Phenylboronic ester-modified anionic micelles for ROS-stimuli response in HeLa cell

Wang, Qi Y; Xu, Yi S; Zhang, Nan X; Dong, Zhi P; Zhao, Bo; Liu, Lin C; Lü, Tao; Wang, Yue

doi:10.1080/10717544.2020.1748761

Cited by 15 publications

(10 citation statements)

References 38 publications

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“…Cystamine dihydrochloride, 1-piperidinepropionic acid, di- tert -butyl dicarbonate (Boc 2 O), α-methyl-ω-amino poly(ethylene glycol) (Mw = 2000), and β-benzyl- l -aspartic acid were purchased from Aladdin (China). N-Carboxy-α-amino acid anhydride of benzyl 2-(2,5-dioxooxazolidin-4-yl) acetate (BLA-NCA) was synthesized from β-benzyl- l -aspartic acid as reported . Glutathione (GSH) and Doxorubicin Hydrochloride (DOX·HCl, 99.8%) were purchased from Sinopharm Chemical Reagent (Shanghai, China).…”

Section: Methodsmentioning

confidence: 99%

“…As shown Table S1, a series of PEG- b -PAsp copolymers with different proportion of hydrophobic segments and hydrophilic segments were synthesized according to the method reported previously …”

Section: Methodsmentioning

confidence: 99%

“…N-Carboxy-α-amino acid anhydride of benzyl 2-(2,5-dioxooxazolidin-4-yl) acetate (BLA-NCA) was synthesized from βbenzyl-L-aspartic acid as reported. 32 Glutathione (GSH) and Doxorubicin Hydrochloride (DOX•HCl, 99.8%) were purchased from Sinopharm Chemical Reagent (Shanghai, China). Characterization.…”

Section: ■ Conclusionmentioning

confidence: 99%

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An Integrated Tumor Microenvironment Responsive Polymeric Micelle for Smart Drug Delivery and Effective Drug Release

et al. 2021

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Tumor microenvironment (TME) responsive polymeric micelles are promising carriers for drug delivery. In order to meet the needs of various applications, multifarious TME-responsive switches are used to construct smart polymeric micelles, which causes the complexity and corpulence of the polymeric micelle system and increases the difficulty of preparation. In this study, we designed and synthesized an ingenious TME-responsive switch through grafting disulfide bond-modified piperidinepropionic acid (CPA) on copolymer poly(ethylene glycol)-b-poly(aspartate)(PEG-b-PAsp) and built a novel pH/reduction-responsive PEG-b-PAsp-g-CPA polymeric micelle delivery system. The CPA-pendants can reverse the surface charge of the polymeric micelle from negative to positive at pH 6.5 because of the protonation of piperidine groups, thereby enhancing the internalization of cell. Subsequently, more piperidine groups are protonated at pH 5.0 which will increase the hydrophilicity of polymeric micelles and cause the hydrophobic core to swell, thus making the disulfide bonds packed in the core to be more easily broken by GSH. With the synergistic effect of the pH-triggered protonation of piperidine groups and reduction triggered break of disulfide bonds, the polymeric micelles will disintegrate and achieve efficient intracellular drug release. The TME-responsive polymeric micelles exhibited good biological safety, enhanced internalization, and rapid intracellular doxorubicin (DOX) release in vitro. Moreover, the PEG-b-PAsp-g-CPA/DOX polymeric micelles showed excellent antitumor efficacy and low systemic toxicity in lung tumor-bearing BALB/C mice. These results indicated that the novel integrated TME-responsive switch CPA helps the PEG-b-PAsp-g-CPA polymeric micelles to obtain excellent TME-responsiveness and antitumor drug delivery capabilities, while it also makes the preparation of TME-responsive polymeric micelles simpler and more convenient. This work provides a new idea for the architecture of TMEresponsive polymeric micelles.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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An Integrated Tumor Microenvironment Responsive Polymeric Micelle for Smart Drug Delivery and Effective Drug Release

et al. 2021

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“…H 2 O 2 can selectively degrade phenyl‐boronic acid/ester to form phenol and boronic acid. The general approach to build phenylboronic acid containing polypeptide is that p ‐hydroxymethyl phenylboronic acid or its derivatives are linked to the side chains of functional polypeptide (Y. Wang, Fan, et al, 2020; Q. Wang, Xu, et al, 2020). For that purpose, Lv et al designed a kind of 4‐(hydroxymethyl) phenylboronic acid pinacol carbonylimidazole modified PEG‐ b ‐poly‐[( N ‐2‐hydroxyethyl)‐aspartamide] (i.e., P‐PBA) (S. Lv et al, 2018).…”

Section: Ros‐responsive Polypeptide Nanoassemblymentioning

confidence: 99%

Stimuli‐responsive polypeptide nanoassemblies: Recent progress and applications in cancer nanomedicine

Song

Ding

Dong

2021

WIREs Nanomed Nanobiotechnol

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Stimuli‐responsive polypeptide nanoassemblies exhibit great potentials for cancer nanomedicines because of desirable biocompatibility and biodegradability, unique secondary conformations, varying functionalities, and especially the stimuli‐enhanced therapeutic efficacy and reduced side effect. This review introduces the design and fabrication of stimuli‐responsive polypeptide nanoassemblies that exhibit endogenous stimuli (e.g., pH, reduction, reactive oxygen species, adenosine triphosphate and enzyme, etc.) and exogenous light stimuli (e.g., UV and near‐infrared light), which are biologically related or applied in the clinic. We also discuss the applications and prospects of those stimuli‐responsive polypeptide nanoassemblies that might overcome the biological barriers of cancer nanomedicines for in vivo administration. Much more effort is needed to accelerate the second‐generation stimuli‐responsive polypeptide nanomedicines for clinical transition and applications. This article is categorized under: Therapeutic Approaches and Drug Discovery > Nanomedicine for Oncologic Disease

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“…This system allows for gradual or temporary release of free active drugs from the nanocarriers in a controlled fashion and a constant drug concentration in the tumor tissue [ 14 – 16 ]. It is well known that poly( l -Aspartic)-polymeric-drug conjugates have consistently been used for drug development as PAsp is biocompatible, biodegradable, and easily modified to be a drug conjugate [ 17 , 18 ]. Similarly, the carboxyl group on the structure of Aspartic acid can be esterified with the hydroxyl group on the CA4 structure to form a nano-prodrug.…”

Section: Introductionmentioning

confidence: 99%

Co-administration of combretastatin A4 nanoparticles and anti-PD-L1 for synergistic therapy of hepatocellular carcinoma

et al. 2021

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Background According to data estimated by the WHO, primary liver cancer is currently the fourth most common malignant tumor and the second leading cause of death around the world. Hepatocellular carcinoma (HCC) is one of the most common primary liver malignancies, so effective therapy is highly desired for HCC. Results In this study, the use of poly(l-Aspartic acid)-poly(ethylene glycol)/combretastatin A4 (CA4-NPs) was aimed to significantly disrupt new blood vessels in tumor tissues for targeted hepatic tumor therapy. Here, PEG-b-PAsp-g-CA4 showed significantly prolonged retention in plasma and tumor tissue. Most importantly, CA4-NPs were mainly distributed at the tumor site because of the triple target effects—enhanced permeability and retention (EPR) effect, acid-sensitive (pH = 5.5) effect to the tumor microenvironment (TME), and good selectivity of CA4 for central tumor blood vessel. Considering that CA4-NPs might induce severe hypoxic conditions resulting in high expression of HIF-1α in tumor tissues, which could induce the overexpression of PD-L1, herein we also used a programmed death-ligand 1 antibody (aPD-L1) to prevent immunosuppression. This way of complementary combination is able to achieve an ideal treatment effect in tumor site where CA4-NPs and aPD-L1 could respond to the inner area and peripheral area, respectively. As a result, a significant decrease in tumor volume and weight was observed in the combination group of CA4-NPs plus aPD-L1 compared with CA4-NPs or aPD-L1 monotherapy in subcutaneous Hepa1-6 hepatic tumor models. Conclusions We presented a new idea that co-administration of CA4-NPs and aPD-L1 possessed notable anti-tumor efficacy for HCC treatment. Graphic abstract

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Phenylboronic ester-modified anionic micelles for ROS-stimuli response in HeLa cell

Cited by 15 publications

References 38 publications

An Integrated Tumor Microenvironment Responsive Polymeric Micelle for Smart Drug Delivery and Effective Drug Release

An Integrated Tumor Microenvironment Responsive Polymeric Micelle for Smart Drug Delivery and Effective Drug Release

Stimuli‐responsive polypeptide nanoassemblies: Recent progress and applications in cancer nanomedicine

Co-administration of combretastatin A4 nanoparticles and anti-PD-L1 for synergistic therapy of hepatocellular carcinoma

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