Dataset Information

Host-guest complexation of cucurbit[8]uril with two enantiomers.

ABSTRACT: Host-guest complexation of cucurbit[8]uril (Q[8]) with two enantiomers, D-3-(2-naphthyl)-alanine (D-NA) and L-3-(2-naphthyl)-alanine (L-NA), has been fully investigated. Experimental data indicate that double guests reside within the cavity of Q[8] in both aqueous solution and solid state, generating highly stable homoternary complexes D-NA₂@Q[8] and L-NA₂@Q[8].

SUBMITTER: Gao ZZ

PROVIDER: S-EPMC5353740 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Host-guest complexation of cucurbit[8]uril with two enantiomers.

Gao Zhong-Zheng ZZ Lin Rui-Lian RL Bai Dong D Tao Zhu Z Liu Jing-Xin JX Xiao Xin X

Scientific reports 20170316

Host-guest complexation of cucurbit[8]uril (Q[8]) with two enantiomers, D-3-(2-naphthyl)-alanine (D-NA) and L-3-(2-naphthyl)-alanine (L-NA), has been fully investigated. Experimental data indicate that double guests reside within the cavity of Q[8] in both aqueous solution and solid state, generating highly stable homoternary complexes D-NA<sub>2</sub>@Q[8] and L-NA<sub>2</sub>@Q[8]. ...[more]

PMID: 28300189

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Project description:BackgroundSupramolecular theranostics have exhibited promising potentials in disease diagnosis and therapy by taking advantages of the dynamic and reversible nature of non-covalent interactions. It is extremely important to figure out the stability of the driving forces in physiological environment for the preparation of theranostic systems.MethodsThe host-guest complexation between cucurbit[8]uril (CB[8]), 4,4'-bipyridinium, and napththyl guest was fully studied using various characterizations, including nuclear magnetic resonance spectroscopy, ultraviolet-visible (UV-vis) spectroscopy, isothermal titration calorimetry (ITC). The association constants of this ternary complex were determined using isothermal titration calorimetry. The stability of the non-covalent interactions and self-assemblies form from this molecular recognition was confirmed by UV-vis spectroscopy and dynamic light scattering (DLS). A supramolecular nanomedicine was constructed on the basis of this 1:1:1 ternary recognition, and its in vitro and in vivo anticancer efficacy were thoroughly evaluated. Positron emission tomography (PET) imaging was used to monitor the delivery and biodistribution of the supramolecular nanomedicine.ResultsVarious experiments confirmed that the ternary complexation between 4,4'-bipyridinium, and napththyl derivative and CB[8] was stable in physiological environment, including phosphate buffered solution and cell culture medium. Supramolecular nanomedicine (SNM@DOX) encapsulating a neutral anticancer drug (doxrubincin, DOX) was prepared based on this molecular recognition that linked the hydrophobic poly(ε-caprolactone) chain and hydrophilic polyethylene glycol segment. The non-covalent interactions guaranteed the stability of SNM@DOX during blood circulation and promoted its tumor accumulation by taking advantage of the enhanced permeability and retention effect, thus greatly improving the anti-tumor efficacy as compared with the free drug.ConclusionArising from the host-enhanced charge-transfer interactions, the CB[8]-based ternary recognition was stable enough in physiological environment, which was suitable for the fabrication of supramolecular nanotheranostics showing promising potentials in precise cancer diagnosis and therapy.

Dataset Information

Host-guest complexation of cucurbit[8]uril with two enantiomers.

Publications

Host-guest complexation of cucurbit[8]uril with two enantiomers.

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