Development of Peptidyl Lysine Dendrons: 1,3‐Dipolar Cycloaddition for Peptide Coupling and Antibody Recognition

Hüttl, Christine; Hettrich, Cornelia; Riedel, Melanie; Henklein, Petra; Rawel, Harshadrai M.; Bier, Frank F.

doi:10.1111/cbdd.12444

Cited by 6 publications

(4 citation statements)

References 46 publications

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“…In this regard, peptides labeled with short-lived positron emitters were synthesized by CuAAC-SP for later use in molecular imaging by positron emission tomography . Another example is peptides loaded with a dendron via CuAAC-SP; these peptide mimotopes are promising candidates as multivalent ligands for antibody B13-DE1 recognition …”

Section: Cu(i)-catalyzed Azide–alkyne Cycloaddition On Solid-phase (...mentioning

confidence: 99%

CuAAC: An Efficient Click Chemistry Reaction on Solid Phase

2015

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Click chemistry is an approach that uses efficient and reliable reactions, such as Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC), to bind two molecular building blocks. CuAAC has broad applications in medicinal chemistry and other fields of chemistry. This review describes the general features and applications of CuAAC in solid-phase synthesis (CuAAC-SP), highlighting the suitability of this kind of reaction for peptides, nucleotides, small molecules, supramolecular structures, and polymers, among others. This versatile reaction is expected to become pivotal for meeting future challenges in solid-phase chemistry.

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Section: Cu(i)-catalyzed Azide–alkyne Cycloaddition On Solid-phase (...mentioning

confidence: 99%

CuAAC: An Efficient Click Chemistry Reaction on Solid Phase

2015

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“…177 Other alkyne-functionalized lysine dendrons using a solid-phase Cu(I)catalyzed for azide peptide conjugation have shown great potential for future immunoassays. 178 The targeting potential of peptide for vectorized drug delivery into prostate cancer cells using PSMA-targeted PAMAM dendrimers has also been reported by other investigators. 136 These nanocarriers were obtained by SPAAC conjugation of N 3 -glutamate urea (GLA) targeting peptides and N 3 -MTX.…”

Section: Other Peptidesmentioning

confidence: 55%

“…Alkyne-functionalized polylysine dendrons were prepared for click chemistry with N 3 –PEG chain-modified χ-MrIA analogues, disulfide-rich χ-conotoxin peptides implicated in the treatment of neurological disorders, by selectively inhibiting the human norepinephrine transporter . Other alkyne-functionalized lysine dendrons using a solid-phase Cu(I)-catalyzed for azide peptide conjugation have shown great potential for future immunoassays . The targeting potential of peptide for vectorized drug delivery into prostate cancer cells using PSMA-targeted PAMAM dendrimers has also been reported by other investigators .…”

Section: Influence Of Active Targeting Using Click Chemistry On Tumor...mentioning

confidence: 89%

Click and Bioorthogonal Chemistry: The Future of Active Targeting of Nanoparticles for Nanomedicines?

et al. 2021

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Over the years, click and bioorthogonal reactions have been the subject of considerable research efforts. These high-performance chemical reactions have been developed to meet requirements not often provided by the chemical reactions commonly used today in the biological environment, such as selectivity, rapid reaction rate and biocompatibility. Click and bioorthogonal reactions have been attracting increasing attention in the biomedical field for the engineering of nanomedicines. In this review, we study a compilation of articles from 2014 to the present, using the terms "click chemistry and nanoparticles (NPs)" to highlight the application of this type of chemistry for applications involving NPs intended for biomedical applications. This study identifies the main strategies offered by click and bioorthogonal chemistry, with respect to passive and active targeting, for NP functionalization with specific and multiple properties for imaging and cancer therapy. In the final part, a novel and promising approach for "two step" targeting of NPs, called pretargeting (PT), is also discussed; the principle of this strategy as well as all the studies listed from 2014 to the present are presented in more detail.

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“…In the studies presented in this paper, we have chosen lysine (Lys) amino acid as the building block for the synthesis of dendrons in view of their known interactions with antibodies. , We have earlier reported on their impact on protein refolding . Since mAb aggregation at higher temperatures is primarily attributed to conformational destabilization or partial to complete unfolding, , this served as the motivation for the present investigation.…”

Section: Introductionmentioning

confidence: 99%

Peptide Dendrons as Thermal-Stability Amplifiers for Immunoglobulin G1 Monoclonal Antibody Biotherapeutics

et al. 2017

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Biotherapeutics such as monoclonal antibodies (mAbs) have a major share of the pharmaceutical industry for treatment of life-threatening chronic diseases such as cancer, skin ailments, and immune disorders. Instabilities such as aggregation, fragmentation, oxidation, and reduction have resulted in the practice of storing these products at low temperatures (-80 to -20 °C). However, reliable storage at these temperatures can be a challenge, particularly in developing and underdeveloped countries; hence, lately, there has been a renewed interest in creating formulations that would offer stability at higher temperatures (25 to 55 °C). Most therapeutic formulations contain excipients such as salts, sugars, amino acids, surfactants, and polymers to provide stability to the biotherapeutic, but their efficacy at high temperatures is limited. The current work proposes the use of peptide dendrons of different generations to create formulations that would be stable at high temperature. Among these dendrons, third-generation lysine dendron L6 has been identified to provide the highest stability to mAbs, as demonstrated by a host of analytical techniques such as size-exclusion chromatography (SEC), dynamic light scattering (DLS), Nanoparticle tracking Analysis (NTA), and circular dichroism (CD). The biocompatibility of these dendrons was confirmed by hemolytic activity tests. Non-interference of the dendrons with the activity of the mAb was confirmed using a surface plasmon resonance (SPR) based activity assay. We hope that this study will stimulate utilization of such higher-generation dendrons for enhancing the thermal stability of mAbs.

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Development of Peptidyl Lysine Dendrons: 1,3‐Dipolar Cycloaddition for Peptide Coupling and Antibody Recognition

Cited by 6 publications

References 46 publications

CuAAC: An Efficient Click Chemistry Reaction on Solid Phase

CuAAC: An Efficient Click Chemistry Reaction on Solid Phase

Click and Bioorthogonal Chemistry: The Future of Active Targeting of Nanoparticles for Nanomedicines?

Peptide Dendrons as Thermal-Stability Amplifiers for Immunoglobulin G1 Monoclonal Antibody Biotherapeutics

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