Helical peptide–polyamine and –polyether conjugates as synthetic ionophores

Benincasa, Monica; Francescon, Marco; Fregonese, Massimo; Gennaro, Renato; Pengo, Paolo; Rossi, Paola; Scrimin, Paolo; Tecilla, Paolo

doi:10.1016/j.bmc.2015.10.034

Cited by 4 publications

(3 citation statements)

References 38 publications

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“…PAAs have excellent biocompatibility and degradability make it brilliant in the fields of prodrug, 1 gene delivery, 2−4 vesicles 5 and ionophores. 6 But PAA is quite different from natural protein synthesis; the strict polymerization conditions limit its development and application.…”

Section: Introductionmentioning

confidence: 99%

“…Poly(amino acid)s (PAAs) are one or several kinds of amino acids connected each other by amido linkage to form a long chain, like proteins. PAAs have excellent biocompatibility and degradability make it brilliant in the fields of prodrug, gene delivery, − vesicles and ionophores . But PAA is quite different from natural protein synthesis; the strict polymerization conditions limit its development and application.…”

Section: Introductionmentioning

confidence: 99%

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Facile Synthesis of High Molecular Weight Poly(ethylene glycol)-b-poly(amino acid)s by Relay Polymerization

Luo,

Yuan,

et al. 2024

Biomacromolecules

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Poly(amino acid)s (PAAs) are one kind of favorable biopolymer that can be used as a drug or gene carrier. However, conventional ring-opening polymerization of PAAs is slow and needs a strict anhydrous environment with an anhydrous reagent as well as the product without enough high molecular weight (M n ), which limits the expanding of PAAs' application. Herein, we took BLG-NCA as the monomer to quickly synthesize one kind of high M n amphiphilic copolymer, poly(ethylene glycol)b-poly(γ-benzyl-L-glutamic acid) (PEG-PBLG), by relay polymerization with a simple one-pot method within 3 h in mild conditions (open air, moisture insensitive). In the polymerization process, ring-opening polymerization-induced self-assembly in sodium bicarbonate aqueous solution first occurred to obtain low M n PEG-PBLG seeds without purification. Then γ-benzyl-L-glutamate N-carboxyanhydride (BLG-NCA) dichloromethane solution was added into PEG-PBLG seeds directly and stirred vigorously to form am emulsion; during this process, the amphiphilic PEG-PBLG seeds will anchor on the interface of DCM and water to ensure the concentration of α-helix rigid PBLG in DCM to maintain the following relay polymerization. Then, high M n PEG-PBLG was obtained in mild conditions in one pot. We found that the α-helix rigid structure was essential for relay polymerization by studying the synthetic speed of amphiphilic copolymer with different secondary structures. MOE simulation results showed that PBLG and BLG-NCA tended to form a double hydrogen bond, which was beneficial to relay polymerization because of higher local concentrations that can produce more double hydrogen bonds. Our strategy can quickly obtain high M n PEG-PBLG (224.9 KDa) within 3 h from PEG-NH 2 and BLG-NCA in one pot and did not need an extra initiator. After deprotection, the poly(ethylene glycol)-b-poly(L-glutamate acid) (PEG-PGA) with high M n as a second product can be used as an excellent antitumor drug carrier. The high M n PEG-PGA can achieve an encapsulation rate of 86.7% and a drug loading rate of 47.3%, which is twice that of the low M n PEG-PGA. As a result, the synthesis of PEG-PBLG by relay polymerization simplified the process of PEG-PAA polymerization and increased the M n . In addition, this method opened a way to obtain other kinds of high M n PEG-PBLG values in the future.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of High Molecular Weight Poly(ethylene glycol)-b-poly(amino acid)s by Relay Polymerization

Luo,

Yuan,

et al. 2024

Biomacromolecules

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“…[36][37][38][39][40] In recent years, polyamine derivatives have attracted increasing attention due to their ability to enhance the selectivity and bioactivity of compounds. [41][42][43][44][45][46] Protein primary structure consists of amino acids linked by peptide bonds. Because amino acids are generally water-soluble and inexpensive, they have been used as capping agents for QDs.…”

Section: Introductionmentioning

confidence: 99%

<p>A Lysosome-Targetable Fluorescence Probe Based on L-Cysteine-Polyamine-Morpholine-Modified Quantum Dots for Imaging in Living Cells</p>

Zhang

Yao

Qiao

et al. 2020

IJN

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Purpose: Quantum dots (QDs) are used as fluorescent probes due to their high fluorescence intensity, longevity of fluorescence, strong light-resistant bleaching ability and high light stability. Therefore, we explore a more precise probe that can target an organelle. Methods: In the current study, a new class of fluorescence probes were developed using QDs capped with 4 different L-cysteine-polyamine-morpholine linked by mercapto groups. Ligands were characterised by Electrospray ionization mass spectrometry (ESI-MS), H-Nuclear Magnetic Resonance (1 H NMR) spectroscopy, and 13 C NMR spectroscopy. Modified QDs were characterized by Transmission Electron Microscope (TEM), Ultraviolet and visible spectrophotometry (UV-Vis), and fluorescence microscopy. And the biological activity of modified QDs was explored by using MTT assay with HeLa, SMMC-7721 and HepG2 cells. The fluorescence imaging of modified QDs was obtained by confocal laser scanning fluorescence microscopy (CLSM). Results: Synthesized QDs ranged between 4 to 5 nm and had strong optical emission properties. UV-Vis and fluorescence spectra demonstrated that the cysteine-polyaminemorpholine were successfully incorporated into QD nanoparticles. The MTT results demonstrated that modified QDs had lesser cytotoxicity when compared to unmodified QDs. In addition, modified QDs had strong fluorescence intensity in HeLa cells and targeted lysosomes of HeLa cells. Conclusion: This study demonstrates the modified QDs efficiently entered cells and could be used as a potential lysosome-targeting fluorescent probe.

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A density functional theory investigation of the interaction of the tetraaqua calcium cation with bidentate carbonyl ligands

et al. 2017

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Calcium complexes with bidentate carbonyl ligands are important in biological systems, medicine and industry, where the concentration of Ca is controlled using chelating ligands. The exchange of two water molecules of [Ca(HO)] for one bidentate monosubstituted and homo disubstituted dicarbonyl ligand was investigated using the B3LYP/6-311++G(d,p) method. The ligand substituents NH, OCH, OH, CH, H, F, Cl, CN and NO are functional groups with distinct electron-donating and -withdrawing effects that bond directly to the sp C atom of the carbonyl group. The geometry, charge and energy characteristics of the complexes were analyzed to help understand the effects of substituents, spacer length and chelation. Coordination strength was quantified in terms of the enthalpy and free energy of the exchange reaction. The most negative enthalpies were calculated for the coordination of bidentate ligands containing three to five methylene group spacers between carbonyls. The chelate effect contribution was analyzed based on the thermochemistry. The electronic character of the substituent modulates the strength of binding to the metal cation, as ligands containing electron-donor substituents coordinate stronger than those with electron-acceptor substituents. This is reflected in the geometric (bond length and chelating angle), electronic (atomic charges) and energetic (components of the total interacting energy) characteristics of the complexes. Energy decomposition analysis (EDA)-an approach for partitioning of the energy into its chemical origins-shows that the electrostatic component of the coordination is predominant, and yields relevant contribution of the covalent term, especially for the electron-withdrawing substituted ligands. The chelate effect of the bidentate ligands was noticeable when compared with substitution by two monodentate ligands. Graphical abstract The affinity of 18 bidentate carbonyl ligands toward the [Ca(HO)] cation is evaluated in terms of energetic, geometric and electronic parameters of the isolated ligands and the substituted aqua complexes. The electronic effects-inductive and mesomeric-intrinsic to the molecular structure of each ligand are found to modulate the strength of the metal-ligand interaction. The effects of polysubstitution, chelation and the length of the alkyl spacers between the anchor points of the ligand are also analyzed.

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Helical peptide–polyamine and –polyether conjugates as synthetic ionophores

Cited by 4 publications

References 38 publications

Facile Synthesis of High Molecular Weight Poly(ethylene glycol)-b-poly(amino acid)s by Relay Polymerization

Facile Synthesis of High Molecular Weight Poly(ethylene glycol)-b-poly(amino acid)s by Relay Polymerization

<p>A Lysosome-Targetable Fluorescence Probe Based on L-Cysteine-Polyamine-Morpholine-Modified Quantum Dots for Imaging in Living Cells</p>

A density functional theory investigation of the interaction of the tetraaqua calcium cation with bidentate carbonyl ligands

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