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

Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers

• Thorbjørn Terndrup Nielsen,
• Catherine Amiel,
• Laurent Duroux,
• Kim Lambertsen Larsen,
• Lars Wagner Städe,
• Reinhard Wimmer and
• Véronique Wintgens

Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

• have shown tremendous potential as drug-delivery vehicles due to their ability to encapsulate drugs and ensure delivery to specific tissues and organs. Nanoparticles in the size range of 50–200 nm have shown very promising results due to their ability to penetrate and accumulate in the highly porous

• group can lead to enhanced stability [5]. An example of such an approach is Cerulean CRLX101, a polymeric CPT conjugate which is currently in clinical trials [6]. Albeit, the CPT polymers reported are potential drug-delivery systems for CPT, they do not by themselves form nanoparticles of the desired

• size. Interaction with suitable correspondent polymers with pendent cyclodextrins may form nanoparticles with the target properties. In recent years cyclodextrin (CD) polymer-based drug-delivery systems have attracted much attention in this field [7][8]. CDs are cyclic sugar molecules constituted of

Release of β-galactosidase from poloxamine/α-cyclodextrin hydrogels

• César A. Estévez,
• José Ramón Isasi,
• Eneko Larrañeta and
• Itziar Vélaz

Beilstein J. Org. Chem. 2014, 10, 3127–3135, doi:10.3762/bjoc.10.330

• absorbing considerable amounts of water, and are suitable for a variety of pharmaceutical and biomedical applications, such as drug delivery and tissue engineering. In particular, hydrogels are excellent vehicles for proteins due to their high water content, good compatibility, and controllable release

• , which can be used as supramolecular drug delivery systems [11]. Thus, cyclodextrin-based physical hydrogels assembled through microcrystalline formation are based upon the aggregation of polypseudorotaxane structures [12]. In the case of reverse Tetronics, α-cyclodextrin (composed of six glucose units

Synthesis and characterization of pH responsive D-glucosamine based molecular gelators

• Navneet Goyal,
• Hari P. R. Mangunuru,
• Bargav Parikh,
• Sonu Shrestha and
• Guijun Wang

Beilstein J. Org. Chem. 2014, 10, 3111–3121, doi:10.3762/bjoc.10.328

• be effective LMWGs, including derivatives from amino acids, carbohydrates, and cholesterols derivatives [8][9][10][11][12][13][14][15][16]. The reversible organogels and hydrogels have been explored for many applications including drug delivery, protein binding and separation, tissue engineering, and

• slowly to the aqueous phase under neutral conditions. Under acidic conditions (pH 1.9), on the other hand, naproxen was released rapidly from the gel phase. The compounds reported on herein may be useful for triggered release drug delivery systems under acidic environment. Experimental Gelation test In

Conjugates of methylated cyclodextrin derivatives and hydroxyethyl starch (HES): Synthesis, cytotoxicity and inclusion of anaesthetic actives

• Lisa Markenstein,
• Antje Appelt-Menzel,
• Marco Metzger and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 3087–3096, doi:10.3762/bjoc.10.325

• was already discussed by Szejli as a very promising candidate for parenteral drug delivery [17], but it was placed back because of its high toxicity [5][18][19]. Therefore our aim was to conjugate DIMEB for the first time to a polymeric backbone, which should hinder cellular uptake. CD polymers are

• like chitosane [29], alginate [24] and dextrane [28] is advantageous for the design of drug delivery systems because of the low toxicities and biodegradabilities of those polymers. Among the various coupling reactions, the [2 + 3] cycloaddition of alkynes and azides, the so-called Huisgen reaction [30

Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers

• Milo Malanga,
• Mihály Bálint,
• István Puskás,
• Kata Tuza,
• Tamás Sohajda,
• László Jicsinszky,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3007–3018, doi:10.3762/bjoc.10.319

• used for layer-by-layer film formation [12]. The synthesis and characterization of a nanosized quaternary ammonium β-CD polymer with high load capacity of the anticancer drug doxorubicin has been described as well as its application as drug delivery carriers across the blood–brain barrier [13]. The

Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery

• Anxo Fernández-Ferreiro,
• Noelia Fernández Bargiela,
• María Santiago Varela,
• Maria Gil Martínez,
• Maria Pardo,
• Antonio Piñeiro Ces,
• José Blanco Méndez,
• Miguel González Barcia,
• Maria Jesus Lamas and
• Francisco.J. Otero-Espinar

Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308

• conjunctiva sac. However, it has been shown that after a single blink, only 10 µL of the solution remains [7]. In this context, pharmaceutical researchers have paid special attention to the development of ophthalmic drug delivery systems during the last decade. Different strategies have been studied to

• patient compliance and comfort [10]. Specifically, stimuli-responsive polymer hydrogels have recently attracted special attention as drug delivery systems due to their capacity to respond to changing environmental conditions such as ion composition, pH, temperature, presence of chemicals, or changes on

• -Hydroxypropyl-β-cyclodextrin (HPBCD) and sulfobutyl ether-β-cyclodextrin (SBECD) are two chemically modified cyclodextrins frequently used as vehicles to improve drug solubility. The aim of this work is to obtain an ophthalmic drug delivery system for the release of fluconazole (FC) based on the use of ion

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

• well-defined structure, low toxicological or pharmacological activity, and good solubility in water. For example, the inclusion of active substances in CDs can reduce their undesirable storage or metabolism degradation, which has led research on CDs to focus on controlled drug delivery [4]. In the food

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

• and forms a hydrophilic layer on the surface of LPs [28]. It is not recognized by RES, which leads to a prolonged retention in circulation (stealth characteristics), and shows the enhanced permeability retention (EPR) effect [36]. PEG-LP is widely used as a drug carrier to realize the targeted drug

• delivery of anticancer drugs [28]. PEG-LP encapsulating DOX is commercially available as DOXIL/CAELYX® [28]. In addition, PEG-LPs are also utilized as long-circulating drug carriers for protein drugs and nucleic acids [37][38]. Thus, PEG-LPs are representative drug carriers and CD PPRXs of PEG-LPs could be