Acyclic CB[n]-type molecular containers: effect of solubilizing group on their function as solubilizing excipients.

ABSTRACT: We report the synthesis and X-ray crystal structures of three acyclic CB[n]-type molecular containers (2a, 2h, 2f) that differ in the charge on their solubilizing groups (SO3(−), OH, NH3(+)). The X-ray crystal structures of compounds 2h and 2f reveal a self-folding of the ArOCH2CH2X wall into the cavity driven by π–π interactions, H-bonds and ion–dipole interactions. The need to reverse this self-folding phenomenon upon guest binding decreases the affinity of 2h and 2f toward cationic guests in water relative to 2a as revealed by direct (1)H NMR and UV/Vis titrations as well as UV/Vis competition experiments. We determined the pKa of 6-aminocoumarin 7 (pKa = 3.6) on its own and in the presence anionic, neutral, and cationic hosts (2a: pKa = 4.9; 2h: pKa = 4.1; 2f, pKa = 3.4) which reflect

SUBMITTER: Zhang B 

PROVIDER: S-EPMC4035228 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature