Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

• peptide sequence, or unmodified PNA [172]. Peschke and co-workers conjugated a dual peptide construct built of penetratin (for cytosolic delivery) and NLS

Automated high-content imaging for cellular uptake, from the Schmuck cation to the latest cyclic oligochalcogenides

• Rémi Martinent,
• Javier López-Andarias,
• Dimitri Moreau,
• Yangyang Cheng,
• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2020, 16, 2007–2016, doi:10.3762/bjoc.16.167

• ), here exemplified by asparagusic acid. A persistent challenge in this evolution is the simultaneous and quantitative detection of cytosolic delivery and cytotoxicity in a high-throughput format. Here, we show that the combination of the HaloTag-based chloroalkane penetration assay (CAPA) with automated

• results can be obtained from dose–response curves of the targeted delivery to selected cells and the cytotoxicity in the same experiment, even with poorly optimized cellular systems. Keywords: automation; cell-penetrating peptides; cellular uptake; cytosolic delivery; cytotoxicity; high-content imaging

• (Figure 5b) [49][50]. The cyclic oligochalcogenides (COCs) 19–22 were introduced to maximize the speed and selectivity of this dynamic covalent exchange chemistry for an efficient cytosolic delivery (Figure 4) [51]. Moving from the original emphasis on the disulfide ring tension into an increasing

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• polymers for 'plug and play' modification and self-assembly. Recognition-mediated assembly of nanoparticle–polymer constructs. Reproduced from [24]. Cytosolic delivery of GFP to cells using nanoparticle-stabilized nanocapsules. Adapted with permission from [63]. Copyright (2013) American Chemical Society

Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery

• Jan Hoyer,
• Ulrich Schatzschneider,
• Michaela Schulz-Siegmund and
• Ines Neundorf

Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204

• , which exert the same effect on cell morphology (Figure 8) and induce an equal amount of LDH release (Figure 9). This is surprising at least for compound 4, since several PAD–CPP conjugates were shown to induce apoptosis upon cytosolic delivery [28][29]. It is possible, though, that the even higher