Polyethylenimine analogs for improved gene delivery: effect of the type of amino groups

Xun, Miao-Miao; Zhang, Ju-Hui; Liu, Yanhong; Zhang, Ji; Xiao, Yaping; Guo, Qin; Li, Shuo; Yu, Xiao‐Qi

doi:10.1039/c5ra23715g

Cited by 8 publications

(10 citation statements)

References 39 publications

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“…The ring opening polymerization of aziridine produces branched PEI (Scheme 1) with primary (1°), secondary (2°), and tertiary (3°) amine groups. 44 Although the theoretical ratio of 1°:2°:3° amines has been reported to be 1:2:1, some variability exists depending on synthetic procedures. 45 Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Post polymer modification of polyethylenimine with citrate esters: selectivity and hydrophobicity

Waggel

Mathers

2016

RSC Adv.

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Citrate esters selectively react with primary (1°) amines on branched polyethylenimine (PEI). As the functionalization occurred, the water soluble PEI transformed into a thermoset. Adjusting stoichiometry and type of citrate ester allowed fine-tuning of hydrophobicity, modulus, and swelling behavior. Based on control experiments of citrate esters with model amines, FTIR analysis of thermosets, swelling experiments, and TGA data, molecular models were constructed to represent the thermosets. Quantifying the hydrophobicity of these molecular models with computational octanol-water (LogPoct) partition coefficients provided a method to assess how hydrophobicity changes during a post polymer modification (PPM) reaction.

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Section: Resultsmentioning

confidence: 99%

Post polymer modification of polyethylenimine with citrate esters: selectivity and hydrophobicity

Waggel

Mathers

2016

RSC Adv.

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“…We also investigated decomplexation of polyplexes by heparin, which is more negatively charged than DNA, and can lead to DNA release by its stronger interaction with cationic polymers. [ 9,33,34 ] As shown in Figure 5 B, DNA is gradually released with increasing concentration of heparin, and the threshold amounts of heparin at which polyplex dissociation occurred were 0.9, 0.6, and 0.2 IU (International Unit) for POEI 1, 2, and 3, respectively, suggesting that polyplexes formed with POEIs bearing more primary/secondary amines have higher DNA binding ability. In addition, DNase I is extremely dangerous for exogenous gene during the movement of DNA through cytosol toward the nucleus.…”

Section: Formation and Stability Of Poeis/dna Polyplexesmentioning

confidence: 96%

Low Molecular Weight PEI‐Based Vectors via Acid‐Labile Ortho Ester Linkage for Improved Gene Delivery

Zhang

Wang

et al. 2016

Macromolecular Bioscience

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A series of novel pH-sensitive gene delivery vectors (POEI 1, 2, and 3) are synthesized through Michael addition from low molecular weight PEI (LMW PEI) via acid-labile ortho ester linkage with terminal acrylates (OEAc) by various feed molar ratios. The obtained POEI 1 and POEI 2 can efficiently condense plasmid DNA into nanoparticles with size range of 200-300 nm and zeta-potentials of about +15 mV while protecting DNA from enzymatic digestion compared with POEI 3. Significantly, ortho ester groups of POEI main-chains can make an instantaneous degradation-response to acidic endosomal pH (≈5.0), resulting in accelerated disruption of polyplexes and intracellular DNA release. MTT assay reveals that all POEIs exhibit much lower cytotoxicity in different cells than branched PEI (25 KDa). As expected, POEI 1 and POEI 2 perform improved gene transfection in vitro, suggesting that such polycations might be promising gene vectors based on overcoming toxicity-efficiency contradiction.

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“…Theoretically, it was proposed that different physicochemical properties of polymers could affect transfection process, including backbone, side chain, molecular weight, hydrophobicity, polydispersity indices, partition‐coefficient, etc . Experimentally, it is well documented that various amine and fluorinated amide groups have different effects on efficiency of gene transfer . Therefore, a systematic understanding of the gene transfection mechanism relating to fluorination is required, which might not be possibly elucidated with fluorinated dendrimers, due to their complex chemical and physical properties.…”

Section: Introductionmentioning

confidence: 99%

Synthetic fluorinated polyamides as efficient gene vectors

Wang

Han

Gao³

et al. 2019

J Biomed Mater Res

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Linear fluorinated polyamides with reversible cationic charges are feasibly prepared to be used as highly efficient gene vectors in HEK293 cell line. Due to the uniform polymer structure, the relationship between the physicochemical properties and transfection efficiency could be unambiguously investigated. The different efficiency in the application of gene delivery between the parent polyethylenimine (PEI) and the polyamides is directly associated with the differences in chemical and physical properties between secondary amines and fluorinated amides. We found that fluorination not only increases the cellular uptake of polymer/DNA polyplexes, but it also decreases cytotoxicity in terms of inducing lower concentrations of proinflammatory cytokine TNF-α.

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Polyethylenimine analogs for improved gene delivery: effect of the type of amino groups

Abstract: The 1°, 2° and 3° amine composition of PEI analogs could be easily adjusted by special synthetic method, and their effects on the gene transfection were studied.

Cited by 8 publications

References 39 publications

Post polymer modification of polyethylenimine with citrate esters: selectivity and hydrophobicity

Post polymer modification of polyethylenimine with citrate esters: selectivity and hydrophobicity

Low Molecular Weight PEI‐Based Vectors via Acid‐Labile Ortho Ester Linkage for Improved Gene Delivery

Synthetic fluorinated polyamides as efficient gene vectors

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