Specific Binding of Liposomal Nanoparticles through Inverse Electron‐Demand Diels–Alder Click Chemistry

Brand, Christian; Iacono, Pasquale; Pérez-Medina, Carlos; Mulder, Willem J. M.; Kircher, Moritz F.; Reiner, Thomas

doi:10.1002/open.201700105

Cited by 6 publications

(4 citation statements)

References 20 publications

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“…The classic chemical method using EDC/NHS is not selective: the free amino group of any protein can react with the activated lipid derivatives, which could introduce steric hindrance to the protein–ligand interaction and even cause cross-linking of the lipid/liposome with the proteins. To address this issue, “two-step click chemistry” dependent on the site-specific functional modification of the proteins has been introduced. − …”

Section: Discussionmentioning

confidence: 99%

Using a Membrane-Penetrating-Peptide to Anchor Ligands in the Liposome Membrane Facilitates Targeted Drug Delivery

Fan

Song

et al. 2019

Bioconjugate Chem.

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Antimicrobial peptides (AMPs) are typical cell penetrating peptides (CPPs) that intercalate into biomembranes and exhibit broad activities. We designed a triple fusion protein consisting of an AMP, Ib-AMP4 at the N-terminus, a fluorescent GFP probe in the center, and the tumor-targeting peptide P1c at the other terminus. After purification from E. coli, the interaction between the Ib-AMP4-GFP-P1c fusion protein (IGP) and the lipid membrane was characterized. Experiments using isothermal titration calorimetry (ITC) and quartz crystal microbalance with dissipation (QCM-D) demonstrated that IGP proteins spontaneously bound the lipid bilayer with a maximal molar ratio of 1:52 (protein:lipid). Furthermore, transmission electron microscopy (TEM) confirmed that the IGP protein was present in the liposome membrane. After decoration with IGP proteins, the DOPC:DOPG liposomes were applied to cancer cells. Microscopy and flow cytometry reveal that the decorated liposomes selectively bound integrin αvβ3-positive A549 cells. In addition, compared with the common chemical conjugation method, the reported method seemed to be superior in certain aspects, such as simple sample preparation and costeffectiveness. Next, the IGP protein was applied to decorate red blood cell (RBC) liposomes for targeted delivery in both in vitro and in vivo applications. The IGP-decorated RBC liposomes preferentially targeted integrin αvβ3 expressing A549 cancer cells. The in vivo imaging showed that IGP-decorated RBC liposomes were concentrated in tumor tissue and were primarily metabolized by the liver and kidney.

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Section: Discussionmentioning

confidence: 99%

Using a Membrane-Penetrating-Peptide to Anchor Ligands in the Liposome Membrane Facilitates Targeted Drug Delivery

Fan

Song

et al. 2019

Bioconjugate Chem.

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“…To circumvent this problem, Brand et al recently designed an IEDDA-based platform for the specific removal of longcirculating radiopharmaceuticals from the systemic circuit. 219 Tz-polydopamine-coated metal disks (Tz-PDA@CoCrMo) were developed to remove the TCO− 89 Zr-radiolabeled liposomes ( 89 Zr-TCO-LNP) that remained in the blood after EPR accumulation in tumor cells. Phosphor autoradiography assays demonstrated 2-fold higher radioactivity on the disk for 89 Zr-TCO-LNP compared with PDA@CoCrMo.…”

Section: Pt Approaches With Nps As a "Platform"mentioning

confidence: 99%

Click and Bioorthogonal Chemistry: The Future of Active Targeting of Nanoparticles for Nanomedicines?

et al. 2021

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Over the years, click and bioorthogonal reactions have been the subject of considerable research efforts. These high-performance chemical reactions have been developed to meet requirements not often provided by the chemical reactions commonly used today in the biological environment, such as selectivity, rapid reaction rate and biocompatibility. Click and bioorthogonal reactions have been attracting increasing attention in the biomedical field for the engineering of nanomedicines. In this review, we study a compilation of articles from 2014 to the present, using the terms "click chemistry and nanoparticles (NPs)" to highlight the application of this type of chemistry for applications involving NPs intended for biomedical applications. This study identifies the main strategies offered by click and bioorthogonal chemistry, with respect to passive and active targeting, for NP functionalization with specific and multiple properties for imaging and cancer therapy. In the final part, a novel and promising approach for "two step" targeting of NPs, called pretargeting (PT), is also discussed; the principle of this strategy as well as all the studies listed from 2014 to the present are presented in more detail.

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“…However, due to long circulation time of liposomes, long-lived radionuclides like zirconium-89 are necessary. Therefore, Brand et al designed the so-called on-demand bioorthogonal removal of circulating TCO-tagged liposomal NPs to decrease exposure to nontargeted tissues and allow imaging at an earlier time point [143]. Most recently, pretargeting has extended its application to the field of liver radioembolization.…”

Section: Novel Applications Of Pretargeting: Beyond Antibodies As mentioning

confidence: 99%

Therapeutic Applications of Pretargeting

2019

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Targeted therapies, such as radioimmunotherapy (RIT), present a promising treatment option for the eradication of tumor lesions. RIT has shown promising results especially for hematologic malignancies, but the therapeutic efficacy is limited by unfavorable tumor-to-background ratios resulting in high radiotoxicity. Pretargeting strategies can play an important role in addressing the high toxicity profile of RIT. Key to pretargeting is the concept of decoupling the targeting vehicle from the cytotoxic agent and administrating them separately. Studies have shown that this approach has the ability to enhance the therapeutic index as it can reduce side effects caused by off-target irradiation and thereby increase curative effects due to higher tolerated doses. Pretargeted RIT (PRIT) has been explored for imaging and treatment of different cancer types over the years. This review will give an overview of the various targeted therapies in which pretargeting has been applied, discussing PRIT with alpha- and beta-emitters and as part of combination therapy, plus its use in drug delivery systems.

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Specific Binding of Liposomal Nanoparticles through Inverse Electron‐Demand Diels–Alder Click Chemistry

Cited by 6 publications

References 20 publications

Using a Membrane-Penetrating-Peptide to Anchor Ligands in the Liposome Membrane Facilitates Targeted Drug Delivery

Using a Membrane-Penetrating-Peptide to Anchor Ligands in the Liposome Membrane Facilitates Targeted Drug Delivery

Click and Bioorthogonal Chemistry: The Future of Active Targeting of Nanoparticles for Nanomedicines?

Therapeutic Applications of Pretargeting

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