Oligomeric epoxide–amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

• Julian Fischer and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2803–2811, doi:10.3762/bjoc.9.315

• solubility, whereas these bondings are increasingly disrupted on heating [3]. These LCST-type polymers are of interest for the development of e.g. hydrogels and drug delivery systems [2][4]. One of the most prominent LCST polymers is poly(N-isopropylacrylamide) (PNIPAM), which exhibits a LCST of about 32 °C

Polymeric redox-responsive delivery systems bearing ammonium salts cross-linked via disulfides

• Christian Dollendorf,
• Martin Hetzer and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 1652–1662, doi:10.3762/bjoc.9.189

• (DEAAm); Introduction Hydrogels with stimuli-responsive properties, in combination with targeted release of embedded drugs, have emerged as a fascinating class of biomedical materials and attracted great interest in medical science, polymeric biotherapeutics and drug delivery in general [1][2][3][4]. In

• delivery [5][6][7]. In general, temperature- and pH-responsive hydrogels containing hydrophilic monomers show low toxicity along with a high efficiency in drug delivery [8]. Besides, cross-linked cationic nanogels have been suggested as DNA delivery systems [9][10][11]. Hamamoto et al. reported a cross

A³-Coupling catalyzed by robust Au nanoparticles covalently bonded to HS-functionalized cellulose nanocrystalline films

• Jian-Lin Huang,
• Derek G. Gray and
• Chao-Jun Li

Beilstein J. Org. Chem. 2013, 9, 1388–1396, doi:10.3762/bjoc.9.155

• for CNCs include nanocomposite formulation, polymer reinforcement, drug delivery [27], enzyme immobilization [28], biomedical applications [29] and as templates for the synthesis of nanomaterials [30]. The deposition of metal nanoparticles onto the surface of CNCs can lead to new nano-heterogeneous

The synthesis of well-defined poly(vinylbenzyl chloride)-grafted nanoparticles via RAFT polymerization

• John Moraes,
• Kohji Ohno,
• Guillaume Gody,
• Thomas Maschmeyer and
• Sébastien Perrier

Beilstein J. Org. Chem. 2013, 9, 1226–1234, doi:10.3762/bjoc.9.139

• preparing highly monodisperse core–shell nanoparticles, which hold great promise for a range of applications such as drug-delivery vectors or colloidal-crystal self-assemblies [10][11]. RAFT polymerization initiated from preformed inorganic nanoparticles enables the grafting of polymer shells from the

Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests

• Sophie Fourmentin,
• Anca Ciobanu,
• David Landy and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1185–1191, doi:10.3762/bjoc.9.133

• contributor to the driving force of complex formation [15]. The accumulation of basic understanding is essential for the formulation of precise docking programs, which estimate and screen the binding of drug candidates for biological receptors [16][17]. Practical applications of native β-CD, such as drug

• delivery [18][19], extraction of pollutants from soil [20][21][22][23], homogenous catalysis [24], and microbial degradation [25] are limited by both its low aqueous solubility (1.8 wt % at 25°C) and its moderate complexing ability. Especially hydrophobic guests form channel inclusion compounds with β-CD

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

• Jiayang Li,
• Yi Kuang,
• Junfeng Shi,
• Yuan Gao,
• Jie Zhou and
• Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

• frequently served as scaffolds for tissue engineering and as carriers for drug delivery [1][2][3][4]. In the applications of drug delivery, it is common to use hydrogels made of biodegradable polymers to encapsulate therapeutic agents for controlled release of drugs by adjusting the pore sizes and

• ][21][22][23][24][25] presents an exciting opportunity for developing new types of biomaterials [26][27][28][29]. While the early works have centered on the use of nanofibers of oligopeptides to form hydrogels as a passive scaffold for tissue engineering and drug delivery [30], the seminal work by

A peptidic hydrogel that may behave as a “Trojan Horse”

• Nicola Castellucci,
• Giorgio Sartor,
• Natalia Calonghi,
• Carola Parolin,
• Giuseppe Falini and
• Claudia Tomasini

Beilstein J. Org. Chem. 2013, 9, 417–424, doi:10.3762/bjoc.9.44

• confocal microscopy, fluorescent hydrogels were prepared, introducing the fluorescent dansyl moiety into the mixture. Keywords: amino acids; confocal microscopy; controlled release; hydrogel; low molecular weight hydrogelator; Introduction Drug delivery is an important topic in the finding of successful

• transition. They have a wide range of applications in biomaterials, biosensors, tissue engineering, and drug delivery [12][13][14][15]. The interest in these materials as tools for the controlled release of drugs is mainly linked to their capability to release gel-entrapped molecules in response to external

Inclusion of the insecticide fenitrothion in dimethylated-β-cyclodextrin: unusual guest disorder in the solid state and efficient retardation of the hydrolysis rate of the complexed guest in alkaline solution

• Dyanne L. Cruickshank,
• Natalia M. Rougier,
• Raquel V. Vico,
• Susan A. Bourne,
• Elba I. Buján,
• Mino R. Caira and
• Rita H. de Rossi

Beilstein J. Org. Chem. 2013, 9, 106–117, doi:10.3762/bjoc.9.14

• ; hydrolysis; inclusion complex; Introduction Whereas cyclodextrins (CDs) have been employed for many years in the pharmaceutical industry to modify drug-delivery properties, the application of CD technology to the improvement of agrochemicals is a more recent innovation [1][2]. Nevertheless, very significant

Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

• Daniel Fürniss,
• Timo Mack,
• Frank Hahn,
• Sidonie B. L. Vollrath,
• Katarzyna Koroniak,
• Ute Schepers and
• Stefan Bräse

Beilstein J. Org. Chem. 2013, 9, 56–63, doi:10.3762/bjoc.9.7

• ][24][25], have emerged as powerful tools in the context of drug delivery [26][27][28][29], peptidomimetics and other biologically relevant applications [28][30][31][32] as well as materials science [33][34]. During the last decade the synthesis of polyamines and peptoids has been well established on

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• ; cross-linked polymers; cyclodextrin; drug delivery; nanosponges; Review Recent advances in nanotechnology demonstrate the increased attention that is now being paid to the supramolecular assembly of simple components for therapeutic and diagnostic purposes. The design of new biomaterials based on

• cyclodextrin nanosponges in drug delivery By virtue of their biocompatibility and versatility, nanosponges have many potential applications in the pharmaceutical field. One recent EU commission report focused on the use of cyclodextrin nanosponges as a promising innovative system for drug delivery. They can be

• side effects. Different drug delivery systems have been designed to modify the release kinetics of medicinal products. The drug release kinetics from nanosponges can be obtained with a prolonged release profile over time. Previous in vitro studies showed that flurbiprofen was released slowly from β-CD

Cyclodextrin-induced host–guest effects of classically prepared poly(NIPAM) bearing azo-dye end groups

• Gero Maatz,
• Arkadius Maciollek and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 1929–1935, doi:10.3762/bjoc.8.224

• techniques. Water-soluble polymers, which exhibit a lower critical solution temperature (LCST), e.g., many poly(N-alkylacrylamides), have found numerous practical applications in waterborne smart materials such as bioactive surfaces, selective bioseparation, or hyperthermia-induced drug delivery [14

Influence of intramolecular hydrogen bonds on the binding potential of methylated β-cyclodextrin derivatives

• Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1890–1895, doi:10.3762/bjoc.8.218

• industrial scale [15]. Methylated CDs have already found several applications in drug delivery [10] and polymer chemistry [16]. They allow radical polymerizations of hydrophobic vinyl monomers in homogenous aqueous solution [17][18][19][20] and living RAFT polymerizations as well [21]. Methylated CDs are

• the future help to design improved hosts based on β-CD for specific applications such as drug delivery [49], removal of pollutants [50][51][52][53], catalysis [54] or smart materials [55]. Experimental 4-tert-Butylbenzoic acid and adamantane-1-carboxylic acid and β-CD derivative 3 were purchased from

Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery

• Jan Hoyer,
• Ulrich Schatzschneider,
• Michaela Schulz-Siegmund and
• Ines Neundorf

Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204

• the specific cell type. Finally, we could show that conjugation of a functionalized cymantrene with (sC18)2 leads to significant reduction of its IC50 value in tumor cells compared to the respective sC18 conjugate, proving that dimerization is a useful method to increase the drug-delivery potential of

• a cell-penetrating peptide. Keywords: anti-tumor agents; cell-penetrating peptides; drug delivery; internalization studies; organometallic complexes; peptides; Introduction A substantial problem concerning promising drug candidates is often their incapacity to reach their full therapeutic

Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2012, 8, 1543–1551, doi:10.3762/bjoc.8.175

• development of drug-delivery systems [3]. Synthetic bilayer vesicles are a versatile model for biological cell membranes, and there are a substantial number of reports on synthetic glycolipids that mimic the glycocalyx [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23]. Multivalent

Restructuring polymers via nanoconfinement and subsequent release

• Alan E. Tonelli

Beilstein J. Org. Chem. 2012, 8, 1318–1332, doi:10.3762/bjoc.8.151

• as drug delivery and suture manufacturing. However, its relatively poor physical properties limit its use in load-bearing applications. An attempt to improve the strength of PCL was made by processing with α-cyclodextrin (α-CD). First an inclusion complex (IC) between PCL and α-CD was formed, and

• preferentially degraded by the enzyme. Regulation of their biodegradation behavior, through formation of and coalescence from CD ICs, may enhance the use of block copolymers in drug delivery and controlled release systems, because of its decisive importance in these applications. Coalesced polymer blends

Organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates of isatins

• Hang Zhang,
• Shan-Jun Zhang,
• Qing-Qing Zhou,
• Lin Dong and
• Ying-Chun Chen

Beilstein J. Org. Chem. 2012, 8, 1241–1245, doi:10.3762/bjoc.8.139

• Hang Zhang Shan-Jun Zhang Qing-Qing Zhou Lin Dong Ying-Chun Chen Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China 10.3762/bjoc.8.139 Abstract The

Cyanoethylation of the glucans dextran and pullulan: Substitution pattern and formation of nanostructures and entrapment of magnetic nanoparticles

• Kathrin Fiege,
• Heinrich Lünsdorf,
• Sevil Atarijabarzadeh and
• Petra Mischnick

Beilstein J. Org. Chem. 2012, 8, 551–566, doi:10.3762/bjoc.8.63

• polymer particle allows for control by magnetic fields. Magnetic separation techniques or magnetic particle imaging can be performed. Applications, such as drug delivery or targeting, hyperthermia and biosensing can be realized [16][17][18]. Binding of stabilizing organic shells to ferric oxide

• years their importance for special biochemical or pharmaceutical applications, such drug delivery or biosensor technology, has grown, due to their special properties such as water solubility, low viscosity and film formation [24][25][26][27]. Pullulan is a homopolysaccharide of D-glucose secreted by

Hyperbranched polyethylenimine bearing cyclodextrin moieties showing temperature and pH controlled dye release

• Indra Böhm,
• Susanne Katharina Kreth and
• Helmut Ritter

Beilstein J. Org. Chem. 2011, 7, 1130–1134, doi:10.3762/bjoc.7.130

• : anthraquinone; cyclodextrin; drug delivery; polyethylenimine; release; Introduction The development of novel materials and their use as drug delivery systems has gained increased interest in the last few decades [1][2][3]. In this context, certain stimuli responsive behaviors are required [4][5]. Hence, the

• compounds for a drug delivery system in combination with hyperbranched cationic polyethylenimine bearing covalently attached β-CDs 3. As outlined in Scheme 1, each dye, 1 and 2, was mixed with 3 in water to form a salt 4 and a host–guest complex 5, respectively. Additionally, both dyes were mixed together

• released separately or simultaneous in response to different external stimuli. Conclusion The controlled release of different dyes from a drug delivery system based on hyperbranched polyethylenimine was investigated. The ionic interactions between the PEI scaffold and the hydroxy moieties of 5,8-dichloro

Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

• Guijun Wang,
• Hao Yang,
• Sherwin Cheuk and
• Sherman Coleman

Beilstein J. Org. Chem. 2011, 7, 234–242, doi:10.3762/bjoc.7.31

• into 3-dimensional networks. The resulting gels may find applications as soft materials for drug delivery, enzyme immobilization, scaffolds for tissue engineering, etc. [10][11][12][13][14]. The structures of LMWGs span a diverse range; carbohydrates have frequently been used in the synthesis of LMWGs

• matrices for enzymes, DNA, and drug delivery systems [22][23][24][25][26][27][28]. Glucose, in particular, is a versatile building block for the preparation of various small molecule gelators [30][31][32][33][34][35][36][37], as it is relatively easy to obtain substituted products by selective

Michael-type addition of azoles of broad-scale acidity to methyl acrylate

• Sławomir Boncel,
• Kinga Saletra,
• Barbara Hefczyc and
• Krzysztof Z. Walczak

Beilstein J. Org. Chem. 2011, 7, 173–178, doi:10.3762/bjoc.7.24

• and which, after acidic hydrolysis [43], can be anchored to drug delivery systems, including, e.g., chemically modified carbon nanotubes, via amide bonds. Examples of azole derivatives as important therapeutic agents. Michael-type addition of azoles of broad-scale acidity 1a–h to methyl acrylate (2

Exceptionally small supramolecular hydrogelators based on aromatic–aromatic interactions

• Junfeng Shi,
• Yuan Gao,
• Zhimou Yang and
• Bing Xu

Beilstein J. Org. Chem. 2011, 7, 167–172, doi:10.3762/bjoc.7.23

• ., response to external stimuli and flow in response to shear force [2]) and applications in several areas (e.g., bioanalysis [3][4], chemical sensing [5][6][7], food processing [8], cosmetics [9], drug delivery [10][11], and tissue engineering [12][13]). Inspired by the existing and potential applications of

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

• since the monomer is very reactive and the polymerization can be conducted in the presence of a large amount of water. Moreover, the polymers were shown to be able to pass the blood brain barrier, making them ideal candidates as vectors for drug delivery. Therefore it is not surprising that several

• polymeric shell in comparison to the traditional monolithic morphology. Such capsular morphologies are suitable for drug delivery applications since the liquid in the core (e.g., water) has usually a higher solvent power than hydrophilic monomers. As for other techniques used to encapsulate drugs such as

Pyridinium based amphiphilic hydrogelators as potential antibacterial agents

• Sayanti Brahmachari,
• Sisir Debnath,
• Sounak Dutta and
• Prasanta Kumar Das

Beilstein J. Org. Chem. 2010, 6, 859–868, doi:10.3762/bjoc.6.101

• ; hydrogel; pyridinium; self-assembly; Introduction Gels are an outstanding group of soft materials lying at the interface of solid and liquid, and find numerous applications in various fields including tissue engineering, biosensors, food processing, cosmetics, photography, controlled drug delivery etc. [1

Chiral gels derived from secondary ammonium salts of (1R,3S)-(+)-camphoric acid

• Tapas Kumar Adalder,
• N. N. Adarsh,
• Ravish Sankolli and
• Parthasarathi Dastidar

Beilstein J. Org. Chem. 2010, 6, 848–858, doi:10.3762/bjoc.6.100

• continuous expanding area on account of their various promising applications [11][12][13]. Broadly, LMOGs are used in cosmetics [14], tissue engineering [15], drug delivery and biomedical applications [16][17][18][19], art conservation [20][21][22], templated synthesis of nanoparticles [23][24], capture and

Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)s

• Richard Hoogenboom,
• Martin W. M. Fijten,
• Guido Kickelbick and
• Ulrich S. Schubert

Beilstein J. Org. Chem. 2010, 6, 773–783, doi:10.3762/bjoc.6.96

• ; Introduction Nowadays, well-defined polymer structures are of major importance for the development of ever more sophisticated and complex materials, e.g., applications in drug delivery or as adaptive materials. Star-shaped polymers are especially interesting since their properties are distinctly different from