期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 43, 页码 15270-15279出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601796
关键词
cation-pi interactions; dyes; glycoluril; hydrophobic effects; molecular clip
资金
- National Natural Science Foundation of China [21272086, CHE-1404911]
- Chinese Scholarship Council
- National Institutes of Health [CA168365]
- Czech Science Foundation [13-15576S]
- Czech Ministry of Education [LM2015051, LO1214]
- program of Employment of Newly Graduated Doctors of Science for Scientific Excellence [CZ.1.07/2.3.00/30.0009]
- European Social Fund
- Czech Republic's state budget
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1404911] Funding Source: National Science Foundation
Molecular clip 1 remains monomeric in water and engages in host-guest recognition processes with suitable guests. We report the K-a values for 32 1.guest complexes measured by H-1 NMR, UV/Vis, and fluorescence titrations. The cavity of 1 is shaped by aromatic surfaces of negative electrostatic potential and therefore displays high affinity and selectivity for planar and cationic aromatic guests that distinguishes it from CB[n] receptors that prefer aliphatic over aromatic guests. Electrostatic effects play a dominant role in the recognition process whereby ion-dipole interactions may occur between ammonium ions and the C=O groups of 1, between the SO3- groups of 1 and pendant cationic groups on the guest, and within the cavity of 1 by cation-pi interactions. Host 1 displays a high affinity toward dicationic guests with large planar aromatic surfaces (e.g. naphthalene diimide NDI + and perylene diimide PDI +) and cationic dyes derived from acridine (e.g. methylene blue and azure A). The critical importance of cation-pi interactions was ascertained by a comparison of analogous neutral and cationic guests (e.g. methylene violet vs. methylene blue; quinoline vs. N-methylquinolinium; acridine vs. N-methylacridinium; neutral red vs. neutral red H+) the affinities of which differ by up to 380-fold. We demonstrate that the high affinity of 1 toward methylene blue (K-a = 3.92 x 10(7) M-1; K-d = 25 nm) allows for the selective sequestration and destaining of U87 cells stained with methylene blue.
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