One‐Step Preparation and pH‐Tunable Self‐Aggregation of Amphoteric Aliphatic Polycarbonates Bearing Plenty of Amine and Carboxyl Groups

Wang, Huafen; Jia, Hui‐Zhen; Zhu, Jingyi; Chu, Yanfeng; Feng, Jie; Zhang, Xian‐Zheng; Zhuo, Ren‐Xi

doi:10.1002/mabi.201200295

Cited by 14 publications

(9 citation statements)

References 31 publications

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“…Some reports suggest even quantitative removal of groups protecting carboxylic functionality [14]. Unfortunately, only few examples of single-step enzymatically catalyzed synthesis of polyacid via copolymerization of carboxylic-acid-functionalized carbonate were found in the literature [16,17].…”

Section: Introductionmentioning

confidence: 99%

Zirconium (IV) Acetylacetonate: Ring-Opening Initiator Mediating One-Step Synthesis of Biodegradable Polyacids

Dobrzyński

Pastusiak

Jaworska

et al. 2019

Advances in Polymer Technology

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Biodegradable polyacid is obtained in one-step ring-opening polymerization (ROP) of carboxylic-acid-functionalized six-membered cyclic carbonate mediated with zirconium (IV) acetylacetonate. Exemplary copolymers with L,L-lactide are described as well. Moreover, zirconium (IV) acetylacetonate is found to be active catalyst of trimethylene carbonate (TMC) ROP in presence of carboxylic acid yielding PTMC end-capped with the acid derivative. Polymerization mechanism is hypothesized demonstrating possibilities of the method in work-saving polycation synthesis and one-step method of conjugate synthesis of well-known biocompatible polyesters and polycarbonates.

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Section: Introductionmentioning

confidence: 99%

Zirconium (IV) Acetylacetonate: Ring-Opening Initiator Mediating One-Step Synthesis of Biodegradable Polyacids

Dobrzyński

Pastusiak

Jaworska

et al. 2019

Advances in Polymer Technology

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“…For example, in the form of an amphiphilic triblock copolymer ABA obtained using tertiary amine-functionalized APC diol as a telechelic initiator of enzymatic ROP of ε-caprolactone [98]. Furthermore, copolymer consisted of PEG and poly(tertiary amine-functionalized carbonate-co-ε-caprolactone) blocks [99], or amphoteric aliphatic copolycarbonates with amine and carboxyl groups in copolymer structure [100] were also reported.…”

Section: Polymers 2020 12 X For Peer Review 4 Of 31mentioning

confidence: 99%

Stimuli-Responsive Aliphatic Polycarbonate Nanocarriers for Tumor-Targeted Drug Delivery

et al. 2020

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Nanoparticles based on amphiphilic copolymers with tunable physicochemical properties can be used to encapsulate delicate pharmaceutics while at the same time improving their solubility, stability, pharmacokinetic properties, reducing immune surveillance, or achieving tumor-targeting ability. Those nanocarriers based on biodegradable aliphatic polycarbonates are a particularly promising platform for drug delivery due to flexibility in the design and synthesis of appropriate monomers and copolymers. Current studies in this field focus on the design and the synthesis of new effective carriers of hydrophobic drugs and their release in a controlled manner by exogenous or endogenous factors in tumor-specific regions. Reactive groups present in aliphatic carbonate copolymers, undergo a reaction under the action of a stimulus: e.g., acidic hydrolysis, oxidation, reduction, etc. leading to changes in the morphology of nanoparticles. This allows the release of the drug in a highly controlled manner and induces a desired therapeutic outcome without damaging healthy tissues. The presented review summarizes the current advances in chemistry and methods for designing stimuli-responsive nanocarriers based on aliphatic polycarbonates for controlled drug delivery.

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“…70 and 90%, respectively. Using lipase, in a one-step reaction, the terpolymers of MTC-COOH with TMC and ADMC (6,14-dimethyl-1,3,9,11-tetraoxa-6,14-diaza-cyclohexadecane-2,10-dione) were also obtained [12]. Importantly, it was also found that coordination complexes such as zirconium IV acetylacetonate Zr(acac) 4 may be successfully used as initiators in the ROP of monomers with active carboxylic groups, such as MTC-COOH.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Polyacids by Copolymerization of l-Lactide with MTC-COOH Using Zn[(acac)(L)H2O] Complex as an Initiator

et al. 2022

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This work presents the results of research on the preparation of bioresorbable functional polyestercarbonates containing side carboxyl groups. These copolymers were synthesized in two ways: the classic two-step process involving the copolymerization of L-lactide and a cyclic carbonate containing a blocked side carboxylate group in the form of a benzyl ester (MTC-Bz) and its subsequent deprotection, and a new way involving the one-step copolymerization of L-lactide with this same carbonate, but containing an unprotected carboxyl group (MTC-COOH). Both reactions were carried out under identical conditions in the melt, using a specially selected zinc chelate complex, with Zn [(acac)(L)H2O] (where: L-N-(pyridin-4-ylmethylene) phenylalaninate ligand) as an initiator. The differences in the kinetics of both reactions and their courses were pictured. The reactivity of the MTC-COOH monomer without a blocking group in the studied co-polymerization was much higher, even slightly higher than L-lactide, which allowed the practically complete conversion of the comonomers in a much shorter time. The basic final properties of the obtained copolymers and the microstructures of their chains were determined. The single-step synthesis of biodegradable polyacids was much simpler. Contrary to the conventional method, this made it possible to obtain copolymers containing all carbonate units with carboxyl groups, without even traces of the heavy metals used in the deprotection of the carboxyl groups, the presence of which is known to be very difficult to completely remove from the copolymers obtained in the two-step process.

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One‐Step Preparation and pH‐Tunable Self‐Aggregation of Amphoteric Aliphatic Polycarbonates Bearing Plenty of Amine and Carboxyl Groups

Cited by 14 publications

References 31 publications

Zirconium (IV) Acetylacetonate: Ring-Opening Initiator Mediating One-Step Synthesis of Biodegradable Polyacids

Zirconium (IV) Acetylacetonate: Ring-Opening Initiator Mediating One-Step Synthesis of Biodegradable Polyacids

Stimuli-Responsive Aliphatic Polycarbonate Nanocarriers for Tumor-Targeted Drug Delivery

Synthesis of Polyacids by Copolymerization of l-Lactide with MTC-COOH Using Zn[(acac)(L)H2O] Complex as an Initiator

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