Fabrication, characterization and adsorption properties of cucurbit[7]uril-functionalized polycaprolactone electrospun nanofibrous membranes

• Changzhong Chen,
• Fengbo Liu,
• Xiongzhi Zhang,
• Zhiyong Zhao and
• Simin Liu

Beilstein J. Org. Chem. 2019, 15, 992–999, doi:10.3762/bjoc.15.97

• present in the PCL fiber matrix in an uncomplexed state. The static adsorption behavior of the PCL/CB[7] nanofibers towards methylene blue (MB) was also preliminary investigated. The results indicate that the adsorption of MB onto the nanofibrous membranes fits the second-order kinetic model and Langmuir

• series of CD-functionalized electrospun nanofibers in the forms of CD-pseudopolyrotaxane [11][12], CDs/polymer [13][14][15], CD-ICs/polymer [16][17], and polymer-free CDs [5][18] or CD-ICs [19] have been fabricated. In addition, calix[8]arene (C[8])/polyacrylonitrile (PAN) composite nanofiber membranes

• the PCL/CB[7] (100:50) nanofibers when compared with the neat PCL nanofibers (Figure 1a and 1b). With the increase of CB[7] loading, a few shuttle-shaped beads in the nanofibrous membranes appeared, and the surface of the composite nanofibers became more and more rough or lumpy (Figure 1c–e

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• ]. Cutaneous, the most common form, causes severe nodular and ulcerative skin lesions, while mucocutaneous destroys mucus membranes, and the most deadly form, visceral leishmaniasis, often results in organ failure [6]. L. major, the parasite used in our in vivo model, causes the cutaneous disease. In each

Cyclopropene derivatives of aminosugars for metabolic glycoengineering

• Jessica Hassenrück and
• Valentin Wittmann

Beilstein J. Org. Chem. 2019, 15, 584–601, doi:10.3762/bjoc.15.54

Olefin metathesis in multiblock copolymer synthesis

• Maria L. Gringolts,
• Yulia I. Denisova,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21

• attract ongoing attention from both experimentalists and theoreticians due to their intrinsic tendency to self-assemble into diverse microstructures [8][9][10][11]. Technological applications of block copolymers cover lithography [12], photovoltaics [13], membranes [14] and many other areas [15]. Most of

Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS

• Sven Thierbach,
• Max Wienhold,
• Susanne Fetzner and
• Ulrich Hennecke

Beilstein J. Org. Chem. 2019, 15, 187–193, doi:10.3762/bjoc.15.18

• OD600 nm of 0.2. Each well contained 1 mL of cell suspension including 100 µM of the AQ derivatives or an equal amount of DMSO. The plates were sealed with optically clear and gas permeable membranes, incubated at 37 °C while shaking and the OD600 nm was measured at certain time points. Experiments were

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

• NO transport, storage and sensing as well as heme metabolism [36]) usually constitute eight to ten antiparallel β-strands and tightly packed hydrophobic or hydrophilic barrel interiors [37]. Membrane-bound β-barrels are confined to mitochondrial and chloroplast membranes and the outer membranes of

• point are relatively small and soluble proteins. As introduced vide supra, membrane-spanning porins and transporters of the all-β-barrel type, which are found in cellular outer membranes, constitute substantially larger “barrel” interiors and were thus utilized as scaffolds to house bulky GH-type

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

• Matthew B. Calvert,
• Varsha R. Jumde and
• Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

• systems exist in bacteria [65] and the Gram-negative specific type III secretion system (TTSS) is a focus of current research. TTSS is a major virulence determinant in a number of pathogens, including P. aeruginosa. In TTSS, toxins are secreted from the bacterial cytosol across the bacterial membranes and

Natural and redesigned wasp venom peptides with selective antitumoral activity

• Marcelo D. T. Torres,
• Gislaine P. Andrade,
• Roseli H. Sato,
• Cibele N. Pedron,
• Tania M. Manieri,
• Giselle Cerchiaro,
• Anderson O. Ribeiro,
• Cesar de la Fuente-Nunez and
• Vani X. Oliveira Jr.

Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

• membranes increased significantly when treated with lead peptides compared to controls. Biophysical features such as helicity, hydrophobicity, and net positive charge were identified to play an important role in the anticancer activity of the peptides. Indeed, abrupt changes in peptide hydrophobicity and

• key for their anticancer activity, as they enable membrane binding [20]. Their anticancer activity typically occurs at micromolar concentrations [21] and is not usually accompanied by hemolytic activity probably because there are structural differences between the membranes of red blood cells and

• cancer cells, which are zwitterionic and negatively charged, respectively. Structure–activity relationship studies have identified amphiphilicity and polar angle as the most important physicochemical properties required for ACPs to invade cancer cells or disturb their membranes [22][23]. In 2007, Konno

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

• Livia Polgár,
• Eszter Lajkó,
• Pál Soós,
• Orsolya Láng,
• Marilena Manea,
• Béla Merkely,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

• environment, due to the electric insulator character of intact surface membranes composed of the phospholipid bilayer. Application of cytotoxic compounds results in disturbed electrophysical integrity (decreasing value of impedance) of surface membranes as a signal of cell death. While cell physiological

Spectroelectrochemical studies on the effect of cations in the alkaline glycerol oxidation reaction over carbon nanotube-supported Pd nanoparticles

• Dennis Hiltrop,
• Steffen Cychy,
• Karina Elumeeva,
• Wolfgang Schuhmann and
• Martin Muhler

Beilstein J. Org. Chem. 2018, 14, 1428–1435, doi:10.3762/bjoc.14.120

• utilization in fuel cells (FCs) converting chemical into electrical energy [5]. In alkaline FCs (AFCs) and proton exchange membrane FCs (PEMFCs), H2 and O2 are converted to H2O, heat and electricity. Since the development of anion exchange membranes the research interest in AFCs has increased again, because

Design and biological characterization of novel cell-penetrating peptides preferentially targeting cell nuclei and subnuclear regions

• Anja Gronewold,
• Mareike Horn and
• Ines Neundorf

Beilstein J. Org. Chem. 2018, 14, 1378–1388, doi:10.3762/bjoc.14.116

• cargo and CPP or by forming non-covalent complexes. Notably, the mechanism of cell entry is still not fully understood, and can only hardly, if in any case, be predicted [9]. In fact, whereas one of the main mechanisms is endocytosis, there exist also CPPs that translocate through cellular membranes by

• C-terminal aa of the cationic antimicrobial peptide CAP18 [18]. When it comes in contact with lipid membranes, it forms a helical structure, probably supporting membrane interaction [19]. However, the main uptake mechanism that was observed followed endocytotic processes, although we have seen that

Oligonucleotide analogues with cationic backbone linkages

• Melissa Meng and
• Christian Ducho

Beilstein J. Org. Chem. 2018, 14, 1293–1308, doi:10.3762/bjoc.14.111

• bioactive agents. However, modifications of the nucleic acid structure are an essential prerequisite for their application in vivo or even in cellulo. The oligoanionic backbone structure of oligonucleotides mainly hampers their ability to penetrate biological barriers such as cellular membranes. Hence

• their oligoanionic phosphate diester backbone, severely hampers the penetration of biological barriers such as cellular membranes, thus leading to low cellular uptake. Second, unmodified ON structures are good substrates for nuclease-mediated degradation. Consequently, it is of vital importance to

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• 1,4-piperazine residue in the oligomethylene linkers (DBP)n, making them tetracations instead of dications for (DB)n at neutral pH. By the virtue of their higher solubility in aqueous media, (DBP)n could easily penetrate cell and nuclear membranes of living cells and inhibit in vitro eukaryotic DNA

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• potent, regarding the growth inhibition of hormone-dependent Dunning R-3327-H prostate cancers in rats, reaching up to 50% of the initial tumor volume in comparison with 2-pyrrolino-DOX. Shortly afterward, they tested the two conjugates in membranes of human breast cancer cells: MCF-7 hormone-dependent

Development of novel cyclic NGR peptide–daunomycin conjugates with dual targeting property

• Andrea Angelo Pierluigi Tripodi,
• Szilárd Tóth,
• Kata Nóra Enyedi,
• Gitta Schlosser,
• Gergely Szakács and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 911–918, doi:10.3762/bjoc.14.78

• CM) up to the 1 mg/mL final concentration. Each conjugate was allowed to incubate at 37 °C. Samples were analyzed at experiment time of 0 h, 6 h and 72 h, respectively, and components were purified with Amicon Ultra Centrifugal Filters (cut off 10K Millipore). The membranes were washed with eluent A

Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies

• Elias Christoforides,
• Andreas Papaioannou and
• Kostas Bethanis

Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69

• shown by molecular modeling, proposing a tail–tail dimer [37] and finally MD calculations concluded that efficient removal of cholesterol from membranes requires the presence of β-CD dimers [27]. In this work, the crystallographic analysis of CHL/β-CD complex conclusively clarifies the inclusion mode of

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

• from normal human pituitary (anterior lobe) and human prostate cancer cells were obtained from a patient at the time of initial surgical treatment. The collection and the use of these specimens for our studies are approved by the local Institutional Ethics Committee. Membranes for receptor binding

An alternative to hydrogenation processes. Electrocatalytic hydrogenation of benzophenone

• Cristina Mozo Mulero,
• Alfonso Sáez,
• Jesús Iniesta and
• Vicente Montiel

Beilstein J. Org. Chem. 2018, 14, 537–546, doi:10.3762/bjoc.14.40

• medium as an optimal reaction medium [5]. Currently, developments in nanostructured materials and polymeric solid exchange membranes have led the field of polymer electrolyte membrane fuel cells (PEMFC) to become a mature technology [18][19][20]. In this regard, a polymer electrolyte membrane

Stimuli-responsive oligonucleotides in prodrug-based approaches for gene silencing

• Françoise Debart,
• Christelle Dupouy and
• Jean-Jacques Vasseur

Beilstein J. Org. Chem. 2018, 14, 436–469, doi:10.3762/bjoc.14.32

• shown to have an important impact on the siRNA solubility and duplex stability. Such designed siRNNs showed a high solubility and serum stability and are not recognized by the innate immune system. On the other hand, due to their large size, they do not passively cross cell membranes. Therefore, to

Microfluidic radiosynthesis of [¹⁸F]FEMPT, a high affinity PET radiotracer for imaging serotonin receptors

• Thomas Lee Collier,
• Steven H. Liang,
• J. John Mann,
• Neil Vasdev and
• J. S. Dileep Kumar

Beilstein J. Org. Chem. 2017, 13, 2922–2927, doi:10.3762/bjoc.13.285

• ). Agonist properties of FEMPT on 5-HT1AR were estimated by [35S]GTPγS binding in membranes of CHO cells which stably express human 5-HT1AR. A dose-dependent increase in [35S]GTPγS binding was induced by FEMPT. Maximal FEMPT stimulated [35S]GTPγS binding Emax was 100% of that seen with 5-HT and an EC50 of 85

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

• dramatically decreased to approximately 5·102, 2·102 and 1.4·104 when the complexes of pDNA with CD1, CD2 and CD3, respectively, were used. This result suggested that the AmCDs may interact with cell membranes, e.g., by electrostatic interaction, or neutralize the anionic nature of pDNA, making the addition of

What contributes to an effective mannose recognition domain?

• Christoph P. Sager,
• Deniz Eriş,
• Martin Smieško,
• Rachel Hevey and
• Beat Ernst

Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255

• for the formation of a homodimer of A (Figure 8B) [40]. It is believed that this dimer enables transport of the lectin from the Golgi apparatus to cell membranes [73]. Due to a dislocated glutamate in the side chain of the homodimer (Figure 8B), the affinity for calcium binding and therefore also

¹⁵N-Labelling and structure determination of adamantylated azolo-azines in solution

• Sergey L. Deev,
• Alexander S. Paramonov,
• Tatyana S. Shestakova,
• Igor A. Khalymbadzha,
• Oleg N. Chupakhin,
• Julia O. Subbotina,
• Oleg S. Eltsov,
• Pavel A. Slepukhin,
• Vladimir L. Rusinov,
• Alexander S. Arseniev and
• Zakhar O. Shenkarev

Beilstein J. Org. Chem. 2017, 13, 2535–2548, doi:10.3762/bjoc.13.250

• membranes. The conjugation of adamantane with heterocyclic compounds also provides a method to modify the pharmacological profile and frequently leads to a new type of bioactivity. For example, N-adamantyl tetrazoles 1 and 2 (Figure 1A) demonstrate lower toxicity and, simultaneously, more potent activity

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• granular staining pattern (Figure 6A and Figure 7A, respectively), which indicate their mitochondrial localization. Furthermore, a weaker (diffuse) emission of 4 and 5 was observed in cytoplasm and plasma membranes of HeLa cells. The mitochondrial staining was confirmed by a co-localization experiment with

Novel approach to hydroxy-group-containing porous organic polymers from bisphenol A

• Tao Wang,
• Yan-Chao Zhao,
• Li-Min Zhang,
• Yi Cui,
• Chang-Shan Zhang and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 2131–2137, doi:10.3762/bjoc.13.211

• potential as heterogeneous catalysts [5][6][7], supports for catalysts [8][9], gas permeable membranes [10][11], and gas storage materials [12][13][14] have attracted much attentions from researchers all over the world as reviewed by Matyjaszewski [15]. During the past years, a large amount of porous