Functionalized triazolopeptoids – a novel class for mitochondrial targeted delivery

Althuon, Daniela; Rönicke, Franziska; Fürniss, Daniel; Quan, Jasmin; Wellhöfer, Isabelle; Jung, Nicole; Schepers, Ute; Bräse, Stefan

doi:10.1039/c5ob00250h

Cited by 22 publications

(17 citation statements)

References 37 publications

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“…2-Azidoacetic acid 53 35 (540 mg, 5.34 mmol) was dissolved in anhydrous dichloromethane (20 mL). The solution was cooled to 0 °C and then TBTU (2.06 g, 6.41 mmol) was added and the solution was stirred for another 15 min at 0 °C.…”

Section: Methodsmentioning

confidence: 99%

A structure–activity relationship of non-peptide macrocyclic histone deacetylase inhibitors and their anti-proliferative and anti-inflammatory activities

Tapadar

Fathi

Raji

et al. 2015

Bioorganic & Medicinal Chemistry

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Inhibition of the enzymatic activity of histone deacetylase (HDAC) is a promising therapeutic strategy for cancer treatment and several distinct small molecule histone deacetylase inhibitors (HDACi) have been reported. We have previously identified a new class of non-peptide macrocyclic HDACi derived from 14- and 15-membered macrolide skeletons. In these HDACi, the macrocyclic ring is linked to the zinc chelating hydroxamate moiety through a para-substituted aryl-triazole cap group. To further delineate the depth of the SAR of this class of HDACi, we have synthesized series of analogous compounds and investigated the influence of various substitution patterns on their HDAC inhibitory, anti-proliferative and anti-inflammatory activities. We identified compounds 25b and 38f with robust anti-proliferative activities and compound 26f (IC50 47.2 nM) with superior anti-inflammatory (IC50 88 nM) activity relative to SAHA.

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Section: Methodsmentioning

confidence: 99%

A structure–activity relationship of non-peptide macrocyclic histone deacetylase inhibitors and their anti-proliferative and anti-inflammatory activities

Tapadar

Fathi

Raji

et al. 2015

Bioorganic & Medicinal Chemistry

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“…Althuon et al [ 101 ] synthesized linear 1,4-triazolopeptoids (e.g., 73 ) as a new class of cell-penetrating peptidomimetics. Repetitive triazole fragments with up to three residues were assembled on solid supports using CuAAC ( Scheme 10 ).…”

Section: 123-triazoles In Other Mimeticsmentioning

confidence: 99%

1,2,3-Triazoles as Biomimetics in Peptide Science

2021

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Natural peptides are an important class of chemical mediators, essential for most vital processes. What limits the potential of the use of peptides as drugs is their low bioavailability and enzymatic degradation in vivo. To overcome this limitation, the development of new molecules mimicking peptides is of great importance for the development of new biologically active molecules. Therefore, replacing the amide bond in a peptide with a heterocyclic bioisostere, such as the 1,2,3-triazole ring, can be considered an effective solution for the synthesis of biologically relevant peptidomimetics. These 1,2,3-triazoles may have an interesting biological activity, because they behave as rigid link units, which can mimic the electronic properties of amide bonds and show bioisosteric effects. Additionally, triazole can be used as a linker moiety to link peptides to other functional groups.

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“…• Straightforward assembly on solid‐support via CuAAC; • Step‐wise addition of azidoacetic acids and propargylic amines [28] …”

Section: Peptide Backbone Modifications and Solid‐phase Synthesis Techniquesmentioning

confidence: 99%

“…Althuon et al . reported on the submonomer‐based solid‐phase synthesis of triazolopeptoids (Table 2, Entry 2) [28] . This approach is based on a direct assembly of the peptoid units on the solid support using click chemistry and copper(I) iodide as a catalyst.…”

Section: Peptide Backbone Modifications and Solid‐phase Synthesis Tec...mentioning

confidence: 99%

“…Althuon et al reported on the submonomer-based solidphase synthesis of triazolopeptoids (Table 2, Entry 2). [28] This approach is based on a direct assembly of the peptoid units on the solid support using click chemistry and copper(I) iodide as a catalyst. This methodology allows for the rapid construction of triazolopeptoids with a wide variety of side chains and accommodates the use of chiral building blocks.…”

Section: Heterocycle-based Peptoid Unit Mimeticsmentioning

confidence: 99%

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Solid‐Phase Synthesis of Peptidomimetics with Peptide Backbone Modifications

2021

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Peptidomimetics are a class of compounds with promising pharmacological properties. Peptidomimetics reduce limitations of peptides including low bioavailability, poor stability, and poor cell‐permeability. Peptide backbone modifications are a frequently used manipulation to reach desirable properties of the peptide molecules. The development of accessible synthetic methodologies plays an important role in peptidomimetic progress. Synthesis of peptidomimetics proceeds via solution and solid‐phase synthesis strategies. Solid‐phase organic synthesis serves as a powerful tool for the preparation of peptidomimetic molecules, thus, numerous strategies have been developed over the years. In this review, we discuss solid‐phase synthetic approaches for peptide backbone modifications that were presented in the last two decades.

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Functionalized triazolopeptoids – a novel class for mitochondrial targeted delivery

Cited by 22 publications

References 37 publications

A structure–activity relationship of non-peptide macrocyclic histone deacetylase inhibitors and their anti-proliferative and anti-inflammatory activities

A structure–activity relationship of non-peptide macrocyclic histone deacetylase inhibitors and their anti-proliferative and anti-inflammatory activities

1,2,3-Triazoles as Biomimetics in Peptide Science

Solid‐Phase Synthesis of Peptidomimetics with Peptide Backbone Modifications

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