molecules. |
| format | Article |
| id | doaj-art-a3d84bcec9a540b5b332879fc1a5741e |
| institution | OA Journals |
| issn | 1932-6203 |
| language | English |
| publishDate | 2015-01-01 |
| publisher | Public Library of Science (PLoS) |
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| series | PLoS ONE |
| spelling | doaj-art-a3d84bcec9a540b5b332879fc1a5741e2025-08-20T02:15:42ZengPublic Library of Science (PLoS)PLoS ONE1932-62032015-01-011010e013870610.1371/journal.pone.0138706Guest-Host Chemistry with Dendrimers—Binding of Carboxylates in Aqueous Solution.Mario FickerJohannes F PetersenJon S HansenJørn B ChristensenRecognition and binding of anions in water is difficult due to the ability of water molecules to form strong hydrogen bonds and to solvate the anions. The complexation of two different carboxylates with 1-(4-carbomethoxypyrrolidone)-terminated PAMAM dendrimers was studied in aqueous solution using NMR and ITC binding models. Sodium 2-naphthoate and sodium 3-hydroxy-2-naphthoate were chosen as carboxylate model compounds, since they carry structural similarities to many non-steroidal anti-inflammatory drugs and they possess only a limited number of functional groups, making them ideal to study the carboxylate-dendrimer interaction selectively. The binding stoichiometry for 3-hydroxy-2-naphthoate was found to be two strongly bound guest molecules per dendrimer and an additional 40 molecules with weak binding affinity. The NOESY NMR showed a clear binding correlation of sodium 3-hydroxy-2-naphthoate with the lyophilic dendrimer core, possibly with the two high affinity guest molecules. In comparison, sodium 2-naphthoate showed a weaker binding strength and had a stoichiometry of two guests per dendrimer with no additional weakly bound guests. This stronger dendrimer interaction with sodium 3-hydroxy-2-naphthoate is possibly a result of the additional interactions of the dendrimer with the extra hydroxyl group and an internal stabilization of the negative charge due to the hydroxyl group. These findings illustrate the potential of the G4 1-(4-carbomethoxy) pyrrolidone dendrimer to complex carboxylate guests in water and act as a possible carrier of such molecules.https://journals.plos.org/plosone/article/file?id=10.1371/journal.pone.0138706&type=printable |
| spellingShingle | Mario Ficker Johannes F Petersen Jon S Hansen Jørn B Christensen Guest-Host Chemistry with Dendrimers—Binding of Carboxylates in Aqueous Solution. PLoS ONE |
| title | Guest-Host Chemistry with Dendrimers—Binding of Carboxylates in Aqueous Solution. |
| title_full | Guest-Host Chemistry with Dendrimers—Binding of Carboxylates in Aqueous Solution. |
| title_fullStr | Guest-Host Chemistry with Dendrimers—Binding of Carboxylates in Aqueous Solution. |
| title_full_unstemmed | Guest-Host Chemistry with Dendrimers—Binding of Carboxylates in Aqueous Solution. |
| title_short | Guest-Host Chemistry with Dendrimers—Binding of Carboxylates in Aqueous Solution. |
| title_sort | guest host chemistry with dendrimers binding of carboxylates in aqueous solution |
| url | https://journals.plos.org/plosone/article/file?id=10.1371/journal.pone.0138706&type=printable |
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