The crystal structure, self-assembly, DNA-binding and cleavage studies of the [2]pseudorotaxane composed of cucurbit[6]uril

Fang-Jun Huo; Cai-Xia Yin; Pin Yang

doi:10.1016/j.bmcl.2006.11.054

The crystal structure, self-assembly, DNA-binding and cleavage studies of the [2]pseudorotaxane composed of cucurbit[6]uril

Bioorg Med Chem Lett. 2007 Feb 15;17(4):932-6. doi: 10.1016/j.bmcl.2006.11.054. Epub 2006 Nov 19.

Authors

Fang-Jun Huo¹, Cai-Xia Yin, Pin Yang

Affiliation

¹ Institute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Shanxi University, Taiyuan 030006, China.

PMID: 17161945
DOI: 10.1016/j.bmcl.2006.11.054

Abstract

The [2]pseudorotaxanes of cucurbit[6]uril with guest molecule 1,6-bis(imidazol-1-yl)hexane (BIMH) were synthesized and characterized by ESI-MS spectrometry, (1)H NMR spectra, and X-ray diffraction crystallography. The influence of different anions on self-assembly in solid-state was discussed by X-ray diffraction crystallography. However, more interestingly, and to our amazement, we discovered the CB[6]/BIMH [2]pseudorotaxane exhibiting efficient cleavage of pBR322 DNA in physiological environment. The cleavage mechanism were studied by fluorescence spectra and the hydrolysis of bis(2,4-dinitrophenyl)-phosphate (BDNPP). From DNA-binding mode being electrostatic force and the first-order kinetics equation, we prove indirectly that the mechanism may be hydrolytic cleavage.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged-Ring Compounds / chemistry*
Chromatography, Agarose
Crystallography, X-Ray
DNA / drug effects*
DNA Fragmentation / drug effects
Hydrolysis
Imidazoles / chemistry*
Kinetics
Magnetic Resonance Spectroscopy
Models, Molecular
Rotaxanes / chemistry*
Spectrometry, Fluorescence
Spectrometry, Mass, Electrospray Ionization

Substances

Bridged-Ring Compounds
Imidazoles
Rotaxanes
cucurbit(6)uril
DNA