Synthesis and self-assembly of amphiphilic and biocompatible poly(vinyl alcohol)-block-poly(l-lactide) copolymer

Mishra, Avnish Kumar; Park, Jicheol; Joseph, K. L. Vincent; Maiti, Suman; Kwak, Jongheon; Choi, Chungryong; Hyun, Seung; Kim, Jin Kon

doi:10.1016/j.polymer.2016.08.005

Cited by 15 publications

(3 citation statements)

References 45 publications

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“…1 H NMR (600 MHz, CDCl 3 ): δ 3.39-3.37 (m, 2H), 2.82-2.80 (m, 2H), 1.76-1.71 (m, 2H); JMOD NMR (150 MHz, CDCl 3 ): δ 32.6, 39.4, 49.2. NMR data were consistent with literature 86 .…”

Section: Methodssupporting

confidence: 88%

Synthesis of vancomycin fluorescent probes that retain antimicrobial activity, identify Gram-positive bacteria, and detect Gram-negative outer membrane damage

et al. 2023

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Antimicrobial resistance is an urgent threat to human health, and new antibacterial drugs are desperately needed, as are research tools to aid in their discovery and development. Vancomycin is a glycopeptide antibiotic that is widely used for the treatment of Gram-positive infections, such as life-threatening systemic diseases caused by methicillin-resistant Staphylococcus aureus (MRSA). Here we demonstrate that modification of vancomycin by introduction of an azide substituent provides a versatile intermediate that can undergo copper-catalysed azide−alkyne cycloaddition (CuAAC) reaction with various alkynes to readily prepare vancomycin fluorescent probes. We describe the facile synthesis of three probes that retain similar antibacterial profiles to the parent vancomycin antibiotic. We demonstrate the versatility of these probes for the detection and visualisation of Gram-positive bacteria by a range of methods, including plate reader quantification, flow cytometry analysis, high-resolution microscopy imaging, and single cell microfluidics analysis. In parallel, we demonstrate their utility in measuring outer-membrane permeabilisation of Gram-negative bacteria. The probes are useful tools that may facilitate detection of infections and development of new antibiotics.

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“…1 H NMR (600 MHz, CDCl 3 ): δ 3.39-3.37 (m, 2H), 2.82-2.80 (m, 2H), 1.76-1.71 (m, 2H); JMOD NMR (150 MHz, CDCl 3 ): δ 32.6, 39.4, 49.2. NMR data were consistent with literature 86 .…”

Section: Methodssupporting

confidence: 88%

Synthesis of vancomycin fluorescent probes that retain antimicrobial activity, identify Gram-positive bacteria, and detect Gram-negative outer membrane damage

et al. 2023

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“…Another prevalent click chemistry is alkyne−azide, which was utilized to couple PVA synthesized through RAFT polymerization and PLLA synthesized through ROP. 171 As xanthates are known to effectively polymerize VAc, azide bearing xanthate was synthesized and used to synthesize azide terminated PVAc, which was then converted into PVA. The RAFT end group was converted into a thiol in the process.…”

Section: Raft First: Combined Approaches For Block Copolymer Synthesismentioning

confidence: 99%

Linear Block Copolymer Synthesis

et al. 2022

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Block copolymers form the basis of the most ubiquitous materials such as thermoplastic elastomers, bridge interphases in polymer blends, and are fundamental for the development of high-performance materials. The driving force to further advance these materials is the accessibility of block copolymers, which have a wide variety in composition, functional group content, and precision of their structure. To advance and broaden the application of block copolymers will depend on the nature of combined segmented blocks, guided through the combination of polymerization techniques to reach a high versatility in block copolymer architecture and function. This review provides the most comprehensive overview of techniques to prepare linear block copolymers and is intended to serve as a guideline on how polymerization techniques can work together to result in desired block combinations. As the review will give an account of the relevant procedures and access areas, the sections will include orthogonal approaches or sequentially combined polymerization techniques, which increases the synthetic options for these materials.

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“…15 Usually, flexible monomers are introduced into PLA to reduce its rigidity and crystallization ability and weaken the interactions between PLA molecules. 16 To improve the toughness of PLA materials, relevant researches focus on copolymerize PLA with other flexible segments, such as polyethylene oxide (PEO), [17][18][19][20] poly(vinyl alcohol) (PVA), [21][22][23] polydimethylsiloxane (PDMS) 24,25 and so forth. However, the introduction of non-renewable petroleum-based materials reduce the biodegradability and eco-friendliness of PLA.…”

Section: Introductionmentioning

confidence: 99%

Poly(L‐lactide)‐b‐poly(ε‐caprolactone)‐b‐poly(D,L‐lactide) copolymers with enhanced toughness and strength by regulating crystallization and phase separation

Chen,

Zhang,

Zhang

et al. 2023

Journal of Polymer Science

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Copolymerizing poly(lactide) with other materials to obtain better comprehensive performance is a effective way to expand its application range. In this work, the precursors of hydroxyl terminated (poly(L‐lactide) [PLLA], poly(ε‐caprolactone) [PCL], poly(D,L‐lactide) [PDLLA]) were prepared, and PLLA‐PCL‐PDLLA copolymer were synthesized by chain extension. The effects of the proportion and molecular weight of each component and the amount of chain extender on crystallization, phase structures, mechanical properties and thermal stabilities of PLLA‐PCL‐PDLLA copolymer were studied in detail. Based on small‐angle X‐ray scattering results, the competition between crystallization and microphase separation was regulated by the composition and chain length of prepolymers. As the ratio of PLLA/PDLLA was 1:1, crystallization was prevailing and no obvious peak was observed in SAXS pattern. The tensile test results showed that as the ratio of PLLA/PDLLA increased from 1:1 to 1:5, the elongation at break of the copolymer changed from 1.8% to 343%. By using shorter length of PCL and PLLA segments in chain extension, improvement in strength and flexibility were obtained due to moderate degree of crystallization and microphase separation. This work used biodegradable materials to prepare extraordinary toughness copolymers without losing the biocompatibility, which may provide a feasible method for obtaining high toughness and biodegradable PLA‐based materials.

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Synthesis and self-assembly of amphiphilic and biocompatible poly(vinyl alcohol)-block-poly(l-lactide) copolymer

Cited by 15 publications

References 45 publications

Synthesis of vancomycin fluorescent probes that retain antimicrobial activity, identify Gram-positive bacteria, and detect Gram-negative outer membrane damage

Synthesis of vancomycin fluorescent probes that retain antimicrobial activity, identify Gram-positive bacteria, and detect Gram-negative outer membrane damage

Linear Block Copolymer Synthesis

Poly(L‐lactide)‐b‐poly(ε‐caprolactone)‐b‐poly(D,L‐lactide) copolymers with enhanced toughness and strength by regulating crystallization and phase separation

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