Molecular Tweezer and Clip in Aqueous Solution: Unexpected Self-Assembly, Powerful Host−Guest Complex Formation, Quantum Chemical1H NMR Shift Calculation

The supramolecular interaction of BPO and ß-CD has been studied by spectrophtometry. The mechanism of the inclusion was studied. The results showed that ß-CD react with BPO to form a 2:1 or 1:1 host-guest complex.The ß-CD reacts with benzoic acid to form a 1:1 host-guest complex after the BPO was reduced by hydroxyl ammonium chloride.Based on the enhancement of the absorbance of BPO produced through complex formation, a spectrophotometric method for determination BPO in bulk aqueous solution in the presence of ß-CD was developed. A linear relationship between the absorbance and BPO concentration was obtained in the range of 0.2～50 μg.ml-1. The proposed method was used to determine the BPO in the flour with satisfactory results. The principal advantage of the proposed method is its excellent selectivity based on molecule recognition of ß-CD and simple.

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Orthogonal self-assembly of an organoplatinum(II) metallacycle and cucurbit[8]uril that delivers curcumin to cancer cells

Proceedings of the National Academy of Sciences ◽

10.1073/pnas.1803800115 ◽

2018 ◽

Vol 115 (32) ◽

pp. 8087-8092 ◽

Cited By ~ 30

Author(s):

Sougata Datta ◽

Santosh K. Misra ◽

Manik Lal Saha ◽

Nabajit Lahiri ◽

Janis Louie ◽

...

Keyword(s):

Complex Formation ◽

Cancer Cells ◽

Self Assembly ◽

Water Solubility ◽

Therapeutic Potential ◽

Water Soluble ◽

Spectroscopic Techniques ◽

Guest Complex ◽

Host Guest Complex ◽

Stat3 Phosphorylation

Curcumin (Cur) is a naturally occurring anticancer drug isolated from the Curcuma longa plant. It is known to exhibit anticancer properties via inhibiting the STAT3 phosphorylation process. However, its poor water solubility and low bioavailability impede its clinical application. Herein, we used organoplatinum(II) ← pyridyl coordination-driven self-assembly and a cucurbit[8]uril (CB[8])-mediated heteroternary host–guest complex formation in concert to produce an effective delivery system that transports Cur into the cancer cells. Specifically, a hexagon 1, containing hydrophilic methyl viologen (MV) units and 3,4,5-Tris[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzoyl groups alternatively at the vertices, has been synthesized and characterized by several spectroscopic techniques. The MV units of 1 underwent noncovalent complexation with CB[8] to yield a host–guest complex 4. Cur can be encapsulated in 4, via a 1:1:1 heteroternary complex formation, resulting in a water-soluble host–guest complex 5. The host–guest complex 5 exhibited ca. 100-fold improved IC50 values relative to free Cur against human melanoma (C32), melanoma of rodents (B16F10), and hormone-responsive (MCF-7) and triple-negative (MDA-MB231) breast cancer cells. Moreover, strong synergisms of Cur with 1 and 4 with combinatorial indexes of <1 across all of the cell lines were observed. An induced apoptosis with fragmented DNA pattern and inhibited expression of phosphor-STAT3 supported the improved therapeutic potential of Cur in heteroternary complex 5.

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Illustration of a computational pipeline for evaluating cyclodextrin host–guest complex formation through conformational capture of bullvalene

The Journal of Chemical Physics ◽

10.1063/5.0045115 ◽

2021 ◽

Vol 154 (15) ◽

pp. 154105

Author(s):

Zahra Shadfar ◽

Oussama Yahiaoui ◽

Thomas A. Collier ◽

Thomas Fallon ◽

Jane R. Allison

Keyword(s):

Complex Formation ◽

Computational Pipeline ◽

Guest Complex ◽

Host Guest Complex

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Enhanced photocatalytic activity of gold nanoparticles driven by supramolecular host–guest chemistry

Chemical Communications ◽

10.1039/c6cc09600j ◽

2017 ◽

Vol 53 (13) ◽

pp. 2126-2129 ◽

Cited By ~ 9

Author(s):

Marc Padilla ◽

Francesca Peccati ◽

José Luis Bourdelande ◽

Xavier Solans-Monfort ◽

Gonzalo Guirado ◽

...

Keyword(s):

Gold Nanoparticles ◽

Photocatalytic Activity ◽

Complex Formation ◽

Guest Complex ◽

Host Guest Complex ◽

Photocatalytic Activities ◽

Guest Chemistry

Gold nanoparticles coated with cyclodextrins show enhanced plasmon-based photocatalytic activities by promoting catalyst–reactant approximationviasupramolecular host–guest complex formation.

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Exciton coupling, intramolecular self-complexation, and host-guest complex formation of 6A,6X-bis-(anthracene-9-carbonyl) derivatives of cyclomalto-octaose

Carbohydrate Research ◽

10.1016/0008-6215(89)85177-8 ◽

1989 ◽

Vol 192 ◽

pp. 173-180 ◽

Cited By ~ 5

Author(s):

Akihiko Ueno ◽

Fumio Moriwaki ◽

Akiko Azuma ◽

Tetsuo Osa

Keyword(s):

Complex Formation ◽

Guest Complex ◽

Exciton Coupling ◽

Carbonyl Derivatives ◽

Host Guest Complex ◽

Derivatives Of

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Taco complex-templated highly regio- and stereo-selective photodimerization of a coumarin-containing crown ether

Chemical Communications ◽

10.1039/c6cc10089a ◽

2017 ◽

Vol 53 (10) ◽

pp. 1688-1691 ◽

Cited By ~ 14

Author(s):

Peifa Wei ◽

Haoze Wang ◽

Kecheng Jie ◽

Feihe Huang

Keyword(s):

Complex Formation ◽

Crown Ether ◽

Quantitative Yield ◽

Guest Complex ◽

Type Host ◽

Host Guest Complex ◽

Stereo Selectivity

We design a coumarin-containing bis(m-phenylene)-32-crown-10 derivative which efficiently controls the regio- and stereo-selectivity of the photodimerization of its two terminal coumarin groups templated by taco-type host–guest complex formation to selectively produce the syn-head-to-tail cryptand isomer in quantitative yield.

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Host-Guest Complexation of Aromatic Carboxylic Acids and their Conjugate Bases by β-Cyclodextrins Monosubstituted at C 6 by Linear and Cyclic Alkyl Triamines in Aqueous Solution

Australian Journal of Chemistry ◽

10.1071/ch99100 ◽

1999 ◽

Vol 52 (12) ◽

pp. 1157 ◽

Cited By ~ 6

Author(s):

Suzanna D. Kean ◽

Bruce L. May ◽

Philip Clements ◽

Christopher J. Easton ◽

Stephen F. Lincoln

Keyword(s):

Aqueous Solution ◽

Carboxylic Acid ◽

Complex Stability ◽

Guest Complex ◽

Acid Complex ◽

K Value ◽

Host Guest Complex ◽

Ph Range ◽

Conjugate Bases ◽

Significant Factors

A pH titrimetric study of the complexation of the guests benzoic acid, 4-methylbenzoic acid and (R)- and (S)-2-phenylpropanoic acids and their conjugate bases by the host 6A-[2-(2-aminoethylamino)ethylamino]-, 6A-[3-(3-aminopropylamino)propylamino]-, 6A-(1,4,7-triazacyclononan-1-yl)-, and 6A-(1,5,9-triazacyclododecan-1-yl)-6A-deoxy-β-cyclodextrins (βCDdien, βCDdipn, βCDtacn and βCDtacdo, respectively) is reported. Over the pH range 3.0–11.0, 49 host–guest complexes were detected. Their stability constants (K) range from 220±50 dm3 mol–1 for the βCDdienH22+ ·benzoate– complex to 48000±11000 dm3 mol–1 for the βCDdipnH22+·(S)-2-phenylpropanoic acid complex at 298.2 K and I = 0.10 mol dm–3 (NaClO4). The latter K value is among the highest reported for a complex of a simple carboxylic acid with a substituted β-cyclodextrin. The charge, hydrophobicity and stereochemistry of both host and guest appear to be significant factors in the variation of host–guest complex stability. 1H ROESY n.m.r. studies of some of the complexes formed are also reported.

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