Interactions of oligomers of organic polyethers with histidine amino acid

Zobnina, V. G.; Kosevich, M. V.; Chagovets, Vitaliy; Boryak, Oleg A.; Vékey, Károly; Gömöry, Ágnes; Kulyk, Anna N.

doi:10.1002/rcm.5342

Cited by 7 publications

(9 citation statements)

References 41 publications

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“…46 Indeed, PEG, with its weakly hydrogen-bonding ether linkages (O ether and terminal OH), is able to interact with charged amino acids side chains, as K and E, through hydrogen-bonding mechanisms. 47,48 …”

Section: Resultsmentioning

confidence: 99%

“…The electrostatic attraction between PEG and positive charges is not surprising because it is well-known that PEG acts as a polyelectrolyte, associating with cations . Indeed, PEG, with its weakly hydrogen-bonding ether linkages (O ether and terminal OH), is able to interact with charged amino acids side chains, as K and E, through hydrogen-bonding mechanisms. , …”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Computational Design of Oligopeptide Containing Poly(ethylene glycol) Brushes for Stimuli-Responsive Drug Delivery

Stanzione

Jayaraman

2015

J. Phys. Chem. B

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Stimuli-responsive biomaterials are used to facilitate drug and gene delivery by shielding the drug/gene during circulation times and selectively releasing the cargo at the desired target. Within stimuli-responsive materials, pH-responsive materials are exploited for delivery to specific organs, intracellular compartments, cancer cells, site of inflammation or infection as those sites are characterized by pH that is different from the blood pH. In this paper we use molecular dynamics (MD) simulations to design such pH-responsive biomaterials where the balance between the various intermolecular interactions (e.g., electrostatics, van der Waals) within the biomaterials allow biofunctional molecules to be reversibly shielded and exposed to the environment with change in pH. In our model the shielding aspect is imparted by a polyethylene glycol (PEG) brush and the pH-responsive component is a PEG-tethered oligopeptide that undergoes changes in conformations via protonation of residues upon changes in pH. Starting with a PEG-tethered peptide in a monodisperse short PEG brush, we first vary the composition and sequence of histidine (H), lysine (K), and glutamate (E) along the oligopeptide sequence to find the design parameters that maximize the shielding and exposure of the oligopeptide at pH ~ 7.0 and pH < 7.0, respectively. Then, we probe the effect of the PEG brush on the conformations of the oligopeptides by simulating PEG-tethered peptide in a bimodal PEG brush containing short PEG and long PEG chains. We characterize the intermolecular interactions involving the PEG, peptide, and solvent that influence the shielded and exposed conformations of the oligopeptides at the two different pHs. In a short monodisperse PEG brush, with a longer PEG-tethered peptide containing large blocks of histidines that undergo change in protonation state as a response to pH change, placed between a protonated lysine and deprotonated glutamate, the PEG brush exhibits maximum shielding and exposure with pH change. This change from shielded to exposed state is driven by electrostatic repulsion upon H protonation. The presence of long PEG chains in a bimodal PEG brush leads to dominating PEG–peptide attractive interactions that reduces the contrast in shielded and exposed conformations of the PEG-tethered peptide upon protonation of histidines.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Computational Design of Oligopeptide Containing Poly(ethylene glycol) Brushes for Stimuli-Responsive Drug Delivery

Stanzione

Jayaraman

2015

J. Phys. Chem. B

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“…Within protocol III, the tissue was loaded with PEG molecules when the 1% SDS solution was introduced (Figure ). Two effects might be important: first, a possible membrane destabilizing effect of PEG (Uchimura et al ., ) and second, a noncovalent intermolecular interaction of PEG molecules with components of the ECM (Zobnina et al ., ; Michel et al ., ). The first effect could speed up lysis of remaining cells, thus SDS molecules could interact with cytoplasmic content quicker compared to protocol II in which no PEG was used.…”

Section: Discussionmentioning

confidence: 98%

Dewaxed ECM: A simple method for analyzing cell behaviour on decellularized extracellular matrices

Ofenbauer

Sebinger

Prewitz

et al. 2012

J Tissue Eng Regen Med

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Decellularization techniques have been used on a wide variety of tissues to create cell-seedable scaffolds for tissue engineering. Finding a suitable decellularization protocol for a certain type of tissue can be laborious, especially when organ perfusion devices are needed. In this study, we report a quick and simple method for comparing decellularization protocols combining the use of paraffin slices and two-dimensional cell cultures. We developed three decellularization protocols for adult murine kidney that yielded decellularized extracellular matrices (ECMs) with varying histological properties. The resulting paraffin-embedded ECM slices were deparaffinized and reseeded with murine embryonic stem cells (mESCs). We analyzed cell attachment four days post seeding via determination of cell numbers, and used quantitative Real-Time PCR 13 days post seeding to measure gene expression levels of two genes associated with renal development, Pax2 and Pou3f3. The three decellularization protocols produced kidney-matrices that showed clearly distinguishable results. We demonstrated that formerly paraffin-embedded decellularized ECMs can effectively influence differentiation of stem cells. This method can be used to identify optimal decellularization protocols for recellularization of three-dimensional tissue-scaffolds with embryonic stem cells and other tissue-specific cell types.

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“…Complexing compounds are very popular because of the wide application range. They are used among other things: in medicine as a capture and neutralize metal ions compounds [3,4,5], as catalysts in polymerization reactions [6,7,8,9,10,11,12,13], as crown ether complex cation ionic liquids catalysts [14,15,16], as activators [17,18], as protecting groups in organic synthesis [19], as chiral gels utilized as memory-erasing recycle system or logic gates based on the stimuli-responsive gel–sol transition, as chiral selectors to separate amino acid enantiomers in capillary electrophoresis analysis of amino acid enantiomers [20,21,22,23], as effective sensors [24,25,26,27,28,29], as a component of ion-selective membrane electrode [30,31], as extractants for various elements [32,33,34,35,36], and as hydraphiles—synthetic ionophores designed to mimic some properties of protein channels that conduct cations such as sodium [37].…”

Section: Introductionmentioning

confidence: 99%

New Kind of Polymer Materials Based on Selected Complexing Star-Shaped Polyethers

Swinarew

Swinarew²,

Gabor

et al. 2019

Polymers

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In today’s analytical trends, there is an ever-increasing importance of polymeric materials for low molecular weight compounds including amines and drugs because they can act as carriers or capture amines or drugs. The use of this type of materials will allow the development of modern materials for the chromatographic column beds and the substrates of selective sensors. Moreover, these kinds of materials could be used as a drug carrier. Therefore, the aim of this study is presenting the synthesis and complexing properties of star-shaped oxiranes as a new sensor for the selective complexation of low molecular weight compounds. Propylene oxide and selected oxirane monomers with carbazolyl in the substituent were selected as the monomers in this case and tetrahydrofuran as its solvent. The obtained polymer structures were characterized using the MALDI-TOF. It was found that in the initiation step potassium hydride deprotonates the monomer molecule and takes also part in the nucleophilic substitution. The resulting polymeric material preferably cross-linked with selected di-oxiranes (1,2,7,8-diepoksyoktan in respect ratio 3:1 according to active center) was then used as a stationary phase in the column and thin layer chromatography for amine separation and identification. Sorption ability of the resulting deposits was determined using a quartz microbalance (QCMB). The study was carried out in stationary mode and flow cells to simulate actual operating phase conditions. Based on changes in electrode vibration frequency, the maximum amount of adsorbed analyte and the best conditions for its sorption were determined.

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Interactions of oligomers of organic polyethers with histidine amino acid

Abstract: The self-organization of polyether chains around the protonated imidazole group of histidine was revealed. This finding should be considered when modelling a pegylated protein structure and polyether-based organic nanoparticles.

Cited by 7 publications

References 41 publications

Computational Design of Oligopeptide Containing Poly(ethylene glycol) Brushes for Stimuli-Responsive Drug Delivery

Computational Design of Oligopeptide Containing Poly(ethylene glycol) Brushes for Stimuli-Responsive Drug Delivery

Dewaxed ECM: A simple method for analyzing cell behaviour on decellularized extracellular matrices

New Kind of Polymer Materials Based on Selected Complexing Star-Shaped Polyethers

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