Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• traditional semiconductor quantum dots (QDs). Particularly in the areas of live imaging and drug delivery, due to their water solubility, low toxicity and photo- and chemical stability. Carbohydrates are readily available chiral biomolecules in nature which offer an attractive and cheap starting material from

• relevant molecules have become very useful for drug delivery, sensing and catalysis to name just a few applications. As a result, nanomaterials exhibiting novel electronic and optical properties, having controlled size, geometry, surface distribution and functionality have been developed as materials for

• fluorescent nanomaterials combined with their myriad of applications, has led to CDs being hailed as the potential non-toxic successors to traditional semiconductor QDs, particularly in the areas of live imaging and drug delivery. Synthetic approaches to access CDs can be classified into two broad categories

Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties

• Maximilian Maier,
• Magnus S. Schmidt,
• Markus Ringwald and
• Christoph P. Fik

Beilstein J. Org. Chem. 2017, 13, 372–383, doi:10.3762/bjoc.13.40

• interest in the field of biomedical applications, e.g., for dental materials, artificial cornea, or drug-delivery systems, for which contact with body fluids is inevitable [17][18]. Whilst some of the resulting secondary di(meth)acrylamides end up being solids, tertiary di(meth)acrylamides can be obtained

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

• Monica Ferro,
• Franca Castiglione,
• Nadia Pastori,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2017, 13, 182–194, doi:10.3762/bjoc.13.21

• many of their formulations, CDNS showed good swelling capability when contacted with water solutions, giving rise to homogeneous hydrogels potentially useful as drug carriers [7]. In order to obtain an effective control over the drug delivery procedure, several efforts have been made to explore how the

A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation

• Wangkhem P. Singh and
• Rajkumar S. Singh

Beilstein J. Org. Chem. 2017, 13, 138–149, doi:10.3762/bjoc.13.17

• such as acids or bases [17], metal ions [18], oxidation and reduction [19], reactive species enzymes, etc. Such responsive gel systems are highly desirable in stimuli-responsive sensor materials, drug delivery, catalysis, nano- and mesoscopic assemblies, light harvesting systems, and many others [20

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• ranging from room temperature to 250 °C [30]. Chemical synthesis by extrusion Extrusion is heavily relied upon within the pharmaceutical industry with regards to the formulation of drugs and their incorporation into drug delivery systems. However, extrusion has not been employed to carry out any organic

Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

• Atsushi Tamura,
• Asato Tonegawa,
• Yoshinori Arisaka and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2016, 12, 2883–2892, doi:10.3762/bjoc.12.287

• drug delivery [31]. Herein, alkynyl group-bearing fluorescent molecules were modified at the terminal azide group of the PRXs, and intracellular fluorescence imaging of the PRXs was performed to verify whether the terminally modified fluorescent molecules could be used for fluorescence imaging. First

• in 6 were almost entirely modified with fluorescent molecules. In our previous study relating to drug delivery applications of PRXs, fluorescent molecules were modified on the threading α-CDs in the PRXs to monitor intracellular uptake and localization of the PRXs [14][32][36][37]. To verify whether

• to be useful candidates in the fabrication or functionalization of supramolecular biomaterials, such as cross-linked hydrogels, surface immobilization, and drug delivery carriers for biomolecules [6]. Further studies relating to the biomaterials applications of azide group-terminated PRXs are

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

• anthryl signals) in the presence of the 1-adamantanol guest. This concept could be very useful in nucleic acid reactions of medicinal and biotechnological importance for new drug delivery systems. Unfortunately, the binding constants between CDs and nucleic acids remain relatively modest and close to

Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

• Eric Buchy,
• Branko Vukosavljevic,
• Maike Windbergs,
• Dunja Sobot,
• Camille Dejean,
• Simona Mura,
• Patrick Couvreur and
• Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

• Eric Buchy Branko Vukosavljevic Maike Windbergs Dunja Sobot Camille Dejean Simona Mura Patrick Couvreur Didier Desmaele Institut Galien (UMR CNRS 8612) Faculté de Pharmacie, Université Paris-Sud, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France Department of Drug Delivery, Helmholtz

• nanometric size confers to drug delivery systems unique properties which improve the pharmacokinetics and the biodistribution of many active compounds, thus increasing specificity, therapeutic efficacy and reducing systemic exposure and toxicity [1][2]. In recent years, many drug delivery systems have been

Stimuli-responsive HBPS-g-PDMAEMA and its application as nanocarrier in loading hydrophobic molecules

• Yongsheng Chen,
• Li Wang,
• Haojie Yu,
• Zain-Ul-Abdin,
• Ruoli Sun,
• Guanghui Jing,
• Rongbai Tong and
• Zheng Deng

Beilstein J. Org. Chem. 2016, 12, 939–949, doi:10.3762/bjoc.12.92

• attractive to academia and industry in recent years due to their special chemical and physical properties. In comparison with their linear counterpart, these polymers afford promising applications such as drug delivery [15][16][17], gene delivery [18][19][20][21] and catalysis [22][23]. Polystyrene is a

• biocompatible material with low polarity. It has been found that a hydrophobic polymer segment with low polarity was helpful in drug delivery systems and in the protection of drugs from degradation [12][24]. Star-like amphiphilic polymers can be prepared by grafting hydrophilic stimuli-responsive chains on

• important, because the LCST of PDMAEMA in water is near the human body temperature; a fact that might be exploited in drug delivery systems. We checked the light transmittance of the HBPS-g-PDMAEMA aqueous solution at a wavelength of 500 nm and a concentration of 10 mg/mL by using a UV–vis spectrophotometer

Optimized methods for preparation of 6^I-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives

• Eva Bednářová,
• Simona Hybelbauerová and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2016, 12, 349–352, doi:10.3762/bjoc.12.38

• industries [4]. These derivatives are usually mixtures of randomly substituted CDs. On the other hand, CD derivatives which are well-defined chemical individuals are well suited for separation science [5], chemosensors [6] or drug delivery [7] applications. These applications often involve a modification of

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

• Qing He,
• Gu Zhan,
• Wei Du and
• Ying-Chun Chen

Beilstein J. Org. Chem. 2016, 12, 309–313, doi:10.3762/bjoc.12.33

• Qing He Gu Zhan Wei Du Ying-Chun Chen Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, China 10.3762/bjoc.12.33 Abstract 7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• -soluble cyanine/β-CD derivatives have been efficiently prepared via CuAAC under simultaneous US/MW irradiation at 75 °C for 2 h (MW 15 W and US 20 W) in good yields (23% and 33%). These dyes were used as versatile carriers for drug delivery and optical imaging. Preparation of CD-grafted materials and CD

• drug delivery systems and toxic compounds scavengers, and have been obtained by grafting CDs into polymeric matrices. A multi-carrier for combined diagnostic and theranostic applications was obtained via the functionalization of carbon nanotubes with CD using a MW-assisted 1,3-dipolar cycloaddition. As

Aggregation behavior of amphiphilic cyclodextrins in a nonpolar solvent: evidence of large-scale structures by atomistic molecular dynamics simulations and solution studies

• Giuseppina Raffaini,
• Fabio Ganazzoli and
• Antonino Mazzaglia

Beilstein J. Org. Chem. 2016, 12, 73–80, doi:10.3762/bjoc.12.8

• have been usually investigated and characterized in water for their potential use as nanocarriers for drug delivery, but they can also aggregate in apolar solvents, as shown in the present paper through atomistic molecular dynamics simulations and dynamic light scattering measurements. The simulations

• molecular recognition [3] or nanocarriers for drug delivery [4]. In the recent past, the aggregation behavior of aCD was investigated in water, getting insights on the structures of free nanoassemblies [5][6] or in combination with therapeutic agents [7]. However, in some stages of preparation and

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

• ], chemical sensors [6] and drug delivery [7][8][9]. As discussed in a range of reviews [10][11][12][13][14] and books [15][16][17][18], cyclodextrins are naturally occurring cyclic oligosaccharides which are also produced industrially through the enzymatic metabolism of starch and related compounds. The

• substituents and the aggregation of the α-CD complexed portions of the AD-PEG chains. Part of the interest in these low molecular weight polymer systems arises because they are able to pass through the kidney membrane [89] and are consequently of interest as components of drug-delivery systems [89][90]. A

Recent advances in metathesis-derived polymers containing transition metals in the side chain

• Ileana Dragutan,
• Valerian Dragutan,
• Bogdan C. Simionescu,
• Albert Demonceau and
• Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

• confer an optimal set of capabilities that recommend them for diverse emerging application areas, e.g., as electro-optical and magnetic devices, for energy storage, nanomaterials, sensing, catalytic and drug-delivery systems [6][12][13][14]. Numerous synthetic routes have been explored to achieve the

• recent study, Tang and coworkers [52] performed a quantitative analysis of counterion exchange in cobaltocene-containing polyelectrolytes that are accessible by an initial ROMP, and subsequently derivatized with cobalt motifs. These results appear to be relevant for self-assembly and drug-delivery

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

• many supramolecular chemistry labs around the world. In addition, the chapter provided a short summary of four emerging themes in biomolecule recognition that are likely to garner increased attention over the next decade; Logic Devices, Biomolecule Responsive Materials, Drug Delivery, and Biomolecule

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

• Giuseppina Raffaini,
• Antonino Mazzaglia and
• Fabio Ganazzoli

Beilstein J. Org. Chem. 2015, 11, 2459–2473, doi:10.3762/bjoc.11.267

• -dependence of the supramolecular structures, or the pH dependence of water solubility, so as to improve our understanding of their activity as drug delivery systems [19][20] and of the biological fate of the assemblies [21][22]. The balance between the hydrophobic and the polar groups on the two CD rims

• or bilayer, or vesicles and nanospheres at appropriate concentrations. In the recent past, some of these structures have been selected to yield versatile and reliable carriers for drug delivery [3][50], and even for molecular recognition of polymers [51]. In this scenario, the proposed study can open

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

• their use as drug delivery vehicles. Here, we aim to form supramolecular nanoparticles (SNPs) by combining advantages of the reversible assembly properties of SNPs using host–guest interactions and of a stimulus-responsive moiety. The SNPs are composed of a core of positively charged poly(ethylene imine

• applications owing to control over their size, their assembly/disassembly, and the modular character for the versatile incorporation of agents aiming for imaging [3], photothermal therapy [4], drug delivery [5][6][7] and gene delivery [8][9][10] applications. Different approaches have been used to form SNPs

• charged polymers and dendrimers. In order to use these SNPs for biomedical applications, in particular for drug delivery, a stimulus-responsive self-assembled system is desired for controlled cargo release. Ferrocene (Fc) is a ubiquitous redox-responsive molecule that is associated with a reversible one

Preparation of Pickering emulsions through interfacial adsorption by soft cyclodextrin nanogels

• Shintaro Kawano,
• Toshiyuki Kida,
• Mitsuru Akashi,
• Hirofumi Sato,
• Motohiro Shizuma and
• Daisuke Ono

Beilstein J. Org. Chem. 2015, 11, 2355–2364, doi:10.3762/bjoc.11.257

• CD nanogels have been increasing in terms of drug delivery systems using the nanoporous cavities of the CDs and hydrogel networks, which can effectively store and release molecules [16][17]. However, to the best of our knowledge, the use of CD nanogels as Pickering emulsifiers has yet to be reported

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• water and could be used for drug delivery (Figure 18) [71]. A few years earlier the same authors used the same principle to synthesize amphiphilic mPEG-block-poly(profenamide-co-ester) copolymers that self-assembled in water and could be used for drug release [72]. As a follow up the same laboratory

Impact of multivalent charge presentation on peptide–nanoparticle aggregation

• Daniel Schöne,
• Boris Schade,
• Christoph Böttcher and
• Beate Koksch

Beilstein J. Org. Chem. 2015, 11, 792–803, doi:10.3762/bjoc.11.89

• controlled assembly of nanoparticles by means of biomolecules is crucial for biological and medical applications such as sensing [4], bioimaging [5], and medical diagnostics [6]. Although nanoparticles are also applied as targeted biomarkers and drug-delivery agents to tumor cells [7], only very little is

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

• Tor E. Kristensen

Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51

• '-diacetyl L-DOPA has since been used by many others as a protected L-DOPA derivative, useful for further synthetic manipulations, such as in biology-oriented materials science and drug delivery. Methods for O-acylation taking place in acetic acid are limited to acetylation, but use of inert organic solvents

C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation

• Roberto Romeo,
• Caterina Carnovale,
• Salvatore V. Giofrè,
• Maria A. Chiacchio,
• Adriana Garozzo,
• Emanuele Amata,
• Giovanni Romeo and
• Ugo Chiacchio

Beilstein J. Org. Chem. 2015, 11, 328–334, doi:10.3762/bjoc.11.38

• assumes particular interest according to its easily access and the well-known biological activity of many derivatives. In these last years, in fact, triazoles have gained considerable attention in medicinal chemistry, bioconjugation, drug-delivery, and materials science [33][34][35][36][37][38]. Moreover

Superstructures with cyclodextrins: Chemistry and applications II

• Gerhard Wenz

Beilstein J. Org. Chem. 2015, 11, 271–272, doi:10.3762/bjoc.11.30

• smart materials and drug delivery. These contributions to Cyclodextrin Chemistry are collected in this Thematic Series of the Beilstein Journal of Organic Chemistry. Gerhard Wenz Saarbrücken, January 2015

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• monodisperse size distribution of nanocapsules with favourable potential for intracellular drug delivery to tumour cells. Surface charges of anionic and cationic nanocapsules were demonstrated as −21 mV and +18 mV, respectively. The stability of CPT in simulated release media, SGF and SIF were maintained

• bioavailability of anticancer drugs should be improved [10]. Nanoparticulate drug delivery systems are promising in this field [11][12]. Nanoparticles are defined as submicron colloidal systems that include both nanospheres and nanocapsules. Nanospheres are defined as matrix systems whereas nanocapsules are core

• consideration of the disadvantages that limit the effectiveness of oral chemotherapy and the advantages of nanoparticular drug delivery systems, developing a strategy with nanoparticles and even nanocapsules might be very promising for oral delivery of anticancer agents. Nanocapsules are especially beneficial