Supramolecular micelle-based nucleoapzymes for the catalytic oxidation of dopamine to aminochrome

Albada, Bauke; Vries, Jan Willem de; Liu, Qing; Golub, Eyal; Klement, W.J.; Herrmann, Andreas; Willner, Itamar

doi:10.1039/c6cc01115b

Cited by 10 publications

(12 citation statements)

References 49 publications

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“… 4 , 5 Further enhancement of the catalytic activity ( k cat ) can be achieved by nucleotide supplements, 6 or by conjugation of the hGQ DNAzyme to an aptamer sequence that binds to the substrate. 7 , 8 Such so-called nucleoapzymes can be subjected to rational design 9 or incorporation into supramolecular assemblies. 8 The predictable formation of the catalytically active DNAzyme nanostructure has resulted in its incorporation into complex oligonucleotide assemblies of which the designed activity depends on an external trigger.…”

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confidence: 99%

“… 7 , 8 Such so-called nucleoapzymes can be subjected to rational design 9 or incorporation into supramolecular assemblies. 8 The predictable formation of the catalytically active DNAzyme nanostructure has resulted in its incorporation into complex oligonucleotide assemblies of which the designed activity depends on an external trigger. 10 Apart from the oxidation of chemical substrates in sensor-type setups, 10 some conversions mimic biological processes such as the oxidation of dopamine to aminochrome or of N -hydroxy- l -arginine to nitric oxide and l -citrulline.…”

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confidence: 99%

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Site-Specific and Trigger-Activated Modification of Proteins by Means of Catalytic Hemin/G-quadruplex DNAzyme Nanostructures

Keijzer

Albada

2020

Bioconjugate Chem.

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Catalytic nanostructures have the potency to mimic enzymatic features. In this paper, we show that the complex between hemin and G-quadruplex DNA efficiently catalyzes the modification of proteins with N -methyl luminol derivatives. Final conversions are reached within 15–30 min, and LC-MS analysis of tryptic digests of the proteins shows that the reaction proceeds with chemoselectivity for electron-rich aromatic residues (Tyr ≫ Trp), and the site-specificity of the modification depends on the sequence and secondary structure folding of the G-quadruplex nanostructure. Furthermore, the modification can be applied on proteins with different biomedical functions, and the nanostructure can be designed to contain a regulatory element in order to regulate protein modification by an external stimulus.

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confidence: 99%

Site-Specific and Trigger-Activated Modification of Proteins by Means of Catalytic Hemin/G-quadruplex DNAzyme Nanostructures

Keijzer

Albada

2020

Bioconjugate Chem.

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“…Over the past years, various strategies have been applied to enhance the enzymatic proficiency of G4-DNAzymes, including the addition of a proximal adenine or cytosine nucleotide to the 3' G-quartet of a parallel G4 (the preferential hemin binding site) [14][15][16][17][18][19][20][21] , the covalent linking of a substrate aptamer to G4 sequences [22][23][24] , or the addition of small-molecular catalytic enhancers [25][26][27][28][29][30] . Interestingly, most if not all G4-DNAzymes described to date are fueled by hydrogen peroxide (H2O2) as the stoichiometric oxidant 9 .…”

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An oxidatively damaged G-quadruplex/hemin DNAzyme

et al. 2020

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“…The authors also pointed out that further optimization of the length of the lipid tails and rigidification of the micelles by crosslinking may make the catalytic performances of the micellar DNAzymes more effective. [ 107 ]…”

Section: Biomedical Applications Of Aoassmentioning

confidence: 99%

Engineered Aptamer‐Organic Amphiphile Self‐Assemblies for Biomedical Applications: Progress and Challenges

Xiong

Liu

Wang

et al. 2021

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Moreover, the characteristic of being nucleic acid molecules provides aptamers with additional distinctive properties: 1) easy modification with a variety of functionalities in a controllable manner; 2) sequence-specific hybridization via Watson−Crick base pairing; 3) conformational changes induced by specific molecular interactions between target and aptamer. All these features make aptamers promising targeting ligands for biomedical applications. Currently, by combining the advantages of nanotechnology and DNA synthesis technology, a wide range of aptamer-functioned nanomaterials have been designed, including 2D nanosheets, gold nanoparticles, liposomes, polymer nanoparticles, DNA nanostructures, which exhibit great potential in bioimaging, biosensing, gene therapy, and targeted drug delivery. [3] Among the aptamer-functionalized nano-systems, aptamer-organic amphiphile self-assemblies (AOASs) have received increasing attention in biomedical field, due to their unique advantages. [4,5] Aptamer-organic amphiphiles (AOAs), prepared by covalently conjugating organic moieties to hydrophilic aptamers, are building blocks to form AOASs via noncovalent driving forces like hydrophobic interactions, hydrogen-bonding, electrostatic interactions, van der Waals forces, and Watson−Crick base pairing. [6,7] The spontaneously shaped AOASs normally have small sizes (10-100 nm) and low critical micelle concentrations (CMCs), which are favorable for tumor accumulation through enhanced permeability and retention (EPR) effect. [8] Generally, AOASs are coreshell nanostructures, where the core and shell are aggregated hydrophobic segment and aptamer corona, respectively. The hydrophobic core can be used to carry multiple water-insoluble compounds, making AOASs serve as versatile carriers for cargo delivery. [9] The aptamer corona renders AOASs with several intriguing merits. First, the high density of aptamers outside endows AOASs with enhanced target binding affinity, called multivalent effect. [10] In addition, the close packing of nucleic acid strands of AOASs can predominantly increase the resistance to nuclease, which is always a big challenge for nucleic acid-based materials. It is speculated that the steric hindrance and a dense anion generated from the close packing of nucleic acid strands could hinder the access of nuclease Currently, nucleic acid aptamers are exploited as robust targeting ligands in the biomedical field, due to their specific molecular recognition, little immunogenicity, low cost, ect. Thanks to the facile chemical modification and high hydrophilicity, aptamers can be site-specifically linked with hydrophobic moieties to prepare aptamer-organic amphiphiles (AOAs), which spontaneously assemble into aptamer-organic amphiphile self-assemblies (AOASs). These polyvalent self-assemblies feature with enhanced target-binding ability, increased resistance to nuclease, and efficient cargo-loading, making them powerful platforms for bioapplications, including targeted drug delivery, cellbased cancer therapy, biosens...

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Supramolecular micelle-based nucleoapzymes for the catalytic oxidation of dopamine to aminochrome

Cited by 10 publications

References 49 publications

Site-Specific and Trigger-Activated Modification of Proteins by Means of Catalytic Hemin/G-quadruplex DNAzyme Nanostructures

Site-Specific and Trigger-Activated Modification of Proteins by Means of Catalytic Hemin/G-quadruplex DNAzyme Nanostructures

An oxidatively damaged G-quadruplex/hemin DNAzyme

Engineered Aptamer‐Organic Amphiphile Self‐Assemblies for Biomedical Applications: Progress and Challenges

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