On-off-on fluorescence detection for biomolecules by a fluorescent cage through host-guest complexation in water

Duan, Honghong; Cao, Fan; Zhang, Minjie; Gao, Meng; Cao, Liping

doi:10.1016/j.cclet.2021.11.010

Cited by 33 publications

(18 citation statements)

References 57 publications

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“…[34][35][36][37] In theory, 1 with a hydrophobic cavity and water solubility could be used as a molecular container for drug delivery in aqueous solution. [38][39][40] On the one hand, 1 has several advantages in aqueous recognition and detection. Its TPE units can endow itself with both fluorescent and chiral responses when binding with chiral drugs, which enables the cage to be used for biological imaging without using additional fluorescent dyes.…”

Section: Introductionmentioning

confidence: 99%

A fluorescent, chirality-responsive, and water-soluble cage as a multifunctional molecular container for drug delivery

et al. 2022

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Section: Introductionmentioning

confidence: 99%

A fluorescent, chirality-responsive, and water-soluble cage as a multifunctional molecular container for drug delivery

et al. 2022

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“…Host–guest chemistry is a subcategory in the field of supramolecular chemistry, which has many and highly varied applications in a broad range of sciences, including the environmental, , pharmaceutical, − chemical, − and biochemical industries. − Specific applications include the removal of toxins from wastewater, improving upon drug delivery and stability, in the preparation of epoxy coatings, and in cancer treatment, to mention only a few. More relevant to the present work is the employment of host compounds for the separation of isomers, both constitutional and stereoisomers.…”

Section: Introductionmentioning

confidence: 99%

Selectivity Considerations of the Roof-Shaped Host Compound trans-α,α,α′,α′-Tetrakis(4-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol in Mixed Anisoles

Barton

Caira

Senekal

et al. 2022

Crystal Growth & Design

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The roof-shaped host compound trans-α,α,α′,α′tetrakis(4-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol H1 was assessed for its selectivity behavior in various anisole (ANI) and ortho-, meta-, and para-methylanisole (oMANI, mMANI, and pMANI) mixtures. Guest/guest competition experiments in equimolar binary mixed guest solvents revealed remarkable host selectivities for ANI or mMANI when oMANI or pMANI was also present (90.7−95.3%). Furthermore, the oMANI/pMANI experiment proved H1 to be nearly completely selective for oMANI (91.8%). In ternary experiments, unexpectedly high selectivities toward ANI (82.6%) and mMANI (89.5%) were noted when the solutions were ANI/oMANI/pMANI and oMANI/mMANI/pMANI. Data obtained from binary competition experiments in which the molar quantity of each guest species was sequentially varied correlated exactly with these equimolar experiments, and high selectivity coefficients were calculated for ANI and mMANI when either oMANI or pMANI was also present. Unfortunately, SCXRD analyses on H1•ANI, 2H1•oMANI, and 2H1•pMANI revealed extreme guest disorder, and these could not be modeled. However, in H1•mMANI, the guest molecules were retained in the crystals by means of a close (host)C−H•••π(guest) contact (2.97 Å, 143°). Finally, thermal analyses proved less useful in explaining the observed host selectivity. This work demonstrates that H1 is an extremely selective host compound in very many of the anisole mixtures used in this investigation and, therefore, is a highly suitable candidate to effectively separate and purify such mixtures.

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“…Host−guest chemistry is an ever-burgeoning field of supramolecular science owing to the diverse range of industries in which it finds application as a result of noncovalent interactions between host and guest molecules. As examples, this chemistry has been used to remove toxins from the environment, 8 to stabilize drug actives and serve as their carriers into the human body, 9 to identify important molecules present in the surrounds through fluorescence, 10 and in spectrophotometric applications. 11 Aside from these important functions, host−guest chemistry also plays a critical role in the separation and purification of closely related compounds such as racemic mixtures and positional isomers with identical or near-identical physical properties.…”

Section: Introductionmentioning

confidence: 99%

Host Compound DED: Guest Accommodation Type, Noncovalent Host···Guest Interactions, Crystal Densities, and Thermal Stabilities Ensure High Host Selectivities for 4-Methylanisole in Anisole and Methylanisole Mixtures

Barton

Senekal

Hosten

2022

Crystal Growth & Design

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trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid (DED), dimethyl trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate (H1), and trans-α,α,α′,α′-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (H2) formed complexes with anisole (ANI) and 2-, 3-, and 4-methylanisole (2-, 3-, and 4-MA) in single-solvent recrystallization experiments. DED was observed to possess an overwhelming selectivity for 4-MA when recrystallized from equimolar binary, ternary, and quaternary mixtures (82.2–99.3%) and nonequimolar binary solutions where this guest species was present. It was therefore demonstrated that DED may serve as an efficient host compound for the separation and purification of many of the mixtures employed in this investigation; extremely high K values (K is a measure of the selectivity of the host compound) were calculated in many instances (137.9, 190.7). However, the selectivity behavior of H1 and H2 in analogous experimental conditions could not be established owing to the extremely slow (months) crystal growth process from these mixtures. Single-crystal X-ray diffraction (SCXRD) experiments revealed that 4-MA interacted with DED via two short stabilizing (host)C–O···π(guest) contacts (3.2782(17), 3.3780(17) Å, 145, 138°). This interaction type was absent in 2(DED)·3-MA and weaker in 2(DED)·2-MA (and only one interaction of this kind was present in the latter complex). Additionally, the crystal density of 2(DED)·4-MA (1.335 g·cm–1) was greater than those of 2(DED)·3(ANI) (1.277 g·cm–1), 2(DED)·2-MA (1.257 g·cm–1), and 2(DED)·3-MA (1.283 g·cm–1), alluding to a tighter packing in the complex with the preferred guest species owing to the shorter contacts in this crystal. The higher density was also explained by a significantly shorter intermolecular (host)π···π(host) interaction in the 4-MA-containing complex. Furthermore, 4-MA experienced more constricted channel accommodation compared with ANI, 2- and 3-MA. Finally, 2(DED)·4-MA possessed the greater thermal stability (the onset of the guest release process, T on = 101.8 °C) compared with 2(DED)·3(ANI) (unstable at room temperature), 2(DED)·2-MA (T on = 90.4 °C), and 2(DED)·3-MA (T on = 85.3 °C).

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On-off-on fluorescence detection for biomolecules by a fluorescent cage through host-guest complexation in water

Cited by 33 publications

References 57 publications

A fluorescent, chirality-responsive, and water-soluble cage as a multifunctional molecular container for drug delivery

A fluorescent, chirality-responsive, and water-soluble cage as a multifunctional molecular container for drug delivery

Selectivity Considerations of the Roof-Shaped Host Compound trans-α,α,α′,α′-Tetrakis(4-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol in Mixed Anisoles

Host Compound DED: Guest Accommodation Type, Noncovalent Host···Guest Interactions, Crystal Densities, and Thermal Stabilities Ensure High Host Selectivities for 4-Methylanisole in Anisole and Methylanisole Mixtures

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