Integration of chemoselective ligation with enzymespecific catalysis: Saccharic colorimetric analysis using aminooxy/hydrazine-functionalized gold nanoparticles

Zhang, Juan; Lv, Jun; Wang, Xiaonan; Li, Defeng; Wang, Zhaoxia; Li, Genxi

doi:10.1007/s12274-015-0885-9

Cited by 12 publications

(6 citation statements)

References 37 publications

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“…In the present study, we introduce a new class of hybrid nucleic acid-based polyacrylamide hydrogels that reveal shape-memory and self-healing functionalities. Two hydrogels are presented in the study: one hydrogel is stabilized by cooperative glucosamine–boronate ester55,56 crosslinking units and reconfigurable K + -ion-stabilized G-quadruplex bridges. The second hydrogel is cooperatively stabilized by the glucosamine–boronate ester bridges and photoresponsive nucleic acid units that undergo light-induced formation or separation of duplex units (DNA “gear”).…”

Section: Introductionmentioning

confidence: 99%

Chemical and photochemical DNA “gears” reversibly control stiffness, shape-memory, self-healing and controlled release properties of polyacrylamide hydrogels

et al. 2019

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Section: Introductionmentioning

confidence: 99%

Chemical and photochemical DNA “gears” reversibly control stiffness, shape-memory, self-healing and controlled release properties of polyacrylamide hydrogels

et al. 2019

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“…To the best of our knowledge, the present study demonstrates the unprecedented switchable thermoplasmonic release of drugs from DNA‐based microcapsules. The hydrogel boundaries of the microcapsules are cross‐linked by the cooperative bridging units, glucosamine–boronate ester complexes [ 57–59 ] and thermoresponsive duplex nucleic acids. By loading the Au NPs‐/Au NRs‐functionalized microcapsules with two different drugs, doxorubicin‐dextran (DOX‐D) and camptothecin‐carboxymethyl cellulose (CPT‐CMC), respectively, the light‐controlled selective release of the drugs from a mixture of drug‐loaded microcapsules is demonstrated.…”

Section: Introductionmentioning

confidence: 99%

Thermoplasmonic‐Triggered Release of Loads from DNA‐Modified Hydrogel Microcapsules Functionalized with Au Nanoparticles or Au Nanorods

Wang

Vázquez‐González

Fadeev

et al. 2020

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Microcapsules consisting of hydrogel shells cross‐linked by glucosamine–boronate ester complexes and duplex nucleic acids, loaded with dyes or drugs and functionalized with Au nanoparticles (Au NPs) or Au nanorods (Au NRs), are developed. Irradiation of Au NPs or Au NRs results in the thermoplasmonic heating of the microcapsules, and the dissociation of the nucleic acid cross‐linkers. The separation of duplex nucleic acid cross‐linkers leads to low‐stiffness hydrogel shells, allowing the release of loads. Switching off the light‐induced plasmonic heating results in the regeneration of stiff hydrogel shells protecting the microcapsules, leading to the blockage of release processes. The thermoplasmonic release of tetramethylrhodamine‐dextran, Texas Red‐dextran, doxorubicin‐dextran (DOX‐D), or camptothecin‐carboxymethylcellulose (CPT‐CMC) from the microcapsules is introduced. By loading the microcapsules with two different drugs (DOX‐D and CPT‐CMC), the light‐controlled dose release is demonstrated. Cellular experiments show efficient permeation of Au NPs/DOX‐D or Au NRs/DOX‐D microcapsules into MDA‐MB‐231 cancer cells and inefficient uptake by MCF‐10A epithelial breast cells. Cytotoxicity experiments reveal selective thermoplasmon‐induced cytotoxicity of the microcapsules toward MDA‐MB‐231 cancer cells as compared to MCF‐10A cells. Also, selective cytotoxicity towards MDA‐MB‐231 cancer cells upon irradiation of the Au NPs‐ and Au NRs‐functionalized microcapsules at λ = 532 or 910 nm is demonstrated.

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“…As the usefulness of oximation chemistry has become apparent, several approaches exploiting nanoparticles fitted with aminooxy surfaces have been reported . The ease of functionalization of gold surfaces, clusters, and nanoparticles with a monolayer of thiol‐ or dithiol‐containing molecules has guided some efforts toward developing and applying thiol ligands containing aminooxy functionality . For example, Nagahori et al prepared aminooxy‐functionalized gold nanoparticles (NPs) for capture and enrichment of glycosphingolipid (GSL)‐generated aldehydes as a means to characterize whole GSLs in living cells .…”

Section: Introductionmentioning

confidence: 99%

Tunable Aminooxy‐Functionalized Monolayer‐Protected Gold Clusters for Nonpolar and Aqueous Oximation Reactions

Sibakoti

Stinger

Adhihetty

et al. 2019

Part & Part Syst Charact

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Aminooxy (–ONH2) groups are well known for their chemoselective reactions with carbonyl compounds, specifically aldehydes and ketones. The versatility of aminooxy chemistry has proven to be an attractive feature that continues to stimulate new applications. This work describes application of aminooxy click chemistry on the surface of gold nanoparticles. A trifunctional amine‐containing aminooxy alkane thiol ligand for use in the functionalization of gold monolayer‐protected clusters (Au MPCs) is presented. Diethanolamine is readily transformed into an organic‐soluble aminooxy thiol (AOT) ligand using a short synthetic path. The synthesized AOT ligand is coated on ≤2‐nm‐diameter hexanethiolate‐(C6S)‐capped Au MPCs using a ligand‐exchange protocol to afford organic‐soluble AOT/C6S (1:1 ratio) Au mixed monolayer‐protected clusters (MMPCs). The synthesis of these Au(C6S)(AOT) MMPCs and representative oximation reactions with various types of aldehyde‐containing molecules is described, highlighting the ease and versatility of the chemistry and how amine protonation can be used to switch solubility characteristics.

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Integration of chemoselective ligation with enzymespecific catalysis: Saccharic colorimetric analysis using aminooxy/hydrazine-functionalized gold nanoparticles

Cited by 12 publications

References 37 publications

Chemical and photochemical DNA “gears” reversibly control stiffness, shape-memory, self-healing and controlled release properties of polyacrylamide hydrogels

Chemical and photochemical DNA “gears” reversibly control stiffness, shape-memory, self-healing and controlled release properties of polyacrylamide hydrogels

Thermoplasmonic‐Triggered Release of Loads from DNA‐Modified Hydrogel Microcapsules Functionalized with Au Nanoparticles or Au Nanorods

Tunable Aminooxy‐Functionalized Monolayer‐Protected Gold Clusters for Nonpolar and Aqueous Oximation Reactions

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