Dataset Information

Photo-responsive cyclodextrin/anthracene/Eu³⁺ supramolecular assembly for a tunable photochromic multicolor cell label and fluorescent ink.

ABSTRACT: A photo-responsive supramolecular assembly was successfully constructed through the stoichiometric 2?:?1 non-covalent association of two 4-(anthracen-2-yl)pyridine-2,6-dicarboxylic acid (1) units in one ?-cyclodextrin (?-CD) cavity, followed by the subsequent coordination polymerization of the ?-CD·1 ₂ (1 ₂ = two 1) inclusion complex with Eu(iii). Interestingly, owing to the photodimerization behavior of anthracene units and the excellent luminescence properties of Eu(iii), the Eu³⁺??-CD·1 ₂ system showed multicolor fluorescence emission from cyan to red by irradiation for 0-16 minutes. Moreover, white light emission with CIE coordinates (0.32 and 0.36) was achieved at 4 min. Importantly, white light-containing multicolor emission could be obtained in water, solid films and living cells. Especially, the Eu³⁺??-CD·1 ₂ system could tag living cells with marvelous white fluorescence and display no obvious cytotoxicity. Thus, this supramolecular assembly offers a new pathway in the fields of tunable photochromic fluorescent ink and cell labelling.

SUBMITTER: Zhou W

PROVIDER: S-EPMC6429777 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Photo-responsive cyclodextrin/anthracene/Eu3+ supramolecular assembly for a tunable photochromic multicolor cell label and fluorescent ink.

Zhou Weilei W Chen Yong Y Yu Qilin Q Li Peiyu P Chen Xuman X Liu Yu Y

Chemical science 20190204 11

A photo-responsive supramolecular assembly was successfully constructed through the stoichiometric 2 : 1 non-covalent association of two 4-(anthracen-2-yl)pyridine-2,6-dicarboxylic acid (1) units in one γ-cyclodextrin (γ-CD) cavity, followed by the subsequent coordination polymerization of the γ-CD·1 2 (1 2 = two 1) inclusion complex with Eu(iii). Interestingly, owing to the photodimerization behavior of anthracene units and the excellent lumines ...[more]

PMID: 30996922

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Project description:UnlabelledBackgroundRecently, various metallocenes were synthesized and analyzed by biological activity point of view (such as antiproliferative properties): ruthenocenes, cobaltoceniums, titanocenes, zirconocenes, vanadocenes, niobocenes, molibdocenes etc. Two main disadvantages of metallocenes are the poor hydrosolubility and the hydrolytic instability. These problems could be resolved in two ways: synthetically modifying the structure or finding new formulations with enhanced properties. The aqueous solubility of metallocenes with cytostatic activities could be enhanced by molecular encapsulation in cyclodextrins, as well as the hydrolytic instability of these compounds could be reduced.ResultsThis study presents a theoretical approach on the nanoencapsulation of a series of titanocenes with cytotoxic activity in ?-, ?-, and ?-cyclodextrin. The HyperChem 5.11 package was used for building and molecular modelling of titanocene and cyclodextrin structures, as well as for titanocene/cyclodextrin complex optimization. For titanocene/cyclodextrin complex optimization experiments, the titanocene and cyclodextrin structures in minimal energy conformations were set up at various distances and positions between molecules (molecular mechanics functionality, MM+). The best interaction between titanocene structures and cyclodextrins was obtained in the case of ?- and ?-cyclodextrin, having the hydrophobic moieties oriented to the secondary face of cyclodextrin. The hydrophobicity of titanocenes (logP) correlate with the titanocene-cyclodextrin interaction parameters, especially with the titanocene-cyclodextrin interaction energy; the compatible geometry and the interaction energy denote that the titanocene/?- and ?-cyclodextrin complex can be achieved. Valuable quantitative structure-activity relationships (QSARs) were also obtained in the titanocene class by using the same logP as the main parameter for the in vitro cytotoxic activity against HeLa, K562, and Fem-x cell lines.ConclusionsAccording to our theoretical study, the titanocene/cyclodextrin inclusion compounds can be obtained (high interaction energy; the encapsulation is energetically favourable). Further, the most hydrophobic compounds are better encapsulated in ?- and ?-cyclodextrin molecules and are more stable (from energetically point of view) in comparison with ?-cyclodextrin case. This study suggests that the titanocene / ?- and ?-cyclodextrin complexes (or synthetically modified cyclodextrins with higher water solubility) could be experimentally synthesized and could have enhanced cytotoxic activity and even lower toxicity.

Dataset Information

Photo-responsive cyclodextrin/anthracene/Eu³⁺ supramolecular assembly for a tunable photochromic multicolor cell label and fluorescent ink.

Publications

Photo-responsive cyclodextrin/anthracene/Eu<sup>3+</sup> supramolecular assembly for a tunable photochromic multicolor cell label and fluorescent ink.

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