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Host−Guest Complexes and Pseudorotaxanes of Cucurbit[7]uril with Acetylcholinesterase Inhibitors

Host−Guest Complexes and Pseudorotaxanes of Cucurbit[7]uril with Acetylcholinesterase Inhibitors

Authors :
Donal H. Macartney
Ian Wyman
Source :
The Journal of Organic Chemistry. 74:8031-8038
Publication Year :
2009
Publisher :
American Chemical Society (ACS), 2009.

Abstract

Pseudorotaxanes may be assembled in aqueous solution using dicationic acetylcholinesterase inhibitors, such as succinylcholine, BW284c51, and alpha,omega-bis(trialkylammonium)alkane dications (or their phosphonium analogues), as bolaform axles and cucurbit[7]uril (CB[7]) as the wheel. With the exceptions of the shorter [(CH(3))(3)N(CH(2))(n)N(CH(3))(3)](2+) (n = 6, 8) dications, the addition of a second CB[7] results in the translocation of the first CB[7], such that the hydrophobic -NR(3)(+) and -PR(3)(+) end groups (R = Me or Et) are located in the cavities of the wheels, while the central portion of the axles extend through the CB[7] portals into the bulk solvent. In the case of the [Quin(CH(2))(10)Quin](2+) (Quin = quinuclidinium) dication, the CB[7] host(s) resides only on the quinuclidinium end group(s). The 1:1 host-guest stability constants range from 8 x 10(6) to 3 x 10(10) M(-1) and are dependent on both the nature of the end group as well as the length and hydrophobicity of the central linker. The magnitude of the stability constants for the 2:1 complexes closely follow the trend observed previously for CB[7] binding with the NR(4)(+) and PR(4)(+) cations.

Details

ISSN :
15206904 and 00223263
Volume :
74
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....d5b29548eeafb75adc8cb7f0ce7509d2
Full Text :
https://doi.org/10.1021/jo901861e