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Advances in 2,3-Dimethylmaleic Anhydride (DMMA)-Modified Nanocarriers in Drug Delivery Systems

Wan, Dong, Wu, Yanan, Liu, Yujun, Liu, Yonghui, Pan, Jie·2024·Pharmaceutics
DOI 10.3390/pharmaceutics16060809PMC PMC11207803
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Abstract

Cancer represents a significant threat to human health. The cells and tissues within the microenvironment of solid tumors exhibit complex and abnormal properties in comparison to healthy tissues. The efficacy of nanomedicines is inhibited by the presence of substantial and complex physical barriers in the tumor tissue. The latest generation of intelligent drug delivery systems, particularly nanomedicines capable of charge reversal, have shown promise in addressing this issue. These systems can transform their charge from negative to positive upon reaching the tumor site, thereby enhancing tumor penetration via transcytosis and promoting cell internalization by interacting with the negatively charged cell membranes. The modification of nanocarriers with 2,3-dimethylmaleic anhydride (DMMA) and its derivatives, which are responsive to weak acid stimulation, represents a significant advance in the field of charge-reversal nanomedicines. This review provides a comprehensive examination of the recent insights into DMMA-modified nanocarriers in drug delivery systems, with a particular focus on their potential in targeted therapeutics. It also discusses the synthesis of DMMA derivatives and their role in charge reversal, shell detachment, size shift, and ligand reactivation mechanisms, offering the prospect of a tailored, next-generation therapeutic approach to overcome the diverse challenges associated with cancer therapy.

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Figure 1 Illustration of the stimulus–response of charge-reversal carriers [58]. Reprinted with permission from [58]. Copyright 2020 BioMed Central.
Figure 1 Illustration of the stimulus–response of charge-reversal carriers [58]. Reprinted with permission from [58]. Copyright 2020 BioMed Central.CC BY · PubMed Central
Figure 2 (a) Charge-reversible targeted PLL conjugated structure and its acid-triggered charge reversal; (b) Schematic diagram of drug delivery to the cell nucleus. The presence of the EPR effect causes these compounds to accumulate in the tumor tissue (A); a large number of folate receptors are present in the tumor tissue, and these folate receptors become the targeting points of the compounds, which are precisely localized and bound with the help of folate-targeting moieties (B1); they are endocytosed into the cell (C); translocation to the endosomes (D) followed by lysosomal uptake (E); the pH in the lysosome is about ~4–5, and this acidic environment favors the hydrolysis reaction of the amide, which in turn leads to PLL regeneration; the regenerated PLL carrier escapes from the lysosome into the cytoplasm (F) and diffuses into the nucleus (G), where the release of the drug it carries is accomplished. When PLLs are regenerated in the tumor tissue, they may adsorb to the cell membrane of the tumor cells, an adsorption process based on electrostatic interactions, which in turn triggers endocytosis (B2), allowing the drug to be taken up by the tumor cells more efficiently. Reprinted with permission from [89]. Copyright 2009 Wiley.
Figure 2 (a) Charge-reversible targeted PLL conjugated structure and its acid-triggered charge reversal; (b) Schematic diagram of drug delivery to the cell nucleus. The presence of the EPR effect causes these compounds to accumulate in the tumor tissue (A); a large number of folate receptors are present in the tumor tissue, and these folate receptors become the targeting points of the compounds, which are precisely localized and bound with the help of folate-targeting moieties (B1); they are endocytosed into the cell (C); translocation to the endosomes (D) followed by lysosomal uptake (E); the pH in the lysosome is about ~4–5, and this acidic environment favors the hydrolysis reaction of the amide, which in turn leads to PLL regeneration; the regenerated PLL carrier escapes from the lysosome into the cytoplasm (F) and diffuses into the nucleus (G), where the release of the drug it carries is accomplished. When PLLs are regenerated in the tumor tissue, they may adsorb to the cell membrane of the tumor cells, an adsorption process based on electrostatic interactions, which in turn triggers endocytosis (B2), allowing the drug to be taken up by the tumor cells more efficiently. Reprinted with permission from [89]. Copyright 2009 Wiley.CC BY · PubMed Central
Figure 3 Hydrolysis of 2,3-dimethylmaleic acid amide bonds triggered by tumor acidity. Reprinted with permission from [79]. Copyright 2018 American Chemical Society.
Figure 3 Hydrolysis of 2,3-dimethylmaleic acid amide bonds triggered by tumor acidity. Reprinted with permission from [79]. Copyright 2018 American Chemical Society.CC BY · PubMed Central
Figure 4 (A) Schematic of the preparation of a photothermal/photodynamic synergistic therapeutic nanomedicine delivery system; (B) Schematic of the in vivo circulation of nanomedicines [92]. Ce6-PLGA@PDA-PAH-DMMA NPs significantly enhance their endocytosis by cells through their surface-exposed positive charge properties, leading to efficient accumulation in tumor tissues. Once these nanoparticles are enriched at the tumor site, by applying 808 nm and 660 nm laser irradiation, these NPs are capable of rapidly generating large amounts of heat (photothermal effect) (i) as well as toxic reactive oxygen species (ROS) (ii). These two mechanisms work together to cause significant damage to the tumor tissue, ultimately effectively killing the tumor cells (iii). Reprinted with permission from [92]. Copyright 2022 Frontiers.
Figure 4 (A) Schematic of the preparation of a photothermal/photodynamic synergistic therapeutic nanomedicine delivery system; (B) Schematic of the in vivo circulation of nanomedicines [92]. Ce6-PLGA@PDA-PAH-DMMA NPs significantly enhance their endocytosis by cells through their surface-exposed positive charge properties, leading to efficient accumulation in tumor tissues. Once these nanoparticles are enriched at the tumor site, by applying 808 nm and 660 nm laser irradiation, these NPs are capable of rapidly generating large amounts of heat (photothermal effect) (i) as well as toxic reactive oxygen species (ROS) (ii). These two mechanisms work together to cause significant damage to the tumor tissue, ultimately effectively killing the tumor cells (iii). Reprinted with permission from [92]. Copyright 2022 Frontiers.CC BY · PubMed Central
Figure 5 Schematic representation of micelles with autophagic flux interference [85]. Reprinted with permission from [85]. Copyright 2023 BioMed Central.
Figure 5 Schematic representation of micelles with autophagic flux interference [85]. Reprinted with permission from [85]. Copyright 2023 BioMed Central.CC BY · PubMed Central
Figure 6 (DOX,PSF)@ZnO-DMMA nanoparticles synthesis strategy and schematic of intracellular drug delivery [93]. The red stars in this Figure are indicated the chemotherapy drug DOX. Reprinted with permission from [93]. Copyright 2020 Elsevier.
Figure 6 (DOX,PSF)@ZnO-DMMA nanoparticles synthesis strategy and schematic of intracellular drug delivery [93]. The red stars in this Figure are indicated the chemotherapy drug DOX. Reprinted with permission from [93]. Copyright 2020 Elsevier.CC BY · PubMed Central
Figure 7 Illustration of charge conversion and reduction-sensitive PVA nanogels for enhanced cellular uptake and intracellular DOX release. Reprinted with permission from [69]. Copyright 2015 Elsevier.
Figure 7 Illustration of charge conversion and reduction-sensitive PVA nanogels for enhanced cellular uptake and intracellular DOX release. Reprinted with permission from [69]. Copyright 2015 Elsevier.CC BY · PubMed Central
Figure 8 (A) Schematic diagram of the preparation of charge convertible CDs-based drug delivery system; (B) Schematic diagram of the drug delivery process. Reprinted with permission from [94]. Copyright 2016 American Chemical Society.
Figure 8 (A) Schematic diagram of the preparation of charge convertible CDs-based drug delivery system; (B) Schematic diagram of the drug delivery process. Reprinted with permission from [94]. Copyright 2016 American Chemical Society.CC BY · PubMed Central
Figure 9 Schematic structure and mechanism of acid-responsive ternary nanocarriers with detachable shells. Reprinted with permission from [95]. Copyright 2017 American Chemical Society.
Figure 9 Schematic structure and mechanism of acid-responsive ternary nanocarriers with detachable shells. Reprinted with permission from [95]. Copyright 2017 American Chemical Society.CC BY · PubMed Central
Figure 10 (A) DOX delivery process with stepwise pH-responsive NPs; (B) pH responsiveness of the polymer Da-cs-Ua [96]. Reprinted with permission from [96]. Copyright 2016 Dovepress.
Figure 10 (A) DOX delivery process with stepwise pH-responsive NPs; (B) pH responsiveness of the polymer Da-cs-Ua [96]. Reprinted with permission from [96]. Copyright 2016 Dovepress.CC BY · PubMed Central
Figure 11 Schematic illustration of intracellular drug release mechanism and lysosomal escape of nanopreparations [97]. Reprinted with permission from [97]. Copyright 2021 Elsevier.
Figure 11 Schematic illustration of intracellular drug release mechanism and lysosomal escape of nanopreparations [97]. Reprinted with permission from [97]. Copyright 2021 Elsevier.CC BY · PubMed Central
Figure 12 Schematic process of PELE-ss-DA micelles loaded with DOX for MDR cancer therapy. Reprinted with permission from [98]. Copyright 2015 Wiley.
Figure 12 Schematic process of PELE-ss-DA micelles loaded with DOX for MDR cancer therapy. Reprinted with permission from [98]. Copyright 2015 Wiley.CC BY · PubMed Central

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Metadata

Authors
Wan, D., Wu, Y., Liu, Y., Liu, Y., & Pan, J.
Venue
Pharmaceutics
Publisher
MDPI AG
Published
2024-06-14
Volume
16
Issue
6
Pages
809
ISSN
1999-4923
DOI
10.3390/pharmaceutics16060809
PMC
PMC11207803
Cited by
7
References
3
Language
en
Licence
creativecommons.org/licenses/by/4.0/ (vor)
Funders
National Natural Science Foundation of China (22178270, 22078246, 82103984)

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

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