Engineering polyzwitterion with acylsulfonamide-based betaine structure for protonated switch of surface chemistry at tumoral pH and reductive responsive drug release of polymeric micelles

Zhou, Baoyuan; Cheng, Peng; Jiang, Junting; Chen, J.; Zhang, L.; Ju, Liang; Wu, Wen-Lan; Meng, Qingshu; Li, J.

doi:10.1016/j.mtchem.2020.100339

Cited by 9 publications

(5 citation statements)

References 38 publications

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“…However, P@DOX cannot fully release DOX within 24 h even at an acidic pH of 5.4 (the release rate was ∼67% within 24 h). On the basis of the existing reports, 44 the reason is that there are probably two different DOX forms, including physical bonded DOX (the electrostatic interaction between PDMAPS moiety and DOX) and embedded DOX inside the micelles. The former one will be rapidly released as the water-soluble segment stretches in acidic solution at pH 5.4, while the encapsulated ones will be released with the diffusion of DOX and the slow degradation of PCL fragments.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Structural Polyfluorene Derivative Nanocarriers with Promising Fluorescence Emission and Antifouling Properties

Zhu

Zhang

et al. 2022

ACS Appl. Polym. Mater.

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Herein, a zwitterionic PF-based copolymer, polyfluorene-a-polybenzothiadiazole-g-polycaprolactone-b-poly[3dimethyl(methacryloxyethyl)-propaneammoniumsulfonate] [PF-a-PBTH-g-(PCL-b-PDMAPS)], was synthesized by combining multiple polymerization techniques and further quaternization. The resultant copolymer with optimized structures (P5) was able to form stabilized unimolecular micelles in an aqueous solution with a diameter of approximately 110 nm. The unique donor− acceptor structure between fluorene and benzothiadiazole group along the conjugated main chains endows copolymers with yellowgreen fluorescence, while the PDMAPS chains with a unique zwitterionic nature enabled not only to enhance water solubility, drug loading efficiency (DLE), and drug loading capacity (DLC) of the whole copolymers but also to present promising antifouling property by preventing nonspecific protein/bacteria adhesion. Further in vivo and in vitro experiments demonstrate that the resultant P5 micelles also present lower cytotoxicity and efficient cellular uptake with the incubation of HeLa and HUVEC cells, which tends to prolong the circulation time of drugs. Our work not only provides a rational combination of zwitterions and polyfluorenes to significantly enhance the water solubility of hydrophobic fluorophores but also exhibits the potential of promising bioimaging for dual stimuli-responsive micelles in vitro (simulated body fluids) and in vivo (open).

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Section: ■ Results and Discussionmentioning

confidence: 99%

Structural Polyfluorene Derivative Nanocarriers with Promising Fluorescence Emission and Antifouling Properties

Zhu

Zhang

et al. 2022

ACS Appl. Polym. Mater.

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“…To overcome this issue, charge-converting zwitterionic polymers have been developed that maintain their zwitterionic nature in circulation but convert to a cationic form in response to endogenous stimuli, most commonly pH, thus improving uptake. [138,139] Ranneh et al developed a pH-responsive polycarboxybetaine based zwitterionic polymer that undergoes charge conversion from neutral at pH 7.4 to cationic at the acidic pH of the tumor microenvironment and inside the endosomes. This charge conversion strategy improved uptake and endosomal escape and enhanced therapeutic efficacy using a polymer based on PEI and a previously developed zwitterionic polymer [140] (Figure 6C).…”

Section: Zwitterionic Polymersmentioning

confidence: 99%

“…• Zwitterionic polymers have enhanced antifouling properties leading to improved serum stability and in vivo circulation times. [126,[129][130][131][134][135][136][137][138][140][141][142][143][144][145] Decationizable polymers…”

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confidence: 99%

Beyond Lipids: Exploring Advances in Polymeric Gene Delivery in the Lipid Nanoparticles Era

Jogdeo,

Siddhanta,

Das

et al. 2024

Advanced Materials

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The recent success of gene therapy during the COVID‐19 pandemic has underscored the importance of effective and safe delivery systems. Complementing lipid‐based delivery systems, polymers present a promising alternative for gene delivery. Significant advances have been made in the recent past, with multiple clinical trials progressing beyond phase I and several companies actively working on polymeric delivery systems which provides assurance that polymeric carriers can soon achieve clinical translation. The massive advantage of structural tunability and vast chemical space of polymers is being actively leveraged to mitigate shortcomings of traditional polycationic polymers and improve the translatability of delivery systems. Tailored polymeric approaches for diverse nucleic acids and for specific subcellular targets are now being designed to improve therapeutic efficacy. This review describes the recent advances in polymer design for improved gene delivery by polyplexes and covalent polymer‐nucleic acid conjugates. The review also offers a brief note on novel computational techniques for improved polymer design. We conclude with an overview of the current state of polymeric gene therapies in the clinic as well as future directions on their translation to the clinic.This article is protected by copyright. All rights reserved

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“…To increase bio-interaction with the targeted side, pH-responsive polyzwitterions with charge reversal have been further developed by tailoring pH-responsiveness of the anionic or cationic moiety in a mildly acidic environment [27]. For instance, Ranneh's group discovered a cationic approach by a synthesized polymer with ethylenediamine-based betaine groups [28]. Stepwise protonation behavior of diamine moiety enabled a zwitterionic structure at physiological pH, which rapidly converted into cationic property at pH 6.5 for increased interaction with the tumor site.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pH-responsive polyzwitterions for activated cellular uptake and tumor accumulation of gold nanoparticles at tumorous acidity

Cheng

Shang

et al. 2023

Biomed. Mater.

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The response sensitivity of surface material plays an important role in adjustable nano-bio interaction in vivo. In this present, a zwitterionic polymer (polyzwitterion) containing quaternary ammonium cation and sulfonamide anion (PMPTSA) was synthesized by RAFT polymerization to explore the pH responsive behavior in tumors. The PMPTSA-coated gold nanoparticles (PMPTSA-@-Au NPs) showed zwitterionic nature such as antifouling ability, low cellular uptake and prolonged circulation time similar with common hydrophilic polymers, including polyethylene glycol (PEG), poly(carboxybetaine methacrylate) (PCBMA) and poly (sulfobetaine methacrylate) (PSBMA) functional gold nanoparticles in physiological environment (pH7.4). A high sensitivity and reversible positive charge conversion of P(MPTSA)-@-Au NPs at tumor slight acidic microenvironment(~pH6.8) leaded to an enhanced cellular internalization than that at pH7.4 and increased tumor accumulation compared with PEG, PCB and PSB functional gold nanoparticles. The highly pH responsive PMPTSA will provide the promising application in cancer nano-medicine.

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Engineering polyzwitterion with acylsulfonamide-based betaine structure for protonated switch of surface chemistry at tumoral pH and reductive responsive drug release of polymeric micelles

Cited by 9 publications

References 38 publications

Structural Polyfluorene Derivative Nanocarriers with Promising Fluorescence Emission and Antifouling Properties

Structural Polyfluorene Derivative Nanocarriers with Promising Fluorescence Emission and Antifouling Properties

Beyond Lipids: Exploring Advances in Polymeric Gene Delivery in the Lipid Nanoparticles Era

Synthesis of pH-responsive polyzwitterions for activated cellular uptake and tumor accumulation of gold nanoparticles at tumorous acidity

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