ArticleInternational journal of nanomedicine2013
A novel application of maleimide for advanced drug delivery: in vitro and in vivo evaluation of maleimide-modified pH-sensitive liposomes.
Article in International journal of nanomedicine, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 42 citations in OpenAlex.
- TagC-RED: An Infrared-Triggered Retro-Ene Reaction for Deep-Tissue Bioconjugation.Journal of the American Chemical Society · 2026Article
- Cell surface thiol-disulfide regulation in cancer: Mechanisms, implications, and theranostic strategies.Redox biology · 2026Review
- Bifunctional Cysteine-Engineered CAR‑T Cells Enable Thiol-Mediated Targeting to Overcome Antigen Escape in B Cell Lymphoma.ACS central science · 2025Article
- Development of Stable, Maleimide-Functionalized Peptidoliposomes Against SARS-CoV-2.International journal of molecular sciences · 2025Article
- Peptide and Protein Cysteine Modification Enabled by Hydrosulfuration of Ynamide.ACS central science · 2024Article
- The Emerging Roles of Nanocarrier Drug Delivery System in Treatment of Intervertebral Disc Degeneration-Current Knowledge, Hot Spots, Challenges and Future Perspectives.Drug design, development and therapy · 2024Review
- Maleimide-Functionalized Liposomes: Prolonged Retention and Enhanced Efficacy of Doxorubicin in Breast Cancer with Low Systemic Toxicity.Molecules (Basel, Switzerland) · 2022Article
- Tumor Microenvironmental Responsive Liposomes Simultaneously Encapsulating Biological and Chemotherapeutic Drugs for Enhancing Antitumor Efficacy of NSCLC.International journal of nanomedicine · 2020Article
- Multifunctional gold nanorods and docetaxel-encapsulated liposomes for combined thermo- and chemotherapy.International journal of nanomedicine · 2017Article
- Effect of the nanoformulation of siRNA-lipid assemblies on their cellular uptake and immune stimulation.International journal of nanomedicine · 2017Article
- Enhanced cellular uptake of maleimide-modified liposomes via thiol-mediated transport.International journal of nanomedicine · 2014Article
- Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier.Beilstein journal of organic chemistry · 2014Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Maleimide is a stable and easy-to-handle moiety that rapidly and covalently conjugates thiol groups of cysteine residues in proteins or peptides. Herein, we use maleimide to modify the surface of liposomes in order to obtain an advanced drug delivery system. Employing a small amount (0.3 mol%) of maleimide-polyethylene glycol (PEG) to modify the surface of the liposomes M-GGLG-liposomes, composed of 1,5-dihexadecyl N,N-diglutamyl-lysyl-L-glutamate (GGLG)/cholesterol/poly(ethylene glycol) 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (PEG5000-DSPE)/maleimide-PEG5000-Glu2C18 at a molar ratio of 5:5:0.03:0.03, drug delivery efficiency was remarkably improved both in vitro and in vivo compared to unmodified liposomes (GGLG-liposomes, composed of GGLG/cholesterol/PEG5000-DSPE/PEG5000-Glu2C18 at a molar ratio of 5:5:0.03:0.03). Moreover, this modification did not elicit any detectable increase in cytotoxicity. The maleimide-modification did not alter the physical characteristics of the liposomes such as size, zeta potential, pH sensitivity, dispersibility and drug encapsulation efficiency. However, M-GGLG-liposomes were more rapidly (≥2-fold) internalized into HeLa, HCC1954, and MDA-MB-468 cells compared to GGLG-liposomes. In vivo, M-GGLG-liposomes encapsulating doxorubicin (M-GGLG-DOX-liposomes) also showed a more potent antitumor effect than GGLG-DOX-liposomes and the widely used 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC)-DOX-liposomes after two subcutaneous injections around breast cancer tissue in mice. The biodistribution of liposomes in this model was observed using an in vivo imaging system, which showed that M-GGLG-liposomes were present for significantly longer at the injection site compared to GGLG-liposomes. The outstanding biological functions of the maleimide-modified liposomes as a novel drug delivery system make them ideally suited to a wide range of applications.
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