From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• two until we settled in. Although a much larger department than UNO, UT Austin had a poorer ratio of NMR instruments to students, and so we focused mostly on isothermal titration calorimetry (ITC) based research. There was the small matter of sneaking into a closed city and slipping under the radar of

Peptide–polymer ligands for a tandem WW-domain, an adaptive multivalent protein–protein interaction: lessons on the thermodynamic fitness of flexible ligands

• Katharina Koschek,
• Vedat Durmaz,
• Oxana Krylova,
• Marek Wieczorek,
• Shilpi Gupta,
• Martin Richter,
• Alexander Bujotzek,
• Christina Fischer,
• Rainer Haag,
• Christian Freund,
• Marcus Weber and
• Jörg Rademann

Beilstein J. Org. Chem. 2015, 11, 837–847, doi:10.3762/bjoc.11.93

• tandem WW-domain of formin-binding protein (FBP21). Polymer carriers were conjugated with 3–9 copies of the proline-rich decapeptide GPPPRGPPPR-NH2 (P1). Binding of the obtained peptide–polymer conjugates to the tandem WW-domain was investigated employing isothermal titration calorimetry (ITC) to

• superior to induce multivalent binding and to increase affinity, while the more flexible and dendritic polymers, pHPMA and hPG are suitable to induce crosslinking upon binding. Keywords: inhibitors of protein–protein interactions; isothermal titration calorimetry; multivalency; peptide–polymer conjugates

• multivalent peptide–polymer conjugate to the tandem WW domain Binding studies with peptide–polymer conjugates were conducted employing isothermal titration calorimetry (ITC). This method enables the determination of the binding affinity of the multivalent ligands and elucidates the composition of the free

Impact of multivalent charge presentation on peptide–nanoparticle aggregation

• Daniel Schöne,
• Boris Schade,
• Christoph Böttcher and
• Beate Koksch

Beilstein J. Org. Chem. 2015, 11, 792–803, doi:10.3762/bjoc.11.89

• with peptide concentration. Isothermal titration calorimetry (ITC) was used to determine the thermodynamic parameters as well as the binding constant for the assembly of Au/MUA nanoparticles (Table 1). By fitting with a one set of binding site mode the binding stoichiometry N, the binding constant KB

Exploring monovalent and multivalent peptides for the inhibition of FBP21-tWW

• Lisa Maria Henning,
• Sumati Bhatia,
• Miriam Bertazzon,
• Michaela Marczynke,
• Oliver Seitz,
• Rudolf Volkmer,
• Rainer Haag and
• Christian Freund

Beilstein J. Org. Chem. 2015, 11, 701–706, doi:10.3762/bjoc.11.80

• which demonstrates that the new carrier provides a venue for the future inhibition of proline-rich sequence recognition by FBP21 during assembly of the spliceosome. Keywords: FBP21-tWW; isothermal titration calorimetry; multivalent polymers; polyglycerol peptide conjugates; proline-rich sequence

• the interaction between hPG-peptide conjugate 2 and FBP21-tWW was measured by isothermal titration calorimetry (ITC) and compared to the KD of the interaction between the monovalent peptide and FBP21-tWW to analyze if multivalent display in form of the hPG-peptide conjugate 2 increases binding

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives – their stability, complexation ability in solution or when deposited on solid anionic surface

• Martin Popr,
• Sergey K. Filippov,
• Nikolai Matushkin,
• Juraj Dian and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20

• PEMPDA-β-CD in solution with a series of simple aromatic guests (salicylic acid, p-methoxyphenol and p-nitroaniline) were determined by isothermal titration calorimetry (ITC) and compared to the native β-CD. Permanently charged cationic CD derivatives were successfully deposited on the anionic solid

Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers

• Thorbjørn Terndrup Nielsen,
• Catherine Amiel,
• Laurent Duroux,
• Kim Lambertsen Larsen,
• Lars Wagner Städe,
• Reinhard Wimmer and
• Véronique Wintgens

Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

• prepared with a degree of substitution of (S)-camptothecin between 3.1 and 10.2%. The binding properties with β-cyclodextrin and β-cyclodextrin polymers were measured by isothermal titration calorimetry and fluorescence spectroscopy, showing no binding with β-cyclodextrin but high binding with β

• ). Binding properties and formation of nanoparticles The ability to form inclusion complexes with β-CD and β-CD-polymers was determined by isothermal titration calorimetry (ITC) and fluorescence spectroscopy. The β-CD polymer (D70HPβ-CD) had been prepared from a 70 kDa dextran backbone modified with 6

• -heptynoic acid in a similar way as already described in literature [17] and had a β-CD content of 58.6% (w/w) (Supporting Information File 1). D10GP-CPT1 (DS 4.6) and D70GP-CPT2 (DS 4.5) were chosen since the similar DS should make comparison possible. Isothermal titration calorimetry The different

Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer

• Florian Hamon,
• Claire Blaszkiewicz,
• Marie Buchotte,
• Estelle Banaszak-Léonard,
• Hervé Bricout,
• Sébastien Tilloy,
• Eric Monflier,
• Christine Cézard,
• Laurent Bouteiller,
• Christophe Len and
• Florence Djedaini-Pilard

Beilstein J. Org. Chem. 2014, 10, 2874–2885, doi:10.3762/bjoc.10.304

• from 2 to 95% of the maximum gradient strength. A 100 ms diffusion time and a 2.2 ms gradient length were used. Isothermal Titration Calorimetry (ITC) was performed using a VP-ITC microcalorimeter at 298 K or 278 K in pure water. Briefly, titration was carried out with 60 injections of 5 µL every 6 min

Improving ITC studies of cyclodextrin inclusion compounds by global analysis of conventional and non-conventional experiments

• Eléonore Bertaut and
• David Landy

Beilstein J. Org. Chem. 2014, 10, 2630–2641, doi:10.3762/bjoc.10.275

• Eleonore Bertaut David Landy Univ Lille Nord de France, F-59000 Lille, France ULCO, UCEIV, F-59140 Dunkerque, France 10.3762/bjoc.10.275 Abstract The study of 1:1 cyclodextrin inclusion compounds by isothermal titration calorimetry was explored in a theoretical and experimental point of view to

• stability, enthalpy, or solubility. Keywords: cyclodextrins; global analysis; inclusion compounds; isothermal titration calorimetry; non-conventional experiments; Introduction The stability and thermodynamics of cyclodextrin inclusion compounds in solutions may be investigated with various analytical

• techniques ranging from spectroscopy to chromatography and including calorimetrical tools [1][2][3][4]. Within this scope, isothermal titration calorimetry (ITC) is gaining more and more importance, as it allows a complete thermodynamic description of the inclusion phenomena (binding constant K, inclusion

Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

• Michael Kurlemann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 2428–2440, doi:10.3762/bjoc.10.253

• complementary and non-complementary strands modified with guest molecules and the investigation of their complexation behavior towards each other by isothermal titration calorimetry (ITC). As complementary binding motifs n-butyl and α-CD and adamantane and β-CD were selected. It was found that it is possible to

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

• Meriem Smadhi,
• Sophie de Bentzmann,
• Anne Imberty,
• Marc Gingras,
• Raoudha Abderrahim and
• Peter G. Goekjian

Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

• . Both homo- and heterobifunctional ligands are obtained by a straightforward preparative route, as an innovative approach. Additionally, isothermal titration calorimetry (ITC) and dynamic light scattering (DLS) helped to better understand lectin–ligand interactions between lecA or lecB and these

• lecB were determined by isothermal titration calorimetry (ITC) by addition of the ligands to a solution of lectin (Figure 3). Dissociation constants (Kd) and thermodynamic parameters (ΔG, ΔH, −TΔS) are listed in Table 1, together with the experimental binding stoichiometry (n), defined as the number of

Photoswitchable precision glycooligomers and their lectin binding

• Daniela Ponader,
• Sinaida Igde,
• Marko Wehle,
• Katharina Märker,
• Mark Santer,
• David Bléger and
• Laura Hartmann

Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166

• modelling for ligand binding. Ongoing studies further investigate ligand binding by additional techniques such as isothermal titration calorimetry and fluorescence spectroscopy. Overall, we have successfully developed photoswitchable glycomimetics that allow for a stimulus-induced change in binding affinity

Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

• Mathieu L. Lepage,
• Alessandra Meli,
• Anne Bodlenner,
• Céline Tarnus,
• Francesco De Riccardis,
• Irene Izzo and
• Philippe Compain

Beilstein J. Org. Chem. 2014, 10, 1406–1412, doi:10.3762/bjoc.10.144

• to 2 orders of magnitude more efficient as CFTR correctors than the clinical candidate miglustat (N-Bu-DNJ, 1, Figure 1). The mechanisms underlying the inhibitory multivalent effect were studied with different methods such as isothermal titration calorimetry, competitive lectin-enzyme assays, X-ray

Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

• Melanie Rauschenberg,
• Eva-Corrina Fritz,
• Christian Schulz,
• Tobias Kaufmann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 1354–1364, doi:10.3762/bjoc.10.138

• the parallel HisHis compared to the antiparallel HisHis [40]. Isothermal titration calorimetry (ITC) confirmed that the interaction of FITC-HisHis (mixture of isomers) and NANA is characterized by the same stoichiometry (1:2) and nearly the same binding constants (K1 = 163 M−1 and K2 = 5.36 × 103 M−1

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton^® X-100

• Melanie Kemnitz and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2176–2183, doi:10.3762/bjoc.8.245

• Acros Organics. They were dried in a microwave drying system SAM 255 (CEM). Methacryloyl chloride (Fluka), acryloyl chloride (Fluka), triethylamine (Acros Organics), AIBN (Sigma-Aldrich), VA-044 (Wako Chemicals) and DMF (VWR) were used as received. Measurements Isothermal titration calorimetry

Influence of intramolecular hydrogen bonds on the binding potential of methylated β-cyclodextrin derivatives

• Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1890–1895, doi:10.3762/bjoc.8.218

• these guests should sensitively respond to changes in the methylation pattern, because they fit tightly into the cavity of β-CD giving rise to high binding constants [26][27]. Binding data were measured by isothermal titration calorimetry (ITC) because it is known to be the most accurate method, and

Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2012, 8, 1543–1551, doi:10.3762/bjoc.8.175

• functions to bind into the cavity of cyclodextrins, the synthesized guest molecules were investigated regarding their 1:1 complexation behavior towards β-cyclodextrin. Isothermal titration calorimetry (ITC) was carried out with β-cyclodextrin and each of the synthesized guest molecules 1–4. The

• literature [30]. Methods: Isothermal titration calorimetry (ITC) measurements were performed on a Nano-Isothermal Titration calorimeter III (model CSC 5300; Calorimetry Sciences Corporation, London, Utah, USA). All samples were measured in distilled water at 23 °C by using a stirring rate of 250 rpm. For

• . Thermodynamic parameters measured with isothermal titration calorimetry. Supporting Information Supporting Information File 284: Synthesis, NMR and mass spectra of guest molecules 1–4. Acknowledgements We acknowledge the synthesis of starting materials by Christian Wendeln. β-Cyclodextrin was kindly donated

Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis

• Hervé Bricout,
• Estelle Léonard,
• Christophe Len,
• David Landy,
• Frédéric Hapiot and
• Eric Monflier

Beilstein J. Org. Chem. 2012, 8, 1479–1484, doi:10.3762/bjoc.8.167

• isothermal titration calorimetry (ITC), at a suitable RAME-β-CD/phosphane concentration ratio ensuring the absence of micelles during the whole experiment. Under these conditions, the values reflect the interaction between a single CD with a single phosphane only. A 1/1 stoichiometry was found whatever the

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

• ion binding processes are direct absorption and emission measurements utilizing chromophores in the receptor or analyte molecule, displacement assays with suitable dyes, NMR titration experiments, isothermal titration calorimetry and transport through an organic phase monitored by HPLC, NMR [37][38

• affinity of benzyl ammonium chloride and 18-crown-6 in several solvents for comparison with other examples found in this review. The data given were determined by isothermal titration calorimetry [9]. These data show that crown ethers bind ammonium ions in different solvents which compete for hydrogen