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Search for "liposomes" in Full Text gives 32 result(s) in Beilstein Journal of Organic Chemistry.

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

Graphical Abstract
  • work was to reveal how CHOL would modulate the CDs effect on the membrane. Hence, liposomes made of dipalmitoyl phosphatidylcholine (DPPC) and various CHOL contents (DPPC/CHOL 100:10, 100:25, 100:50, and 100:100) encapsulating the hydrophilic fluorophore, sulforhodamine B (SRB), were prepared and
  • encapsulated in the aqueous core of liposomes which is generally known as “drug-in-cyclodextrin-in-liposomes” (DCL) [6]. This novel delivery system has gained popularity in the past few decades and many publications proved its importance and significance. Actually, the use of the two delivery systems
  • (liposomes and CDs) was shown to combine the advantages of each separate system and to circumvent the drawbacks of liposomes and the problems associated with CDs: for instance, studies reported that the DCL increased the entrapment of hydrophobic drugs in liposomes and enhanced the vesicle stability. The DCL
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Published 17 Oct 2023

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

Graphical Abstract
  • work includes, in addition to the oxidation of such type of polyunsaturated EL incorporated in liposomes [99], the formal synthesis of some oxidized derivatives. As an illustration, lyso-PAF 15.1 (extracted from egg albumin) was acylated using Steglich conditions with ω-unsaturated carboxylic acid to
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Published 08 Sep 2023
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  • 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
  • photosynthesis using liposomes was thoroughly reviewed with special attention paid to donors and redox mediators [38]. Species such as methyl viologen were employed as redox mediators in some of the systems reviewed, however, the regeneration still required consumption of species other than water, such as EDTA
  • of artificial photosynthesis research investigating the compartmentalization of different reactions using liposomes and membranes [38]. Another alternative could be to use redox-active polymers as recyclable donors which would allow microporous membrane separation. Redox-active polymers are a very
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Published 08 Aug 2023

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

Graphical Abstract
  • forces. DAC has mainly been used to create drug composites but recently found application in the formulation of liposomes or the direct nanodispersion of pharmaceutically active ingredients [24][25][26][27][28]. The technique resembles nanomilling methods but allows a much smaller sample scale, which
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Published 21 Oct 2021

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

Graphical Abstract
  • Tat to PEG 2000 and found that in their liposomal formulations, those containing 10% PEG 2000–Tat had the most efficient uptake in a BBB model [9]. Several studies have used transferrin-conjugated PEG analogs. In 2011, in a series of papers, Pang et al. observed that liposomes comprised of 5–10% PEG
  • –transferrin increased brain delivery by 2.8-fold compared to liposomes without transferrin in a BBB model and in vivo [15] and further when loaded with the chemotherapeutic agent doxorubicin. They observed increased delivery of this compound and subsequently a significant tumor regression in mouse xenografts
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Published 26 Apr 2021

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

Graphical Abstract
  • ; Introduction Various nano- and microsystems, including micelles, liposomes, and microbubbles, have been developed as imaging agents and to selectively deliver chemotherapeutics to tumor cells [1][2][3][4][5][6]. An increased specificity for tumor cells can be gained through ligand-mediated active targeting
  • step by washing. The human epidermal growth factor receptor-2 (HER2)-targeting KCCYSL peptide–(SG)n–lipids in which the (SG)n (n = 3, 5, 7) sequence was used as a spacer allowed the reduction of the steric hindrance when compared to the conventional PEG2000 spacer [28]. Liposomes containing these
  • peptide ligands dramatically increased cellular association in HER2-positive cells. Other lipids grafted to the RGD peptide and SG spacer were integrated in PEGylated liposomes and were efficiently associated with integrin αvβ3-expressing Colon-26 cells [25]. One of our general objectives is to synthesize
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Published 19 Feb 2021

Selected peptide-based fluorescent probes for biological applications

  • Debabrata Maity

Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247

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  • in nature as it contains minimum six fatty acid chains. It is toxic at higher concentration and has been identified in sepsis or septic shock in humans [58]. It induces a strong immune response in normal mammalian cells. Schmuck et al. reported cationic peptide-based polydiacetylene (PDA) liposomes
  • for the turn on fluorescent detection of LPS in mixed solvent (DMSO/TBS buffer, 1:4) (Figure 10A) [59]. The liposomes are created by mixing two lipids in a ratio of 9:1. First lipid 12 is designed by attaching 10,12-tricosadiyonic acid to a penta-lysine oligopeptide bearing an aminonaphthalimide
  • fluorophore on one lysine. The four cationic lysine residues are closely mimicking the structure of polymyxin B, which has a strong affinity to the negative LPS. The second lipid 13 is designed by connecting 10,12-tricosadiyonic acid to histidine. PDA liposomes are formed after UV-light-irradiated
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Published 03 Dec 2020

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

Graphical Abstract
  • hydrophilic and a lipophilic domain, thereby rendering them amphiphilic. This dual functionality gives surfactants unique properties such as being able to stabilize emulsions (emulsifiers) or forming large self-assembled aggregates that can take the shape of, for example, micelles or liposomes [1]. The latter
  • reactions in water, thereby giving rise to a greener approach to organic synthesis [2][3]. Furthermore, the micelles act as a mini-reactor in which the reagents exist in a very high concentration, giving cleaner and faster reactions [1]. The larger aggregates, liposomes, have shown great potential as drug
  • 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
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Published 17 Nov 2020

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

Graphical Abstract
  • dendritic cells) [22][23]. It has been shown that uptake of liposomes displaying mannose ligands attached to the surface enhanced the uptake in human monocyte-derived dendritic cells [24]. Here we describe a structure–activity relationship (SAR) study on novel mannosylated desmuramyl peptide derivatives in
  • antigens and regulate the immune reaction by specific binding to CLRs. Therefore, compounds with expressed CRL agonist or antagonist properties could also be considered as potential agents for cancer immunotherapy [49][50]. Mannosylated liposomes with incorporated MDP have proved to be effective carriers
  • for target inhibition of liver metastasis [51]. Therefore, the presented mannosylated desmuramyl peptides with incorporated adamantane will be further explored in order to get a better insight into possible PRR crosstalk. Namely, inclusion of adamantane into carriers such as liposomes can additionally
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Published 29 Jul 2019

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

Graphical Abstract
  • with high affinity to lectins and with antibiotic activities [34], lectin recognition by n-alkyl thioglycoside liposomes remains unprecedented [33][34]. Moreover, the calculated distance between the two sugar moieties of compound 8 (up to 13 Å, Figure 6) and the presence of flexible arms make these
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Published 17 Apr 2019

Nanoreactors for green catalysis

  • M. Teresa De Martino,
  • Loai K. E. A. Abdelmohsen,
  • Floris P. J. T. Rutjes and
  • Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

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  • -isopropylacrylamide)-b-poly(ethylene oxide) (PNIPAM-b-PEO) [78]. The term “polymersomes” is derived from liposomes because of the structural resemblance. Compared to liposomes, polymersomes are mechanically robust vesicles and therefore considered to be highly attractive for nanoreactor applications [24][40
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Published 29 Mar 2018

Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion

  • Susanne Huhmann,
  • Anne-Katrin Stegemann,
  • Kristin Folmert,
  • Damian Klemczak,
  • Johann Moschner,
  • Michelle Kube and
  • Beate Koksch

Beilstein J. Org. Chem. 2017, 13, 2869–2882, doi:10.3762/bjoc.13.279

Graphical Abstract
  • stable towards proteolysis by trypsin and chymotrypsin in the presence of liposomes [29]. In the absence of liposomes, the fluorinated variants were as rapidly degraded as the non-fluorinated control, suggesting that the incorporation of HfLeu is not the only factor that prevents the peptide from being
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Published 22 Dec 2017

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

Graphical Abstract
  • resulting in a low oral bioavailability. This limitation can be overcome by using micro or nano-encapsulation methods that allow preparing fisetin oral liquid formulations that are well absorbed. Previously reported encapsulation strategies include liposomes [18], nanoemulsions [19], nanocochleates (which
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Published 13 Oct 2017

Remarkable functions of sn-3 hydroxy and phosphocholine groups in 1,2-diacyl-sn-glycerolipids to induce clockwise (+)-helicity around the 1,2-diacyl moiety: Evidence from conformation analysis by 1H NMR spectroscopy

  • Yoshihiro Nishida,
  • Mengfei Yuan,
  • Kazuo Fukuda,
  • Kaito Fujisawa,
  • Hirofumi Dohi and
  • Hirotaka Uzawa

Beilstein J. Org. Chem. 2017, 13, 1999–2009, doi:10.3762/bjoc.13.196

Graphical Abstract
  • properties, as glycerophospholipids comprise elements of fluid membrane [5] and nanoscale vesicles called liposomes [6]. In addition, the chiral sn-glycerol backbone is composed of acyclic polyols that produce several conformers through the free rotation about each of the C–C single bonds. For example, the
  • (C/M = 2:1), the solvation by methanol-d4 might be partly replaced with D2O. Hamilton et al. [30] employed 13C NMR spectroscopy to examine the dynamic molecular behavior of 1,2-dilauroyl-sn-glycerol located in liposomes mixed with glycerophospholipids. Their 13C NMR analysis revealed that the
  • hydration occurring around the carbonyl groups in the 1,2-diacyl moiety triggers the dynamics of the molecular alignments in liposomes. Probably, an analogous phenomenon related to the solvation around sn-3 OH was observed. Thus, solvation is thought to play a key role in the dynamic conformation change
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Published 25 Sep 2017

A recursive microfluidic platform to explore the emergence of chemical evolution

  • David Doran,
  • Marc Rodriguez-Garcia,
  • Rebecca Turk-MacLeod,
  • Geoffrey J. T. Cooper and
  • Leroy Cronin

Beilstein J. Org. Chem. 2017, 13, 1702–1709, doi:10.3762/bjoc.13.164

Graphical Abstract
  • , a few recent examples in the literature report the utilisation of pico- and nanolitre microfluidic water-in-oil droplets and liposomes as artificial cell analogues [14][15]. Aqueous, single emulsion microdroplets can be produced at kilohertz frequencies, and provide compartmentalisation on a similar
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Published 17 Aug 2017

Chemical systems, chemical contiguity and the emergence of life

  • Terrence P. Kee and
  • Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

Graphical Abstract
  • acid monomers has been achieved in this manner: When amphiphile vesicles or liposomes are dried in the presence of solutes on a silicate support, a system of stacked lipid bilayers with intercalated solutes is formed [52]. In this arrangement, the nucleotides are optimally spaced to react and form
  • membrane architecture, amphiphile vesicles or liposomes, became the main type of compartment models for the study of the origins of life, although other systems could also serve the very same purpose [77][78][79][80][81]. Besides the chemical continuity arguments, amphiphile bilayers offer a very fine
  • reconstitute photosynthetic machinery in phospholipid liposomes [91][92] and polymersomes [93]. In these experiments, the use of photosensitizer triads or bacteriorhodopsin has allowed for the conversion of light energy into a proton gradient, which in turn could be utilized to power an ATP synthase to produce
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Published 07 Aug 2017

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

Graphical Abstract
  • create construct 6. The liposomes were composed of dipalmitoyl-3-trimethylammoniumpropane and phosphatidylethanolamine. The whole system was characterized by atomic force microscopy, the average size of the liposomes was 150 nm in width and 30 nm in height. We evaluated the biological activity of
  • encapsulation of construct 6 into the liposomes improved the drug distribution in cancer cells and was followed by cell death. This new liposomal trilobolide derivative not only retains the biological properties of pure trilobolide, but also enhances the bioavailability, and thus has potential for the use in
  • theranostic applications. Keywords: BODIPY conjugates; cancer targeting; drug delivery; liposomes; natural compounds; sesquiterpene lactone trilobolide; Introduction Targeted (smart) drug delivery is a method for specific delivering of an active compound preferentially to some cells or tissues in the human
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Published 04 Jul 2017

Glyco-gold nanoparticles: synthesis and applications

  • Federica Compostella,
  • Olimpia Pitirollo,
  • Alessandro Silvestri and
  • Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

Graphical Abstract
  • -glycolic acid)-PLGA NPs, liposomes), many examples in literature report on the development of gold-based glyco nanoparticles as efficient system to delivery payloads. In this contest, AuNPs modified with lactose moieties and β-cyclodextrins have been reported by Vargas-Berenguel et al. [87]. The authors
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Published 24 May 2017

Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids

  • Simon Drescher,
  • Vasil M. Garamus,
  • Christopher J. Garvey,
  • Annette Meister and
  • Alfred Blume

Beilstein J. Org. Chem. 2017, 13, 995–1007, doi:10.3762/bjoc.13.99

Graphical Abstract
  • bilayers, they can be used to stabilize liposomes for drug delivery purposes. The applicability of this approach was already tested for a large variety of natural and artificial bolalipids [12][16][17][18][19][20][21][22]. The isolation of archaeal bolalipids from natural sources is expensive and often
  • unmodified bolalipids, such as PC-C32-PC, could not be incorporated into bilayers of DMPC or POPC [28]. In contrast, bolalipids with an alkyl chain modification, e.g., PC-C17pPhC17-PC, were partially miscible with DPPC and DSPC. But, closed lipid vesicles (liposomes) and a pronounced stabilization of the
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Published 23 May 2017

The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil

  • Joyce Azzi,
  • Pierre-Edouard Danjou,
  • David Landy,
  • Steven Ruellan,
  • Lizette Auezova,
  • Hélène Greige-Gerges and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2017, 13, 835–844, doi:10.3762/bjoc.13.84

Graphical Abstract
  • to produce functional foods with enhanced functionality and stability [6]. Various encapsulation materials are used for food applications such as liposomes, phytosomes, cyclodextrins, dendrimers and many others [7][8][9]. The use of cyclodextrins (CDs) in food industry is currently flourishing due to
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Published 05 May 2017

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

Graphical Abstract
  • , sterols, fat-soluble vitamins, phospholipids, mono-, di- and triglycerides, etc. Their amphiphilic nature causes the molecules of certain lipids to organize into liposomes when they are in aqueous medium. This property allows the formation of biological membranes. Indeed, cells and organelles membranes
  • 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
  • with DNA [109][110]. As consequence, CDs can be used to complex DNA and to encapsulate it into liposomes for potential gene therapy applications [111]. However, other formulation can be used to obtain non-viral vectors [112]. Since anthrylamines have potent DNA-intercalating properties, Ikeda et al
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Published 07 Dec 2016

Thermal and oxidative stability of Atlantic salmon oil (Salmo salar L.) and complexation with β-cyclodextrin

  • Daniel I. Hădărugă,
  • Mustafa Ünlüsayin,
  • Alexandra T. Gruia,
  • Cristina Birău (Mitroi),
  • Gerlinde Rusu and
  • Nicoleta G. Hădărugă

Beilstein J. Org. Chem. 2016, 12, 179–191, doi:10.3762/bjoc.12.20

Graphical Abstract
  • various matrices. Matrices such as chitosan and N-lauroyl chitosan [25], N-stearoyl-O-butylglycerylchitosan [26], mixtures of soybean soluble polysaccharide and octenyl succinic anhydride [27], hydrolyzed soy protein isolate and maltodextrin [20][28], liposomes [29] and even yeast cell autolysate [30
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Published 02 Feb 2016

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

  • Mohamed Ramadan El Sayed Aly,
  • Hosam Ali Saad and
  • Shams Hashim Abdel-Hafez

Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208

Graphical Abstract
  • bioavailability of anticancer drugs. Thus, SuberAniloHydroxamic acid–cholesterol conjugates (SAHA–cholesterol) [11], cholesterol-based charged liposomes encaging doxorubicin [12] or curcumin [13] showed higher activity compared with the native drugs. Synthetic coumarin-caged cholesterol derivatives, for instance
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Published 16 Oct 2015

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

Graphical Abstract
  • have been partially neutralized by the liposomes, either by attachment and/or incorporation into the lipid bilayer. Very likely, in case of stearylated peptides, we surmise incorporation into the bilayer via the fatty acyl chain. To verify the association with lipid membranes exemplarily, we
  • hemagglutination by acylated antiviral peptides was drastically reduced in the presence of additional membranes (here liposomes). Taken into consideration that the in vivo situation is characterized by an excess of cell membrane surfaces serving as targets for the amphiphilic peptides, the multivalent presentation
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Published 29 Apr 2015

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

Graphical Abstract
  • 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
  • useful as sustained gene transfer carriers [26][27]. Liposomes (LPs) are microscopic phospholipid vesicles with a bilayered membrane structure and are used as a promising drug carrier [28]. When conventional LPs are administrated intravenously, they are coated with plasma proteins, which results in a
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Published 25 Nov 2014
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