Tunable nanostructures by directional assembly of donor–acceptor supramolecular copolymers and antibacterial activity

Chakraborty, Saptarshi; Barman, Ranajit; Ghosh, Suhrit

doi:10.1039/c9tb02772f

Cited by 12 publications

(12 citation statements)

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“…74 As such, the implications of the above results on a broader range of chemistries involving trimethylanilinium salts is also worth delineating. In our estimation, the fundamental understanding of the structural parameters affecting anilinium salt degradation hold implications for: (i) the design of anilinium-derived ionic liquids used as solvents, electrolytes, and in electropolymerisation strategies, 75,76 (ii) the design and understanding of anilinium-derived compounds used in antibacterial technologies, 77,78 (iii) understanding the reaction conditions and range of anilinium substitution patterns amenable to metal-catalysed chemistries (including but not limited to arylation, alkynylation, silylation, and ortho-methylation), 7,8,23,29,31,79 (iv) understanding substrate design for 18 F radiolabelling mediated by S N Ar chemistries on anilinium cores, 12,80 and (v) a fuller understanding of the range of anilinium structures applicable to ion-pair directed regiocontrol of C-H activation methods. Fig.…”

Section: Discussionmentioning

confidence: 99%

Trialkylammonium salt degradation: implications for methylation and cross-coupling

et al. 2021

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Section: Discussionmentioning

confidence: 99%

Trialkylammonium salt degradation: implications for methylation and cross-coupling

et al. 2021

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“…(a) Structure of donor and acceptor amphiphiles (reported in refs − ). Representative negatively stained TEM images of (b) NDI-25, (c) Py-2, and (d) NDI-25 + Py-2 (1:1).…”

Section: Co-assembly Of Donor and Acceptor Containing Amphiphilesmentioning

confidence: 99%

“…(e) Schematic showing formation of unsymmetric two-component donor–acceptor supramolecular polymersome. Adapted with permission from refs and . Copyright 2018 Wiley VCH and Copyright 2020 Royal Society of Chemistry.…”

Section: Co-assembly Of Donor and Acceptor Containing Amphiphilesmentioning

confidence: 99%

Molecular Recognition Driven Bioinspired Directional Supramolecular Assembly of Amphiphilic (Macro)molecules and Proteins

et al. 2021

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Metrics & MoreArticle Recommendations CONSPECTUS: Bioinspired self-assembly has been explored with diverse synthetic scaffolds, among which amphiphiles are perhaps the most extensively studied systems. Classical surfactants or amphiphilic block copolymers, depending on the hydrophobic− hydrophilic balance, produce distinct nanostructures, which hold promise for applications ranging from biology to materials sciences. Nevertheless, their immiscibility-driven aggregation does not provide the opportunity to precisely regulate the internal order, morphology, or functional group display, which is highly desirable, especially in the context of biological applications.A new class of amphiphiles have emerged in the recent past in which the hydrophilic segment(s) is appended with a hydrophobic supramolecular-structure-directing-unit (SSDU), consisting of a π-conjugated chromophore and a H-bonding group. Selfrecognition of the SSDU by attractive directional interactions governs the supramolecular assembly, which is fundamentally different than the repulsive solvent-immiscibility driven aggregation of traditional amphiphiles. Such SSDU-appended hydrophilic polymers exhibit entropy-driven highly stable self-assembly producing distinct nanostructures depending on the H-bonding functional group. For example, polymers with the hydrazide-functionalized SSDU attached form a polymersome, while in a sharp contrast, the same polymers when connected to an amide containing SSDU produce a cylindrical micelle via a spherical-micelle intermediate. This relationship holds true for a series of SSDU-attached hydrophilic polymers irrespective of the hydrophobic/hydrophilic balance or chemical structure, indicating that the supramolecular-assembly is primarily controlled by the specific molecular-recognition motif of the SSDU, instead of the packing parameter-based norms. Beyond synthetic polymers, SSDU-attached proteins also exhibit similar molecular-recognition driven self-assembly as well as coassembly with SSDU-attached polymers or hydrophilic wedges, producing multi-stimuli-responsive nanostructures in which the protein gains remarkable protection from thermal denaturation or enzymatic hydrolysis and exhibits redox-responsive enzymatic activity. Furthermore, SSDU-derived bola-shape π-amphiphiles have been recognized as a useful scaffold for the synthesis of unsymmetric polymersomes, rarely reported in the literature. The building block consists of a hydrophobic naphthalene-diimide (NDI) π-system attached to a hydrophilic functional group (ionic or nonionic) and a nonionic wedge on its two opposite arms. Extended H-bonding among the hydrazide groups, placed only on one side of the central chromophore by design, ensures stacking of the NDIs with parallel orientation and induces a preferred direction of curvature so that the H-bonded chain and consequently the functional groups attached to the same side remain at the inner-wall of the supramolecular polymersome. Automatically, the functional groups, located on the other side, are displayed ...

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“…Du and coworkers reported pioneering studies of polymer vesicles in the application of antibacterial [ 38 , 88 ]. In general, the polymer vesicles with positively charged surface exhibited both Gram-positive and Gram-negative bacteria inhibition activity due to the non-selectivity of the physical damage of the cell membrane of bacteria [ 83 , 103 , 104 , 105 ]. Comparing to their linear counterparts, polymer vesicles usually showed better antimicrobial activity due to the enhanced local charge density and reduced cytotoxicity toward mammalian cell, owing to the shield effect of the coronas, which was described in the previous sections.…”

Section: Antimicrobial Applications Of Polymer Vesiclesmentioning

confidence: 99%

Polymer Vesicles for Antimicrobial Applications

2021

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Polymer vesicles, hollow nanostructures with hydrophilic cavity and hydrophobic membrane, have shown significant potentials in biomedical applications including drug delivery, gene therapy, cancer theranostics, and so forth, due to their unique cell membrane-like structure. Incorporation with antibacterial active components like antimicrobial peptides, etc., polymer vesicles exhibited enhanced antimicrobial activity, extended circulation time, and reduced cell toxicity. Furthermore, antibacterial, and anticancer can be achieved simultaneously, opening a new avenue of the antimicrobial applications of polymer vesicles. This review seeks to highlight the state-of-the-art of antimicrobial polymer vesicles, including the design strategies and potential applications in the field of antibacterial. The structural features of polymer vesicles, preparation methods, and the combination principles with antimicrobial active components, as well as the advantages of antimicrobial polymer vesicles, will be discussed. Then, the diverse applications of antimicrobial polymer vesicles such as wide spectrum antibacterial, anti-biofilm, wound healing, and tissue engineering associated with their structure features are presented. Finally, future perspectives of polymer vesicles in the field of antibacterial is also proposed.

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Tunable nanostructures by directional assembly of donor–acceptor supramolecular copolymers and antibacterial activity

Abstract: This manuscript reports supramolecular copolymerization of amphiphilic donor (D) and acceptor (A) units and their antibacterial activity.

Cited by 12 publications

References 63 publications

Trialkylammonium salt degradation: implications for methylation and cross-coupling

Trialkylammonium salt degradation: implications for methylation and cross-coupling

Molecular Recognition Driven Bioinspired Directional Supramolecular Assembly of Amphiphilic (Macro)molecules and Proteins

Polymer Vesicles for Antimicrobial Applications

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