Indicator Displacement Assays Inside Live Cells

Norouzy, Amir; Azizi, Zahra; Nau, Werner M.

doi:10.1002/anie.201407808

Cited by 112 publications

(102 citation statements)

References 76 publications

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“…26,27,29,30 These CB[8] controlled systems have been used to advantage in the preparation of supramolecular polymeric systems for biological and materials applications, chemical sensing ensembles, molecular machines, non-covalent promotors of biological dimerization, and supramolecular catalysis. 27,31,32 Given their excellent biocompatibility, other recent efforts have sought to use CB[n]-type receptors to enhance drug solubility, for imaging applications, and as a drug reversal agent. 31,33 Pioneering work in this area was performed by Yang, Zink, and Stoddart based on mesoporous silica nanoparticles that are gated by host•guest recognition processes.…”

Section: Introductionmentioning

confidence: 99%

“…27,31,32 Given their excellent biocompatibility, other recent efforts have sought to use CB[n]-type receptors to enhance drug solubility, for imaging applications, and as a drug reversal agent. 31,33 Pioneering work in this area was performed by Yang, Zink, and Stoddart based on mesoporous silica nanoparticles that are gated by host•guest recognition processes. 23,34 In this paper, we decorate the external surface of Fujita-type Pd 12 L 24 metal organic polyhedra (MOP) with MV ligands, explore their non-covalent functionalization with CB[n], and demonstrate their ability to deliver doxorubicin to cancer cells.…”

Section: Introductionmentioning

confidence: 99%

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Metal–Organic Polyhedron Capped with Cucurbit[8]uril Delivers Doxorubicin to Cancer Cells

et al. 2016

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Self-assembly of ligand 1 and Pd(NO3)2 delivers Fujita-type metal organic polyhedron (MOP) 3 which bears 24 covalently attached methyl viologen units on its external surface as evidenced by 1H NMR, DOSY NMR, electrospray mass spectrometry, TEM, and AFM measurements. MOP 3 undergoes non-covalent complexation with cucurbit[n]urils to yield MOPs 4 – 6 with diameter ≈ 5–6 nm. MOP 5 can be fully loaded with doxorubicin prodrug 2 via hetero ternary complex formation to yield 7. The MOPs exhibit excellent stability toward neutral to slightly acidic pH in 10 mM sodium phosphate buffer mitigating the concern of disassembly during circulation. The results of MTS assays show that MOP 7 is 10-fold more cytotoxic toward HeLa cells than equimolar quantities of doxorubicin prodrug 2. The enhanced cytotoxicity can be traced to a combination of enhanced cellular uptake of 7 and DOX release as demonstrated by flow cytometry and confocal fluorescence microscopy. The confluence of properties imparted by the polycationic MOP architecture and plug-and-play CB[n] complexation provides a potent new platform for drug delivery application.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Metal–Organic Polyhedron Capped with Cucurbit[8]uril Delivers Doxorubicin to Cancer Cells

et al. 2016

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“…67 Sulfonated calixarenes look like terrible candidates for cellbased studies. 29,56,[70][71][72][73][74] Our collaborators in the Strahl lab used a proximity ligation assay that probes the co-localization of H3K4me3 and MLL5 in C2C12 cells (Fig. 68 They are highly charged at neutral pH.…”

Section: Cell-based Studiesmentioning

confidence: 99%

Host–guest chemistry that directly targets lysine methylation: synthetic host molecules as alternatives to bio-reagents

Hof

2016

Chem. Commun.

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Post-translational methylation is a chemically simple modification, but regulates the function of hundreds of proteins in profound ways. This Feature Article will report on the basic aspects of protein methylation, and will offer a personal perspective on our recent efforts at making supramolecular hosts that can bind and discriminate among post-translationally methylated partners. The article highlights several general lessons drawn from these efforts and related work by other groups. It also describes some ways in which supramolecular approaches are inherently well suited to provide tools that drive new research in the life sciences.

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“…pH, chemical, electrochemical, photochemical). 15 For example, unfunctionalized CB[n] containers have featured prominently in a variety of applications including drug delivery, 16 chemical sensing ensembles, 17 supramolecular catalysis, peptide and protein recognition, 18 supramolecular materials, 11,19 and affinity capture materials. 20 In order to further augment the recognition properties of the CB[n] systems, the development of methods for the selective (mono)functionalization of CB[n] have been pursued.…”

Section: Introductionmentioning

confidence: 99%

Cationic acyclic cucurbit[n]uril-type containers: synthesis and molecular recognition toward nucleotides

Sigwalt

Zavalij

Isaacs

2016

Supramolecular Chemistry

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We report the synthesis of M2NH3 which is a tetracationic analogue of our prototypical acyclic CB[n]-type molecular container M2. Both M1NH3 and M2NH3 possess excellent solubility in D2O and do not undergo intermolecular self-association processes that would impinge on their molecular recognition properties. Compounds M1NH3 and M2NH3 do, however, undergo an intramolecular self-complexation process driven by ion-dipole interactions between the ureidyl C=O portals and the OCH2CH2NH3 arms along with inclusion of one aromatic wall in its own hydrophobic cavity. The Ka values for M1NH3 and M2NH3 toward seven nucleotides were determined by 1H NMR titration and found to be quite modest (Ka in the 102 – 103 M−1 range) although M2NH3 is slightly more potent. The more highly charged guests (e.g. ATP) form stronger complexes with M1NH3 and M2NH3 than the less highly charged guest (e.g. ADP, AMP). The work highlights the dominant influence of the ureidyl C=O portals on the molecular recognition behavior of acyclic CB[n]-type receptors and suggests routes (e.g. more highly charged arms) to enhance their recognition behavior toward anions.

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Indicator Displacement Assays Inside Live Cells

Cited by 112 publications

References 76 publications

Metal–Organic Polyhedron Capped with Cucurbit[8]uril Delivers Doxorubicin to Cancer Cells

Metal–Organic Polyhedron Capped with Cucurbit[8]uril Delivers Doxorubicin to Cancer Cells

Host–guest chemistry that directly targets lysine methylation: synthetic host molecules as alternatives to bio-reagents

Cationic acyclic cucurbit[n]uril-type containers: synthesis and molecular recognition toward nucleotides

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