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

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

• . It was emphasized that the increased plasma membrane fluidity due to the decrease of lipid rafts and, moreover, cholesterol in the biological membrane plays a role in inducing apoptosis [58]. When the literature information and the findings are evaluated, it can be said that the use of CD

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• –517. Keywords: Appel reaction; azidolysis; cholesterol; crystal structure; Walden inversion; Introduction 3β-Hydroxycholest-5-ene (cholesterol) is a structural and physiologic amphipathic steroid in human and animals as well. Cholesterol is an essential component of the plasma membrane, where it

Biological properties and conformational studies of amphiphilic Pd(II) and Ni(II) complexes bearing functionalized aroylaminocarbo-N-thioylpyrrolinate units

• Samet Poyraz,
• Samet Belveren,
• Sabriye Aydınoğlu,
• Mahmut Ulger,
• Abel de Cózar,
• Maria de Gracia Retamosa,
• Jose M. Sansano and
• H. Ali Döndaş

Beilstein J. Org. Chem. 2021, 17, 2812–2821, doi:10.3762/bjoc.17.192

• cellular targets known for antituberculosis drugs and all the different chemical structures (inhibition of cell wall synthesis, disruption of the plasma membrane, DNA-gyrase, etc.) the next work focused on determining the exact biological mechanism and docking studies could not be executed. Conclusion The

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

• Marco Keller,
• Karl Sauvageot-Witzku,
• Franz Geisslinger,
• Nicole Urban,
• Michael Schaefer,
• Karin Bartel and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

• plate reader (FLIPR) built into a robotic liquid handling station (Fluent, Tecan, Switzerland) and a HEK293 cell line stably expressing the human TPC2 (C-terminally RFP-tagged) rerouted to the plasma membrane as previously described [57]. Trypsinized HEK293 cells (stably expressing hTPC2L11A/L12A

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

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

Simulating the enzymes of ganglioside biosynthesis with Glycologue

• Andrew G. McDonald and
• Gavin P. Davey

Beilstein J. Org. Chem. 2021, 17, 739–748, doi:10.3762/bjoc.17.64

• then to subsequent ceramide-linked glycoconjugate acceptors, before transport and eventual incorporation into the plasma membrane via vesicular fusion. Gangliosides, which function as antigenic determinants [4], may play a role in membrane organization [5], cell signaling [6], apoptosis [7], and in

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

• Sambasivarao Kotha,
• Gaddamedi Sreevani,
• Lilya U. Dzhemileva,
• Milyausha M. Yunusbaeva,
• Usein M. Dzhemilev and
• Vladimir A. D’yakonov

Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269

• surface of the plasma membrane is an exact and reliable indication of cell apoptosis or necrosis. The difference between these two forms of cell death is that in the early stages of apoptosis, the cell membrane remains relatively undamaged, whereas upon necrosis, the cell membrane loses integrity. In the

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

• -soluble and selective bioprobe for plasma membrane imaging. The new compound was efficiently synthesized in a two-step procedure with good yields. The photophysical properties were evaluated and the dye proved to have an excellent photostability in several solvents. DFT calculations were found in

• agreement with the experimental data and helped to understand the stabilizing intramolecular charge-transfer process from the first excited state. The new fluorescent derivative could be applied as selective bioprobe in several cell lines and displayed plasma-membrane affinity during the imaging experiments

• for all tested models. Keywords: benzothiadiazole; bioprobe; cell imaging; fluorescence; mitochondria; molecular architecture; plasma membrane; Introduction The selective staining of plasma membranes is of paramount importance to study cellular processes and events associated with this dynamic

Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement

• Jessica Matthias,
• Thines Kanagasundaram,
• Klaus Kopka and
• Carsten S. Kramer

Beilstein J. Org. Chem. 2019, 15, 2333–2343, doi:10.3762/bjoc.15.226

• . Lipophilic cations such as the phosphonium cation or rhodamines are known to accumulate selectively within the mitochondria, driven by the mitochondrial plasma membrane potential [39][40]. Thereby, the high lipophilicity facilitates the diffusion through the lipid bilayers of the cell and mitochondrial

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• (Ac)]-GnRH-III(Dau=Aoa). Dau served as a positive control in this experiment and showed a high level of intracellular fluorescence. Considering that Dau is a small molecule and can diffuse through the plasma membrane while the conjugates can enter the cells by receptor-mediated endocytosis with low

• of conjugates requires their receptor-mediated internalization and the lysosomal degradation, while Dau could diffuse through the plasma membrane and exerts its antitumor activity by intercalating directly to DNA. Furthermore, it was previously demonstrated that the smallest Dau-containing fragment

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

• -sC18* and NrTP-sC18* formed α-helices that showed amphipathic character with a clear hydrophilic and hydrophobic face (Figure 1C). This property might support the interaction with the plasma membrane. Cytotoxic profile of novel CPPs In the next step, the cytotoxicity profiles of the novel peptide

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

• overall shape of the molecule. Further, cholesterol is one of the basic natural components of eukaryotic cells, thus some portion of construct 6 could be fixed in plasma membrane, which decreases the possibility of manifesting the known biological effects of Tb inside cells [42]. Liposome preparation and

• with U-2 OS cells (Supporting Information File 1, Figure S16), on which they were bound at the plasma membrane. After 2 h of incubation, there were two populations of cells with liposomes bound either on the plasma membrane or inside the cells (Figure 6). The intracellular localization of liposomes was

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• biomimetic plasma membrane incorporating glycolipid rafts. The in situ chemical conversion of GD1a gangloside into its metabolic product under the action of sialidase was investigated. The outcome of the sialidase action is not limited to the creation of GM1 and AsialoGM1 gangliosides as it is accompanied by

Expression, purification and structural analysis of functional GABA transporter 1 using the baculovirus expression system

• Jing Hu,
• Chris Weise,
• Christoph Böttcher,
• Hua Fan and
• Jian Yin

Beilstein J. Org. Chem. 2017, 13, 874–882, doi:10.3762/bjoc.13.88

• membrane. GAT1 dimers were expressed and examined as a distinct population of 9 nm freeze-fracture particles in the plasma membrane of Xenopuslaevis oocytes by freeze-fracture and electron microscopy [33]. The GAT1 protein monomer was determined to be the functional unit since each monomer functions

• concentration (CMC) of DDM:0.009% or 0.18 mM), no significant population of micelles could be found. These results suggest that the observed particles most likely correspond to a monodisperse preparation of GAT1/GFP. Several studies have demonstrated that GAT1 expresses in an oligomeric formation in the plasma

Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

• Malte Hilsch,
• Ivan Haralampiev,
• Peter Müller,
• Daniel Huster and
• Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

• maintaining the membrane’s barrier function by increasing the bilayer packing density through condensing the phospholipids. Furthermore, cholesterol is an important player in the dynamic domain structure of the plasma membrane and the formation of lateral lipid domains with relevance to membrane protein

• the membrane bilayer, which guides their ability to cross the blood–brain barrier. This process consists of three steps at the membrane level, (i) incorporation of sterols into the plasma membrane, (ii) their transbilayer diffusion and (iii) their release from the membrane. With regard to the transfer

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• the order carbohydrates << nucleic acids << proteins < lipids. Consequently, the majority of biological investigations about CDs involved their ability to extract lipids (cholesterol or phospholipids) from the plasma membrane. As expected, this capacity can be very useful for numerous applications

Synthesis of cyclic N¹-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells

• Ahmed Mahal,
• Stefano D’Errico,
• Nicola Borbone,
• Brunella Pinto,
• Agnese Secondo,
• Valeria Costantino,
• Valentina Tedeschi,
• Giorgia Oliviero,
• Vincenzo Piccialli and
• Gennaro Piccialli

Beilstein J. Org. Chem. 2015, 11, 2689–2695, doi:10.3762/bjoc.11.289

• transient increase of intracellular concentration of Ca2+ when added to the cells, thus demonstrating their ability to cross the plasma membrane. Results and Discussion Chemistry The key step for the preparation of all cADPR/cIDPR analogues is the macrocyclization via pyrophosphate bond formation, which is

• analogues 3 and 4 retained the ability to pass the plasma membrane of neuronal cells. Conclusion cADPR is a second messenger synthesized by neuronal cells that modulates the Ca2+ homeostasis in the nervous system [42]. Unfortunately, cADPR is characterized by a low ability to cross the plasma membranes

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• electrochemistry [18] or by adding an oxidizing agent [19]. Different studies have employed this concept to form redox-responsive systems applied, for example, in self-healing materials [19], polymeric hydrogels [20][21], voltage-responsive vesicles [22], ultrasentive enzyme sensors [23], and as a plasma membrane

Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Yumi Hirai,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224

• effects of CyDs in NPC cells are as follows; 1) CyDs may extract the free form of cholesterol from plasma membranes of lipid rafts, and then cholesterol in endolysosomes are transported to plasma membrane to supply, 2) the endocytosed CyDs may transport cholesterol from endolysosomes, and 3) the

• endocytosed CyDs may elicit a perturbation in endolysosomes membranes through the interaction with membrane components, which would result in the efflux of cholesterol from endolysosomes. In our preliminary study, 1 mM Lac-β-CyD could not extract cholesterol from the plasma membrane of U18666A-treated HepG2

Regulation of integrin and growth factor signaling in biomaterials for osteodifferentiation

• Qiang Wei,
• Theresa L. M. Pohl,
• Anja Seckinger,
• Joachim P. Spatz and
• Elisabetta A. Cavalcanti-Adam

Beilstein J. Org. Chem. 2015, 11, 773–783, doi:10.3762/bjoc.11.87

• cells [18]. Therefore, the integrins serve to link the two compartments, namely the ECM and the intracellular actin filamentous cytoskeleton across the plasma membrane. The interactions between integrins and ligands result in two major functions. First, the interactions physically integrate the ECM

Synthesis of a hexasaccharide partial sequence of hyaluronan for click chemistry and more

• Marina Bantzi,
• Stephan Rigol and
• Athanassios Giannis

Beilstein J. Org. Chem. 2015, 11, 604–607, doi:10.3762/bjoc.11.67

• not form PGs, in contrast to the other GAGs, which are synthesized in the Golgi apparatus or the endoplasmic reticulum [8]. HA is enzymatically produced by three glycosyltransferases (HA synthases: HAS 1, 2 and 3) in the cellular plasma membrane and its chain can reach a mass of 102–104 kDa [9

Potential of acylated peptides to target the influenza A virus

• Daniel Lauster,
• Damian Pawolski,
• Julian Storm,
• Kai Ludwig,
• Rudolf Volkmer,
• Henry Memczak,
• Andreas Herrmann and
• Sumati Bhatia

Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65

• results show that acylated peptides, e.g., C18-PeBGF, could readily insert into biological membranes. As we observed association with the plasma membrane of red blood cells we surmise that those peptides could also insert into the virus envelope. Conclusion Here, we investigated the potential of a

Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

• Anne-Katrin Späte,
• Verena F. Schart,
• Julia Häfner,
• Andrea Niederwieser,
• Thomas U. Mayer and
• Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

• ], followed by labeling with streptavidin–AlexaFluor647 (streptavidin–AF647) (Scheme 3). With all three sugars staining of the plasma membrane was detected by confocal laser scanning microscopy of living cells (Figure 2A, B, C). Only the solvent control did not show any membrane staining (Figure 2D, for