Ag@polyDOPA-b-polysarcosine hybrid nanoparticles with antimicrobial properties from in-situ reduction and NTA polymerization

Cen, Jiayu; Zheng, Biao; Yang, Yang; Wu, Jindan; Mao, Zhengwei; Ling, Jun; Han, Gaorong

doi:10.1016/j.eurpolymj.2019.109269

Cited by 10 publications

(7 citation statements)

References 58 publications

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“…In addition, DOPA repeating units reduced Ag + to Ag so that Ag@PDOPA-b-PSar nanoparticles were formed and applied as antimicrobials. 25 Besides mono-amino initiator, di-amino initiators were used to prepare polypept(o)ides as well. 22c One amino group initiated the first block while the other was protected.…”

Section: Sequential Rop Approachmentioning

confidence: 99%

Synthesis and properties of polypeptoid‐containing block copolymers: A review

Zhou

Shen

Ling

2021

Journal of Polymer Science

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Polypeptoids, with similar structure to polypeptides, are nowadays rising stars due to their excellent solubility, processibility, enzymatic stability, and biocompatibility. Attractive properties of polypeptoid-containing copolymers endow them with various applications in surface antifouling, biosensing, microreactor, drug delivery, and stimuli-response. The syntheses of block copolymers containing polypeptoids have attracted a great amount of interest so far. The review summarizes the synthetic strategies of polypeptoid-containing copolymers, that is, polypeptoid-b-polypeptoid, Àpolypeptide, Àpolyester, Àpolyether and -polyolefin developed recently, as well as their phase-separation, assembly and stimuli-response properties.

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Section: Sequential Rop Approachmentioning

confidence: 99%

Synthesis and properties of polypeptoid‐containing block copolymers: A review

Zhou

Shen

Ling

2021

Journal of Polymer Science

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“…Self-assembly MRI contrast reagent Antimicrobial nanoparticles [82,9] Tyrosine-NTA (Tyr-NTA) vii (60 °C, tetramethylene sulfone) - [9] Sar-NTA i, ii, iii Hydrophilic block Stealth property, antifouling [4] NEG-NTA i, iii, iv Omnisoluble in solvents Mechanism research [83,84] NBG-NTA i, ii, iii, iv Temperature responsiveness Hydrophobic block [85][86][87] NAG-NTA i Self-assembly Postmodification [88] MeSPG-NTA i Self-assembly Oxidation responsiveness Ref.…”

Section: Polymerization Of Ntasmentioning

confidence: 99%

“…[86] As the controlled polymerizations of NNTAs initiated by primary amine are realized, the robustness of this system is investigated. The stability study reveals that NNTAs and amine-initiated NNTA polymerizations are stable to various nucleophiles including alcohols, [96] mercaptans, [97] phenols, [9,82,98] carboxylic acids, [81,99] and water. [84] Mercaptans, alcohols without activation, phenols, and water cannot initiate the polymerization of NNTAs (Scheme 6).…”

Section: Polymerization Of Ntasmentioning

confidence: 99%

“…DoS was also able to reduce silver cation and form Ag@DoS as an antibacterial reagent. [82] Poly(Nallylglycine)-b-polysarcosine (PNAG-b-PSar) was synthesized through benzylamine-initiated ROP of N-allylglycine NTA (NAG-NTA) and Sar-NTA. Further postpolymerization modification of allyl group attached tetraphenylethylene (TPE) group, the emblematic luminogen with aggregation-induced emission (AIE), to PNAG side chains.…”

Section: Nta Monomers and Applicationmentioning

confidence: 99%

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An Inspection into Multifarious Ways to Synthesize Poly(Amino Acid)s

Zheng

Bai

Tao

et al. 2021

Macromol. Rapid Commun.

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Poly(𝜶-amino acid)s (PAAs) attract growing attention due to their essential role in the application as biomaterials. To synthesize PAAs with desired structures and properties, scientists have developed various synthetic techniques with respective advantages. Here, different approaches to preparing PAAs are inspected. Basic features and recent progresses of these methods are summarized, including polymerizations of amino acid N-carboxyanhydrides (NCAs), amino acid N-thiocarboxyanhydrides (NTAs), and N-phenoxycarbonyl amino acids (NPCs), as well as other synthetic routes. NCA is the most classical monomer to prepare PAAs with high molecular weights (MWs). NTA polymerizations are promising alternative pathways to produce PAAs, which can tolerate nucleophiles including alcohols, mercaptans, carboxyl acids, and water. By various techniques including choosing appropriate solvents or using organic acids as promoters, NTAs polymerize to produce polypeptoids and polypeptides with narrow dispersities and designed MWs up to 55.0 and 57.0 kg mol −1 , respectively. NPC polymerizations are phosgene-free ways to synthesize polypeptides and polypeptoids. For the future prospects, detail investigations into polymerization mechanisms of NTA and NPC are expected. The synthesis of PAAs with designed topologies and assembly structures is another intriguing topic. The advantages and unsettled problems in various synthetic ways are discussed for readers to choose appropriate approaches for PAAs.

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“…Moreover, polymerization initiated by biomolecules, including amino acids and peptides, could be a potential approach to preparing functional polypeptoids without tedious postmodification. Recently, ring-opening polymerization (ROP) of N -substituted glycine N -thiocarboxyanhydrides (NNTAs) has been developed as a versatile method to prepare polypeptoids. − Comparing with classical ROP of α-amino acid N -carboxyanhydrides (NCA), − ROP of NNTA has excellent tolerance to nucleophilic impurities, including water, , alcohols, phenols, , and mercaptans . NNTA polymerization is therefore a promising way to synthesize functional polypeptoids from unprotected monomers and biomolecule initiators.…”

Section: Introductionmentioning

confidence: 99%

Understanding Acid-Promoted Polymerization of the N-Substituted Glycine N-Thiocarboxyanhydride in Polar Solvents

Zheng

et al. 2021

Biomacromolecules

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Polymerization of N-substituted glycine N-thiocarboxyanhydrides (NNTAs) is a promising pathway to prepare functional polypeptoids benefiting from their tolerance to nucleophilic impurities. However, controlled NNTA polymerization is hard to achieve in amide polar solvents, including N,Ndimethylacetamide (DMAc), N,N-dimethylformamide (DMF), and N-methyl pyrrolidone (NMP), the only aprotic solvents for many biomacromolecules and polypeptoids. In the present work, we successfully achieve controlled NNTA polymerization in amide polar solvents by adding acetic acid as a promoter. The promotion is applied to the polymerization of sarcosine NTA, N-ethyl glycine NTA, and N-butyl glycine NTA. DMAc, DMF, and NMP are suitable solvents to prepare polypeptoids with designable molecular weights and low dispersities (1.06−1.21). The polysarcosines with high molecular weights are prepared up to 35.2 kg/mol. A kinetic investigation quantitatively reveals that the presence of acetic acid not only accelerates the polymerization, but also suppresses H 2 S-catalyzed decomposition of NNTAs by decreasing the concentration of H 2 S dissolved in polar solvents. Benzoic acid is also able to promote the polymerization, while trifluoroacetic acid, phosphoric acid, and phenol are not appropriate promoters. The moderate acidity of acids is essential. L-Methionine, L-tryptophan, and L-phenylalanine, which are dissolved in DMF, initiate the controlled polymerization of sarcosine-NTA in the presence of acetic acid and introduce functional end groups to polysarcosines quantitatively. In DMAc, hydrophilic vancomycin is grafted by poly(N-butyl glycine). The amphiphilic product dissolves in dichloromethane and stabilizes water-in-oil emulsion.

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Ag@polyDOPA-b-polysarcosine hybrid nanoparticles with antimicrobial properties from in-situ reduction and NTA polymerization

Cited by 10 publications

References 58 publications

Synthesis and properties of polypeptoid‐containing block copolymers: A review

Synthesis and properties of polypeptoid‐containing block copolymers: A review

An Inspection into Multifarious Ways to Synthesize Poly(Amino Acid)s

Understanding Acid-Promoted Polymerization of the N-Substituted Glycine N-Thiocarboxyanhydride in Polar Solvents

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