LDL-mimetic lipid nanoparticles prepared by surface KAT ligation for<i>in vivo</i>MRI of atherosclerosis

Fracassi, Alessandro; Cao, Jianbo; Yoshizawa-Sugata, Naoko; Tóth, Éva; Archer, Corey; Gröninger, Olivier G.; Ricciotti, Emanuela; Tang, Soon Yew; Handschin, Stephan; Bourgeois, Jean‐Pascal; Ray, Ankita; Liosi, Korinne; Oriana, Sean; Stark, Wendelin J.; Masai, Hisao; Zhou, Rong; Yamakoshi, Yoko

doi:10.1039/d0sc04106h

Cited by 15 publications

(16 citation statements)

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“…Furthermore, the reaction can be performed at low concentrations of the reactants, forming natural amide bonds without involving coupling reagents or producing toxic byproducts. Our recent results also demonstrated this approach successfully provides hybrid nanoparticles for in vivo imaging. , The use of KAT ligation in surface modification was thought to provide several advantages compared to other chemical reactions. The chemoselective and orthogonal KAT ligation reaction could facilitate surface modification with biomolecules bearing unprotected functional groups.…”

Section: Introductionmentioning

confidence: 71%

“…Our recent results also demonstrated this approach successfully provides hybrid nanoparticles for in vivo imaging. 18,19 The use of KAT 2) was synthesized from dibromooctane as a starting material (Scheme S1). The obtained compound 1 was purified, and characterized by HR-MS, IR, and 1 H, 13 C, 19 F, and 11 B NMR.…”

Section: Introductionmentioning

confidence: 99%

“…18,19 The use of KAT 2) was synthesized from dibromooctane as a starting material (Scheme S1). The obtained compound 1 was purified, and characterized by HR-MS, IR, and 1 H, 13 C, 19 F, and 11 B NMR. 2.2.…”

Section: Introductionmentioning

confidence: 99%

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KAT Ligation for Rapid and Facile Covalent Attachment of Biomolecules to Surfaces

Fracassi

Ray

Nakatsuka

et al. 2021

ACS Appl. Mater. Interfaces

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The efficient and bioorthogonal chemical ligation reaction between potassium acyltrifluoroborates (KATs) and hydroxylamines (HAs) was used for the surface functionalizationof a self-assembled monolayer (SAM) with biomolecules. An alkane thioether molecule with one terminal KAT group (S-KAT) was synthesized and adsorbed onto a gold surface, placing a KATgroup on the top of the monolayer (KAT-SAM). As an initial test case, an aqueous solution of a hydroxylamine (HA) derivative of PEG (HA-PEG) was added to this KAT-SAM at room temperature to perform the surface KAT ligation. Quartz crystal microbalance with dissipation (QCM-D) monitoring confirmed the rapid attachment of the PEG moiety onto the SAM.The covalent conjugation of PEG by amide-bond formation was established by complementary surface characterization methods including contact angle, ellipsometry, and X-ray photoelectron spectroscopy (XPS). To test the applicability of this surface KAT ligation for the attachment of biomolecules to the surfaces, this KAT-SAM was subjected to the reaction with HA derivative of protein. A HA-derivatized green fluorescent protein (HA-GFP) was added in dilute concentrations to the KAT-SAM under aqueous conditions and rapid protein attachment was observed in real-time by QCM. Despite the fact that such biomolecules have a variety of unprotected functional groups within their structures, the surface KAT reaction proceeded efficiently in a selective manner. Our results clearly demonstrate the versatile applicability of the KAT ligation for the covalent attachment of a variety of biomolecules onto surfaces under dilute and biocompatible conditions to form stable, natural amide bonds.File list (2) download file view on ChemRxiv Surface_KAT_ACS_Mater_interface_main_text_25Mar20... (2.08 MiB) download file view on ChemRxiv Surface KAT_SI_25Mar2021_final.pdf (4.32 MiB)

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Section: Introductionmentioning

confidence: 71%

Section: Introductionmentioning

confidence: 99%

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KAT Ligation for Rapid and Facile Covalent Attachment of Biomolecules to Surfaces

Fracassi

Ray

Nakatsuka

et al. 2021

ACS Appl. Mater. Interfaces

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“…In particular, while nonpolar molecules can spontaneously localize to the hydrophobic lipid bilayer, the enrichment of lipid compartments with polar hydrophilic molecules such as water‐soluble proteins is more challenging. Ideally, the incorporation of hydrophilic proteins into lipid membranes should be achieved using robust bioconjugation methods that enable the stable attachment of proteins to the bilayer, and ensure adequate exposure of the protein to the aqueous bulk [37–42] …”

Section: Resultsmentioning

confidence: 99%

“…Ideally, the incorporation of hydrophilic proteins into lipid membranes should be achieved using robust bioconjugation methods that enable the stable attachment of proteins to the bilayer, and ensure adequate exposure of the protein to the aqueous bulk. [37][38][39][40][41][42] Along these lines, we explored the feasibility of using SNAPtag conjugation for controlling protein localization into our lipid sponge phase droplets (Figure 3A). [43,44] SNAP-tag bioconjugation offers several advantages compared to other protein anchoring methods.…”

Section: Chembiochemmentioning

confidence: 99%

Controlling Protein Enrichment in Lipid Sponge Phase Droplets using SNAP‐Tag Bioconjugation

et al. 2022

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All cells use organized lipid compartments to facilitate specific biological functions. Membrane‐bound organelles create defined spatial environments that favor unique chemical reactions while isolating incompatible biological processes. Despite the fundamental role of cellular organelles, there is a scarcity of methods for preparing functional artificial lipid‐based compartments. Here, we demonstrate a robust bioconjugation system for sequestering proteins into zwitterionic lipid sponge phase droplets. Incorporation of benzylguanine (BG)‐modified phospholipids that form stable covalent linkages with an O6‐methylguanine DNA methyltransferase (SNAP‐tag) fusion protein enables programmable control of protein capture. We show that this methodology can be used to anchor hydrophilic proteins at the lipid‐aqueous interface, concentrating them within an accessible but protected chemical environment. SNAP‐tag technology enables the integration of proteins that regulate complex biological functions in lipid sponge phase droplets, and should facilitate the development of advanced lipid‐based artificial organelles.

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Engineering Nanoplatforms for Theranostics of Atherosclerotic Plaques

Liu,

Jiang,

Yang

et al. 2024

Adv Healthcare Materials

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Atherosclerotic plaque formation is considered the primary pathological mechanism underlying atherosclerotic cardiovascular diseases, leading to severe cardiovascular events such as stroke, acute coronary syndromes, and even sudden cardiac death. Early detection and timely intervention of plaques are challenging due to the lack of typical symptoms in the initial stages. Therefore, precise early detection and intervention play a crucial role in risk stratification of atherosclerotic plaques and achieving favorable post‐interventional outcomes. The continuously advancing nanoplatforms have demonstrated numerous advantages including high signal‐to‐noise ratio, enhanced bioavailability, and specific targeting capabilities for imaging agents and therapeutic drugs, enabling effective visualization and management of atherosclerotic plaques. Motivated by these superior properties, we comprehensively summarize various noninvasive imaging modalities for early recognition of plaques in the preliminary stage of atherosclerosis. Additionally, we propose several therapeutic strategies to enhance the efficacy of treating atherosclerotic plaques. Finally, we discuss existing challenges and promising prospects for accelerating clinical translation of nanoplatform‐based molecular imaging and therapy for atherosclerotic plaques. In conclusion, this review provides an insightful perspective on the diagnosis and therapy of atherosclerotic plaques.This article is protected by copyright. All rights reserved

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LDL-mimetic lipid nanoparticles prepared by surface KAT ligation forin vivoMRI of atherosclerosis

Abstract: The low-density lipoprotein (LDL)-mimetic lipid nanoparticles (LNPs), decorated with MRI contrast agents, and fluorescent dyes, were prepared by the covalent attachment of apolipoprotin-mietic peptide (P), Gd(III)-chelate (Gd), and sulforhodamine B...

Cited by 15 publications

References 47 publications

KAT Ligation for Rapid and Facile Covalent Attachment of Biomolecules to Surfaces

KAT Ligation for Rapid and Facile Covalent Attachment of Biomolecules to Surfaces

Controlling Protein Enrichment in Lipid Sponge Phase Droplets using SNAP‐Tag Bioconjugation

Engineering Nanoplatforms for Theranostics of Atherosclerotic Plaques

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