Preparation of poly(serine ester)s by ring-opening polymerization of N-trityl serine lactone under catalysis of ZnEt2

Wei, Ying; Li, Xiaoyuan; Jing, Xiabin; Chen, Xuesi; Huang, Yubin

doi:10.1007/s40242-013-2355-9

Cited by 4 publications

(6 citation statements)

References 36 publications

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“…Differing from CARTs with oligocationic backbones, Ser-CARTs incorporate a charge-altering side-chain amine to complex the mRNA cargo and produce neutral serine-based byproducts upon degradation, resulting in mRNA release (Scheme B). In addition to their biocompatibility and expected rearrangement into peptides 4 , − oligo(serine esters) were selected for study over other degradable amine-functionalized polyesters , because of their activating α-amino ester motif. Studies suggest that the rapid rearrangement of morpholinone-derived oligo(α-amino esters) is partially due to the activation of a backbone ammonium group positioned α to the ester repeating unit .…”

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confidence: 99%

Oligo(serine ester) Charge-Altering Releasable Transporters: Organocatalytic Ring-Opening Polymerization and their Use for in Vitro and in Vivo mRNA Delivery

et al. 2019

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RNA technology is transforming life science research and medicine, but many applications are limited by the accessibility, cost, efficacy, and tolerability of delivery systems. Here we report the first members of a new class of dynamic RNA delivery vectors, oligo(serine ester)-based chargealtering releasable transporters (Ser-CARTs). Composed of lipid-containing oligocarbonates and cationic oligo(serine esters), Ser-CARTs are readily prepared (one flask) by a mild ring-opening polymerization using thiourea anions and, upon simple mixing with mRNA, readily form complexes that degrade to neutral serine-based products, efficiently releasing their mRNA cargo. mRNA/Ser-CART transfection efficiencies of >95% are achieved in vitro. Intramuscular or intravenous (iv) injections of mRNA/Ser-CARTs into living mice result in in vivo expression of a luciferase reporter protein, with spleen localization observed after iv injection.Messenger RNA (mRNA) is advancing fundamental research and medicine through its ability to induce the transient catalytic expression of target proteins in vitro, in vivo, and ex vivo. Applications of mRNA include protein replacement therapy, gene editing, vaccination, and cancer immunotherapy. 1 However, the challenge of developing synthetically accessible, affordable, safe, and effective delivery vectors that extracellularly protect and intracellularly release mRNA have hampered applications, driving demand for improved delivery systems. 2,3 Current delivery strategies focus on mechanical methods and viral and nonviral vectors. [4][5][6] Mechanical methods that temporarily render the cellular membrane permeable are limited to accessible tissues and ex vivo techniques, often suffer from poor cell viability, and *

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confidence: 99%

Oligo(serine ester) Charge-Altering Releasable Transporters: Organocatalytic Ring-Opening Polymerization and their Use for in Vitro and in Vivo mRNA Delivery

et al. 2019

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“…studies demonstrated the non-cytotoxicity of γ-Fe 2 O 3 -PAA, [33,34] and the low cytotoxicity of pSe-b-PEG. [36] PEG 10K , as well as the hydrolytic product serine, are nontoxic at low doses and would probably be excreted in vivo. [65] Cell viability assays show convincing results regarding short term non-toxicity of γ- objects into ≈ 500 nm dense clusters within 24 h, [33] nanoassembly involving hydrolysable poly(ester serine) leads to almost complete separation of the γ-Fe 2 O 3 -PAA nanoparticles from each other in the same duration.…”

Section: Determination Of the Amount Of Iron Oxide Adsorbed And Intermentioning

confidence: 99%

“…In the present study, issues arising from the long-term fate of γ-Fe 2 O 3 -PAA/polyelectrolyte PICs are overcome by replacing industrial cationic polyelectrolytes with biocompatible and biodegradable ones. [36] Poly(acrylic acid) (PAA) coated iron oxide nanoparticles were prepared following reported protocols. In brief, magnetite (Fe 3 O 4 ) nanocrystals were synthesized by co-precipitation of iron (II) and iron (III) salts in aqueous alkaline medium at room temperature.…”

Section: Introductionmentioning

confidence: 99%

“…pSe homopolyelectrolytes and pSe-b-PEG diblock copolymer were synthesized according to previously reported protocol. [36] The M w were determined by gel permeation chromatography (GPC). Briefly, poly(N-trityl serine lactone) with M w (pTSL) = 33050 g mol -1 (pTSL 33K ), and poly(N-trityl serine lactone)-b-PEG with M w (pTSL) = 33050 g mol - 1 and M w (PEG) = 10000 g mol -1 (pTSL 33K -b-PEG 10K ), were synthesized via ring-opening polymerization of N-trityl serine lactone with diethyl zinc as catalyst.…”

Section: Introductionmentioning

confidence: 99%

“…This de-protection procedure induces a polyelectrolyte backbone degradation about 20 % whereas the PEG 10K block did not degrade. [36,49] The obtained pSe and pSe-b-PEG with acetate counter-ions are characterized by a M w (pSe, Acetate) = 11840 g mol -1 , corresponding to an average degree of polymerization DP(pSe) = 80. (Table S1 and S2).…”

Section: Introductionmentioning

confidence: 99%

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Auto-degradable and biocompatible superparamagnetic iron oxide nanoparticles/polypeptides colloidal polyion complexes with high density of magnetic material

Wang

Sandre

Wang

et al. 2019

Materials Science and Engineering: C

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Hypothesis: superparamagnetic iron oxide nanoparticles (SPIONs) are extensively used as building block of colloidal nanocomposites for biomedical applications. Strategies employed to embed them in a biodegradable and biocompatible polymer matrix often fail to achieve a high density of loading which would greatly benefit to applications such as imaging and hyperthermia. In this study, poly(acrylic acid) coated SPION (γ-Fe 2 O 3-PAA) are self-assembled with hydrolysable poly(serine ester) by electrostatic complexation, leading to perfectly defined spherical particles with ultra-high density of magnetic material and an ability to auto-degrade into individual SPION and biocompatible byproducts. Experiments: self-assembly and auto-degradation of γ-Fe 2 O 3-PAA/poly(serine ester) and γ-Fe 2 O 3-PAA/poly(serine ester)-b-PEG colloidal particles are studied by light scattering and microscopy. Colloidal stability in bio-fluids, hyperthermia under alternating magnetic field, cellular uptake, cytotoxicity and degradation of γ-Fe 2 O 3-PAA/poly(serine ester)-b-PEG in living cells are investigated. Findings: a remarkably slow electrostatic complexation leads to dense superparamagnetic γ-Fe 2 O 3-PAA/poly(serine ester)-b-PEG polyion complexes (PICs) with controlled sizes (150-500 nm) and times of degradation in aqueous solvents (700-5000 h). The material shows good sustainability during hyperthermia, is well taken up by MC3T3 cells and non-cytotoxic. TEM images reveal a mechanism of degradation by "peeling" and fragmentation. In cells, PICs are reduced into individual SPIONs within 72 h.

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Synthesis and characterization of amino-functional polyesters composed of lactic acids and serine amino acids

Wei,

Li,

Yuan

et al. 2024

Polymer

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Preparation of poly(serine ester)s by ring-opening polymerization of N-trityl serine lactone under catalysis of ZnEt2

Cited by 4 publications

References 36 publications

Oligo(serine ester) Charge-Altering Releasable Transporters: Organocatalytic Ring-Opening Polymerization and their Use for in Vitro and in Vivo mRNA Delivery

Oligo(serine ester) Charge-Altering Releasable Transporters: Organocatalytic Ring-Opening Polymerization and their Use for in Vitro and in Vivo mRNA Delivery

Auto-degradable and biocompatible superparamagnetic iron oxide nanoparticles/polypeptides colloidal polyion complexes with high density of magnetic material

Synthesis and characterization of amino-functional polyesters composed of lactic acids and serine amino acids

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