Towards synthetic adrenaline receptors.
The authors have designed a new host mol. (I) for substrates of the adrenergic receptor; this mol. has a flexible bisphosphonate as chelating unit for the amino alc. part and an electron-poor nonpolar macrocyclic cavity for the catechol ring. I forms complexes with amino alcs., amines, and amino acid esters with high assocn. consts. in polar org. solvents. Exertion of solvophobic interactions inside the macrocyclic cavity in DMSO and methanol leads to specificity for guest mols. with hydrophobic moieties. Exptl. evidence is presented for the insertion of the guest mols.' nonpolar groups into the macrocycle's hydrophobic cavity. NMR spectra of complexes with 2 in DMSO show a mol. imprint of the guest mol.; this gives information about its location inside the macrocycle. In aq. solns. strong self-assocn. of 2 occurs, which is explained by distinct structural similarities between 2 and micelle-forming phospholipids.
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