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

• . Specific drug targeting can be achieved by using, for example, antibodies, peptides, polyethylene glycol polymers, and last but not least, liposomes, which have been nowadays extensively investigated [1][2]. In general, liposomes are employed in order to enhance the therapeutic index of an applied drug by

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

• intracellular stability. Liz-Marzan et al. assessed the ability of glycan ligands to reduce the protein corona formation around rod-shaped AuNPs [71]. Lactose- and polyethylene glycol (PEG)-functionalized gold nanorods demonstrated similar ability in reducing the interaction with proteins, when compared to

• protein component. In a different example, Barchi and co-workers focused on the Thomsen Friedenreich tumor-associated antigen (TFag) and synthesized TFag-amino acid-coated AuNPs by means of a thiol-polyethylene glycol spacer. Among the synthesized GAuNPs, TFag-Thr-AuNPs showed, in vitro, an increased

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

• Adrián A. Heredia and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2017, 13, 910–918, doi:10.3762/bjoc.13.92

• , we performed a screening of solvents under oxygen atmosphere (Table 1). Best yields were obtained with DMF, isopropanol or polyethylene glycol (PEG) as the solvents (Table 1, entries 1, 10, 12 and 13), whereas only moderate yields below 50% were obtained when the reaction was conducted in

Towards potential nanoparticle contrast agents: Synthesis of new functionalized PEG bisphosphonates

• Souad Kachbi-Khelfallah,
• Maelle Monteil,
• Margery Cortes-Clerget,
• Evelyne Migianu-Griffoni,
• Jean-Luc Pirat,
• Olivier Gager,
• Julia Deschamp and
• Marc Lecouvey

Beilstein J. Org. Chem. 2016, 12, 1366–1371, doi:10.3762/bjoc.12.130

• is a procedure developed in our laboratory to introduce the bisphosphonate from acyl chloride and tris(trimethylsilyl)phosphite in one step. Keywords: bisphosphonate; Fe2O3 nanoparticle; polyethylene glycol derivatives; surface ligand synthesis; Introduction Numerous researchers are interested in

Artificial Diels–Alderase based on the transmembrane protein FhuA

• Hassan Osseili,
• Daniel F. Sauer,
• Klaus Beckerle,
• Marcus Arlt,
• Tomoki Himiyama,
• Tino Polen,
• Akira Onoda,
• Ulrich Schwaneberg,
• Takashi Hayashi and
• Jun Okuda

Beilstein J. Org. Chem. 2016, 12, 1314–1321, doi:10.3762/bjoc.12.124

• (polyethylene-polyethylene glycol), SDS (sodium dodecyl sulfate), TEV (Tobacco Etch Virus), MALDI–TOF–MS (matrix-assisted laser desorption/ionisation and time-of-flight mass spectrometry), FhuAΔCVFtev (FhuA Δ1-159_C545_V548_F501_tev), CD (circular dichroism), ESI-MS (electrospray ionization-mass spectrometry

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• , these clusters grow into stable crystal-like structures such that the hydrogel functions similarly to a block copolymer with hard segments composed of micro-crystalline methylated α-CD and softer segments composed of polyethylene glycol in the hydrogel. The preparations of the copolymers of either N,N

Synthesis, structure, and mechanical properties of silica nanocomposite polyrotaxane gels

• Kazuaki Kato,
• Daisuke Matsui,
• Koichi Mayumi and
• Kohzo Ito

Beilstein J. Org. Chem. 2015, 11, 2194–2201, doi:10.3762/bjoc.11.238

• progress. Experimental Materials Crude polyrotaxane consisting of polyethylene glycol (PEG, Mn = 32,000) and α-cyclodextrin (CD) were purchased from Advanced Softmaterials, Inc. The crude polyrotaxane was purified by repeated reprecipitation from its DMSO solution into deionized water. The obtained

Hexacoordinate Ru-based olefin metathesis catalysts with pH-responsive N-heterocyclic carbene (NHC) and N-donor ligands for ROMP reactions in non-aqueous, aqueous and emulsion conditions

• Shawna L. Balof,
• K. Owen Nix,
• Matthew S. Olliff,
• Sarah E. Roessler,
• Arpita Saha,
• Kevin B. Müller,
• Ulrich Behrens,
• Edward J. Valente and
• Hans-Jörg Schanz

Beilstein J. Org. Chem. 2015, 11, 1960–1972, doi:10.3762/bjoc.11.212

• monomer liquidity and polyethylene glycol (PEG) based Emulgin® B3 as surfactant which was previously vigorously stirred for 1 h and then further emulsified using a sonication probe for another 5 min establishing the microemulsion. The emulsion polymerization reactions were conducted at less favorable

Influence of length and flexibility of spacers on the binding affinity of divalent ligands

• Susanne Liese and
• Roland R. Netz

Beilstein J. Org. Chem. 2015, 11, 804–816, doi:10.3762/bjoc.11.90

• ratio lp/L ≈ 10 and thus correspond to the very stiff limit. Polyethylene glycol (PEG) with a persistence length of about lp = 0.38 nm on the other hand is characterized by a ratio smaller than lp/L = 0.08 and thus correspond to the flexible limit [23]. Effective concentration – harmonic spring and

Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer

• Florian Hamon,
• Claire Blaszkiewicz,
• Marie Buchotte,
• Estelle Banaszak-Léonard,
• Hervé Bricout,
• Sébastien Tilloy,
• Eric Monflier,
• Christine Cézard,
• Laurent Bouteiller,
• Christophe Len and
• Florence Djedaini-Pilard

Beilstein J. Org. Chem. 2014, 10, 2874–2885, doi:10.3762/bjoc.10.304

• over a typical range of 4000–100 Da. The mass spectra were collected as a continuum profile data. Accurate mass measurement was achieved using polyethylene glycol as the internal reference mass with a resolving power set to a minimum of 10,000 (10% valley). NMR experiments were performed at 300.13 and

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

• et al. have reported that a number of α-CDs spontaneously thread onto polyethylene glycol (PEG) and form necklace-like supramolecular assemblies [6][7]. The latter are referred to as polypseudorotaxanes (PPRXs), since the release of α-CD from the polymer chain can be achieved upon dissolution in

Synthesis of graft polyrotaxane by simultaneous capping of backbone and grafting from rings of pseudo-polyrotaxane

• Kazuaki Kato,
• Katsunari Inoue,
• Masabumi Kudo and
• Kohzo Ito

Beilstein J. Org. Chem. 2014, 10, 2573–2579, doi:10.3762/bjoc.10.269

• , 277-0882, Japan 10.3762/bjoc.10.269 Abstract Graft polyrotaxanes, with poly(ε-caprolactone) (PCL) graft chains on the ring components were synthesized by the simultaneous ring-opening polymerization of ε-caprolactone from both ends of the backbone polymer, an end-functionalized polyethylene glycol

Efficient CO₂ capture by tertiary amine-functionalized ionic liquids through Li⁺-stabilized zwitterionic adduct formation

• Zhen-Zhen Yang and
• Liang-Nian He

Beilstein J. Org. Chem. 2014, 10, 1959–1966, doi:10.3762/bjoc.10.204

• (mol CO2 absorbed per mol of base) through the formation of zwitterionic adducts being stabilized by Li+. Keywords: carbon capture and sequestration; CO2 chemistry; coordination effect; ionic liquid; polyethylene glycol; zwitterionic adducts; Introduction Carbon capture and sequestration (CCS) from

• ). Notably, equimolar CO2 absorption was obtained using task-specific ionic liquids (TSILs) with the phosphonium cation containing long alkyl chains and anions derived from AAs (prolinate and methioninate) [36], or AA salts with bulky N-substituents in polyethylene glycol (PEG) solution [37]. However

Carbohydrate PEGylation, an approach to improve pharmacological potency

• M. Eugenia Giorgi,
• Rosalía Agusti and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147

• polyethylene glycol (PEG), known as PEGylation, has been widely used to improve the bioavailability of proteins and low molecular weight drugs. The covalent conjugation of PEG to the carbohydrate moiety of a protein has been mainly used to enhance the pharmacokinetic properties of the attached protein while

• multiarm PEGs, with the aim to increase the loading of the active sugar. Multivalent glycomolecules have proven to mediate or inhibit a variety of biological or pathological processes [17][23]. Review Polyethylene glycol (PEG) derivatives Polyethyleneglycol is an amphiphilic polymer consisting of repeating

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• styrene and cross-linked divinylbenzene [20]. At present, there are mainly three classes of solid carriers: traditional polystyrene (PS), polyethylene glycol (PEG)-functionalized PS (such as TentaGel-supports [47]) and pure PEG-based resins such as PEGA resin [48] and ChemMatrix [49]. Shelton et al

• (lipidation) or methoxy polyethylene glycol (PEG) polymers (PEGylation) [14]. These two strategies are based on substantially different mechanisms, which can lead to a remarkable increase of the potential utility of peptides as pharmaceuticals. Lipidation of peptides: In general, the half-life extension of

• be selectively modified with activated (mainly N-hydroxysuccinimidyl (NHS) esters) PEG. Small polyethylene glycol units up to 2 kDa can be introduced on the solid support [99]. The introduction of larger PEG units has to be carried out in solution. Therefore, side-chain protecting groups during the

Amyloid-β probes: Review of structure–activity and brain-kinetics relationships

• Todd J. Eckroat,
• Abdelrahman S. Mayhoub and
• Sylvie Garneau-Tsodikova

Beilstein J. Org. Chem. 2013, 9, 1012–1044, doi:10.3762/bjoc.9.116

• the BBB in vivo. This disappointing result could be appointed to the excessively high lipophilicity of the compound. To improve the pharmacokinetic profile of 94, the [18F]-labeled analogue 96 was designed as an imaging probe [72]. Compound 96, which contains an [18F] end-capped polyethylene glycol

Synthesis and evaluation of cell-permeable biotinylated PU-H71 derivatives as tumor Hsp90 probes

• Tony Taldone,
• Anna Rodina,
• Erica M. DaGama Gomes,
• Matthew Riolo,
• Hardik J. Patel,
• Raul Alonso-Sabadell,
• Danuta Zatorska,
• Maulik R. Patel,
• Sarah Kishinevsky and
• Gabriela Chiosis

Beilstein J. Org. Chem. 2013, 9, 544–556, doi:10.3762/bjoc.9.60

• cancer cell decreased. With regards to linker nature, the polyethylene glycol linker containing derivatives (i.e., 2a, 2h and 2i) performed poorest by this measure. Unexpectedly, derivatives 2g and 2f both containing the same 15-atom linker and differing only by the presence of H (on derivative 2g) or

Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker

• Mayeul Collot,
• Steffen Eller,
• Markus Weishaupt and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 97–105, doi:10.3762/bjoc.9.13

• hydrolysis or enzymatic reactions. There are different variations of pure polystyrene resins. Jandajel resin for example features crosslinking of PS chains by tetrahydrofuran derivatives [29][30]. To improve the swelling behavior of PS resins in polar solvents, the PS core was grafted with polyethylene

• glycol (PEG) chains [31], resulting in solid supports such as Tentagel, Hypogel or Argogel. These resins were successfully used for the synthesis of peptides [31]. Meldal and co-workers developed PEGA resins [32] with good swelling behavior in water and polar solvents. Since the amide bonds of this solid

An improved synthesis of a fluorophosphonate–polyethylene glycol–biotin probe and its use against competitive substrates

• Hao Xu,
• Hairat Sabit,
• Gordon L. Amidon and
• H. D. Hollis Showalter

Beilstein J. Org. Chem. 2013, 9, 89–96, doi:10.3762/bjoc.9.12

• ). In this study we have designed a novel synthetic route to a known FP probe linked by polyethylene glycol to a biotin tag (FP–PEG–biotin). Our route markedly increases the efficiency of the probe synthesis and overcomes several problems of a prior synthesis. As a proof of principle, FP–PEG–biotin was

Chemical modification allows phallotoxins and amatoxins to be used as tools in cell biology

• Jan Anderl,
• Hartmut Echner and
• Heinz Faulstich

Beilstein J. Org. Chem. 2012, 8, 2072–2084, doi:10.3762/bjoc.8.233

• derivative (8 residues) are comparable, we argue that arginine residues are more effective in mediating internalization of phalloidin than are lysine residues. For phalloidin bound to methoxy-polyethylene-glycol we found that cytotoxicity strictly depended on the molecular weight of the polymer chain (Figure

Combined bead polymerization and Cinchona organocatalyst immobilization by thiol–ene addition

• Kim A. Fredriksen,
• Tor E. Kristensen and
• Tore Hansen

Beilstein J. Org. Chem. 2012, 8, 1126–1133, doi:10.3762/bjoc.8.125

• dithiol 5 was easily obtained from esterification of 3-mercaptopropionic acid and propane-1,3-diol [14]. Trivinyl ether 6, polyethylene glycol (PEG) dimethacrylate 7, diacrylate 8 and diallyl ether 9 are all commercially available compounds. For thiol–ene additions via the radical pathway, the order of

Coupled chemo(enzymatic) reactions in continuous flow

• Ruslan Yuryev,
• Simon Strompen and
• Andreas Liese

Beilstein J. Org. Chem. 2011, 7, 1449–1467, doi:10.3762/bjoc.7.169

• (Scheme 1). Retention of the cofactor was achieved by its covalent binding to polyethylene glycol (PEG) with a molecular weight of 10 kDa. The reactor was operated continuously for 48 days under sterile conditions. A maximal conversion of 99.7% and a space-time yield (STY) of 42.5 g L−1 day−1 were reached

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

• surface active initiator. By contrast, the surface active polyethylene glycol azo-initiator yielded polymers almost free of homopolymers with a low blockiness when acrylamide and styrene were copolymerized. Wu et al. used the same principle but with monomers having the ability to copolymerize alternately

• require very high polymerization temperatures. Star copolymers of polyethylene glycol and polypropylene glycol were crosslinked in inverse miniemulsion via an esterification reaction with a dithiodicarboxylic acid to yield nanogels [124]. The disulfide bonds were subsequently cleaved by reduction to yield

Poly(glycolide) multi-arm star polymers: Improved solubility via limited arm length

• Florian K. Wolf,
• Anna M. Fischer and
• Holger Frey

Beilstein J. Org. Chem. 2010, 6, No. 67, doi:10.3762/bjoc.6.67

• via calibration with polyethylene glycol (PEG) standards. The obvious underestimation of the molecular weight by SEC is attributed to the peculiar spherical geometry of the multi-arm star copolymer and has also been observed with other star polymers. The polydispersities of the materials are in the