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

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

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

• Information Supporting Information File 258: Analytical techniques, in vitro experiments, polymer synthesis, analysis of critical micelle concentration, and fluorescence microscopy of non-TPP micelles. Acknowledgements The authors would like to acknowledge the NMR and microscopy facility within the Mark

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

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

• the alga produces ectoine. In summary, ectoine is indicative of Roseovarius sp. MS2 in the tripartite community and can serve for localisation studies. Localisation of bacterial symbionts of Ulva mutabilis using fluorescence microscopy and imaging mass spectrometry Based on the above results, we

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• -aggregates (96 nm) [56][57], indicating efficient exciton hopping. The 10% THF assembly showed almost no power dependence, in striking difference to other systems. This can be attributed to the exciton trapping [24], probably at the large aromatic “edges” in the 10% THF crystals. Superresolution fluorescence

• microscopy measurements were carried out in order to further study the photonic behavior of the systems. Interestingly, the 5% THF system displayed an emission that was localized at regions that appeared to be matching the shape and dimensions of the crystal edges (Figure S13, Supporting Information File 1

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

• Lorenzo Sansalone,
• Jun Zhao,
• Matthew T. Richers and
• Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

• transfected with either wild-type (WT) α4β2 or mutant (E61C) nicotinic acetylcholine receptors [16]. Cells with successful ion channel expression co-expressed YFP visualized using epi-fluorescence microscopy. Cover slips were treated with all trans-1 (0.05 mM in physiological buffer) for 20 min in the dark

Mono- and bithiophene-substituted diarylethene photoswitches with emissive open or closed forms

• A. Lennart Schleper,
• Mariano L. Bossi,
• Vladimir N. Belov and
• Stefan W. Hell

Beilstein J. Org. Chem. 2019, 15, 2344–2354, doi:10.3762/bjoc.15.227

• large fluorescence quantum yield, compound SyOTh1 emerged as a candidate for single-molecule based super-resolution fluorescence microscopy. Keywords: diarylethenes; dyes; fluorescence; organic synthesis; photochromism; photoswitching; Introduction Reversibly photoswitchable diarylethenes (DAEs) with

• resistance and large fluorescence quantum yield, compound SyOTh1 may be an excellent marker for single-molecule based super-resolution fluorescence microscopy, e.g., MINFLUX and STORM. In addition, SyOTh1 presents a remarkable on-switching of 10% of its maximal fluorescence signal with 470 nm light, and the

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

• Anne-Marie Caminade,
• Artem Zibarov,
• Eduardo Cueto Diaz,
• Aurélien Hameau,
• Maxime Klausen,
• Kathleen Moineau-Chane Ching,
• Jean-Pierre Majoral,
• Jean-Baptiste Verlhac,
• Olivier Mongin and
• Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

• widespread popularity of TPE (also named TPA, for two-photon absorption) in the biology community, with on one side, the advent of two-photon excitation fluorescence microscopy [4], even for research clinical uses [5], and on the other side with the discovery of the TPA properties of quantum dots (inorganic

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• , the endoplasmic reticulum was visualized by transfection with a plasmid DNA coding mCherry-ER (0.5 µg) using Fugene HD (Promega, USA; DNA/Fugene HD = 1:3). Fluorescence microscopy The intracellular localization of compound 5 was studied by real-time live-cell fluorescence microscopy using an inverse

• sesquiterpene lactones archangelolide (1) and trilobolide (2). Intracellular localization of archangelolide-dansyl (5) in human cells from osteosarcoma (U-2 OS). A, C) Bright-field images; B, D) fluorescence microscopy of living cells treated with 1 µM concentration of compound 5 for 90 min. Co-localization of

• dansylarchangelolide 5 with a marker of endoplasmic reticulum (top row) and with a mitochondrial marker (bottom row) in human cells from osteosarcoma (U-2 OS). A, E) Bright-field images. Fluorescence microscopy of living cells treated with 1 µM concentration of compound 5 (90 min; images B and F) and a mitochondria

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• light using a fluorescence microscope (BIOREVO BZ-9000, Keyence, Osaka, Japan), intracellular ROS were detected using the ROS-ID Oxidative Stress Detection Kit (Enzo Life Sciences, Farmingdale, NY, USA) in conjunction with fluorescence microscopy. Intracellular ROS was detected in the form of green

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

• were incubated with Tz-biotin, followed by incubation with streptavidin-AlexaFluor 555 (strep-AF555) for visualization (Scheme 1). In confocal fluorescence microscopy experiments, all sugars showed a distinct cell membrane staining in comparison to the negative control (Figure 3A). As expected [25][27

• , resuspended in buffer, and then subjected to flow cytometry analysis. The obtained results coincided with those of the fluorescence microscopy experiments (Figure 3B,C). Ac4ManNCyc gave a significantly higher fluorescence intensity than the negative control, which, however, is exceeded by far from that of

• . Ac4GlcNCp was obtained in 19% yield and Ac4GalNCp in 16% yield over two steps. We next explored the suitability of Ac4GlcNCp and Ac4GalNCp in MGE. Applying the same protocol used for the mannosamine derivatives, we first performed fluorescence microscopy experiments after MGE. As a positive control, we

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

• Andrejs Šišuļins,
• Jonas Bucevičius,
• Yu-Ting Tseng,
• Irina Novosjolova,
• Kaspars Traskovskis,
• Ērika Bizdēna,
• Huan-Tsung Chang,
• Sigitas Tumkevičius and
• Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

• biocompatibility could be applied for the cell staining in fluorescence microscopy. Applications in the cell studies The newly prepared compound library with purine and 7-deazapurine derivatives was submitted to the screening of their biological activity. The compounds of interest were studied on two cancer cell

Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents

• Mingjun Yuan,
• Song Lin Chua,
• Yang Liu,
• Daniela I. Drautz-Moses,
• Joey Kuok Hoong Yam,
• Thet Tun Aung,
• Roger W. Beuerman,
• May Margarette Santillan Salido,
• Stephan C. Schuster,
• Choon-Hong Tan,
• Michael Givskov,
• Liang Yang and
• Thomas E. Nielsen

Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284

• incubation of the macrophages at 37 °C, 5% CO2 for 4 h was ensued. A solution containing 20 µM propidium iodide (PI) was added to the macrophages to stain for dead macrophages killed by PAO1 treated with cisplatin or ΔpscJ. Live and dead macrophages were imaged by fluorescence microscopy (Zeiss, Germany) at

Impact of Pseudomonas aeruginosa quorum sensing signaling molecules on adhesion and inflammatory markers in endothelial cells

• Carmen Curutiu,
• Florin Iordache,
• Veronica Lazar,
• Aurelia Magdalena Pisoschi,
• Aneta Pop,
• Mariana Carmen Chifiriuc and
• Alina Maria Hoban

Beilstein J. Org. Chem. 2018, 14, 2580–2588, doi:10.3762/bjoc.14.235

• cellular substrata of PAO1 strain treated with 20 µM of tested purified QSSMs. Fluorescence microscopy images of QSSMs treated euckariote cells, revealing attachment patterns. (Ctrl- = untreated control cells, P.a ctrl = P. aeruginosa control treated cells, ODdHL = P. aeruginosa + OddHL treated cells

Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril

• Mohammad A. Alnajjar,
• Jürgen Bartelmeß,
• Robert Hein,
• Pichandi Ashokkumar,
• Mohamed Nilam,
• Werner M. Nau,
• Knut Rurack and
• Andreas Hennig

Beilstein J. Org. Chem. 2018, 14, 1961–1971, doi:10.3762/bjoc.14.171

• BODIPYs introduced herein matches the emission wavelength of an Ar laser, which is still the most common excitation source in fluorescence correlation spectroscopy (FCS) and fluorescence microscopy. FCS has been established to study dynamic processes in biological systems and, more recently, also in

• complex formation of the BODIPY core, the photostability of the dyes was not affected by CB7 complex formation (Figure S20, Supporting Information File 1). The compatibility of BODIPYs with common excitation sources and filter sets also enables their use in fluorescence microscopy. To demonstrate, we have

• fluorophore. After centrifugation and washing of the polymer particles, surface-bound 5 could be clearly visualized by fluorescence microscopy on CB7-functionalized polymer particles, whereas polymer particles lacking CB7 on the surface did not show any fluorescence (Figure 7). This result is consistent with

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

• , all following uptake experiments were conducted at peptide concentrations between 1 and 10 μM, where no significant effect on cell viability was observed in both cell lines. Cellular uptake studies Next, we analyzed the intracellular fate of the new peptide variants using confocal fluorescence

• microscopy. Thus, MCF-7 and HeLa cells were incubated with 10 µM peptide solutions at 37 °C and inspected after 30 min (Figure 3). Surprisingly, both new peptide variants, N50-sC18* and NrTP-sC18*, entered the cells extremely efficiently compared to sC18* alone. For sC18*, only small dots were detectable

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

• . Fluorescence microscopy revealed a cytoplasmic localization of the oligonucleotide without accumulation in the nuclei. This indicated an endocytotic uptake mechanism with (at least partial) retention of the material in the endocytotic vesicles. No unspecific cytotoxic effect of the guanidinylated

• nuclease and serum stability as well as significantly enhanced cellular uptake relative to their native congeners. As for the aforementioned phosphoramidates, fluorescence microscopy indicated a cytoplasmic localization of the tested zwitterionic oligonucleotide without significant accumulation in the

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

• -DNA by fluorescence microscopy with preference for A·T-rich sequences [106]. Two positively charged lysine residues are expected to interact with ds-DNA electrostatically. Upon binding to the minor groove of ds-DNA, the conformation of conjugate 43 was changed from an extended to a folded form

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

• -side chain cycle). In vitro fluorescence microscopy studies of an Oregon Green (OG) labeled c[KNGRE]-NH2 (OG attached to the side chain of Lys) revealed selective binding to CD13-receptor positive (CD13+) HT-1080 human fibrosarcoma cells and minimal binding to receptor negative (CD13−) MCF-7 human

Halogen-containing thiazole orange analogues – new fluorogenic DNA stains

• Aleksey A. Vasilev,
• Meglena I. Kandinska,
• Stanimir S. Stoyanov,
• Stanislava B. Yordanova,
• David Sucunza,
• Juan J. Vaquero,
• Obis D. Castaño,
• Stanislav Baluschev and
• Silvia E. Angelova

Beilstein J. Org. Chem. 2017, 13, 2902–2914, doi:10.3762/bjoc.13.283

• [12][13], DNA fragment sizing [14][15], as reporter groups in hybridization probes [16][17][18][19][20][21][22][23], single DNA molecule fluorescence microscopy [24][25], gel staining [26], in real-time PCR analysis [27][28]) because of their excellent staining properties. Unsymmetrical cyanines have

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

• Jan Podlesný,
• Lenka Dokládalová,
• Oldřich Pytela,
• Adam Urbanec,
• Milan Klikar,
• Numan Almonasy,
• Tomáš Mikysek,
• Jaroslav Jedryka,
• Iwan V. Kityk and
• Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

• utilized in two-photon excited fluorescence microscopy and bioimaging [13][14], most often upon their further structural tuning towards higher polar character and solubility in water [20][21][22]. Their linking to porphyrins proved to be a useful strategy for two-photon photodynamic therapy [23][24][25

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• construct 6 and its liposomal formulation, both of which showed immunomodulatory properties in primary rat macrophages. The uptake and intracellular distribution of construct 6 and its liposomal formulation was monitored by means of live-cell fluorescence microscopy in two cancer cell lines. The

• potency of the fluorescent construct Tb-ChL and BODIPY and its liposome derivative to enter cancer cells was tested by live-cell fluorescence microscopy using two human cell line models: cells were derived from osteosarcoma (U-2 OS) and cervical carcinoma (HeLa). Inside U-2 OS cells, construct 6 was

• represents the arithmetic average of the deviations from the centre plane of the sample. Panel of images from live-cell fluorescence microscopy: intracellular localization of construct 6 in U-2 OS cells after 48 h of incubation: A) 200 nM; C) 500 nM concentration of construct 6; B) and D) merges of A and C

Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface

• Frederik Neuhaus,
• Fabio Zobi,
• Gerald Brezesinski,
• Marta Dal Molin,
• Stefan Matile and
• Andreas Zumbuehl

Beilstein J. Org. Chem. 2017, 13, 1099–1105, doi:10.3762/bjoc.13.109

• using fluorescence microscopy, grazing-incidence angle X-ray diffraction, and infrared reflection–absorption spectroscopy. An increase of the lateral membrane pressure leads to a well-packed layer of the ‘flipper’ mechanophores and a clear change in hue above 18 mN/m. The fluorescent probes had no