Safety‐catch linkers for Fmoc solid‐phase synthesis of peptide thioesters and hydrazides by amide‐to‐imide activation

Paprocki, Maciej P; Rasmussen, Jacob; Sørensen, Kasper K.; Jensen, Knud J.

doi:10.1002/psc.3364

Cited by 2 publications

(2 citation statements)

References 34 publications

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“…Synthesis of Angiopep-2 was based on conventional Fmoc-solid phase peptide synthesis (SPPS. 32 Our laboratory has explored efficient means for synthesizing PLHSpT which contains non-natural amino acids. The synthesis method for PLHSpT which contains non-natural amino acids was based on Lin et al 33 The Fmoc-Thr (HPO 3 Bzl)-OH of PLHSpT with spatial steric hindrance should be three times coupling reactions by treatment with different coupling reagents.…”

Section: Methodsmentioning

confidence: 99%

Novel dual targeting cubosomes modified with angiopep-2 for co-delivery GNA and PLHSpT to brain glioma

Lin,

Wei,

Zhang

et al. 2023

J Biomater Appl

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3Glioblastoma multiforme is the most aggressive malignant brain tumor. However, the treatment of glioblastoma multiforme faces great challenges owing to difficult penetration of the blood-brain barrier. Therefore, more effective treatment strategies are desired quite urgently. In our study, a dual-targeting drug delivery system for co-loading with hydrophobic Gambogenic acid and hydrophilic PLHSpT was developed by cubosomes with angiopep-2 decorating. The Ang-cubs-(GNA + PLHSpT) was prepared by high-temperature emulsification-low-temperature solidification demonstrating excellent physical properties.Transmission electron microscopy revealed that Ang-cubs-(GNA + PLHSpT) was nearly spherical with a “core-shell” double-layer structure. Differential scanning calorimetry suggested that a new phase was formed. Small-angle X-ray scattering also verified that Ang-cubs-(GNA + PLHSpT) retains the Pn3m cubic. Moreover, laser confocal indicated that Ang-cubs-(GNA + PLHSpT) was capable of crossing BBB via binding to lipoprotein receptor-related protein-1, likely suggesting the potential tumor-specific targeting characteristic. Compared to free drug and cubs-(GNA + PLHSpT), Ang-cubs-(GNA + PLHSpT) was easily taken up by C6 cell and exhibited better anti-glioma effects in vitro. Importantly, GNA and PLHSpT co-loaded Ang-cubs could suppress tumor growth and significantly prolong survival in vivo. In conclusion, Ang-cubs-(GNA + PLHSpT) acts as a new dual-targeting drug delivery system for the treatment of GBM.

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Section: Methodsmentioning

confidence: 99%

Novel dual targeting cubosomes modified with angiopep-2 for co-delivery GNA and PLHSpT to brain glioma

Lin,

Wei,

Zhang

et al. 2023

J Biomater Appl

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“…To address this issue of poor reactivity, Jensen's group introduced a more reactive aromatic pyrrolidinone resin in a later publication [92]. This resin, based on the same five-member ring principle, exhibits enhanced reactivity in the presence of a nucleophile (Scheme 16).…”

Section: Pyroglutamyl/pyrrolidinone Amidementioning

confidence: 99%

Safety-Catch Linkers for Solid-Phase Peptide Synthesis

Noki,

de la Torre,

Albericio

2024

Molecules

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Solid-phase peptide synthesis (SPPS) is the preferred strategy for synthesizing most peptides for research purposes and on a multi-kilogram scale. One key to the success of SPPS is the continual evolution and improvement of the original method proposed by Merrifield. Over the years, this approach has been enhanced with the introduction of new solid supports, protecting groups for amino acids, coupling reagents, and other tools. One of these improvements is the use of the so-called “safety-catch” linkers/resins. The linker is understood as the moiety that links the peptide to the solid support and protects the C-terminal carboxylic group. The “safety-catch” concept relies on linkers that are totally stable under the conditions needed for both α-amino and side-chain deprotection that, at the end of synthesis, can be made labile to one of those conditions by a simple chemical reaction (e.g., an alkylation). This unique characteristic enables the simultaneous use of two primary protecting strategies: tert-butoxycarbonyl (Boc) and fluorenylmethoxycarbonyl (Fmoc). Ultimately, at the end of synthesis, either acids (which are incompatible with Boc) or bases (which are incompatible with Fmoc) can be employed to cleave the peptide from the resin. This review focuses on the most significant “safety-catch” linkers.

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Safety‐catch linkers for Fmoc solid‐phase synthesis of peptide thioesters and hydrazides by amide‐to‐imide activation

Cited by 2 publications

References 34 publications

Novel dual targeting cubosomes modified with angiopep-2 for co-delivery GNA and PLHSpT to brain glioma

Novel dual targeting cubosomes modified with angiopep-2 for co-delivery GNA and PLHSpT to brain glioma

Safety-Catch Linkers for Solid-Phase Peptide Synthesis

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