scholarly journals Peptides – Molecular Allrounders

2021 ◽  
Vol 75 (6) ◽  
pp. 525-529
Author(s):  
Helma Wennemers
Keyword(s):  
Amino Acids ◽  
Supramolecular Chemistry ◽  
Asymmetric Catalysis ◽  
Functional Diversity ◽  
Chemical Biology ◽  
Cell Penetrating Peptides ◽  
Peptide Catalysts ◽  
Collagen Peptides ◽  
Cell Penetrating

The enormous structural and functional diversity available through combining different amino acids into peptides offers numerous exciting opportunities. This article summarizes recent research highlights from my laboratory in the areas of asymmetric catalysis, supramolecular chemistry, and chemical biology. This scope includes the development of bioinspired peptide catalysts, synthetic collagen peptides, supramolecular porous assemblies, and cell-penetrating peptides.

Development of helix-stabilized cell-penetrating peptides containing cationic α,α-disubstituted amino acids as helical promoters

2017 ◽  
Vol 25 (6) ◽  
pp. 1846-1851 ◽  
Author(s):  
Hiroko Yamashita ◽  
Takashi Misawa ◽  
Makoto Oba ◽  
Masakazu Tanaka ◽  
Mikihiko Naito ◽  
...  
Keyword(s):  
Amino Acids ◽  
Cell Penetrating Peptides ◽  
Cell Penetrating ◽  
Disubstituted Amino Acids

Stereochemistry as a determining factor for the effect of a cell-penetrating peptide on cellular viability and epithelial integrity

2018 ◽  
Vol 475 (10) ◽  
pp. 1773-1788 ◽  
Author(s):  
Ditlev Birch ◽  
Malene V. Christensen ◽  
Dan Staerk ◽  
Henrik Franzyk ◽  
Hanne Mørck Nielsen
Keyword(s):  
Amino Acids ◽  
Cell Viability ◽  
Mammalian Cells ◽  
Membrane Integrity ◽  
Cell Penetrating Peptides ◽  
Proliferating Cells ◽  
Epithelial Integrity ◽  
Cell Penetrating ◽  
Culture Models ◽  
Well Differentiated

Cell-penetrating peptides (CPPs) comprise efficient peptide-based delivery vectors. Owing to the inherent poor enzymatic stability of peptides, CPPs displaying partial or full replacement of l-amino acids with the corresponding d-amino acids might possess advantages as delivery vectors. Thus, the present study aims to elucidate the membrane- and metabolism-associated effects of l-Penetratin (l-PEN) and its corresponding all-d analog (d-PEN). These effects were investigated when exerted on hepatocellular (HepG2) or intestinal (Caco-2 and IEC-6) cell culture models. The head-to-head comparison of these enantiomeric CPPs included evaluation of their effects on cell viability and morphology, epithelial membrane integrity, and cellular ultrastructure. In all investigated cell models, a rapid decrease in cell viability, pronounced membrane perturbation and an altered ultrastructure were detected upon exposure to d-PEN. At equimolar concentrations, these observations were less pronounced or even absent for cells exposed to l-PEN. Both CPPs remained stable for at least 2 h during exposure to proliferating cells (cultured for 24 h), although d-PEN exhibited a longer half-life when compared with that of l-PEN when exposed to well-differentiated cell monolayers (cultured for 18–20 days). Thus, the stereochemistry of the CPP penetratin significantly influences its effects on cell viability and epithelial integrity when profiled against a panel of mammalian cells.

Plasmid DNA delivery by arginine-rich cell-penetrating peptides containing unnatural amino acids

2016 ◽  
Vol 24 (12) ◽  
pp. 2681-2687 ◽  
Author(s):  
Takuma Kato ◽  
Hiroko Yamashita ◽  
Takashi Misawa ◽  
Koyo Nishida ◽  
Masaaki Kurihara ◽  
...  
Keyword(s):  
Amino Acids ◽  
Plasmid Dna ◽  
Unnatural Amino Acids ◽  
Dna Delivery ◽  
Cell Penetrating Peptides ◽  
Cell Penetrating

scholarly journals Steroid diversification by multicomponent reactions

2019 ◽  
Vol 15 ◽  
pp. 1236-1256 ◽  
Author(s):  
Leslie Reguera ◽  
Cecilia I Attorresi ◽  
Javier A Ramírez ◽  
Daniel G Rivera
Keyword(s):  
Amino Acids ◽  
Drug Discovery ◽  
Carboxylic Acid ◽  
Supramolecular Chemistry ◽  
Boronic Acid ◽  
Chemical Biology ◽  
Multicomponent Reactions ◽  
Naturally Occurring ◽  
Almost All ◽  
Structural Diversification

Reports on structural diversification of steroids by means of multicomponent reactions (MCRs) have significantly increased over the last decade. This review covers the most relevant strategies dealing with the use of steroidal substrates in MCRs, including the synthesis of steroidal heterocycles and macrocycles as well as the conjugation of steroids to amino acids, peptides and carbohydrates. We demonstrate that steroids are available with almost all types of MCR reactive functionalities, e.g., carbonyl, carboxylic acid, alkyne, amine, isocyanide, boronic acid, etc., and that steroids are suitable starting materials for relevant MCRs such as those based on imine and isocyanide. The focus is mainly posed on proving the amenability of MCRs for the diversity-oriented derivatization of naturally occurring steroids and the construction of complex steroid-based platforms for drug discovery, chemical biology and supramolecular chemistry applications.

scholarly journals Chemical-Functional Diversity in Cell-Penetrating Peptides

PLoS ONE ◽  
2013 ◽  
Vol 8 (8) ◽  
pp. e71752 ◽  
Author(s):  
Sofie Stalmans ◽  
Evelien Wynendaele ◽  
Nathalie Bracke ◽  
Bert Gevaert ◽  
Matthias D’Hondt ◽  
...  
Keyword(s):  
Functional Diversity ◽  
Cell Penetrating Peptides ◽  
Cell Penetrating

scholarly journals Oligoalanine helical callipers for cell penetration

2018 ◽  
Vol 54 (50) ◽  
pp. 6919-6922 ◽  
Author(s):  
Marta Pazo ◽  
Marisa Juanes ◽  
Irene Lostalé-Seijo ◽  
Javier Montenegro
Keyword(s):  
Amino Acids ◽  
Rational Design ◽  
Chemical Space ◽  
Cell Penetrating Peptides ◽  
Short Peptides ◽  
Cell Penetration ◽  
Basic Amino Acids ◽  
Cell Penetrating ◽  
Natural Amino Acids

Even for short peptides that are enriched in basic amino acids, the large chemical space that can be spanned by combinations of natural amino acids hinders the rational design of cell penetrating peptides.

scholarly journals Molecular dynamics study of the internalization of cell-penetrating peptides containing unnatural amino acids across membranes

2021 ◽  
Author(s):  
Joan Gimenez-Dejoz ◽  
Keiji Numata
Keyword(s):  
Molecular Dynamics ◽  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Biological Membranes ◽  
Cell Penetrating Peptides ◽  
Delivery Systems ◽  
Cell Penetrating ◽  
Target Molecules

Peptide-based delivery systems that deliver target molecules into cells have been gaining traction. These systems need cell-penetrating peptides (CPPs), which have the remarkable ability to penetrate into biological membranes and...

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