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A Supramolecular Catalyst Self-Assembled From Polyoxometalates and Cationic Pillar[5]arenes for the Room Temperature Oxidation of Aldehydes.

ABSTRACT: Oxidizing aldehydes to generate carboxylic acids is a crucial reaction in nature and in chemical industry. The aldehyde oxidation, an easily achieved process in liver cells, is inert toward autoxidation in industrial production and difficultly achieved under enzymatic condition (in water, at pH 7, at room temperature). Herein, we prepared a supramolecular catalyst which are nanospheres assembled in aqueous media by chromium centered Anderson polyoxometalates Na3[CrMo6O18(OH)3] (namely, CrMo6) and cationic pillar[5]arenes (namely, P5A) with 10 positive charges which can be used as the phase transfer catalysts (PTCs). This supramolecular catalyst was exploited on aldehydes oxidation under enzymatic condition with relatively good conversion. Through DLS monitoring, the diameters of nanospheres were variable while changing the charge ratios of the ionic complexes (P5A-CrMo6), and it is probably because of the closer charge ratios causing the more compact assemblies. Also, the nano-morphologies were monitored by TEM and SEM, and the nanostructures were characterized by zeta potential, the X-ray energy-dispersive spectroscopy (EDS), elemental analysis.

SUBMITTER: Zeng M

PROVIDER: S-EPMC6198131 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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A Supramolecular Catalyst Self-Assembled From Polyoxometalates and Cationic Pillar[5]arenes for the Room Temperature Oxidation of Aldehydes.

Zeng Mengyan M Chen Kun K Tan Junyan J Zhang Jie J Wei Yongge Y

Frontiers in chemistry 20181016

Oxidizing aldehydes to generate carboxylic acids is a crucial reaction in nature and in chemical industry. The aldehyde oxidation, an easily achieved process in liver cells, is inert toward autoxidation in industrial production and difficultly achieved under enzymatic condition (in water, at pH 7, at room temperature). Herein, we prepared a supramolecular catalyst which are nanospheres assembled in aqueous media by chromium centered Anderson polyoxometalates Na3[CrMo6O ...[more]

PMID: 30386765

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Project description:Bacterial biofilms are a major threat to human health, causing persistent infections that lead to millions of fatalities worldwide every year. Biofilms also cause billions of dollars of damage annually by interfering with industrial processes. Recently, cationic pillararenes were found to be potent inhibitors of biofilm formation in Gram-positive bacteria. To identify the structural features of pillararenes that result in antibiofilm activity, we evaluated the activity of 16 cationic pillar[5]arene derivatives including that of the first cationic water-soluble pillar[5]arene-based rotaxane. Twelve of the derivatives were potent inhibitors of biofilm formation by Gram-positive pathogens. Structure activity analyses of our pillararene derivatives indicated that positively charged head groups are critical for the observed antibiofilm activity. Although certain changes in the lipophilicity of the substituents on the positively charged head groups are tolerated, dramatic elevation in the hydrophobicity of the substituents or an increase in steric bulk on these positive charges abolishes the antibiofilm activity. An increase in the overall positive charge from 10 to 20 did not affect the activity significantly, but pillararenes with 5 positive charges and 5 long alkyl chains had reduced activity. Surprisingly, the cavity of the pillar[n]arene is not essential for the observed activity, although the macrocyclic structure of the pillar[n]arene core, which facilitates the clustering of the positive charges, appears important. Interestingly, the compounds found to be efficient inhibitors of biofilm formation were nonhemolytic at concentrations that are ∼100-fold of their MBIC50 (the minimal concentration of a compound at which at least 50% inhibition of biofilm formation was observed compared to untreated cells). The structure-activity relationship guidelines established here pave the way for a rational design of potent cationic pillar[n]arene-based antibiofilm agents.

Dataset Information

A Supramolecular Catalyst Self-Assembled From Polyoxometalates and Cationic Pillar[5]arenes for the Room Temperature Oxidation of Aldehydes.

Publications

A Supramolecular Catalyst Self-Assembled From Polyoxometalates and Cationic Pillar[5]arenes for the Room Temperature Oxidation of Aldehydes.

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