Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine

• Xiayang Huang,
• Xinghua Zhang,
• Tianxin Qian,
• Junwei Ma,
• Lei Cui and
• Chunju Li

Beilstein J. Org. Chem. 2018, 14, 2236–2241, doi:10.3762/bjoc.14.198

• specific structures and interesting host–guest properties [21][22][23][24][25][26][27][28][29][30][31][32]. Water-soluble pillar[n]arene derivatives, especially those containing carboxylato moieties, showed low cell toxicity and good biocompatibility, and have been applied in biomedical applications such

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• lumiflavin (3Lum Ered*(cat/cat•−) ≈ +1.5 V vs SCE) as the photocatalyst in aqueous buffer (Scheme 4) [44]. This work highlights the great biocompatibility of organophotoredox methodology and also is an excellent demonstration of the type of chemoselectivity achievable using these methods. Apart from the

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• ][31][32][33][34][35]. Cyclodextrins (CDs), in particular, constitute appealing systems due to their biocompatibility, which allowed them to be approved by the FDA as human friendly products [36]. Thus, polycationic CDs might be used in principle as bimodal ligands for the simultaneous internalization

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• trifluoroethoxy group in suppressing the aggregation of phthalocyanine is extremely remarkable. Therefore, it is expected that an effective medical dye can be developed by using this excellent aggregation suppressing effect. On the other hand, improving the biocompatibility of phthalocyanine is as important as

• suppressing its aggregation property. It is also necessary to improve the water solubility of the lipophilic phthalocyanine in order to increase its biocompatibility [88][89]. One frequent method to increase the water solubility of phthalocyanine involves the combination of a biomolecule such as a sugar [90

• laser only to the target tumor cells. The features of ideal PDT agents include, among others: i) strong absorption in the red wavelength region; ii) non-aggregation property; iii) high biocompatibility; iv) good selectivity to cancer cells; v) high quantum yield of singlet oxygen [96]. Since the PDT

New bio-nanocomposites based on iron oxides and polysaccharides applied to oxidation and alkylation reactions

• Daily Rodríguez-Padrón,
• Alina M. Balu,
• Antonio A. Romero and
• Rafael Luque

Beilstein J. Org. Chem. 2017, 13, 1982–1993, doi:10.3762/bjoc.13.194

• have been widely reported for the preparation of nanocomposites with a great range of applications, due to their low cytotoxicity and notable biocompatibility and stability [33][34][35][36][37], their catalytic application is still lacking. In addition, these natural products are easily and

An efficient Pd–NHC catalyst system in situ generated from Na₂PdCl₄ and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

• Nan Sun,
• Meng Chen,
• Liqun Jin,
• Wei Zhao,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 1735–1744, doi:10.3762/bjoc.13.168

• polymers from the polymerization of ethylene oxide [67]. Owing to their significant advantages, including widely commercial availability, biocompatibility, chemical and thermal stability and ease to be derived, PEGs have been widely used as phase-transfer catalysts (PTC) or in the preparation of water

One-pot synthesis of block-copolyrotaxanes through controlled rotaxa-polymerization

• Jessica Hilschmann,
• Gerhard Wenz and
• Gergely Kali

Beilstein J. Org. Chem. 2017, 13, 1310–1315, doi:10.3762/bjoc.13.127

• because of its high biocompatibility and biodegradability [31][32][33]. Here should be noted that polyisoprene was already subjected to pseudopolyrotaxane formation, with limited success, i.e., with β-CD only oligoisoprenes (degree of polymerization < 9) could form complexes with low coverage (3.0%) [34

• monomers and CD derivatives. The resulting triblock-copolyrotaxanes might be good stocks for the synthesis of highly elastic slide-ring gels and hydrogels. Due to the biocompatibility of the constituents and the ability of the polyrotaxanes to self-assemble, these materials might also be applicable for

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

• comparison to spherical and star-shaped AuNPs. Saccharidic functionalization: the coating density Besides the inorganic core, the surrounding organic shell plays a crucial role in GAuNP chemical-physical properties. The organic functionalization, in fact, impart the stealth ability and biocompatibility of

• inspired by the availability of novel nanomaterials with specific capabilities [95]. AuNPs have attracted great attention in this field due to their unique characteristics of biocompatibility and easy fabrication, already outlined previously. In the last five years, significant examples on the use of

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

• Barbara Dmochowska,
• Karol Sikora,
• Anna Woziwodzka,
• Jacek Piosik and
• Beata Podgórska

Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138

• [22][23][24]. To overcome many problems associated with QASs, they were combined with sugars. We intended to obtain biologically active compounds – especially antibacterial and antifungal – with high biocompatibility and good biodegradation properties. Some examples of fused molecules containing QASs

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

• the development of superparamagnetic iron oxide nanoparticles (SPIONPs) because of their biocompatibility which allows there in vivo use both for diagnosis in magnetic resonance imaging and in therapy [1][2]. Most often, it is necessary to modify the surface of SPIONPs to increase the metabolic

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

• form hydrogels [84][85]. In particular, hydrogels formed by PEG and cyclodextrins have been investigated intensively because of the biocompatibility of their components. Interestingly, local crystallization of the polyrotaxane threaded cyclodextrins, sometimes called molecular necklaces [86], may form

Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides

• Madhuri Vangala and
• Ganesh P. Shinde

Beilstein J. Org. Chem. 2015, 11, 2289–2296, doi:10.3762/bjoc.11.249

• ) [4][5][6]. The strong affinity of the nitrogen in oxazoline towards metal makes the chiral derivatives excellent catalysts for asymmetrical transformations [7][8][9][10]. The amphiphilicity and biocompatibility of poly-2-substituted-2-oxazolines gained them recognition as biomaterials for polymer

Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Yumi Hirai,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224

• mice through a reduction in cholesterol levels [7][8][9]. Most recently, it was reported that HP-γ-CyD, which has great advantages in biocompatibility compared to HP-β-CyD, can also reduce the cholesterol accumulation in NPC-like cells [10]. However, a high dose of HP-β-CyD or HP-γ-CyD was necessary to

Synthesis and evaluation of the biostability and cell compatibility of novel conjugates of nucleobase, peptidic epitope, and saccharide

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum,
• Khalid Omar Al Footy,
• Khadija Omar Badahdah and
• Bing Xu

Beilstein J. Org. Chem. 2015, 11, 1352–1359, doi:10.3762/bjoc.11.145

• proteolytic stabilities of the conjugates depend on the functional peptidic epitopes. We found that TTPV is proteolytic resistant and LGFNI is susceptible to proteolysis. In addition, all the conjugates are compatible to the mammalian cells tested. Keywords: biocompatibility; biostability; nucleobase

Multivalent dendritic polyglycerolamine with arginine and histidine end groups for efficient siRNA transfection

• Fatemeh Sheikhi Mehrabadi,
• Hanxiang Zeng,
• Mark Johnson,
• Cathleen Schlesener,
• Zhibin Guan and
• Rainer Haag

Beilstein J. Org. Chem. 2015, 11, 763–772, doi:10.3762/bjoc.11.86

• and degrees of branching [5]. Additionally, dPG has multiple groups for further functionalization, high chemical stability, and good biocompatibility in vitro and in vivo [6][7][8]. All these characteristics make dPG an ideal scaffold for a broad range of applications from anti fouling [9] to

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

• Franziska Klitsche,
• Julian Ramcke,
• Julia Migenda,
• Andreas Hensel,
• Tobias Vossmeyer,
• Horst Weller,
• Silvia Gross and
• Wolfgang Maison

Beilstein J. Org. Chem. 2015, 11, 678–686, doi:10.3762/bjoc.11.77

• derivatives bearing an additional effector moiety may be used to generate stable particles with tailored properties, good solubility and biocompatibility. Suitable effectors in this context are PEG [31][32][33], zwitterions [34][35] or polyglycerols [36][37] which, when immobilized on NPs, may be used to tune

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

• al. [28]. We intended to conjugate the corresponding methylated mono-azido-β-CD derivatives to propargylated hydroxyethyl starch (HES). Advantages of HES are its very high aqueous solubility paired with good biocompatibility and its very low allergenic potential [33]. HES is in use for a long time

Detonation nanodiamonds biofunctionalization and immobilization to titanium alloy surfaces as first steps towards medical application

• Juliana P. L. Gonçalves,
• Afnan Q. Shaikh,
• Manuela Reitzig,
• Daria A. Kovalenko,
• Jan Michael,
• René Beutner,
• Gianaurelio Cuniberti,
• Dieter Scharnweber and
• Jörg Opitz

Beilstein J. Org. Chem. 2014, 10, 2765–2773, doi:10.3762/bjoc.10.293

• -existent toxicity and improved biocompatibility, in comparison to the unmodified DND, extends the applications of this carbon material from microelectronics, polishing and optical monitoring to biomedicine. Titanium and titanium-based alloys have been used as bone implant material for a long time, because

• achieve improved surface properties with enhanced wear behavior, corrosion resistance, and biocompatibility. Scharnweber et al. worked on biofunctionalization of titanium implant materials by immobilizing collagen type I and studied conformational changes caused by adsorptive immobilization [17][18

• oxide layer. Stability and biocompatibility investigations of the achieved coatings will then follow. Experimental Chemicals DND were purchased from Plasmachem GmbH (purity degree: 95%). All buffers where made from p.a. grade chemicals supplied by Merck KGaA and autoclaved before use. All other

A promising cellulose-based polyzwitterion with pH-sensitive charges

• Thomas Elschner and
• Thomas Heinze

Beilstein J. Org. Chem. 2014, 10, 1549–1556, doi:10.3762/bjoc.10.159

• with trimethylsilyl methacrylate [8][9]. Polybetaines, for example sulfobetaines, could be prepared from the reaction of a tertiary amine (monomer or polymer) and a sultone [10]. Due to their biocompatibility and hemocompatibility polybetaines are attributed to be materials with biomimetic properties

• repeating unit, but not in the same side chain. Moreover, regioselective functionalization is possible [13]. In contrast to synthetic polybetaines an increased solubility could be expected for polysaccharide derivatives and, furthermore, biopolymers possess an inherent biocompatibility and biodegradability

An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards ‘clickable’ biodegradable polylactide

• Quanxuan Zhang,
• Hong Ren and
• Gregory L. Baker

Beilstein J. Org. Chem. 2014, 10, 1365–1371, doi:10.3762/bjoc.10.139

• Aliphatic polyesters, in particular polylactide (PLA), are now widely used for biomedical applications, such as surgery sutures [1], implants for bone fixation [2], drug delivery vehicles [3][4] and tissue engineering scaffolds [5] because of their excellent biocompatibility, biodegradability and mechanical

Synthesis of a sucrose dimer with enone tether; a study on its functionalization

• Zbigniew Pakulski,
• Norbert Gajda,
• Magdalena Jawiczuk,
• Jadwiga Frelek,
• Piotr Cmoch and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2014, 10, 1246–1254, doi:10.3762/bjoc.10.124

• designed for such receptors, sugars are the most promising due to their availability and biocompatibility. Up to date only monosaccharides have found a wide application in the synthesis of crown ether analogs [5][6]. The disaccharide scaffold is much less pronounced [7]. During the past decade we have

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

• Jun Hu,
• Jindan Wu,
• Qian Wang and
• Yong Ju

Beilstein J. Org. Chem. 2013, 9, 2877–2885, doi:10.3762/bjoc.9.324

• the form of free acids or aglycones, has been noted by its low toxicity, biocompatibility and bioactivity [31][32]. A wide array of papers has been published to report its anti-inflammatory, antiviral, and antitumor effects [33][34]. In recent years, it has been found that triterpenoids can serve as

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

• tris(hydroxypropyltriazolylmethyl)amine (THPTA, Figure 1) was present [64]. In bioorganic chemistry, research efforts have focused on developing ligands that can prevent the copper ions from causing biological damage [68][69][70]. Apart from TBTA that had been shown to increase the biocompatibility of

3D-printed devices for continuous-flow organic chemistry

• Vincenza Dragone,
• Victor Sans,
• Mali H. Rosnes,
• Philip J. Kitson and
• Leroy Cronin

Beilstein J. Org. Chem. 2013, 9, 951–959, doi:10.3762/bjoc.9.109

• chemistry because of its biocompatibility; however, from a chemical point of view its use is limited to a few solvents and organic compounds, and to preserve its integrity it can only be used up to temperatures of 60–66 °C [19]. Polyacrylates consist of a vast group of polymers with different physical and

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

• inherently easily biodegradable. To meet the prerequisites for self-delivery systems, besides biodegradability, the hydrogelators should preserve the pharmacological efficacy of the therapeutic building blocks, any side effects should be minimized and the biocompatibility maximized. Therefore, a convenient

• biocompatibility of these NSAID hydrogelators, we select 1a, 1c, and 1d to test their cytotoxicity by incubating them with HeLa cells for 72 h at 37 °C. As shown in Figure 4, 1a, 1c, and 1d exhibit IC50 values of 206 µM, 321 µM, and 294 µM, respectively. Among these three hydrogels, 1a lacks the tyrosine residue