On the synthesis of cyclodextrin–peptide conjugates by the Huisgen reaction

Lartia, Rémy; Jankowski, Christopher K.; Arseneau, Sébastien

doi:10.1002/psc.2899

Cited by 3 publications

(5 citation statements)

References 23 publications

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“…Both types of additives promoted ɑ-helix formation for the parent peptides, however there were no significant changes for the conjugates. In summary, the obtained bis-conjugates exposed ɑ-helix formation without the need for any additives [ 27 ].…”

Section: Cyclodextrin-peptide Conjugatesmentioning

confidence: 99%

Cyclodextrins-Peptides/Proteins Conjugates: Synthesis, Properties and Applications

2021

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Cyclodextrins (CDs) are a family of macrocyclic oligosaccharides mostly composed of six, seven, or eight α-D-glucopyranose units with α-1,4-glycosidic bonds to form toroidal structures. The CDs possess a hydrophilic exterior and hydrophobic interior with the ability to form an inclusion complex, especially with hydrophobic molecules. However, most existing studies are about conjugation CDs with peptide/protein focusing on the formation of new systems. The CD-peptide/protein can possess new abilities; particularly, the cavity can be applied in modulation properties of more complexed proteins. Most studies are focused on drug delivery, such as targeted delivery in cell-penetrating peptides or co-delivery. The co-delivery is based mostly on polylysine systems; on the other hand, the CD-peptide allows us to understand biomolecular mechanisms such as fibryllation or stem cell behaviour. Moreover, the CD-proteins are more complexed systems with a focus on targeted therapy; these conjugates might be controllable with various properties due to changes in their stability. Finally, the studies of CD-peptide/protein are promising in biomedical application and provide new possibilities for the conjugation of simple molecules to biomolecules.

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Section: Cyclodextrin-peptide Conjugatesmentioning

confidence: 99%

Cyclodextrins-Peptides/Proteins Conjugates: Synthesis, Properties and Applications

2021

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“…This is another reason βCD was chosen as an ideal candidate for the desired application. There are several examples in the literature that use the hydroxyl group of βCD to conjugate different biological moieties including peptides, antibody fragments, fluorophores, drugs, etc. − The desired chemical modifications can be either done for all of the hydroxyls at the primary surface or it can be done on a single hydroxyl group, which provides more site-specific functionalization. − ,, For example, Hu and co-workers conjugated folic acid (FA) to single amine functional, drug-loaded βCD through EDC/NHS coupling to use it as a targeted drug delivery system . Lartia et al conjugated an alkyne functional peptide to single azide functional βCD via “click” chemistry as another example …”

Section: Introductionmentioning

confidence: 99%

“…19−22 The desired chemical modifications can be either done for all of the hydroxyls at the primary surface or it can be done on a single hydroxyl group, which provides more site-specific functionalization. [19][20][21]23,24 For example, Hu and co-workers conjugated folic acid (FA) to single amine functional, drugloaded βCD through EDC/NHS coupling to use it as a targeted drug delivery system. 19 Lartia et al conjugated an alkyne functional peptide to single azide functional βCD via "click" chemistry as another example.…”

Section: ■ Introductionmentioning

confidence: 99%

“…19 Lartia et al conjugated an alkyne functional peptide to single azide functional βCD via "click" chemistry as another example. 20 In this study, we aimed to show the bioconjugation potential of NCCs through the example of multiple commonly used functionalizations such as targeting, PEGylation, and fluorescent labeling. For this purpose, a monofunctionality like azide, alkyne, or amine was obtained at the primary surface of βCD as the first step to produce a functional precursor for later conjugation using effective coupling reactions.…”

Section: ■ Introductionmentioning

confidence: 99%

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Bioconjugated β-Cyclodextrin–Perfluorohexane Nanocone Clusters as Functional Nanoparticles for Nanoparticle-Mediated Histotripsy

et al. 2022

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Nanocone clusters (NCCs) are new-generation agents of nanoparticle-mediated histotripsy (NMH) recently developed to address the limitations of previously designed nanodroplets (NDs). NCCs can be obtained by simply mixing FDA-approved cyclodextrins (CD) and suitable perfluorocarbons (PFCs), which result in smaller size aggregates, detectable PFC amount, and more stable long-term storage since the obtained powder can be stored and redispersed as needed. Previous experimental and computational studies showed that NCCs consist of an organization of inclusion complexes of CD and PFC around free PFC droplets, and their aggregate behavior depends on the localization of PFC in the cavity and the water solubility of CD derivatives. It has been shown that β-cyclodextrin (βCD) and perfluorohexane (PFH) are ideal candidates for NCCs that can be isolated as a powder with high PFC content among various CD and PFC derivatives. This study focuses on the further development of the selected NCC composition to enhance the potential of NMH therapy while also enabling more detailed future experiments in vitro and in vivo. It is aimed to show the bioconjugation potential of NCCs through the example of the most commonly used functionalization methods such as targeting, PEGylation, and fluorescent labeling. For this purpose, βCD as a building block was monofunctionalized with groups such as azide, alkyne, and amine groups that allow for effective coupling reactions such as the "click" reaction and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride/N-hydroxysuccinimide (EDC/NHS) coupling. These monofunctional βCDs were used as building blocks of NCCs in the presence of PFH to obtain functional NCCs as precursors of bioconjugation. EPPT1 as a synthetic peptide specific to uMUC1 and folic acid (FA) as the most commonly used targeting agent along with PEGylation were successfully shown as bioconjugation examples. Lastly, fluorescently labeled NCCs were obtained via fluorescein isothiocyanate (FITC) and alkyne functional NCC reaction through propargyl amine and isothiocyanate group reaction. The obtained bioconjugates were tested in vitro to validate the conjugation, and the ability to lower the histotripsy cavitation threshold, which is necessary for NMH, was demonstrated for all bioconjugates. Overall, the results showed that all obtained bioconjugates successfully lowered the cavitation threshold pressure while also fulfilling the desired bioconjugation metrics to serve as improved tools to enhance NMH as a targeted noninvasive ablation method.

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“…Despite a wide range of potential uses of CD–peptide conjugates, the lack of robust and reliable synthetic methodologies limits the range of scaffolds that can be accessed. The majority of reported constructs are mono‐ or di‐functionalized and are assembled through direct coupling of protected amino acids, protected peptides, or through azide–alkyne cycloaddition chemistry of unprotected peptides . Few hepta‐peptide functionalized β‐CDs have been reported, and these have been synthesized by coupling of pre‐assembled protected peptides or azide–alkyne cycloaddition in low to moderate yields …”

Section: Introductionmentioning

confidence: 99%

Highly Functionalized β‐Cyclodextrins by Solid‐Supported Synthesis

Vurgun

Nitz

2018

Chemistry A European J

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Using covalent capture, a high yielding selective mono-functionalization of heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-CD with a 5-mercaptopentyl functional group has been achieved. Here, we demonstrate the immobilization of the mono-thiol functionalized β-CD on PEGA resin via a disulfide bond, enabling solid-phase elaboration of the remaining six primary amines. To showcase the potential of this method, the amines were elaborated to tripeptides through standard Fmoc-peptide chemistry. A small library of CD-tripeptide conjugates was generated which, when reduced from the solid support, could be tagged at the released thiol with an environmentally sensitive fluorophore. The resulting library of sensors showed potential for the differential sensing of various bile salts. The described methodology provides a rapid and versatile route to synthesize highly functionalized libraries of CD derivatives that may be tailored towards applications in sensing, catalysis, and multivalent displays.

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On the synthesis of cyclodextrin–peptide conjugates by the Huisgen reaction

Cited by 3 publications

References 23 publications

Cyclodextrins-Peptides/Proteins Conjugates: Synthesis, Properties and Applications

Cyclodextrins-Peptides/Proteins Conjugates: Synthesis, Properties and Applications

Bioconjugated β-Cyclodextrin–Perfluorohexane Nanocone Clusters as Functional Nanoparticles for Nanoparticle-Mediated Histotripsy

Highly Functionalized β‐Cyclodextrins by Solid‐Supported Synthesis

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