Host−[2]Rotaxanes as Cellular Transport Agents
Host−[2]rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 m...
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Veröffentlicht in: | Journal of the American Chemical Society 2003-07, Vol.125 (27), p.8290-8301 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Host−[2]rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K A's) in the range of 1 × 104 to 5 × 104 M-1, whereas the K A range for the fluorophores is 1 × 104 to 9 × 105 M-1. Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 × 103 to 5 × 103 M-1 range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane−[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft−[2]rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability. |
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ISSN: | 0002-7863 1520-5126 |
DOI: | 10.1021/ja034918c |