Accelerated Polypeptide Synthesis via <i>N</i>‐Carboxyanhydride Ring Opening Polymerization in Continuous Flow

Vrijsen, Jeroen H.; Mazo, Alicia Rasines; Junkers, Thomas; Qiao, Greg G.

doi:10.1002/marc.202000071

Cited by 9 publications

(5 citation statements)

References 55 publications

(74 reference statements)

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“…Polypeptides could be prepared by the ROP of amino acid NCA monomers in a controlled manner (Liu et al, 2020;Lv et al, 2020;Vrijsen et al, 2020). In this study, the Y-shaped co-polypeptide mPEG-(PLeu…”

Section: Resultsmentioning

confidence: 99%

Enhanced Anticancer Efficacy of Chemotherapy by Amphiphilic Y-Shaped Polypeptide Micelles

Cong

Zhang

Liu

2021

Front. Bioeng. Biotechnol.

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Although the treatment modalities of cancers are developing rapidly, chemotherapy is still the primary treatment strategy for most solid cancers. The progress in nanotechnology provides an opportunity to upregulate the tumor suppression efficacy and decreases the systemic toxicities. As a promising nanoplatform, the polymer micelles are fascinating nanocarriers for the encapsulation and delivery of chemotherapeutic agents. The chemical and physical properties of amphiphilic co-polymers could significantly regulate the performances of the micellar self-assembly and affect the behaviors of controlled release of drugs. Herein, two amphiphilic Y-shaped polypeptides are prepared by the ring-opening polymerization of cyclic monomer l-leucine N-carboxyanhydride (l-Leu NCA) initiated by a dual-amino-ended macroinitiator poly(ethylene glycol) [mPEG-(NH2)2]. The block co-polypeptides with PLeu8 and PLeu16 segments could form spontaneously into micelles in an aqueous solution with hydrodynamic radii of 80.0 ± 6.0 and 69.1 ± 4.8 nm, respectively. The developed doxorubicin (DOX)-loaded micelles could release the payload in a sustained pattern and inhibit the growth of xenografted human HepG2 hepatocellular carcinoma with decreased systemic toxicity. The results demonstrated the great potential of polypeptide micellar formulations in cancer therapy clinically.

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Section: Resultsmentioning

confidence: 99%

Enhanced Anticancer Efficacy of Chemotherapy by Amphiphilic Y-Shaped Polypeptide Micelles

Cong

Zhang

Liu

2021

Front. Bioeng. Biotechnol.

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“…[51] Qiao and co-workers sped up ROP of NCA by designing a silicon microflow reactor with highly efficient permeation of CO 2 through tubing. [52] Zhao et al used fluorinated alcohol as an organocatalyst to enable alcohol-initiated NCA polymerizations. [53,54] Liu and co-workers reported alkali hexamethyldisilazide saltinitiated NCA polymerizations, which produced polypeptides with medium dispersities in open air.…”

Section: Advances In Polymerizations Of Ncasmentioning

confidence: 99%

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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“…However, the scalability of these processes remains challenging [1] . In contrast, the Ring Opening Polymerisation (ROP) of N ‐carboxyanhydrides (NCAs) has emerged as an atom efficient one‐pot route to polypeptides under living polymerisation conditions [2, 3] . This approach allows the scalable synthesis of peptidomimetics that gather the main features needed for a certain function such as charge, hydrophilicity/hydrophobicity or secondary structure.…”

Section: Figurementioning

confidence: 99%

On‐POM Ring‐Opening Polymerisation of N‐Carboxyanhydrides

et al. 2021

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The ring‐opening polymerisation of α‐amino acid N‐carboxyanhydrides (NCAs) offers a simple and scalable route to polypeptides with predicted and narrow molecular weight distributions. Here we show how polyoxometalates (POMs)—redox‐active molecular metal‐oxide anions—can serve as inorganic scaffold initiators for such NCA polymerisations. This “On‐POM polymerisation” strategy serves as an innovative platform to design hybrid materials with additive or synergistic properties stemming from the inorganic and polypeptide component parts. We have used this synthetic approach to synthesise a library of bactericidal poly(lysine)–POM hybrid derivatives that can be used to prevent biofilm formation. This versatile “On‐POM polymerisation” method provides a flexible synthetic approach for combining inorganic scaffolds with amino acids, and the potential to tailor and improve the specificity and performance of hybrid antimicrobial materials.

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Accelerated Polypeptide Synthesis via N‐Carboxyanhydride Ring Opening Polymerization in Continuous Flow

Cited by 9 publications

References 55 publications

Enhanced Anticancer Efficacy of Chemotherapy by Amphiphilic Y-Shaped Polypeptide Micelles

Enhanced Anticancer Efficacy of Chemotherapy by Amphiphilic Y-Shaped Polypeptide Micelles

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

On‐POM Ring‐Opening Polymerisation of N‐Carboxyanhydrides

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