Tyrosine based cationic acrylates as potent antimicrobial agents against shigellosis

Datta, Lakshmi Priya; Dutta, Dipak; Chakraborty, Arpita; Das, Tapan Kumar

doi:10.1039/c8bm01588k

Cited by 18 publications

(11 citation statements)

References 58 publications

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“…Synthesis of a polyampholyte copolymer with a well-defined and regular structure can be achieved by the reversible addition–fragmentation chain transfer (RAFT) polymerization technique . The incorporation of biological moieties within an artificial or synthetic polymeric system is of particular interest to integrate the biomimetic features. − Herein, we employed RAFT polymerization protocols to synthesize a block copolymer containing two polymethacrylate blocks with carboxylic side chains in one of the blocks functionalized with tryptophan (Trp). The incorporation of Trp units at the side chains allows for the utilization of free amine and indole groups to infuse polyampholytic character to the block copolymer.…”

Section: Introductionmentioning

confidence: 99%

Polyampholyte-Based Synthetic Chaperone Modulate Amyloid Aggregation and Lithium Delivery

Datta

Samanta

Govindaraju

2020

ACS Chem. Neurosci.

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Protein misfolding and aggregation is the pathological hallmark of Alzheimer’s disease (AD). The etiopathogenesis of AD involves the accumulation of amyloid-β (Aβ) plaques in the brain, which disrupt the neuronal network and communication, causing neuronal death and severe cognitive impairment. Modulation of Aβ aggregation by exogenous therapeutic agents is considered an effective strategy to treat AD. Frequent failure of drug candidates in various phases of clinical trials reiterates the need for alternative therapeutic strategies for AD treatment. Polyampholytes with cationic and anionic segments are considered as artificial protein mimics capable of modulating the protein misfolding and aggregation. We report a diblock copolymer of tryptophan-functionalized methacrylic acid (PTMA) polyampholyte synthesized through reversible addition–fragmentation chain transfer (RAFT) polymerization. Investigation revealed that PTMA acts as a synthetic chaperone to protect the native structure of the lysozyme under heat-induced aggregation conditions. PTMA effectively modulates Aβ aggregation and rescues neuronal cells. Lithium has been shown to exhibit therapeutic efficacy in chronic neurological diseases including AD. PTMA sequesters and releases lithium ions in response to neuropathological pH stimuli, making it a promising candidate for lithium transport and delivery. The detailed studies demonstrate PTMA as aggregation modulator and lithium carrier with implications for combinational therapy to treat AD.

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Section: Introductionmentioning

confidence: 99%

Polyampholyte-Based Synthetic Chaperone Modulate Amyloid Aggregation and Lithium Delivery

Datta

Samanta

Govindaraju

2020

ACS Chem. Neurosci.

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“…Keeping this in mind, in a recent work a series of side-chain tyrosine-based polyacrylate polymers have been synthesized by Datta et al by employing the RAFT method. 74 Interestingly, the polymers showed potent antibacterial activity against the bacterial strain Shigella flexneri and antifungal activity against the fungus Aspergillus niger. Also, they found that the biocidal activity increases with increase in the molecular weight of the polymers as the number of cationic charges increases which in turn affects the biocidal activity.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Side‐chain amino‐acid‐based polymers: self‐assembly and bioapplications

Nayak

Ghosh

Khan

et al. 2021

Polymer International

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The design and development of side-chain amino-acid-based polymeric nanostructures have attracted a significant research interest as they bring a remarkable revolution in various territories of the biomedical field. The incorporation of amino acid moieties into the side chain of synthetic polymeric scaffolds exhibits several beneficial properties like aqueous solubility, chiral recognition, high biocompatibility, stimuli responsiveness, antifouling properties, as well as their capability to form higher ordered self-assembled architectures. Considering the important features and widespread applications of side-chain aminoacid-containing polymers, here we shed light on the self-assembled characteristics of side-chain amino-acid-containing polymers and their implications. The primary aim of this review article is to highlight the recent achievements of this bright area of research. We describe the numerous aspects of side-chain amino-acid-containing polymers focusing mainly on self-assembly properties and the biomedical applications, which include drug and gene delivery, antimicrobial activity, antifouling coating, wound healing, tissue engineering etc.

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“…For this reason, a protection group, which can be removed under mild acidic conditions, is preferred over those being labile to basic conditions. [122,123] Thus, no degradation of the polymer side chain esters during the deprotection process is to be expected. Typically, the 𝛼-amino group is protected with a BOC group.…”

Section: Amino Acid-derived Poly(meth)acrylatesmentioning

confidence: 99%

A Guideline for the Synthesis of Amino‐Acid‐Functionalized Monomers and Their Polymerizations

Leiske

Kempe

2021

Macromol. Rapid Commun.

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Amino acids have emerged as a sustainable source for the design of functional polymers. Besides their wide availability, especially their high degree of biocompatibility makes them appealing for a broad range of applications in the biomedical research field. In addition to these favorable characteristics, the versatility of reactive functional groups in amino acids (i.e., carboxylic acids, amines, thiols, and hydroxyl groups) makes them suitable starting materials for various polymerization approaches, which include step-and chain-growth reactions. This review aims to provide an overview of strategies to incorporate amino acids into polymers. To this end, it focuses on the preparation of polymerizable monomers from amino acids, which yield main chain or side chain-functionalized polymers. Furthermore, postpolymerization modification approaches for polymer side chain functionalization are discussed. Amino acids are presented as a versatile platform for the development of polymers with tailored properties.

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Tyrosine based cationic acrylates as potent antimicrobial agents against shigellosis

Abstract: Design of tyrosine-based cationic polymers with antimicrobial activities.

Cited by 18 publications

References 58 publications

Polyampholyte-Based Synthetic Chaperone Modulate Amyloid Aggregation and Lithium Delivery

Polyampholyte-Based Synthetic Chaperone Modulate Amyloid Aggregation and Lithium Delivery

Side‐chain amino‐acid‐based polymers: self‐assembly and bioapplications

A Guideline for the Synthesis of Amino‐Acid‐Functionalized Monomers and Their Polymerizations

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