Acid hydrolysis of polymers and copolymers of N‐vinyl‐N‐methylacetamide

Buys, H. C. W. M.; Vercauteren, F.F.; Elven, A. van; Tinnemans, A. H. A.

doi:10.1002/recl.19891080402

Cited by 4 publications

(13 citation statements)

References 13 publications

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“…The PMVAm precursor was synthesized by FRP of NMVA at 30 °C in MeOH followed by acidic hydrolysis with 3 n HCl at 100 °C (Table , entry 3, PM155‐F). Under this moderated condition, hydrolysis reached 76% (Table , entry 3) . Then, 1 H ‐pyrazole‐carboxamidine hydrochloride was reacted at 30 °C in water with the secondary amines of the PMVAm.…”

Section: Resultsmentioning

confidence: 99%

“…In contrast, the hydrolysis the PNVA homopolymer was performed under milder conditions (5% w/v, 2 n HCl, 120 °C, 14 h, soft conditions, indicated by the suffix s) according to Dréan et al P(NMVA‐ co ‐NVA) copolymers were hydrolyzed by both the sets of conditions. Finally, the PMVAm for guanidinylation was hydrolyzed using 3 n HCl at 100 °C (medium conditions, suffix m, Table , entry 3) . The determination of the percentage of deacetylation for each polymer was achieved using EA.…”

Section: Methodsmentioning

confidence: 99%

“…[17] PMVAms were readily obtained by free radical polymerization (FRP) of Nmethylvinylacetamide (NMVA), followed by acidic hydrolysis of the amide groups. [25][26][27] A series of PMVAms with controlled molar masses and low molar mass distribu tion prepared by organometallic mediated radical polymeri zation (OMRP) of NMVA and subsequent acidic hydrolysis was tested. [28,29] We also found that the molar mass and the distribution of the PMVAm had a negligible impact on the transfection efficiency.…”

Section: Doi: 101002/mabi201700353mentioning

confidence: 99%

“…Finally, the PMVAm for guanidinylation was hydrolyzed using 3 n HCl at 100 °C (medium conditions, suffix m, Table 1, entry 3). [27] The determination of the percentage of deacetylation for each pol ymer was achieved using EA. The method was based on the C/N ratio in the polymer before and after acidic treatment rather than on absolute mass percentage of C and N in order to prevent mistakes coming from the hydroscopic character of the polymer (Table S1, Supporting Information).…”

Section: General Procedures For Hydrolysismentioning

confidence: 99%

“…Indeed, we reported that polymethylvinylamine (PMVAm)‐based pDNA polyplexes reached transfection efficiency in the same order as the gold standard lPEI, yet with improved cell viability (>60%) . PMVAms were readily obtained by free radical polymerization (FRP) of N ‐methylvinylacetamide (NMVA), followed by acidic hydrolysis of the amide groups . A series of PMVAms with controlled molar masses and low molar mass distribution prepared by organometallic mediated radical polymerization (OMRP) of NMVA and subsequent acidic hydrolysis was tested .…”

Section: Introductionmentioning

confidence: 99%

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Poly(N‐methylvinylamine)‐Based Copolymers for Improved Gene Transfection

Dréan

Debuigne

Jérôme

et al. 2018

Macromolecular Bioscience

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Poly(N-methylvinylamines) with secondary amines can form complexes with plasmid DNA (pDNA) and provide transfection efficiency in HeLa cells in the same order as linear polyethyleneimine but with higher cell viability. Chemical modifications of poly(N-methylvinylamine) backbones are performed to further improve transfection efficiency while maintaining low degree of cytotoxicity. In a first type of polymer, primary amino groups are incorporated via a copolymerization strategy. In a second one, primary amino and imidazole groups are incorporated also via a copolymerization strategy. In a third one, secondary amino groups are substituted with methylguanidine functions through a postpolymerization reaction. Thus, novel polymers of various molecular masses are synthesized, characterized, and their interaction with pDNA studied. Then, their transfection efficiency and cytotoxicity are tested in HeLa cells. Two polymethylvinylamine-based copolymers, one containing 20% of imidazole moieties and another one composed of 12% of guanidinyl units allow remarkable transfection efficiency of HeLa, pulmonary (16HBE), skeletal muscle (C2C12), and dendritic (DC2.4) cells. Overall, this work thus identifies new promising DNA carriers and chemical modifications that improve the transfection efficiency while maintaining low degree of cytotoxicity.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Doi: 101002/mabi201700353mentioning

confidence: 99%

Section: General Procedures For Hydrolysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Poly(N‐methylvinylamine)‐Based Copolymers for Improved Gene Transfection

Dréan

Debuigne

Jérôme

et al. 2018

Macromolecular Bioscience

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Use of Primary and Secondary Polyvinylamines for Efficient Gene Transfection

et al. 2017

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Gene transfection with polymeric carrier remains a challenge; particularly, high transfection levels combined with low toxicity are hard to achieve. We herein revisit polyvinylamines, an old and neglected family of cationic polymers. They can be readily obtained by controlled hydrolysis of polyvinylamides prepared through (controlled) radical polymerization. A series of tailor-made and well-defined polyvinylamines bearing primary amino groups, and poly(N-methylvinylamine) bearing secondary amines, were evaluated for the transfection of cells with pDNA as a function of their molar mass, molar mass distribution, and degree of deacetylation. Unexpected high transfection levels, in combination with low cytotoxicity were recorded for both series. Surprisingly, a great impact of the molar mass was observed for the primary amine polyvinylamine series, whereas the results were mostly independent of molar mass or dispersity for the polymer bearing secondary amine. It was further established that a certain percentage of acetamide groups increased the transfection level, while maintaining low cytotoxicity. These results highlight for the first time the real potential of polyvinylamines as gene carriers, and make these polymers very attractive for further development in gene therapy.

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Far beyond primary poly(vinylamine)s through free radical copolymerization and amide hydrolysis

et al. 2016

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Due to their affinity for many supports, their pH responsiveness, metal binding capacity and polyelectrolytes complexation, poly(vinylamine) derivatives have attracted attention for many applications including coatings, water purification, or gas membrane separation. Nevertheless, most of them possess only pendant primary amines despite the possible benefits of incorporating different amino groups along the chain. In this work, a straightforward and scalable synthesis route towards polymers bearing primary and secondary amines, as well as imidazole groups, is reported. The general strategy relies on the radical copolymerization of different vinylamides and vinyl imidazole followed by the hydrolysis of the resulting poly(vinylamide) derivatives. Binary and ternary free radical copolymerizations of Nvinylacetamide (NVA), N-methyl vinylacetamide (NMVA) and 1-vinylimidazole (VIm) were investigated and the reactivity ratios for each copolymerization system were determined. Thanks to these values a series of statistical copolymers with predictable composition and low deviation over the chain distribution could then be synthesized. Finally, the acidic hydrolysis of the acetamide functions towards the corresponding amine was performed and optimized. Copolymers containing various pendant amino groups and with low dispersity in the chain composition could be obtained, which opens new perspectives for the above mentioned applications.polyvinylimidazole 55 , as well as the dependence of the antimicrobial efficiency on the charge density and hydrophobicity. 54 Finally, these novel polyamines might also outperform primary PVAm in applications like paper strengthening or coating applications 9-11 . In other words, much can be expected from this poly(vinylamine) based synthetic platform. Notes and references

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Acid hydrolysis of polymers and copolymers of N‐vinyl‐N‐methylacetamide

Cited by 4 publications

References 13 publications

Poly(N‐methylvinylamine)‐Based Copolymers for Improved Gene Transfection

Poly(N‐methylvinylamine)‐Based Copolymers for Improved Gene Transfection

Use of Primary and Secondary Polyvinylamines for Efficient Gene Transfection

Far beyond primary poly(vinylamine)s through free radical copolymerization and amide hydrolysis

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