Bioorthogonal Copper‐Free Click Chemistry In Vivo for Tumor‐Targeted Delivery of Nanoparticles

Koo, Heebeom; Lee, Sang‐Min; Na, Jin Hee; Kim, Sun Hwa; Hahn, Sei Kwang; Choi, Kuiwon; Kwon, Ick Chan; Jeong, Seo Young; Kim, Kwangmeyung

doi:10.1002/anie.201206703

Cited by 241 publications

(224 citation statements)

References 35 publications

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“…1–6 The structure, composition, and core and surface property of micelles can be easily tuned through controlled polymerization and conjugation chemistry. 7, 8 However, one issue central to the self-assembled micelles is their intrinsic instability under physiological conditions: micelles potentially undergo dynamic dissociation upon dilution and high shearing force in the circulation system in vivo . 9–12 To improve the stability of micelles in the biological systems, various approaches have been employed, including chemical cross-linking of the shell 13–16 or the core 17–20 of self-assembled micelles.…”

Section: Introductionmentioning

confidence: 99%

Redox-Responsive, Core-Cross-Linked Micelles Capable of On-Demand, Concurrent Drug Release and Structure Disassembly

et al. 2013

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We developed camptothecin (CPT)-conjugated, core-cross-linked (CCL) micelles that are subject to redox-responsive cleavage of the built-in disulfide bonds, resulting in disruption of the micellar structure and rapid release of CPT. CCL micelles were prepared via co-precipitation of disulfide-containing CPT-poly(Tyrosine(alkynyl)-OCA) conjugate and monomethoxy poly(ethylene glycol)-b-poly(Tyrosine(alkynyl)-OCA), followed by cross-linking of the micellar core via azide–alkyne click chemistry. CCL micelles exhibited excellent stability under physiological conditions while underwent rapid dissociation in reduction circumstance, resulting in burst release of CPT. These redox-responsive CCL micelles showed enhanced cytotoxicity against human breast cancer cells in vitro.

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Section: Introductionmentioning

confidence: 99%

Redox-Responsive, Core-Cross-Linked Micelles Capable of On-Demand, Concurrent Drug Release and Structure Disassembly

et al. 2013

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“…35 These trisaccharides were conjugated to one of the two lipid anchors, 16:0 Caproylamine PE, which is short for 1,2-dipalmitoyl- sn -glycero-3-phosphoethanolamine-N-(hexanoylamine), or 16:0 succinyl PE, which is short for 1,2-dipalmitoyl- sn -glycero-3-phosphoethanolamine-N-(succinyl) (Avanti Polar Lipids, Alabaster, AL). The conjugation was done via oligo(ethylene glycol) (OEG) linkers either through Cu-free click chemistry with a dibenzocyclooctyne (ϕ) group, 36 or through an N -hydroxysuccinimide (NHS) coupling reaction to the amine functionality generated by reducing the azides. To change the membrane environments, we used six different functionalities anchored to lipids: the hydrophilic mannose or fucose linked to OEG-lipid via Cu-free click chemistry ( Man -ϕ-OEG-lipid or Fuc -ϕ-OEG-lipid), the hydrophobic cyclooctyne group conjugated with or without OEG linker to the lipid molecule (ϕ-OEG-lipid or ϕ-lipid), and the acidic −COOH or basic −NH 2 terminated lipids ( HOOC -OEG-lipid or H 2 N -lipid).…”

Section: Resultsmentioning

confidence: 99%

Membrane Environment Can Enhance the Interaction of Glycan Binding Protein to Cell Surface Glycan Receptors

Shen

Wang

Lin³

et al. 2014

ACS Chem. Biol.

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The binding of lectins to glycan receptors on the host cell surface is a key step contributing to the virulence and species specificity of most viruses. This is exemplified by the viral protein hemagglutinin (HA) of the influenza A virus, whose binding specificity is modulated by the linkage pattern of terminal sialic acids on glycan receptors of host epithelial cells. Such specificity dictates whether transmission is confined to a particular animal species or jumps between species. Here, we show, using H5N1 avian influenza as a model, that the specific binding of recombinant HA to α2-3 linked sialic acids can be enhanced dramatically by interaction with the surface of the lipid membrane. This effect can be quantitatively accounted for by a two-stage process in which weak association of HA with the membrane surface precedes more specific and tighter binding to the glycan receptor. The weak protein–membrane interaction discovered here in the model system may play an important secondary role in the infection and pathogenesis of the influenza A virus.

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“…Scheme 3 shows a short list of dialdehyde containing molecules and their corresponding conjugates. As an example for bioconjugation, we synthesized dialdehyde molecules tethered to lysine (34) and to the well-known biomolecular binding ligands biotin (37) and DNP (dinitrophenol) (35). 63,64 To demonstrate the biotin and DNP dialdehyde molecules as click-chemistry bioconjugation reagents, we used the inverse liposome strategy to Figure 4, i.e., using dialdehyde reagents to click with amine lipids.…”

Section: Bioconjugate Chemistrymentioning

confidence: 99%

General Dialdehyde Click Chemistry for Amine Bioconjugation

et al. 2017

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The development of methods for conjugating a range of molecules to primary amine functional groups has revolutionized the fields of chemistry, biology, and material science. The primary amine is a key functional group and one of the most important nucleophiles and bases used in all of synthetic chemistry. Therefore, tremendous interest in the synthesis of molecules containing primary amines and strategies to devise chemical reactions to react with primary amines has been at the core of chemical research. In particular, primary amines are a ubiquitous functional group found in biological systems as free amino acids, as key side chain lysines in proteins, and in signaling molecules and metabolites and are also present in many natural product classes. Due to its abundance, the primary amine is the most convenient functional group handle in molecules for ligation to other molecules for a broad range of applications that impact all scientific fields. Because of the primary amine's central importance in synthetic chemistry, acid-base chemistry, redox chemistry, and biology, many methods have been developed to efficiently react with primary amines, including activated carboxylic acids, isothiocyanates, Michael addition type systems, and reaction with ketones or aldehydes followed by in situ reductive amination. Herein, we introduce a new traceless, high-yield, fast click-chemistry method based on the rapid and efficient trapping of amine groups via a functionalized dialdehyde group. The click reaction occurs in mild conditions in organic solvents or aqueous media and proceeds in high yield, and the starting dialdehyde reagent and resulting dialdehyde click conjugates are stable. Moreover, no catalyst or dialdehyde-activating group is required, and the only byproduct is water. The initial dialdehyde and the resulting conjugate are both straightforward to characterize, and the reaction proceeds with high atom economy. To demonstrate the broad scope of this new click-conjugation strategy, we designed a straightforward scheme to synthesize a suite of dialdehyde reagents. The dialdehyde molecules were used for applications in cell-surface engineering and for tailoring surfaces for material science applications. We anticipate the broad utility of the general dialdehyde click chemistry to primary amines in all areas of chemical research, ranging from polymers and bioconjugation to material science and nanoscience.

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Bioorthogonal Copper‐Free Click Chemistry In Vivo for Tumor‐Targeted Delivery of Nanoparticles

Cited by 241 publications

References 35 publications

Redox-Responsive, Core-Cross-Linked Micelles Capable of On-Demand, Concurrent Drug Release and Structure Disassembly

Redox-Responsive, Core-Cross-Linked Micelles Capable of On-Demand, Concurrent Drug Release and Structure Disassembly

Membrane Environment Can Enhance the Interaction of Glycan Binding Protein to Cell Surface Glycan Receptors

General Dialdehyde Click Chemistry for Amine Bioconjugation

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