New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• ) resembles those of other amphiphilic marine siderophores such as marinobactins and aquachelins exhibiting the membrane affinity [21] as well as the self-assembling ability to form iron-containing vesicles [22]. This study presents another suite of amphiphilic peptidic siderophores originating in the

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

• arms, can encapsulate planar aromatic molecules, making this system promising for drug delivery. The advancement of pH-switchable molecular tweezers laid the groundwork for the development of switchable lipids [20]. When such lipids are incorporated in lipid vesicles, they provide means for controlled

• their open conformation. This causes fluctuations and local defects in the packing of a bilayer (Figure 3), leading to membrane disruption and release of active components from within the vesicles [22]. Such concept makes these tweezers good candidates for controlled drug delivery. The group of F. Wang

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• assemblies as well as precise switching of the biological activity of the photoswitchable derivative. Along these lines, in 2023, Leung and co-workers prepared amphiphilic indigo-based photoswitches and incorporated them into vesicles [88]. Irradiation of the vesicles with red light resulted in the E–Z

• isomerization of the indigo derivatives that led to the disassembly of well-shaped vesicles and formation of irregular aggregates. The thermal Z–E relaxation of the indigo scaffold provided the restoration of the vesicle structure. The system contributed to the development of red-light-controllable biomedical

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• solution as well as contradictory propensity to form luminescent nanostructure suspensions in hexane (Figure 5) [137]. It was posited that 65 features hollow vesicles, with vesicle fusion releasing curvature energy, leading to a thermodynamically more stable tubular structure. Such aggregation-induced

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• dose-dependent manner [15]. Additionally, the CHOL content was demonstrated to reduce and sometimes to inhibit the permeability of DPPC vesicles induced by bioactive agents [16][17]. Given the condensing and ordering effect that CHOL exerts on the membrane, the presence of CHOL in the lipid bilayer

• obtained by subtracting the SRB release from vesicles in the presence of CDs from that obtained in their absence as explained earlier. Results are presented in Figures 3, 4, and 5. The obtained data are also reported in Tables S1–S4 (Supporting Information File 1) in which the vertical reading points out

• 1 h of incubation whereas those from membranes containing higher CHOL contents did not exceed 5% after the same time. After 4 h of incubation, the SRB release reached 16.41% for 10% CHOL liposomal membranes and less than 10% for vesicles composed of higher CHOL content. After 48 h of incubation, 63

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• ) KO mouse which is a mouse model that stop the biosynthesis of ELs [22]. In that case, a reduction of the levels of various neurotransmitters were evidenced likely due to an alteration of the transport efficacy assumed by the synaptic vesicles. The phenotype of these KO mouse shows impaired social

• mesenchymal transition of breast epithelium cell lines [33], the fusion of membranes with extracellular or intracellular vesicles [34] including neurotransmission vesicles [35]. ELs could also be used as a probe to evaluate climate change [36]. All the articles and reviews reporting the description of natural

Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors

• Grace A. Lowe

Beilstein J. Org. Chem. 2023, 19, 1198–1215, doi:10.3762/bjoc.19.88

• microscopy [36][37]. In nature, chemical gradients and phase separation are maintained by compartmentalization in liposomes, micelles, and vesicles rather than at interfaces such as ITIES. Artificial photosynthesis systems are being designed to mimic this behavior and recently the field of artificial

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• construct pH-responsive supramolecular vesicles and molecule-scale drug carriers, respectively. Both of them exhibited pH-responsive properties, with the host–guest binding disintegrating when the pH of the solution is adjusted to 5.5 and the binding regenerated when the pH is restored to 7.4. These

• stimulus-responsive supramolecular vesicles and molecule-scale drug carriers are considered to have potential for cancer drug delivery. However, such supramolecular systems are not suitable for oral administration, which is a convenient and patient-preferred method of drug delivery, especially for patients

• in the range of 200 to 800 nm at 25 °C. Fluorescence spectroscopy. The solid-state fluorescence intensities of three CS-TPE bioconjugates and their fluorescence intensities at different pH values, as well as those of the three TBTQ-C6/CS-TPE supramolecular vesicles at different pH values were

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• -containing amphiphile (trans-AZO) to produce the TBTQ-C6-trans-AZO supra-amphiphile by host–guest interactions in water. The supra-amphiphile was further self-assembled into photo and pH dual-responsive supramolecular vesicles that have a potential to serve as drug nanocarriers to enable controlled drug

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

• tunable self-assembly, such as vesicles [14][15][16], micelles [17][18][19], nanocrystals [20], coordination-driven assemblies [9][21][22], host–guest interactions [15][23][24][25], etc. In the above systems, catalysts are encapsulated by supramolecular assemblies and thus provide a suitable environment

• acceptors. The obtained vesicles could be utilized as a nanoreactor for photocatalyzed dehalogenation reactions in water. However, the above reported supramolecular nanosystem requires a long time to produce the dehalogenated product with high yield. Therefore, the development of a potential nanoreactor for

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

• Mathias B. Danielsen and
• Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

• , ASOs carrying the novel guanidinium modification were mainly localized in the cytoplasm, indicating that the ASOs are taken up by endocytosis but are retained in part in the endocytic vesicles [112]. Utilizing the phosphorus atom as an attachment point for cationic aminoalkyl groups has been employed

DNA with zwitterionic and negatively charged phosphate modifications: Formation of DNA triplexes, duplexes and cell uptake studies

• Yongdong Su,
• Maitsetseg Bayarjargal,
• Tracy K. Hale and
• Vyacheslav V. Filichev

Beilstein J. Org. Chem. 2021, 17, 749–761, doi:10.3762/bjoc.17.65

• transfection reagent, whereas, N+ONs remain concentrated in vesicles within the cytoplasm. These results indicate that both N+ and Ts-modified ONs are promising for various in vivo applications. Keywords: cell uptake; charge neutral modification; DNA; modified phosphates; Staudinger reaction; Introduction

• microscopy. Figure 3 shows that FAM-labelled Ts and N+-modified DNAs are concentrated in vesicles (punctate foci in the oligo/FAM panel) that accumulate around the edge of the nucleus. Interestingly, the Ts-modified oligo is also present in the nucleus as indicated by the colocalisation of the ON (Figure 3E

• ) with the nuclear DNA (Figure 3D). The diffuse nuclear pattern of the Ts-modified ON suggests they can escape the endocytic vesicles and enter the nucleus via the nuclear pores. This is in contrast to the lack of colocalisation of the FAM signal with the nuclear DNA in the negative control (no oligo

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• nuclei such as 1H or 15N PREs. 19F NMR has also been applied to study the conformational heterogeneity and dynamics of a broad range of proteins and peptides upon their interaction with model lipid vesicles [59], micelles [60] and bicelles [61]. It has enabled the quantification and mechanistic

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

• David Straßburger,
• Svenja Herziger,
• Katharina Huth,
• Moritz Urschbach,
• Rainer Haag and
• Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

• to its functionalization with negatively charged sulfate groups. The binding behavior of dPGS to L-selectin has been thoroughly probed as dendrimer [26][27], conjugated to a polymer [28] or as amphiphilic adamantyl conjugates that are able to self-assemble on cyclodextrin vesicles [29]. Our group

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

• Giovanni Picca,
• Markus Probst,
• Simon M. Langenegger,
• Oleg Khorev,
• Peter Bütikofer,
• Anant K. Menon and
• Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

• of MPD across the ER. Although the activity of MPD scramblase has been described in microsomal vesicles and reconstituted systems [1][2][9], the molecular identity of this protein remains unknown. To circumvent the need for traditional purification strategies to identify the scramblase, we considered

Plasma membrane imaging with a fluorescent benzothiadiazole derivative

• Pedro H. P. R. Carvalho,
• Jose R. Correa,
• Karen L. R. Paiva,
• Daniel F. S. Machado,
• Jackson D. Scholten and
• Brenno A. D. Neto

Beilstein J. Org. Chem. 2019, 15, 2644–2654, doi:10.3762/bjoc.15.257

• its selectivity seems to be smaller than the one observed for the new green emitter. Although the plasma membrane separates the interior of the cell from the extracellular environment, there is a massive material transfer between both sides [59]. These materials typically are transported by vesicles

Probing of local polarity in poly(methyl methacrylate) with the charge transfer transition in Nile red

• Aydan Yadigarli,
• Qimeng Song,
• Sergey I. Druzhinin and
• Holger Schönherr

Beilstein J. Org. Chem. 2019, 15, 2552–2562, doi:10.3762/bjoc.15.248

• -controlled drug delivery systems [4][6][7][8][9][10], as well as dynamics of polymers at interfaces [11]. To be able to understand local properties of polymers, in particular in nanoenvironments of polymeric vesicles (polymersomes), comprising a hydrophilic corona and a hydrophobic wall [1][12], or in

Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

• Sachin S. Burade,
• Sushil V. Pawar,
• Tanmoy Saha,
• Navanath Kumbhar,
• Amol S. Kotmale,
• Manzoor Ahmad,
• Pinaki Talukdar and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2019, 15, 2419–2427, doi:10.3762/bjoc.15.234

• [17][18], we investigated the ion transport activity of 1 and 2a across lipid bilayer membranes. In this study, the collapse of the pH gradient (pHout = 7.8 and pHin = 7.0), created across egg yolk ʟ-α-phosphatidylcholine (EYPC) vesicles with entrapped 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium

• 2b. The influx of Cl‒ ion by these transporters were monitored using EYPC-LUVslucigenin. Additionally, compound 9, which has a free amino group and a free carboxylic acid group, was also subjected to the Cl‒ transport study. The Cl– sensitive dye lucigenin, was entrapped within the lipid vesicles and

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• phospholipid unilamellar vesicles at low concentrations (5 µg/mL), and in a dose and molecular weight dependent fashion, indicating their potential antimicrobial properties. Further studies revealed that co-polymerisation of norbornene imide monomers with different alkyl groups provided optimal antimicrobial

Reversible end-to-end assembly of selectively functionalized gold nanorods by light-responsive arylazopyrazole–cyclodextrin interaction

• Maximilian Niehues,
• Patricia Tegeder and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2019, 15, 1407–1415, doi:10.3762/bjoc.15.140

• -to-end aggregates. Ma et al. suggested that the host–guest interaction is not strong enough to assemble the particles if not preformed. Yet, this is not consistent with publications that report photoswitchable azobenzene–CD interaction on surfaces [28], in hydrogels [29], the assembly of CD vesicles

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

• vesicles, alone or in mixture with phospholipids, mimicking bacterial outer membrane vesicles (OMV) with potential antiadhesive properties. Keywords: glycolipids; outer membrane vesicles; synthetic vaccines; Introduction Outer membrane vesicles (OMV) [1], lipid bilayer vesicles released from the outer

• -glycosylated compounds were observed. Preparation of vesicles upon hydration of a thin film of phospholipids and glycolipids Once synthesized, the compounds 5 and 8 bearing GlcNAc residues were used to produce giant vesicles (GVs) upon hydration with PBS (pH 7.4) by modifying reported procedures [28][29][30

• ). Moreover, a thin layer of compounds 5 or 8 without POPC, hydrated in the same conditions, gave similar giant vesicles (Figure 3, images f,g and i). Microscopic observation suggested that those supramolecular assemblies microscopically resemble the well-known outer membrane vesicles (OMV) [1]. The tentative

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

• Keishiro Tahara,
• Ling Pan,
• Toshikazu Ono and
• Yoshio Hisaeda

Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232

• B12 [30]. Indeed, in the crystal structure, 1 maintained the same corrin framework as natural B12 [31]. We combined the hydrophobic B12 derivatives with bilayer vesicles [32][33], a protein [34], organic polymers [35][36][37][38][39][40], and metal organic frameworks (MOFs) [41]. Furthermore, to

• vesicles composed of synthetic lipids and alkylated complexes of heptapropyl cobyrinate (Scheme 3) [32][33]. The alkylated B12 model complexes were introduced into the vesicle in aqueous solutions through non-covalent hydrophobic interactions and irradiated with a 500 W tungsten lamp to result in the

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

• for nucleotides sensing through a dye replacement procedure. It is unusual that disubstituted macrocycles 10a,b bind more effectively a less charged adenosine 5'-diphosphate (ADP) than adenosine 5'-triphosphate (ATP). A simple colorimetric method based on polydiacetylene vesicles decorated with 10b

• vesicles [41]. The inflection point in the plot of EY λmax vs surfactant concentration should be treated as the CAC of the amphiphile [42]. As can be seen from Table 1 the CAC values determined by the two methods are significantly different, especially in the case of macrocycles 10a,b. These differences

• the aggregate. Therefore, a different packing of aggregates is the main reason for the observed ADP/ATP selectivity of calixarene 10b. Polydiacetylene–10b vesicles for ADP/ATP sensing Polydiacetylenes (PDAs), alternating ene-yne conjugated molecules, induce a blue-to-red color transition by the

Lanyamycin, a macrolide antibiotic from Sorangium cellulosum, strain Soce 481 (Myxobacteria)

• Lucky S. Mulwa,
• Rolf Jansen,
• Dimas F. Praditya,
• Kathrin I. Mohr,
• Patrick W. Okanya,
• Joachim Wink,
• Eike Steinmann and
• Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 1554–1562, doi:10.3762/bjoc.14.132

• of this class, bafilomycin A1 (Figure 3) is a useful biochemical tool as it prevents the re-acidification of synaptic vesicles once they have undergone exocytosis [14]. Bafilomycins are also known to be cytotoxic, inhibitors of autophagy, active against Gram-positive bacteria, yeast and fungi

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

• , which were probably representing vesicles, since an endocytotic uptake pathway for this CPP and its longer version sC18 was already demonstrated [13][18][19]. In addition, the nuclear localization sequence N50 alone was not noticeable present within both cell lines at the tested concentration (Figure S6

• high enough to escape from the vesicles and to reach the nuclei. This might indicate that a certain concentration threshold is indispensable for efficient internalization, a phenomenon that was already discussed for other CPPs [29][35]. Considering all these observations, it was presumed that the