Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

• Josipa Matić,
• Tana Tandarić,
• Marijana Radić Stojković,
• Filip Šupljika,
• Zrinka Karačić,
• Ana Tomašić Paić,
• Lucija Horvat,
• Robert Vianello and
• Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

• exhibited a micromolar and submicromolar binding affinity for ds-polynucleotides and inactivated a mutant of dipeptidyl peptidase enzyme E451A. Confocal microscopy revealed that the conjugate with the longer linker entered the HeLa cell membranes and blue fluorescence was visualized as the dye accumulated

• cellular uptake and intracellular distribution of Phen-Py-1 in HeLa cells by TCS SP8 X confocal microscopy. The results showed that the dye entered the HeLa cell membranes fast, and after 1 hour of incubation at 1 µM concentration, blue fluorescence was visualized as the dye accumulated in the cell

• binding (∆rH). The reaction Gibbs energies (∆rG) were calculated by using the following equation: ∆rG = −RTln(Ka). The entropic contribution to the binding Gibbs energy was calculated by the equation: T∆rS = ∆rH − ∆rG. Confocal microscopy: HeLa cells were cultured and maintained in complete high glucose

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• . These prepared porphyrin nanowires were subjected to surface microscopy and fluorescence energy transfer experiments, which elucidated their stability and resistance to disassembly. Conclusion Cu(I)-catalyzed “click chemistry” is a well-established protocol for the facile access of complexes from simple

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• correlated to the foam stability. Morphology of the matrices studied by scanning electron microscopy (SEM) The different microstructures of the samples have been analysed for the three polysaccharide combinations. Those of β-cyclodextrin/LBG matrices will be shown here, since all the polysaccharides

• different times and the percent emergence of the liquid fraction was plotted vs time (see also Figure 1). Characterization of matrices: Scanning electron microscopy (SEM) of gold-sputter-coated samples was carried out using a Phenom Pro 739 microscope. Infrared analysis was carried out for the crushed

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• microscopy (HSM) analyses for all four complexes (Figures S9–S12 in Supporting Information File 1) and variable temperature powder X-ray diffraction (VTPXRD) analyses for β-CD·BES and β-CD·PRO (Figures S13 and S14 in Supporting Information File 1). The precise temperature onset values did not always

• performed on a Bruker Ultrashield 400 Plus Spectrometer (Billerica, Massachusetts, U.S.A.) and the program MestReNova was used to analyse the resulting data [48]. Thermal analysis Hot stage microscopy (HSM): The crystals were immersed in a small amount of silicone oil and heated at a constant rate of 10

• microscopy (HSM), variable temperature powder X-ray diffraction (VTPXRD) patterns, TGA, dTGA and DSC analytical data, details of electron counts derived from the Squeeze procedure, and geometrical parameters of the β-CD host molecules. Acknowledgements The authors acknowledge the University of Cape Town for

Formal total synthesis of macarpine via a Au(I)-catalyzed 6-endo-dig cycloisomerization strategy

• Jiayue Fu,
• Bingbing Li,
• Zefang Zhou,
• Maosheng Cheng,
• Lu Yang and
• Yongxiang Liu

Beilstein J. Org. Chem. 2022, 18, 1589–1595, doi:10.3762/bjoc.18.169

• -inflammatory [4][5][6][7][8], insecticidal, fungicidal, etc [9]. In addition to the above-mentioned activities, macarpine was also used as a DNA probe for flow cytometry and fluorescence microscopy due to its fluorescent properties [10]. Despite some research on the activities of macarpine had been performed

Mechanochemical bottom-up synthesis of phosphorus-linked, heptazine-based carbon nitrides using sodium phosphide

• Blaine G. Fiss,
• Georgia Douglas,
• Michael Ferguson,
• Jorge Becerra,
• Jesus Valdez,
• Trong-On Do,
• Tomislav Friščić and
• Audrey Moores

Beilstein J. Org. Chem. 2022, 18, 1203–1209, doi:10.3762/bjoc.18.125

• University, Québec City, Québec, Canada Facility for Electron Microscopy Research (FEMR), McGill University, Montréal, Québec, Canada Department of Materials Engineering, McGill University, 3610 University Street, Montréal, Québec, Canada 10.3762/bjoc.18.125 Abstract Herein, we present the bottom-up

• electron microscopy-electron energy loss spectroscopy (STEM-EELS). The STEM-EELS data for a g-h-PCN sample prior to annealing showed equal distribution of carbon and nitrogen with minimal phosphorus present, and particles roughly 400 nm in length (Supporting Information File 1, Figure S4a). Upon annealing

• Electron Microscopy Research (FEMR), the MC2 facility, McGill University Institute for Advanced Material (MIAM) for the use of their microscopy and spectroscopy equipment. Funding We are grateful for the support of the Natural Science and Engineering Research Council of Canada (NSERC) Discovery Grant and

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

• Ashish Kumar Mazumdar,
• Gyana Prakash Nanda,
• Nisha Yadav,
• Upasana Deori,
• Upasha Acharyya,
• Bahadur Sk and
• Pachaiyappan Rajamalli

Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

• % water/THF) of BPy-pTC were characterized using scanning electron microscopy (SEM). The SEM image showed the spherical nanoaggregates of BPy-pTC, with 95 nm diameter (Figure 3f). The BPy-p3C compound emitted in the green region at λem = 530 nm in THF, with a PLQY of 3.6% (Figure 3a). Similar to BPy-pTC

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

• Maxime Pypec,
• Laurent Jouffret,
• Claude Taillefumier and
• Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

• length, corresponding to the amide I C=O stretching of the N-(methylamino)amides functions. Preliminary transmission electron microscopy (TEM) analysis of dimer 2 seems to suggest ordered self-assembled multilayered structures (Figure S5 in Supporting Information File 1). This observation now needs to be

Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water

• Zhihang Bai,
• Krishnasamy Velmurugan,
• Xueqi Tian,
• Minzan Zuo,
• Kaiya Wang and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2022, 18, 429–437, doi:10.3762/bjoc.18.45

• binding interaction between m-TPEWP5 and G is strong enough to form a stable complex in an aqueous solution. The morphology of the supramolecular m-TPEWP5G and m-TPEWP5G-EsY systems was monitored by using transmission electron microscopy (TEM). As shown in Figure 3, m-TPEWP5G self-assembled to form a worm

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• polymer) (Co@imine-POP) has been synthesized by immobilizing cobalt onto a nitrogen-rich porous organic polymer (Scheme 20) [35]. Using scanning electron microscopy, the surface morphology of the catalyst was evaluated. Nowadays, covalent organic frameworks (COF) were found to be a suitable support in

Synthesis and bioactivity of pyrrole-conjugated phosphopeptides

• Qiuxin Zhang,
• Weiyi Tan and
• Bing Xu

Beilstein J. Org. Chem. 2022, 18, 159–166, doi:10.3762/bjoc.18.17

• derivatives. Enzymatic conversion To further investigate the reason for the different activities in cell assays among the three compounds, 1, 4a and 6b, we employed transmission electron microscopy (TEM) to study the morphologies of the assemblies of these compounds before and after enzymatic

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• characterized by powder Fourier-transform infrared (FTIR) spectroscopy, X-ray diffraction (XRD) analysis, scanning electron microscopy (SEM), high-resolution transmission electron microscopy (HRTEM), energy-dispersive X-ray (EDX) spectroscopy, etc. It was effectively utilized in the eco-friendly synthesis of

Adjusting the length of supramolecular polymer bottlebrushes by top-down approaches

• Tobias Klein,
• Franka V. Gruschwitz,
• Maren T. Kuchenbrod,
• Ivo Nischang,
• Stephanie Hoeppener and
• Johannes C. Brendel

Beilstein J. Org. Chem. 2021, 17, 2621–2628, doi:10.3762/bjoc.17.175

• ][27][28]. Both methods are applied for fragmentation of initially µm-long SPBs based on BTU–PEO and BTP–PEO conjugates. The resulting nanofibers were characterized in detail by cryogenic transmission electron microscopy (cryoTEM), as well as by asymmetrical flow field-flow fractionation measurements

• ). cryoTEM investigations were performed at the electron microscopy facilities of the Jena Center for Soft Matter (JCSM), which were purchased with grants from the DFG and the European funds for Regional Development (EFRE). The funding of the collaborative research center PolyTarget, projects A05 and Z01

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• detector was calibrated with polystyrene standards having narrow molecular-weight distributions. The data were analyzed using Eco-SEC analysis software. A Hitachi HT7700 (TEM) with EXALENS (120 kV) working at a high-resolution (HR) mode was used to obtain transmission electron microscopy (TEM) images, high

Post-functionalization of drug-loaded nanoparticles prepared by polymerization-induced self-assembly (PISA) with mitochondria targeting ligands

• Janina-Miriam Noy,
• Fan Chen and
• Martina Stenzel

Beilstein J. Org. Chem. 2021, 17, 2302–2314, doi:10.3762/bjoc.17.148

• at the start of the reaction and after 45 min tuned to 8.3 to allow maximum conjugation efficiency. After removing excess TPP-COOH and coupling reagents via dialysis in Milli-Q water, the particles were adjusted to 4 mg mL−1 and analysed using DLS experiments and TEM microscopy (Figure 1). The

• mitochondria target containing nanoparticles PPM-NP4-TPP and MPM-NP2-TPP were further analysed using 3D spheroid tumour models [47]. The samples were incubated with 143B and SW982 cells and the penetration profiles of the micelles were investigated using laser scanning confocal microscopy. After 3 hours of

• zwitterionic drug particles similar anticancer efficiency than that of the non-conjugated PPM-NP4 micelles. The co-localization of the TPP-variants into the mitochondria, lysosomes and nuclei were analysed using laser scanning confocal microscopy. Surprisingly, there was no improvement in mitochondria

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

An initiator- and catalyst-free hydrogel coating process for 3D printed medical-grade poly(ε-caprolactone)

• Jochen Löblein,
• Thomas Lorson,
• Miriam Komma,
• Tobias Kielholz,
• Maike Windbergs,
• Paul D. Dalton and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2021, 17, 2095–2101, doi:10.3762/bjoc.17.136

• ), however, this morphology is highly irregular. A change in wetting behavior could be demonstrated, and toluidine blue staining indicates successful SIPGP of HEMA on PCL scaffolds. However, to prove that this material is indeed PHEMA, we performed confocal Raman microscopy on the samples, which allows a

• , the high PCL signal intensity covers most of the signals originating from the thin PHEMA coating directly deposited on fibers (Supporting Information File 1, Figure S4; a 3D Raman reconstruction is provided in Supporting Information File 2). Scanning electron microscopy (SEM) corroborates this fiber

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

• triplex, most likely due to reduced ability of R to π-stack [103]. As expected, fluorescence microscopy showed improved cellular uptake of the cationic guanidinium-modified PNAs [103]. PNA nucleobases for Hoogsteen recognition of adenine: Because the T•A–T triplets are reasonably stable under

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• experiments were performed. In brief, HeLa cells were incubated with carboline 3ac (10 μM and 100 nM), and the cellular uptake was examined using confocal microscopy (λex = 405 nm; λem = 420–470 nm). Compound 3ac showed excellent cytosolic uptake in cancer cells when incubated at a 10 μM concentration (Figure

• derivative 3ac (10 nM, 100 nM, 1 μM, 10 μM, and 100 μM), the cellular uptake and distribution was monitored by using confocal microscopy (λex = 405 nm; λem range = 420–470 nm). Selected examples of compounds containing the γ-carboline core. Single-crystal XRD structure of 3ac (CCDC: 1897787). UV–vis

• , 3ca, 3ga in the breast cancer cell line, MCF7 and (B) doxorubicin against the panel of tested cancer cell lines. Dose–response curve of γ-carbolines 3ac, 3bc, 3ca, 3ga in macrophage cell line, RAW264.7. Laser scanning confocal microscopy studies (λex = 405 nm; collection range = 420–470 nm) for uptake

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• in a horizontal agarose gel system (FBSB710 Fisher Scientific) for 4 h at 50 volts (virus buffer), 4 °C and then, the gel was stained with ethidium bromide. The image was captured using a documentation system (MS Major Science). Transmission electron microscopy analysis of VLPs. 6 µL of VLP-dsRNAvp28

• to the wild type CCMV (lane 2 and 3, respectively, in Figure 1). In contrast, the free dsRNAvp28 ran faster (lane 4 in Figure 1) in comparison with the sample and wild type CCMV, as an indication of VLPs formation. The VLPs assembly at each stage was analyzed by transmission electron microscopy (TEM

Icilio Guareschi and his amazing “1897 reaction”

• Gian Cesare Tron,
• Alberto Minassi,
• Giovanni Sorba,
• Mara Fausone and
• Giovanni Appendino

Beilstein J. Org. Chem. 2021, 17, 1335–1351, doi:10.3762/bjoc.17.93

• differential scanning microscopy studies [64]. In connection with the work on the restauration of parchments, Guareschi developed an interest in the chemistry and technology of ancient inks and dyes, a topic he covered in some monumental monographs [65]. These, and the study on the history of chemistry, filled

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

• Cansu Esen and
• Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

• analysis to evaluate the vTA incorporation, and microscopy techniques were employed to examine the impact on their morphology. In terms of applicability, water contact angle measurement, equilibrium swelling ratio analysis, and dye releasing efficiency experiment were also conducted. All hydrogel samples

• , Figure S1). Scanning electron microscopy was performed to investigate the morphology of freeze-dried HGCM and HGCM-vTA. As shown in Figure 2a, HGCM exhibits a significantly porous and uniform morphology. Formation of accessible pores for vTA was the key point to reach in order to activate g-CN nanosheets

• performed via inductively coupled plasma optical emission spectroscopy (ICP-OES Optima 8000). Scanning electron microscopy (SEM) and EDX elemental mapping were performed using a JSM-7500F (JEOL) microscope equipped with an Oxford Instruments X-Max 80 mm2 detector for the determination of both elemental

A new glance at the chemosphere of macroalgal–bacterial interactions: In situ profiling of metabolites in symbiosis by mass spectrometry

• Marine Vallet,
• Filip Kaftan,
• Veit Grabe,
• Fatemeh Ghaderiardakani,
• Simona Fenizia,
• Aleš Svatoš,
• Georg Pohnert and
• Thomas Wichard

Beilstein J. Org. Chem. 2021, 17, 1313–1322, doi:10.3762/bjoc.17.91

• -pyrimidinecarboxylic acid) was found in bacterial presence. Ectoine was used as a metabolic marker for localisation studies of Roseovarius sp. within the tripartite community because it was produced exclusively by these bacteria. By combining confocal laser scanning microscopy (cLSM) and AP-SMALDI-HRMS, we proved that

• reveal any information on the metabolically active bacteria and the spatial distribution of substances exchanged. While the study of bacterial symbiosis is often limited to either chemistry or microscopy work, recent functional and metabolomics methods are available to enable chemical imaging of

• profile fingerprint matching [26][27][28]. Our research combines cutting-edge laser scanning microscopy and high-resolution mass spectrometry to uncover Ulva/bacteria interactions and specialised metabolites at the microscale level. In this study, we demonstrate that the chemosphere of U. mutabilis

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• assessed by nanoparticle tracking analysis (NTA, Table 3) and transmission electron microscopy (TEM, Supporting Information File 1, Figure S2). After postinsertion, LNP sizes were found by NTA to range from 54–66 nm (Table 3), while TEM analysis revealed average sizes between 45–52 nm (Supporting

• a tight junction barrier has formed within these cells and can be used to determine the ability of the LNPs to pass through the BBB (Supporting Information File 1, Figure S3A). Additionally, we further confirmed our junctions using fluorescent microscopy on the barrier layers to confirm expression

• (phosphate-buffered saline, PBS) conditions (Figure 4A). Additionally, we confirmed LNP uptake by the monocyte-derived macrophages (MDMs) using fluorescent microscopy (Figure 4B). We found that all LNPs containing the Cy5 oligonucleotide were observable under the microscope (Figure 4B) and that all