Design, synthesis and application of carbazole macrocycles in anion sensors

• Alo Rüütel,
• Ville Yrjänä,
• Sandip A. Kadam,
• Indrek Saar,
• Mihkel Ilisson,
• Astrid Darnell,
• Kristjan Haav,
• Tõiv Haljasorg,
• Lauri Toom,
• Johan Bobacka and
• Ivo Leito

Beilstein J. Org. Chem. 2020, 16, 1901–1914, doi:10.3762/bjoc.16.157

• residues (from glutaric to thapsic acid) with different chain lengths, allowing manipulation of the ring size. Similar strategies for closing macrocycles have previously been published [26][27][28]. To predict possible binding properties, all methylene-bridged macrocycles and their binding to several

• coupling of the corresponding amino derivatives according to Scheme 1. The synthesis of CZ016 is also described in Scheme 1. Details of all synthetic procedures can be found in Supporting Information File 1. Binding measurements The binding properties of the macrocycles are expressed by the logarithms of

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors

• Abimelek Cortes-Pacheco,
• María Adelina Jiménez-Arellanes,
• Francisco José Palacios-Can,
• José Antonio Valcarcel-Gamiño,
• Rodrigo Said Razo-Hernández,
• María del Carmen Juárez-Vázquez,
• Adolfo López-Torres and
• Oscar Abelardo Ramírez-Marroquín

Beilstein J. Org. Chem. 2020, 16, 1277–1287, doi:10.3762/bjoc.16.108

• the binding properties of a molecule. Besides the dipole moment, 3 and 4 have the greatest chemical hardness of the bisphosphonates. This descriptor is related to the chemical susceptibility to an external potential. Therefore, the antiinflammatory activity of these compounds can be related to the

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

• Phil M. Pithan,
• Sören Steup and
• Heiko Ihmels

Beilstein J. Org. Chem. 2020, 16, 904–916, doi:10.3762/bjoc.16.82

• -binding properties to be used as DNA-sensitive fluorescent probes in cell imaging [60][61][62] or as photoswitchable DNA ligands [63]. Therefore, we were interested in a combination of the photochromic properties of the spirooxazine moiety with the advantageous photophysical and biological properties of

Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2 + 2] cycloaddition and cycloreversion

• Sarah Kölsch,
• Heiko Ihmels,
• Jochen Mattay,
• Norbert Sewald and
• Brian O. Patrick

Beilstein J. Org. Chem. 2020, 16, 111–124, doi:10.3762/bjoc.16.13

• structural changes of the nucleic acid. In turn, both of these processes interfere with biologically relevant recognition processes between DNA and enzymes, e.g., topoisomerase [10]. Therefore, many potential lead structures of chemotherapeutic anticancer drugs exhibit DNA-binding properties [1][2][3][4][5

• switching of binding properties [36]. Apparently, styryl-substituted aromatic derivatives could fill this gap because the [2 + 2] photocyclization reaction of stilbenes and derivatives thereof is a well-established reversible photoreaction [37][38][39][40][41][42][43][44][45][46], and styryl dyes, in

• release the DNA-binding ligand have not been reported so far. Herein, we report on the photochemical and DNA-binding properties of the selected styrylquinolizinium derivatives 3a–d and demonstrate their ability to operate as photoswitchable DNA ligands. Results and Discussion Synthesis 2

Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides

• Sabrina Müller,
• Jannik Paulus,
• Jochen Mattay,
• Heiko Ihmels,
• Veronica I. Dodero and
• Norbert Sewald

Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8

• contacts to the bottom of the cognate minor groove. However, previous studies on distamycin A-like derivatives containing only pyrrole moieties and 4,4'-substituted azobenzene as a photoswitchable linker showed that the binding properties of the Z- and E-isomers were quite similar. Hence, there was no

Design, synthesis and investigation of water-soluble hemi-indigo photoswitches for bioapplications

• Daria V. Berdnikova

Beilstein J. Org. Chem. 2019, 15, 2822–2829, doi:10.3762/bjoc.15.275

• solubility in aqueous medium and potential RNA-binding properties, the dimethylaminopropyl substituent [19] was introduced to hemi-indigo Z-1c. Two synthetically straightforward approaches of the alkylamino group introduction were considered: (i) N-alkylation of the indoxyl core and (ii) O-alkylation of the

A toolbox of molecular photoswitches to modulate the CXCR3 chemokine receptor with light

• Xavier Gómez-Santacana,
• Sabrina M. de Munnik,
• Tamara A. M. Mocking,
• Niels J. Hauwert,
• Shanliang Sun,
• Prashanna Vijayachandran,
• Iwan J. P. de Esch,
• Henry F. Vischer,
• Maikel Wijtmans and
• Rob Leurs

Beilstein J. Org. Chem. 2019, 15, 2509–2523, doi:10.3762/bjoc.15.244

• samples at 434 nm or 460 nm, the π–π* transition band of the trans-isomer re-appears, indicating a high percentage of trans-isomer at that PSS. The use of 494 nm affords less trans compound and is less efficient in achieving PSS trans. Next, the CXCR3 binding properties of 2a–e were measured (Table 1) in

• electron delocalization of π-electrons that is translated to a bathochromic shifting of the band to lower energy wavelength (337 nm). PSS values of 81–92% are obtained when illuminating with 360 nm light. The binding properties of 3a–h also result in outcomes similar to those of 2a–e. That is, Ki values

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

• Lei Zhang,
• Greta Linden and
• Olalla Vázquez

Beilstein J. Org. Chem. 2019, 15, 2500–2508, doi:10.3762/bjoc.15.243

• an improved TM difference between the trans- and cis-PNA15(oF4Azo)2 10 (up to ≈3.7 °C), which was the best for our system. Azobenzene (Azo)-containing PNAs behaved similarly to PNA(oF4Azo) (Table 2), which verified that the fluorine substitution did not affected the binding properties. The

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

• Anniina Kiesilä,
• Jani O. Moilanen,
• Anneli Kruve,
• Christoph A. Schalley,
• Perdita Barran and
• Elina Kalenius

Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241

• the pyridine[4]arene dimer, and all mass spectrometric data and theoretical calculations show undoubtedly that the cation is located inside the cavity of the dimer in the gas phase. It is an interesting fact, that the binding properties of pyridine[4]arene differ from earlier reports [7][8]. However

• , cation binding to pyridinearene is clearly not as strong as with resorcin[4]arene, which is known for its excellent cation receptor properties. A comparison of these two macrocyclic hosts reveals significant differences in their binding properties. Pyridine[4]arene appears to have a better affinity

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

• Meng-Di Gu,
• Yao Lu and
• Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes

• Li-Li Wang,
• Yi-Kuan Tu,
• Huan Yao and
• Wei Jiang

Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146

• interesting new binding properties. During the last six years, our group have developed a series of naphthol-based macrocyclic receptors [24][25][26][27][28][29]. Of them, oxatub[4]arene [30][31] and zorb[4]arene [32][33] show multiple conformations due to the flipping of naphthalenes and thus resulted in a

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• ) were used to evaluate the binding properties of compounds 5 and 8 towards wheat germ agglutinin (WGA), a lectin from Triticum vulgaris that is specific for N-acetylneuraminic acid and N-acetylglucosamine. This assay consists in measuring the ability of the compounds to inhibit the binding of WGA

Polyaminoazide mixtures for the synthesis of pH-responsive calixarene nanosponges

• Antonella Di Vincenzo,
• Antonio Palumbo Piccionello,
• Alberto Spinella,
• Delia Chillura Martino,
• Marco Russo and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2019, 15, 633–641, doi:10.3762/bjoc.15.59

• the binding properties of CaNSs examined in our previous work [22], because they have been considered good models of organic pollutants [26][27][28][29][30]; moreover, they have been largely used as probes to investigate the microscopic interactions involved in the binding equilibria with other

Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes

• Krzysztof M. Zwoliński and
• Julita Eilmes

Beilstein J. Org. Chem. 2019, 15, 617–622, doi:10.3762/bjoc.15.57

• prepared and their binding properties toward sodium and potassium ions were studied in addition to transition metals. Sakata et al. reported the syntheses and characterization of nickel(II), copper(II) [25] and oxovanadium(IV) [26] complexes of crown ether-annulated DBTAAs, which caused dimerization in the

• binding properties of the crown ether-capped DBTAA receptors are under investigation and will be reported elsewhere. Experimental General procedure for the synthesis of crown ether-capped DBTAA’s 3a and 3b 1,7-Diaza-15-crown-5 (0.1 mmol, 22 mg) together with triethylamine (0.05 mL) was added to a

Olefin metathesis catalysts embedded in β-barrel proteins: creating artificial metalloproteins for olefin metathesis

• Daniel F. Sauer,
• Johannes Schiffels,
• Takashi Hayashi,
• Ulrich Schwaneberg and
• Jun Okuda

Beilstein J. Org. Chem. 2018, 14, 2861–2871, doi:10.3762/bjoc.14.265

• very similar structural patterns, β-barrel and TIM-barrel proteins occupy a tremendous sequence space and are highly versatile in terms of metabolic functions, binding properties, transport and catalytic activities. The compact barrel structure can be regarded as a prototype of stable protein scaffolds

Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine

• Xiayang Huang,
• Xinghua Zhang,
• Tianxin Qian,
• Junwei Ma,
• Lei Cui and
• Chunju Li

Beilstein J. Org. Chem. 2018, 14, 2236–2241, doi:10.3762/bjoc.14.198

• guests exhibit a significant fluorescence intensity enhancement and the intensity is strong enough to be distinguished by the naked eye. The easy accessibility, good water-solubility and nice binding properties make 2,2’-CBP4 be applicable in the biomedical field, for example, chemical sensors, drug

Synthesis and post-functionalization of alternate-linked-meta-para-[2ⁿ.1ⁿ]thiacyclophanes

• Wout De Leger,
• Koen Adriaensen,
• Koen Robeyns,
• Luc Van Meervelt,
• Joice Thomas,
• Björn Meijers,
• Mario Smet and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2190–2197, doi:10.3762/bjoc.14.192

• amide derivative 20 and acid derivative 21 was performed with good overall yields (three steps), 80% and 54%. In the near future, the binding properties of these interesting alternate-linked-meta-para-thiacyclophanes will be investigated. X-ray crystal structure of alternate-linked-meta-para

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

• Vladimir A. Burilov,
• Guzaliya A. Fatikhova,
• Mariya N. Dokuchaeva,
• Ramil I. Nugmanov,
• Diana A. Mironova,
• Pavel V. Dorovatovskii,
• Victor N. Khrustalev,
• Svetlana E. Solovieva and
• Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

• macrocycles 10a, 12a,b (Figure 3) can be rationalized in terms of the binding properties of the investigated nucleotides. Moreover, the presence of intramolecular hydrogen bonding (Figure 4a and b) can explain the protonation of only one nitrogen atom despite the close protonation constants of both primary

Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

• Siva Sankar Murthy Bandaru,
• Darinka Dzubiel,
• Heiko Ihmels,
• Mohebodin Karbasiyoun,
• Mohamed M. A. Mahmoud and
• Carola Schulzke

Beilstein J. Org. Chem. 2018, 14, 1871–1884, doi:10.3762/bjoc.14.161

• binding properties towards G4-DNA because of the biological importance of G4-DNA [9][10][11][12][13]. Along these lines, we and others have established the class of annelated quinolizinium derivatives as versatile ligands that bind to duplex, triplex and quadruplex DNA depending on their shape and size

• [14][15][16][17][18] and whose interaction with the nucleic acid may be used for fluorimetric detection of the latter [19][20]. To further exploit the DNA-binding properties of this specific class of cationic hetarenes, synthetic routes to novel derivatives with the desired substitution pattern and

• since they were proposed to have ideal photophysical and DNA-binding properties. Herein, we present the successful Suzuki–Miyaura and Sonogashira coupling reactions of benzo[b]quinolizinium substrates. In addition, the absorption and emission properties of the novel arylalkynylbenzo[b]quinolizinium

Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

• Sabine Schuster,
• Beáta Biri-Kovács,
• Bálint Szeder,
• Viktor Farkas,
• László Buday,
• Zsuzsanna Szabó,
• Gábor Halmos and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

• and do not differ widely. Especially, the binding affinity on prostate cancer tissue deviate only slightly (3.0–11.6 nm) indicating that the incorporation of D-Asp or D-Glu in position 6 did not substantially affect the receptor binding properties of the GnRH-III derivatives. In addition, the

• . It turned out that the 4Lys(Bu)-containing conjugates 4 and 5 have a higher binding affinity to the GnRH receptors in comparison to the 4Ser-containing ones. Furthermore, the D-Asp derivatives 1 and 4 show slightly improved receptor binding properties than the D-Glu derivatives 2 and 5 which might be

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• ed. 18, 90128 Palermo, Italy 10.3762/bjoc.13.271 Abstract Three polyaminocyclodextrin materials, obtained by direct reaction between heptakis(6-deoxy-6-iodo)-β-cyclodextrin and the proper linear polyamines, were investigated for their binding properties, in order to assess their potential

• our materials to exploit both the cavity and the polycationic branches, thus functioning as bimodal ligands. Keywords: aminocyclodextrins; binding properties; nitroanilines; pDNA; polarimetry; supramolecular chemistry; Introduction Polyamine macromolecules have attracted a widespread interest for

Binding abilities of a chiral calix[4]resorcinarene: a polarimetric investigation on a complex case of study

• Marco Russo and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2698–2709, doi:10.3762/bjoc.13.268

• within a couple of days, even if stored at low temperature (4 °C). Therefore, the proline subunits easily undergo racemization under alkaline conditions. Binding properties of CAP Based on the previous results, we preliminarily tested the interaction of guests 1–12 with CAP−2. We observed that anions 1

• ), whereas the binding properties of the tetra-anion are only fair. Then, on the grounds of these preliminary data, guests 6–12 were selected for a more detailed study considering also the other anionic forms of the host. The complete results are collected in Table 1. As a first observation, we can notice

Metal-mediated base pairs in parallel-stranded DNA

• Jens Müller

Beilstein J. Org. Chem. 2017, 13, 2671–2681, doi:10.3762/bjoc.13.265

• –Crick base pairing was enforced to ensure the formation of parallel-stranded duplexes. Formal replacement of one C–H group in pyrrolocytosine by a nitrogen atom leads to imidazolocytosine. A series of substituted imidazolocytosine (XIC) nucleobases were investigated with respect to their metal-binding

• properties, too [72]. In analogy to XPC, XIC forms dinuclear metal-mediated homo base pairs with Ag(I). Table 3 lists representative changes in the melting temperature upon formation of an XIC–Ag(I)2–XIC base pair within a DNA duplex. As can be seen, these base pairs are extremely stabilizing both in

Synthesis and metal binding properties of N-alkylcarboxyspiropyrans

• Alexis Perry and
• Christina J. Kousseff

Beilstein J. Org. Chem. 2017, 13, 1542–1550, doi:10.3762/bjoc.13.154

• materials – and as interesting molecules in themselves – we describe herein an efficient synthesis of N-alkylcarboxyspiropyrans (analogous to C4SP) with alkyl chain lengths from C2 to C12, and a systematic analysis of their metal-binding properties across a range of metal cations. It was envisaged that

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• binding properties of the glucose moiety displayed on a metal surface with insulin, a peptide hormone [86]. By means of a UV–vis spectroscopy assay, the authors confirmed the successful use of dextran-coated AuNPs to selectively bind low concentrations of insulin (at 1 pM), even in serum samples, and