Guanidiniocarbonyl‐Pyrroles (GCP) – 20 Years of the Schmuck Binding Motif

Abstract

In this Minireview, an overview about the past 20 years of the guanidiniocarbonyl‐pyrrole (GCP) binding motif, which was designed, investigated and applied by Prof. Dr. Carsten Schmuck, is presented. Here we highlight the first steps from design and discovery, initial binding studies, applications in material science to advanced biomedical use in protein modulation and delivery of genetic material.

Supramolecular polymers with reversed viscosity/temperature profile for application in motor oils

“…Based on our working hypothesis, a supramolecular VII system requires a BU with strong dimerization tendency and a LU with precoordinating properties. For our purpose, we initially employed the guanidiniocarbonyl pyrrole (GCP) motif as a binding unit [19]. The GCP unit is a self-complementary zwitterion, which forms dimers with high association constants, based on a sixfold hydrogen-bonding interaction, strengthened by coulombic interactions (see Figure 2a) [20,21].…”

Cationic dynamic covalent polymers for gene transfection

“…98 Some artificial derivatives of guanidiniums such as the guanidiniocarbonyl pyrrole motif show improved oxoanion binding and thus bears a strong potential for nucleic acid delivery applications. [99][100][101] Histidine also can be grafted to cationic polymers. Thanks to the low pKa of its imidazole ring(≈ 6), it often partake in an acid-dependent fusion and leakage of liposomes.…”

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

“…Selfassembly into supramolecular structures and molecular recognition processes have been established based on different noncovalent interactions such as hydrogen bonding [9][10][11][12], π-π interaction [13][14][15][16][17], hydrophobic effects, and amphiphilicity [18][19][20][21]. It has been highly desirable to establish concepts that could be applied in aqueous solution, with the Schmuck binding motif -the guanidiniocarbonyl-pyrrole zwitterion binding motif -representing a most versatile binding motif with potential from nanostructure design to biomedicine [22][23][24][25]. In addition, it is desirable to establish general concepts that do not rely on specific binding motifs.…”