Hot shape transformation: the role of PSar dehydration in stomatocyte morphogenesis

• Remi Peters,
• Levy A. Charleston,
• Karinan van Eck,
• Teun van Berlo and
• Daniela A. Wilson

Beilstein J. Org. Chem. 2025, 21, 47–54, doi:10.3762/bjoc.21.5

• systems like PEG-PS [20] or PEG-PDLLA [31]. This wrinkled morphology suggests that the membrane may possess greater flexibility compared to the aforementioned systems (Supporting Information File 1, Figure S22). This effect is more often observed in liposome systems that have thinner and more flexible

• membranes. In this example by Buscema et al. it was observed that liposome vesicles can deform under mechanical stress to yield similar structures as the PSar-PBLG vesicles [32]. It was attempted to change the shape of the assembled vesicles following a similar method as previously developed for PEG-PS

Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions

• Hayato Takagi,
• Çetin Çelik,
• Ryosuke Fukuda,
• Qi Guo,
• Tomohiro Higashino,
• Hiroshi Imahori,
• Yoko Yamakoshi and
• Tatsuya Murakami

Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231

• , respectively. In this study, by mimicking our previous system of triad molecules and living cells, we report a simplified model system with a cationic C60 derivative (catC60) and a liposome with embedded 1-pyrenebutyric acid (PyBA) to demonstrate that the addition of PyBA was important to achieve fast and

• safer control of Vm. Keywords: liposome; π–π interaction; reactive oxygen species; superoxide radical anion; Introduction The [60]fullerene (C60) is known as an excellent electron acceptor [1][2] and is commonly used in organic solar cell applications [3]. Taking advantage of the fact that C60 can be

• Figure 4a, the intensity decreased upon increasing the concentration of the catC60 in the liposomes, showing the quench of PyBA fluorescence by catC60, presumably by interacting in the liposome membrane. The incomplete quenching after the addition of PyBA at a concentration comparable to that of catC60

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

• content membrane increase. Keywords: cholesterol; cyclodextrins; liposome; membrane permeability; Introduction Cyclodextrins (CDs) are a family of cyclic oligosaccharides made of glucopyranose units connected by α-1,4-glycosidic bonds. They possess a cone-shaped molecular structure with a hydrophobic

• the best of our knowledge, this work is the first study investigating the effect of CDs on the permeability of DPPC liposome membranes of various CHOL content. The CDs effect was examined at various CD/DPPC molar ratios. This work will provide a better understanding of the influence of CHOL content on

• the CDs effect with regards to their affinity to lipid membrane components. It will also allow us to point out if the CDs-induced lipid extraction may occur in “lipid rafts”. Results and Discussion In this study, liposome membranes made of DPPC and various CHOL contents were prepared (10%, 25%, 50

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

• mitochondria binding ligand does not induce any damaging effects to these cell lines. Many studies have reported that attaching targeting ligands on nanoparticle or liposome surfaces play a key role in overcoming biological barriers and reducing targeting effects. Active targeting or retention can increase

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

• Masayori Hagimori,
• Estefanía E. Mendoza-Ortega and
• Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

• serine–glycine (SG)n segments rather than classical poly(oxyethylene) linkers between the lipid polar head and a targeting ligand were proposed for the liposome-mediated, selective delivery of anticancer drugs. Here, we report the synthesis of perfluoroalkylated lipopeptides (F-lipopeptides) bearing two

• particular cell surface receptor [7][9][10][11][12][13][14]. To this aim, ligand–lipid conjugates have been developed in research and preclinical development for liposome targeting for decades. In particular, peptide ligands offer significant advantages, including efficient synthesis routes, versatility, and

Easy access to a carbohydrate-based template for stimuli-responsive surfactants

• Thomas Holmstrøm,
• Daniel Raydan and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2020, 16, 2788–2794, doi:10.3762/bjoc.16.229

• -delivery system owing to their size and the ability to carry drugs, both in the polar (core) or apolar (lipid bilayer) interior [4][5]. A challenge in liposome-based drug delivery systems is to release the drug at the place of function. This challenge has led to the development of stimuli-responsive

• mechanical impulse that can increase or decrease the distance between the two lipophilic tails, thus changing the amphiphilic properties of the molecule. Incorporating such molecules into the lipid bilayer of liposomes can result in the decomposition of the whole liposome when the stimuli-responsive

Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

• Rosana Ribić,
• Ranko Stojković,
• Lidija Milković,
• Mariastefania Antica,
• Marko Cigler and
• Srđanka Tomić

Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174

• most suitable position of adamantane in this class of compounds is at the peptide N-terminus. Adamantane can act as membrane anchor for mannose structures and thus be exposed on liposome surfaces and as such used in targeted drug delivery [37]. It can be also incorporated into a β-cyclodextrine cavity

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

• Joana M. Pais,
• Maria João Barroca,
• Maria Paula M. Marques,
• Filipe A. Almeida Paz and
• Susana S. Braga

Beilstein J. Org. Chem. 2017, 13, 2138–2145, doi:10.3762/bjoc.13.212

• are liposome derivatives) [20], and cyclodextrin inclusion complexes [21][22][23]. Cyclodextrins (CDs) are naturally occurring cyclic oligosaccharides produced by bacterial degradation of starch. Native CDs have six to eight α-D-glucose units linked by α-1,4 bonds, being called α-, β- and γ-CDs

Framing major prebiotic transitions as stages of protocell development: three challenges for origins-of-life research

• Ben Shirt-Ediss,
• Sara Murillo-Sánchez and
• Kepa Ruiz-Mirazo

Beilstein J. Org. Chem. 2017, 13, 1388–1395, doi:10.3762/bjoc.13.135

• , the majority of ‘compartment-first’ approaches have focused on a second research objective: capturing cell-like behaviours by means of vesicle model systems. Compartmentalization could initially be tried with a two-phase system (e.g., droplets or micro-emulsions) but liposome research techniques

• be grown and multiplied under lab conditions [31]; their rich inherent dynamics [32]; and the competition–selection experiments they make possible, if mixed with different liposome populations [33][34][35][36]. Thus, the interest of working with these model systems stems from the fact that they

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

• reduces its potential medicinal applications. The targeted delivery of hydrophobic drugs can be achieved using liposome-based carriers. Therefore, we designed a traceable liposomal drug delivery system for trilobolide. The fluorescent green-emitting dye BODIPY, cholesterol and trilobolide were used to

• describe the synthesis and application of a fluorescent construct (further called construct 6, depicted in Scheme 1) based on a green-emitting BODIPY dye and trilobolide–cholesterol (Tb-ChL) in a liposome formulation. Trilobolide (Tb, Figure 1) is a potent natural compound of the sesquiterpene lactone

• ) in the proposed structure is based on its routine exploitation in production of artificial liposome vehicles. Incorporation of ChL into liposomes was shown to ‘tighten’ the fluid bilayers, and thus, to reduce the leakage of an active content from the liposomes [1]. Taken together, a construct 6 probe

A postsynthetically 2’-“clickable” uridine with arabino configuration and its application for fluorescent labeling and imaging of DNA

• Heidi-Kristin Walter,
• Bettina Olshausen,
• Ute Schepers and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2017, 13, 127–137, doi:10.3762/bjoc.13.16

• , Germany) to a final volume of 9 µL. 12 µL of a 1:10 dilution of ScreenFect®A in dilution buffer were added to the diluted DNA and rapidly mixed. A subsequent incubation time of 20 min at room temperature allowed the formation of lipoplexes (liposome–DNA complexes). The transfection mixture was then added

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

• that α-CD has the strongest affinity to phospholipids (e.g., phosphatidylinositol) [64][65]. In 2000, Nishijo et al. studied the interactions of various CDs with dipalmitoyl, distearoyl, and dimyristoylphosphatidylcholine liposomes. This study highlights that the liposome-CD interaction depends on the

• monolayers [57] or liposome bilayers [60]. For instance, a typical paper has been published in 2001 by Leventis and Silvius [60]. In order to characterize the CDs capacity to bind cholesterol, the authors examined the catalytic transfer of cholesterol between liposomes composed of 1-stearoyl-2-oleoyl

Smart molecules for imaging, sensing and health (SMITH)

• Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

• develop a series of mobile carriers for chloride ions across liposome and cell membranes [6]. There continues to be a strong community interest in chloride transporters as they are expected to exhibit interesting biological activity [7]. In addition, my group developed some of the first synthetic

Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier

• Kayoko Hayashida,
• Taishi Higashi,
• Daichi Kono,
• Keiichi Motoyama,
• Koki Wada and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292

• such as polyethylene glycol (PEG). On the other hand, PEGylated liposomes have been utilized as a representative anticancer drug carrier. However, little is known about the formation of CD PPRX with PEGylated liposome. In the present study, we first report the formation of CD PPRX with PEGylated

• liposome and evaluate it as a sustained release drug carrier. PEGylated liposome encapsulating doxorubicin was disrupted by the addition of α-CD. Meanwhile, γ-CD included two PEG chains and/or one bending PEG chain of PEGylated liposome and formed PPRX without the disruption of the membrane integrity of

• the PEGylated liposome. Moreover, the release of doxorubicin and/or PEGylated liposome encapsulating doxorubicin from the PPRX was prolonged in accordance with the matrix type release mechanism. These findings suggest the potential of γ-CD PPRX as sustained release carriers for PEGylated liposome

Photo, thermal and chemical degradation of riboflavin

• Muhammad Ali Sheraz,
• Sadia Hafeez Kazi,
• Sofia Ahmed,
• Zubair Anwar and
• Iqbal Ahmad

Beilstein J. Org. Chem. 2014, 10, 1999–2012, doi:10.3762/bjoc.10.208

• observed in neutral or negatively charged liposomes while a decrease was noted in positively charged liposomes. The photodegradation of RF followed first-order kinetics both in the presence and absence of liposomes [138]. Highest stability of RF in a liposome was observed when the vitamin was complexed and

Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family

• Hirofumi Dohi,
• Takeru Kanazawa,
• Akihiro Saito,
• Keita Sato,
• Hirotaka Uzawa,
• Yasuo Seto and
• Yoshihiro Nishida

Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155

• notable biological and physical properties. For example, bis(α-D-mannopyranosyl)-[60]fullerene is capable of forming a liposome-like supramolecule in aqueous media and exhibits a strong binding activity to an α-mannose-binding lectin (concanavalin A, Con A) as the result not only of carbohydrate cluster

Synthetic glycopeptides and glycoproteins with applications in biological research

• Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

• of a MUC1 TN-glycopeptide, a polio peptide T-cell epitope and the Pam3CSK4 lipopeptide immune-stimulant was prepared by liposome-mediated native chemical ligation. Mice immunized with the three-component vaccine were injected with breast-cancer tumor cells, and were found to be significantly more

Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• vesicle or liposome formation or solvent evaporation, the solvent used initially can be removed by dialysis or evaporation and exchanged with water to build the new dispersion medium. The capsules could be obtained with different wall thicknesses depending on the concentration of monomers and with a large