Synthesis and evaluation of a novel adapter lipid derivative for preparation of cyclic peptide-modified PEGylated liposomes: Application of cyclic RGD peptide

Kato, Naoya; Sato, Toshio; Fuchigami, Yuki; Suga, Tadaharu; Longjian, Geng; Tsurumaru, Masako; Hagimori, Masayori; Mukai, Hidefumi; Kawakami, Shigeru

doi:10.1016/j.ejps.2022.106239

Cited by 19 publications

(19 citation statements)

References 40 publications

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“…International Journal of Nanomedicine 2022:17 6680 mixing for 1 h using HFQ lipids with (SG) 5 as spacer. 5,6,8,9 Our HFQ lipids might form unstable micelles compared to those observed with conventional PEG lipids. Therefore, we hypothesized that HFQ lipids would be rapidly inserted into PEGylated liposomes without any additional destabilization of the liposomal membrane.…”

Section: Dovepressmentioning

confidence: 82%

“…We recently reported the targeting of PEGylated liposomes by modifying HFQ lipid with cyclic RGDfK (cRGD) as a ligand peptide using bulk mixing for 1 h. 9 In our study, we evaluated whether short-time preparation by the microfluidic post-insertion method can be applied to the modification of functional lipids with cyclic ligand peptides into PEGylated liposomes. cRGD-(SG) 5 /PEGylated liposomes prepared by the microfluidic post-insertion method showed almost the same particle size and PDI as those of PEGylated liposomes ( Table 2 ), suggesting that cRGD was modified into PEGylated liposomes using the microfluidic post-insertion method without substantially changing the physicochemical properties of PEGylated liposomes.…”

Section: Discussionmentioning

confidence: 99%

“…RGD-(SG) 5 -lipid and cRGD-(SG) 5 -lipid were synthesized and characterized by a previously described method. 6 , 9 The sequence of RGD and cRGD are shown in the introduction.…”

Section: Methodsmentioning

confidence: 99%

“…Colon 26 (murine colorectal carcinoma) cells from the Cell Resource Center for Biomedical Research (Tohoku University, Sendai, Japan) were cultured as previously described. 6 , 9 …”

Section: Methodsmentioning

confidence: 99%

“…In addition, HFQ lipids were designed to meet the criteria for dispersibility in water (0.2 mM and above to enable ligand modification using the post-insertion method (bulk mixing)). [7][8][9] In the bulk mixing method, lipid composition of the nanoparticles, mixing temperature, and duration may affect the physicochemical properties. 10,11 For the large-scale preparation of targeted liposomes, it is necessary to change the preparation conditions, including the conditions mentioned above, and change the volume.…”

Section: Introductionmentioning

confidence: 99%

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Microfluidic Post-Insertion Method for the Efficient Preparation of PEGylated Liposomes Using High Functionality and Quality Lipids

Sugimoto

Suga

Kato

et al. 2022

IJN

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Targeted liposomes using ligand peptides have been applied to deliver therapeutic agents to the target sites. The postinsertion method is commonly used because targeted liposomes can be prepared by simple mixing of ligand peptide-lipid and liposomes. A large-scale preparation method is required for the clinical application of ligand-peptide-modified liposomes. Largescale preparation involves an increase in volume and a change in the preparation conditions. Therefore, the physicochemical properties of liposomes may change owing to large alterations in the preparation conditions. To address this issue, we focused on a microfluidic device and developed a novel ligand peptide modification method, the microfluidic post-insertion method. Methods: We used integrin αvβ3-targeted GRGDS (RGD) and cyclic RGDfK (cRGD)-modified high functionality and quality (HFQ) lipids, which we had previously developed. First, the preparation conditions of the total flow rate in the microfluidic device for modifying HFQ lipids to polyethylene glycol (PEG)-modified (PEGylated) liposomes were optimized by evaluating the physicochemical properties of the liposomes. The targeting ability of integrin αvβ3-expressing colon 26 murine colorectal carcinoma cells was evaluated by comparing the cellular association properties of the liposomes prepared by the conventional post-insertion method. Results: When the RGD-HFQ lipid was modified into PEGylated liposomes by varying the total flow rate (1, 6, and 12 mL/min) of the microfluidic device, as the total flow rate increased, the polydispersity index also increased, whereas the particle size did not change. Furthermore, the RGD-and cRGD-modified PEGylated liposomes prepared at a total flow rate of 1 mL/min showed high cellular association properties equivalent to those prepared by the conventional post-insertion method. Conclusion: Microfluidic post-insertion method of HFQ lipids might be useful for clinical application and large-scale preparation of targeted liposomes.

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Section: Dovepressmentioning

confidence: 82%

Section: Discussionmentioning

confidence: 99%

“…RGD-(SG) 5 -lipid and cRGD-(SG) 5 -lipid were synthesized and characterized by a previously described method. 6 , 9 The sequence of RGD and cRGD are shown in the introduction.…”

Section: Methodsmentioning

confidence: 99%

“…Colon 26 (murine colorectal carcinoma) cells from the Cell Resource Center for Biomedical Research (Tohoku University, Sendai, Japan) were cultured as previously described. 6 , 9 …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Microfluidic Post-Insertion Method for the Efficient Preparation of PEGylated Liposomes Using High Functionality and Quality Lipids

Sugimoto

Suga

Kato

et al. 2022

IJN

Self Cite

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RGD peptide in cancer targeting: Benefits, challenges, solutions, and possible integrin–RGD interactions

Javid,

Oryani,

Rezagholinejad

et al. 2024

Cancer Medicine

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RGD peptide can be found in cell adhesion and signaling proteins, such as fibronectin, vitronectin, and fibrinogen. RGD peptides' principal function is to facilitate cell adhesion by interacting with integrin receptors on the cell surface. They have been intensively researched for use in biotechnology and medicine, including incorporation into biomaterials, conjugation to medicinal molecules or nanoparticles, and labeling with imaging agents. RGD peptides can be utilized to specifically target cancer cells and the tumor vasculature by engaging with these integrins, improving drug delivery efficiency and minimizing adverse effects on healthy tissues. RGD‐functionalized drug carriers are a viable option for cancer therapy as this focused approach has demonstrated promise in the future. Writing a review on the RGD peptide can significantly influence how drugs are developed in the future by improving our understanding of the peptide, finding knowledge gaps, fostering innovation, and making drug design easier.

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Mechanisms of extracellular vesicle uptake and implications for the design of cancer therapeutics

Jackson Cullison,

Flemming,

Karagoz

et al. 2024

J of Extracellular Bio

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The translation of pre‐clinical anti‐cancer therapies to regulatory approval has been promising, but slower than hoped. While innovative and effective treatments continue to achieve or seek approval, setbacks are often attributed to a lack of efficacy, failure to achieve clinical endpoints, and dose‐limiting toxicities. Successful efforts have been characterized by the development of therapeutics designed to specifically deliver optimal and effective dosing to tumour cells while minimizing off‐target toxicity. Much effort has been devoted to the rational design and application of synthetic nanoparticles to serve as targeted therapeutic delivery vehicles. Several challenges to the successful application of this modality as delivery vehicles include the induction of a protracted immune response that results in their rapid systemic clearance, manufacturing cost, lack of stability, and their biocompatibility. Extracellular vesicles (EVs) are a heterogeneous class of endogenous biologically produced lipid bilayer nanoparticles that mediate intercellular communication by carrying bioactive macromolecules capable of modifying cellular phenotypes to local and distant cells. By genetic, chemical, or metabolic methods, extracellular vesicles (EVs) can be engineered to display targeting moieties on their surface while transporting specific cargo to modulate pathological processes following uptake by target cell populations. This review will survey the types of EVs, their composition and cargoes, strategies employed to increase their targeting, uptake, and cargo release, and their potential as targeted anti‐cancer therapeutic delivery vehicles.

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Synthesis and evaluation of a novel adapter lipid derivative for preparation of cyclic peptide-modified PEGylated liposomes: Application of cyclic RGD peptide

Cited by 19 publications

References 40 publications

Microfluidic Post-Insertion Method for the Efficient Preparation of PEGylated Liposomes Using High Functionality and Quality Lipids

Microfluidic Post-Insertion Method for the Efficient Preparation of PEGylated Liposomes Using High Functionality and Quality Lipids

RGD peptide in cancer targeting: Benefits, challenges, solutions, and possible integrin–RGD interactions

Mechanisms of extracellular vesicle uptake and implications for the design of cancer therapeutics

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