Guanidiniocarbonyl-Pyrroles (GCP) - 20 Years of the Schmuck Binding Motif.

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.

[1]  C. Schmuck,et al.  Functional Disruption of the Cancer‐Relevant Interaction between Survivin and Histone H3 with a Guanidiniocarbonyl Pyrrole Ligand , 2020, Angewandte Chemie.

[2]  C. Ottmann,et al.  A Supramolecular Stabilizer of the 14‐3‐3ζ/ERα Protein‐Protein Interaction with a Synergistic Mode of Action , 2019, Angewandte Chemie.

[3]  Yasser B. Ruiz-Blanco,et al.  Multivalent Ligands with Tailor‐Made Anion Binding Motif as Stabilizers of Protein–Protein Interactions , 2019, Chembiochem : a European journal of chemical biology.

[4]  C. Schmuck,et al.  A stimuli responsive two component supramolecular hydrogelator with aggregation-induced emission properties. , 2019, Soft matter.

[5]  C. Ottmann,et al.  Arginine mimetic appended peptide-based probes for fluorescence turn-on detection of 14-3-3 proteins. , 2019, Organic & biomolecular chemistry.

[6]  D. Hoffmann,et al.  A new class of supramolecular ligands stabilizes 14-3-3 protein-protein interactions by up to two orders of magnitude. , 2019, Chemical communications.

[7]  C. Schmuck,et al.  A dual pH-responsive supramolecular gelator with aggregation-induced emission properties. , 2018, Soft matter.

[8]  Xiao‐Yu Hu,et al.  Formation of Twisted β-Sheet Tapes from a Self-Complementary Peptide Based on Novel Pillararene-GCP Host-Guest Interaction with Gene Transfection Properties. , 2018, Chemistry.

[9]  C. Schmuck,et al.  Hierarchical self-assembly of a small monomer with two orthogonal binding sites: from discrete hexagonal containers to a stimuli-responsive supramolecular gel , 2018 .

[10]  D. Hoffmann,et al.  Rational Design, Binding Studies, and Crystal‐Structure Evaluation of the First Ligand Targeting the Dimerization Interface of the 14‐3‐3ζ Adapter Protein , 2018, Chembiochem : a European journal of chemical biology.

[11]  C. Schmuck,et al.  A Systematic Structure–Activity Study of a New Type of Small Peptidic Transfection Vector Reveals the Importance of a Special Oxo‐Anion‐Binding Motif for Gene Delivery , 2017, Chembiochem : a European journal of chemical biology.

[12]  C. Schmuck,et al.  Efficient Gene Transfection through Inhibition of β-Sheet (Amyloid Fiber) Formation of a Short Amphiphilic Peptide by Gold Nanoparticles. , 2017, Angewandte Chemie.

[13]  C. Schmuck,et al.  Self-Assembly of a Tripodal Triszwitterion Forms a pH-Switchable Hydrogel that Can Reversibly Encapsulate Hydrophobic Guests in Water. , 2017, Chemistry.

[14]  C. Schmuck,et al.  Two-Component Self-Assembly: Hierarchical Formation of pH-Switchable Supramolecular Networks by π-π Induced Aggregation of Ion Pairs. , 2016, Chemistry.

[15]  C. Schmuck,et al.  Guanidiniocarbonyl pyrrole (GCP) conjugated PAMAM-G2, a highly efficient vector for gene delivery: the importance of DNA condensation. , 2016, Chemical communications.

[16]  C. Schmuck,et al.  Incorporation of a Non-Natural Arginine Analogue into a Cyclic Peptide Leads to Formation of Positively Charged Nanofibers Capable of Gene Transfection. , 2016, Angewandte Chemie.

[17]  C. Schmuck,et al.  Two-component self-assembly of a tetra-guanidiniocarbonyl pyrrole cation and Na4EDTA: formation of pH switchable supramolecular networks. , 2015, Chemical communications.

[18]  C. Schmuck,et al.  Chapter 8:Synthetic Receptors for Amino Acids and Peptides , 2015 .

[19]  M. Fleischer,et al.  Transforming polyethylenimine into a pH-switchable hydrogel by additional supramolecular interactions. , 2014, Chemical communications.

[20]  Hannes Y. Kuchelmeister,et al.  Utilizing combinatorial chemistry and rational design: peptidic tweezers with nanomolar affinity to DNA can be transformed into efficient vectors for gene delivery by addition of a lipophilic tail. , 2013, Angewandte Chemie.

[21]  T. Govindaraju,et al.  A supramolecular gel from a quadruple zwitterion that responds to both acid and base. , 2013, Angewandte Chemie.

[22]  H. Vieker,et al.  Cooperative self-assembly of discoid dimers: hierarchical formation of nanostructures with a pH switch. , 2013, Journal of the American Chemical Society.

[23]  D. Hoffmann,et al.  A new approach to inhibit human β-tryptase by protein surface binding of four-armed peptide ligands with two different sets of arms. , 2013, Organic & biomolecular chemistry.

[24]  Hannes Y. Kuchelmeister,et al.  Efficient gene delivery into cells by a surprisingly small three-armed peptide ligand , 2012 .

[25]  C. Schmuck,et al.  Advances in switchable supramolecular nanoassemblies. , 2012, Chemistry.

[26]  C. Schmuck.  A Journey Through 12 Years of Interacting Molecules: From Artificial Amino Acid Receptors to the Recognition of Biomolecules and Switchable Nanomaterials. , 2011 .

[27]  C. Schmuck.  A Journey through 12 Yearsof Interacting Molecules: From Artificial Amino Acid Receptors tothe Recognition of Biomolecules and Switchable Nanomaterials , 2011 .

[28]  C. Böttcher,et al.  Switchable supramolecular polymers from the self-assembly of a small monomer with two orthogonal binding interactions. , 2011, Journal of the American Chemical Society.

[29]  C. Schmuck,et al.  Carboxylate Binding by Indole-Based Guanidinium Receptors: Acylguanidinium Cations are Better than Aromatic Guanidinium Cations† , 2011 .

[30]  R. Haag,et al.  pH-triggered self-assembly of zwitterionic polyglycerol dendrons into discrete and highly stable supramolecular dendrimers in water. , 2010, Chemistry.

[31]  C. Schmuck,et al.  pH‐schaltbare Vesikel aus einem von Serin abgeleiteten Guanidiniocarbonylpyrrol‐Carboxylat‐Zwitterion in DMSO , 2010 .

[32]  C. Schmuck,et al.  pH-switchable vesicles from a serine-derived guanidiniocarbonyl pyrrole carboxylate zwitterion in DMSO. , 2010, Angewandte Chemie.

[33]  F. Würthner,et al.  Step-wise self-assembly of a small molecule with two orthogonal binding interactions leads to single stranded linear polymers in DMSO. , 2009, Chemical communications.

[34]  C. Cavallotti,et al.  Oxoanion binding by guanidiniocarbonylpyrrole cations in water: a combined DFT and MD investigation. , 2008, Chemistry.

[35]  F. Würthner,et al.  A new type of soft vesicle-forming molecule: an amino acid derived guanidiniocarbonyl pyrrole carboxylate zwitterion. , 2008, Organic letters.

[36]  T. Schrader,et al.  Artificial ditopic Arg-Gly-Asp (RGD) receptors. , 2007, Chemistry.

[37]  C. Schmuck,et al.  Oxoanion binding by flexible guanidiniocarbonyl pyrrole-ammonium bis-cations in water. , 2007, The Journal of organic chemistry.

[38]  C. Schmuck,et al.  Formation of vesicular structures through the self-assembly of a flexible bis-zwitterion in dimethyl sulfoxide. , 2007, Angewandte Chemie.

[39]  C. Schmuck,et al.  Solid phase synthesis of a prototype of a new class of biomimetic receptors for anionic carbohydrates. , 2007, Organic & biomolecular chemistry.

[40]  C. Schmuck,et al.  The Development of Artificial Receptors for Small Peptides Using Combinatorial Approaches , 2007 .

[41]  C. Schmuck,et al.  Sequence-dependent binding of dipeptides by an artificial receptor in water. , 2006, Chemistry.

[42]  C. Schmuck.  How to improve guanidinium cations for oxoanion binding in aqueous solution?: The design of artificial peptide receptors , 2006 .

[43]  C. Schmuck,et al.  Combinatorial receptor finding-large and random vs. small and focused libraries , 2006 .

[44]  C. Schmuck,et al.  2-(Guanidiniocarbonyl)furans as a New Class of Potential Anion Hosts: Synthesis and First Binding Studies , 2006 .

[45]  C. Schmuck,et al.  Sequence-dependent stereoselectivity in the binding of tetrapeptides in water by a flexible artificial receptor. , 2006, Angewandte Chemie.

[46]  Carsten Schmuck Prof.,et al.  Sequence-Dependent Stereoselectivity in the Binding of Tetrapeptides in Water by a Flexible Artificial Receptor† , 2006 .

[47]  C. Schmuck,et al.  A naked-eye sensing ensemble for the selective detection of citrate--but not tartrate or malate--in water based on a tris-cationic receptor. , 2006, Organic & biomolecular chemistry.

[48]  C. Schmuck,et al.  One-armed artificial receptors for the binding of polar tetrapeptides in water: probing the substrate selectivity of a combinatorial receptor library. , 2006, Chemistry.

[49]  Carsten Schmuck,et al.  Ion pair driven self-assembly of a flexible bis-zwitterion in polar solution: formation of discrete nanometer-sized cyclic dimers. , 2006, Journal of the American Chemical Society.

[50]  C. Schmuck,et al.  Ladungswechselwirkungen machen es möglich: ein kombinierter statistischer und kombinatorischer Ansatz zur Auffindung künstlicher Rezeptoren für die Bindung von Tetrapeptiden in Wasser† , 2005 .

[51]  J. Scheiber,et al.  Charge interactions do the job: a combined statistical and combinatorial approach to finding artificial receptors for binding tetrapeptides in water. , 2005, Angewandte Chemie.

[52]  Sebastian Schlund,et al.  "Knock-out" analogues as a tool to quantify supramolecular processes: a theoretical study of molecular interactions in guanidiniocarbonyl pyrrole carboxylate dimers. , 2005, Journal of the American Chemical Society.

[53]  C. Schmuck,et al.  Recognition of anionic carbohydrates by an artificial receptor in water. , 2005, Organic letters.

[54]  C. Schmuck,et al.  Efficient complexation of N-acetyl amino acid carboxylates in water by an artificial receptor: unexpected cooperativity in the binding of glutamate but not aspartate. , 2005, Journal of the American Chemical Society.

[55]  C. Schmuck,et al.  A molecular flytrap for the selective binding of citrate and other tricarboxylates in water. , 2005, Journal of the American Chemical Society.

[56]  C. Schmuck,et al.  Amino acid binding by 2-(guanidiniocarbonyl)pyridines in aqueous solvents: a comparative binding study correlating complex stability with stereoelectronic factors. , 2005, Chemistry.

[57]  M. J. Chalmers,et al.  Structurally related non-covalent complexes examined by quadrupole ion trap (QIT) MS2 and infrared multiphoton dissociation Fourier transform ion cyclotron resonance mass spectrometry IRMPD-FT-ICR MS: evidence for salt-bridge structures in the gas phase , 2004 .

[58]  C. Schmuck,et al.  Dipeptide binding in water by a de novo designed guanidiniocarbonylpyrrole receptor. , 2004, Journal of the American Chemical Society.

[59]  C. Schmuck,et al.  Peptide Binding by One‐Armed Receptors in Water: Screening of a Combinatorial Library for the Binding of Val‐Val‐Ile‐Ala , 2003, Chembiochem : a European journal of chemical biology.

[60]  M. J. Chalmers,et al.  Determination of the activation energy for unimolecular dissociation of a non-covalent gas-phase peptide: Substrate complex by infrared multiphoton dissociation fourier transform ion cyclotron resonance mass spectrometry , 2003, Journal of the American Society for Mass Spectrometry.

[61]  C. Schmuck,et al.  N'-alkylated guanidiniocarbonyl pyrroles: new receptors for amino acid recognition in water. , 2003, Organic letters.

[62]  Carsten Schmuck and Lars Geiger.  Carboxylate Binding by Guanidiniocarbonyl Pyrroles: From Self- Assembly to Peptide Receptors , 2003 .

[63]  C. Schmuck,et al.  Using combinatorial methods to arrive at a quantitative structure-stability relationship for a new class of one-armed cationic peptide receptors targeting the C-terminus of the amyloid beta-peptide. , 2003, Organic & biomolecular chemistry.

[64]  C. Schmuck,et al.  Using combinatorial methods to arrive at a quantitative structure–stability relationship for a new class of one-armed cationic peptide receptors targeting the C-terminus of the amyloid β-peptideElectronic supplementary information (ESI) available: quantitative on bead binding assay. See http://www.r , 2003 .

[65]  J. Lex,et al.  C−H···O Interactions as Isofunctional Replacements for N−H···O Interactions − Dimer Formation of Methyl 5-Amidopyrrole-2-carboxylates in the Solid State , 2001 .

[66]  C. Schmuck.  Carboxylate binding by 2-(guanidiniocarbonyl)pyrrole receptors in aqueous solvents: improving the binding properties of guanidinium cations through additional hydrogen bonds. , 2000, Chemistry.

[67]  C. Schmuck.  Highly Stable Self‐Association of 5‐(Guanidiniocarbonyl)‐1H‐pyrrole‐2‐carboxylate in DMSO – The Importance of Electrostatic Interactions , 1999 .

[68]  C. Schmuck.  Side chain selective binding of N-acetyl-α-amino acid carboxylates by a 2-(guanidiniocarbonyl)pyrrole receptor in aqueous solvents , 1999 .

[69]  C. Schmuck,et al.  The mechanism of thiazolium catalysis , 1996 .

[70]  C. Schmuck,et al.  GOODNESS OF FIT IN COMPLEXES BETWEEN SUBSTRATES AND RIBONUCLEASE MIMICS : EFFECTS ON BINDING, CATALYTIC RATE CONSTANTS, AND REGIOCHEMISTRY , 1996 .

[71]  W. Roth,et al.  Radikal-Stabilisierungsenergie – das MMEVBH-Kraftfeld , 1995 .