Iodide-Selective Synthetic Ion Channels Based on Shape-Persistent Organic Cages

Benke, Bahiru Punja; Aich, Pulakesh; Kim, Young-Hoon; Kim, Kyung Lock; Rohman, Rumum; Hong, Seongwon; Hwang, In‐Chul; Lee, Eun Hui; Roh, Joon Ho; Kim, Kimoon

doi:10.1021/jacs.7b02708

Cited by 120 publications

(104 citation statements)

References 43 publications

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“…To compare with Kim's highly selective iodide channel based on a porphyrin‐derived covalent organic cage, the same assay conditions used by Kim were applied to 1 a (see Figure S22). The resulting quenching of HPTS fluorescence follows the same selectivity sequence as reported.…”

Section: Resultsmentioning

confidence: 99%

“…The first iodide channel was reported by the group of Gin and is based on a β‐cyclodextrin, exhibiting low activity and low selectivity among halides (I − >Br − >Cl − ) . Recent work by the group of Kim has shown that a porphyrin‐based covalent organic cage can achieve high I − /Cl − selectivity but with quite moderate iodide transport activity . As such, there is a need to develop highly active and selective artificial iodide transporters for potential medical treatment of IDD.…”

Section: Introductionmentioning

confidence: 99%

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Polyhydrazide‐Based Organic Nanotubes as Efficient and Selective Artificial Iodide Channels

Roy¹,

Joshi

et al. 2020

Angew Chem Int Ed

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Reported herein is a series of pore‐containing polymeric nanotubes based on a hydrogen‐bonded hydrazide backbone. Nanotubes of suitable lengths, possessing a hollow cavity of about a 6.5 Å diameter, mediate highly efficient transport of diverse types of anions, rather than cations, across lipid membranes. The reported polymer channel, having an average molecular weight of 18.2 kDa and 3.6 nm in helical height, exhibits the highest anion‐transport activities for iodide (EC50=0.042 μm or 0.028 mol % relative to lipid), whcih is transported 10 times more efficiently than chlorides (EC50=0.47 μm). Notably, even in cholesterol‐rich environment, iodide transport activity remains high with an EC50 of 0.37 μm. Molecular dynamics simulation studies confirm that the channel is highly selective for anions and that such anion selectivity arises from a positive electrostatic potential of the central lumen rendered by the interior‐pointing methyl groups.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Polyhydrazide‐Based Organic Nanotubes as Efficient and Selective Artificial Iodide Channels

Roy¹,

Joshi

et al. 2020

Angew Chem Int Ed

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“…To date, DCC has been successfully appliedt oar ange of biological templates,i ncluding enzymes, receptors, transmembrane transporters, nucleotides, and polymer-supported targets. [11][12][13][14][15][16][17] However, most, if not all, such biologicallyt emplated DCC approaches employ only as inglet emplate to directt he self-assembly process;t his severelyl imits the applications of DCC approaches.…”

Section: Introductionmentioning

confidence: 99%

Multiprotein Dynamic Combinatorial Chemistry: A Strategy for the Simultaneous Discovery of Subfamily‐Selective Inhibitors for Nucleic Acid Demethylases FTO and ALKBH3

Das

Yang

Dong

et al. 2018

Chemistry An Asian Journal

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Dynamic combinatorial chemistry (DCC) is a powerful supramolecular approach for discovering ligands for biomolecules. To date, most, if not all, biologically templated DCC systems employ only a single biomolecule to direct the self-assembly process. To expand the scope of DCC, herein, a novel multiprotein DCC strategy has been developed that combines the discriminatory power of a zwitterionic "thermal tag" with the sensitivity of differential scanning fluorimetry. This strategy is highly sensitive and could differentiate the binding of ligands to structurally similar subfamily members. Through this strategy, it was possible to simultaneously identify subfamily-selective probes against two clinically important epigenetic enzymes: FTO (7; IC =2.6 μm) and ALKBH3 (8; IC =3.7 μm). To date, this is the first report of a subfamily-selective ALKBH3 inhibitor. The developed strategy could, in principle, be adapted to a broad range of proteins; thus it is of broad scientific interest.

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“…[15] Large, rigid POCs have the potential to incorporate multiple non-interacting active sites. This broad structural diversity in combination with soluble processing that is not possible with most heterogeneous materials has led to POC applications in gas separation, [16] artificial ion channels, [17] nanoparticle encapsulation, [18] batteries, [19] and supramolecular allostery. [20] The molecular structure of POCs also facilitates post-synthetic modifications where more robust and intricate cages can be obtained.…”

mentioning

confidence: 99%

Supramolecular Tuning Enables Selective Oxygen Reduction Catalyzed by Cobalt Porphyrins for Direct Electrosynthesis of Hydrogen Peroxide

et al. 2020

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We report a supramolecular strategy for promoting the selective reduction of O2 for direct electrosynthesis of H2O2. We utilized cobalt tetraphenylporphyrin (Co‐TPP), an oxygen reduction reaction (ORR) catalyst with highly variable product selectivity, as a building block to assemble the permanently porous supramolecular cage Co‐PB‐1(6) bearing six Co‐TPP subunits connected through twenty‐four imine bonds. Reduction of these imine linkers to amines yields the more flexible cage Co‐rPB‐1(6). Both Co‐PB‐1(6) and Co‐rPB‐1(6) cages produce 90–100 % H2O2 from electrochemical ORR catalysis in neutral pH water, whereas the Co‐TPP monomer gives a 50 % mixture of H2O2 and H2O. Bimolecular pathways have been implicated in facilitating H2O formation, therefore, we attribute this high H2O2 selectivity to site isolation of the discrete molecular units in each supramolecule. The ability to control reaction selectivity in supramolecular structures beyond traditional host–guest interactions offers new opportunities for designing such architectures for a broader range of catalytic applications.

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Iodide-Selective Synthetic Ion Channels Based on Shape-Persistent Organic Cages

Cited by 120 publications

References 43 publications

Polyhydrazide‐Based Organic Nanotubes as Efficient and Selective Artificial Iodide Channels

Polyhydrazide‐Based Organic Nanotubes as Efficient and Selective Artificial Iodide Channels

Multiprotein Dynamic Combinatorial Chemistry: A Strategy for the Simultaneous Discovery of Subfamily‐Selective Inhibitors for Nucleic Acid Demethylases FTO and ALKBH3

Supramolecular Tuning Enables Selective Oxygen Reduction Catalyzed by Cobalt Porphyrins for Direct Electrosynthesis of Hydrogen Peroxide

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