Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• processes is well documented, as in the case of embryogenesis, fertilization, inflammation and metastasis. Lectins play a key role in parasite-symbiotic recognition in microbes and invertebrates of plants and vertebrates. The present role assigned to lectin lies in their ability to decipher sugar-encoded

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

• represent a promising candidate for developing theranostic agents, able to carry drugs to a selected tissue and to act as a sensitive probe. In fact, the metallic core of GAuNPs has been exploited to design and develop promising early detecting agents of cancer or inflammation. In this contest, Andresen and

• mice, the authors demonstrated that GAuNPs selectively targeted overexpressed glucose receptors (GLUT1) and accumulated in the damaged lung, while PEGylated AuNPs did not show any relevant accumulation in the inflammation site. Moreover, another study on the synthesis of glucose-functionalized AuNPs

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

• catalyze the exchange of cholesterol between serum lipoproteins and cells [56]. ii) Cardiovascular diseases The atherosclerosis vascular disease (ASVD) is caused by an inflammation of the arterial wall that is caused by increased cholesterol blood levels and an accumulation of cholesterol crystals in the

• ® CRYSMEB (a mixture of methylated β-CD where 2-O-methylations are dominant) in atherosclerotic mouse models [131]. As expected, their interfering action with cholesterol metabolism has a positive impact on atherogenesis, lipid profile and atherosclerotic plaque inflammation. In addition to reduce

• , the researchers suspect that the CD boosts the activity of macrophages, enabling them to attack excess cholesterol without causing inflammation. Indeed, CD increases liver X receptor (LXR) involved in the antiatherosclerotic and anti-inflammatory effects as well as in the RCT improvement. Moreover, α

Biradical vs singlet oxygen photogeneration in suprofen–cholesterol systems

• Fabrizio Palumbo,
• Francisco Bosca,
• Isabel M. Morera,
• Inmaculada Andreu and
• Miguel A. Miranda

Beilstein J. Org. Chem. 2016, 12, 1196–1202, doi:10.3762/bjoc.12.115

• from inflammation to cardiovascular and Alzheimer diseases [1][2]. This type of damage can be induced via free radicals or singlet oxygen (1O2) [3][4]. The former generally involves hydrogen abstraction (HA) of an allylic hydrogen and can be achieved by photosensitizing agents in combination with UVA

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• herbs, widely distributed from Central to South America, including Southern Brazil. Species such as J. paniculata and J. polita are used in South America to disinfect and cure external wounds, to treat inflammation [1][2], and as a blood depurative [3]. Pharmacological studies demonstrated that the anti

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• involved in inflammation reactions. The authors isolated 23, 24 and 27 from the feces of Trogopterus xanthipes (flying squirrel) by bioactivity-guided fractionation, and determined IC50 values for the pure compounds to be in the low mM range (1.33, 1.07 and 2.33 mM, respectively) [31]. Also estrogenic and

Physical properties and biological activities of hesperetin and naringenin in complex with methylated β-cyclodextrin

• Waratchada Sangpheak,
• Jintawee Kicuntod,
• Roswitha Schuster,
• Thanyada Rungrotmongkol,
• Peter Wolschann,
• Nawee Kungwan,
• Helmut Viernstein,
• Monika Mueller and
• Piamsook Pongsawasdi

Beilstein J. Org. Chem. 2015, 11, 2763–2773, doi:10.3762/bjoc.11.297

• the effect of free compounds and their inclusion complexes on inflammation as described previously [59]. Cells were seeded at a density of 2 × 106 cells per well in 24 well plates, and incubated at 37 °C for 24 hours. After that, samples were added to obtain a final concentration of 0.1, 0.05 and

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

• Ana Čikoš,
• Irena Ćaleta,
• Dinko Žiher,
• Mark B. Vine,
• Ivaylo J. Elenkov,
• Marko Dukši,
• Dubravka Gembarovski,
• Marina Ilijaš,
• Snježana Dragojević,
• Ivica Malnar and
• Sulejman Alihodžić

Beilstein J. Org. Chem. 2015, 11, 1447–1457, doi:10.3762/bjoc.11.157

• well as inflammation [36][37][38]. In the search for novel scaffolds to be used as a fresh starting point for further derivatisation [39], we explored modifications to the macrocyclic ring. Oxidative deoximation of 1 in mild acidic media, shown in Scheme 1, led us to an unexpected macrolide-spiroketal

Synthesis of alpha-tetrasubstituted triazoles by copper-catalyzed silyl deprotection/azide cycloaddition

• Zachary L. Palchak,
• Paula T. Nguyen and
• Catharine H. Larsen

Beilstein J. Org. Chem. 2015, 11, 1425–1433, doi:10.3762/bjoc.11.154

• cruzi, which causes Chagas’ disease [6]. An alpha-tetrasubstituted triazole that inhibits cathepsin S can potentially treat ailments ranging from inflammation to autoimmune disorders [7][8]. The core of the cathepsin S inhibitor is synthesized in six steps. Synthesis and isolation of an N-sulfinyl

Regulation of integrin and growth factor signaling in biomaterials for osteodifferentiation

• Qiang Wei,
• Theresa L. M. Pohl,
• Anja Seckinger,
• Joachim P. Spatz and
• Elisabetta A. Cavalcanti-Adam

Beilstein J. Org. Chem. 2015, 11, 773–783, doi:10.3762/bjoc.11.87

• ); be timed biodegradable; neither cause acute nor chronic inflammation; be easily stored and handled (sterilized); and the last be cost-effective [75][80]. The present delivery systems and methods have been systematically reviewed in recent literature [8][9][81]. In brief, growth factors in living

Discrete multiporphyrin pseudorotaxane assemblies from di- and tetravalent porphyrin building blocks

• Mirko Lohse,
• Larissa K. S. von Krbek,
• Sebastian Radunz,
• Suresh Moorthy,
• Christoph A. Schalley and
• Stefan Hecht

Beilstein J. Org. Chem. 2015, 11, 748–762, doi:10.3762/bjoc.11.85

• significant attention mediated in particular by the desire to understand biological phenomena, such as virus docking to cells [27], toxin inhibition [28], or leucocyte recruitment in inflammation processes of the endothelium [29]. Multivalency has also inspired synthetic supramolecular architecture as it not

Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates

• Qinggang Mei,
• Chun Wang,
• Weicheng Yuan and
• Guolin Zhang

Beilstein J. Org. Chem. 2015, 11, 288–293, doi:10.3762/bjoc.11.33

• kaempferol have attracted attention for a long time due to their broad spectrum of biological activities, including induction of apoptosis in adipocytes, anti-inflammation and anti-atherogenic properties [6][7]. 3-O-Methylkaempferol evidently possesses antiviral [8], antimicrobial [9] and cytotoxic [10

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• from preexisting ones. Under physiological conditions, angiogenesis is vital for foetal development, tissue regeneration and wound healing. From a pathophysiologic perspective, massive vascular growth or abnormal shape formation promotes many ailments including cancer, inflammation, and eye illnesses

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

• Éva Rajnavölgyi,
• Renáta Laczik,
• Viktor Kun,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

• component of the phospholipid membranes found everywhere in the body [2]. Changes in the balance of n−3 and n−6 PUFAs in the diet upon low intake of n−3 PUFAs have been linked to several inflammation-related chronic diseases and certain mental illnesses [3]. Greenland Inuits with traditionally high seafood

• diseases [7]. Intake of dietary fats may influence inflammation in the gastrointestinal tract. In a long-term study conducted on 170 805 women a reduced risk of ulcerative colitis was observed for the participants with high intake of n−3 PUFAs [8]. The fatty acid composition of the diet, in particular, the

• proportion of different types of PUFAs, has an influence on the fatty acid composition of immune cells which is a chemical trigger for immune response, such as inflammation [9]. Supplementation of the diet of healthy human volunteers with n−3 PUFAs was unambiguously beneficial: the number of monocytes and

The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon–carbon bond formation via electrogenerated N-acyliminium ions

• Alan M. Jones and
• Craig E. Banks

Beilstein J. Org. Chem. 2014, 10, 3056–3072, doi:10.3762/bjoc.10.323

• important target in the inflammation response (Scheme 18). The α-methoxy group introduced could then be intercepted via an N-acyliminium ion intermediate with a variety of C–C bond forming reagents. The compounds prepared were interrogated for bioactivity against α-L-fucosidase and related targets and IC50

A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives

• Debabrata Samanta,
• Anup Rana,
• Jan W. Bats and
• Michael Schmittel

Beilstein J. Org. Chem. 2014, 10, 2989–2996, doi:10.3762/bjoc.10.317

• ], acetylcholinesterase inhibitors [3], and antibacterial agents [4][5]. Due to the strong inhibitory activity of 1,2,4-thiadiazoles against kinase-3β, they can be used for treatment of diabetes (type II) and chronic inflammation [6][7]. Therefore, their synthesis is a field of continuing interest for many chemists [1][8

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• inflammation and traumatic bleeding. The leaves and stems of this plant contain oleoside-type secoiridoid glucosides with structurally interesting tetrasubstituted cyclopentanoid monoterpene units [116]. Two representative examples of these glycosides are nudifloside A (151) and D (13), which share a common

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

• Maja Kandziora and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

• involved in different diseases such as cancer [4], inflammation [5], and infections [6]. However, the use of carbohydrates as drugs has been strongly limited due to the hydrolytic lability of the glycosidic bond [7] and the weak binding affinities of single molecules. With the development of artificial C

Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands

• Silvia Bernardi,
• Paola Fezzardi,
• Gabriele Rispoli,
• Stefania E. Sestito,
• Francesco Peri,
• Francesco Sansone and
• Alessandro Casnati

Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175

• activation, cell growth, differentiation and apoptosis. Among different families of lectins, the ones showing a selectivity for β-D-galactoside and β-D-galactose-terminating oligosaccharides are called galectins and play important roles in a series of pathological events such as inflammation, fibrosis, heart

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

• osteoporosis, cardiovascular diseases and inflammation can be treated by peptide-based drugs [4][5]. Within the last decades, the fast development of omics technologies such as genomics, proteomics and transcriptomics led to the identification of a great number of target peptides or proteins [6]. This trend

Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin

• John Li,
• May May Leong,
• Alastair Stewart and
• Mark A. Rizzacasa

Beilstein J. Org. Chem. 2013, 9, 2762–2766, doi:10.3762/bjoc.9.310

• Abstract The total synthesis of the endogenous inflammation resolving eicosanoid resolvin D2 (1) is described. The key steps involved a Wittig reaction between aldehyde 5 and the ylide derived from phosphonium salt 6 to give enyne 17 and condensation of the same ylide with aldehyde 7 to afford enyne 11

• ; resolvin D2; Sonogashira coupling; total synthesis; Wittig reaction; Introduction The resolution of inflammation is a tightly governed active process effectively mediated by a range of bioactive polyunsaturated fatty acids, peptides and proteins. In 2002, a new family of endogenously generated lipid

• mediators involved in the resolution of inflammation named the resolvins (resolution phase interaction products) were identified by Serhan and co-workers in the inflammatory exudates of aspirin treated mice [1][2][3]. The resolvins are divided into 2 groups, the D-series resolvins D2 (1) and D1 (2) [3

Total synthesis of (−)-epimyrtine by a gold-catalyzed hydroamination approach

• Thi Thanh Huyen Trinh,
• Khanh Hung Nguyen,
• Patricia de Aguiar Amaral and
• Nicolas Gouault

Beilstein J. Org. Chem. 2013, 9, 2042–2047, doi:10.3762/bjoc.9.242

• alkaloid; total synthesis; Findings (−)-Epimyrtine, isolated from Vaccinium myrtillus (Ericaceae) [1][2], is a quinolizidine alkaloid. This alkaloid family exhibits potential pharmacological properties such as anticancer, antibacterial, antiviral and anti-inflammation activities [3][4][5]. This alkaloid

Synthesis and quantitative structure–activity relationship study of substituted imidazophosphor ester based tetrazolo[1,5-b]pyridazines as antinociceptive/anti-inflammatory agents

• Wafaa M. Abdou,
• Neven A. Ganoub and
• Eman Sabry

Beilstein J. Org. Chem. 2013, 9, 1730–1736, doi:10.3762/bjoc.9.199

• , showed a notable antinociceptive and anti-inflammatory activity without toxic side-effects. Keywords: antinociceptive/anti-inflammatory agents; imidazophosphor esters; phosphonyl carbanions; ring closure; tetrazolo[1,5-b]pyridazine; Introduction Inflammation is a characteristic feature of disease

• the cyclooxygenase (COX) enzymes. Later on, it was reported that the second isoform of cyclooxygenase (COX-2) has a better effect on the inflammation with fewer side-effects [6][7][8][9]. Despite their widespread use, none of the presently available agents is ideal; each has its own shortcomings [3

• ]. Subsequently, to improve the efficacy/safety profile of new NSAIDs, the structural–activity relationship (SAR) has been extensively studied, taking into account up-to-date knowledge about the mechanism of inflammation that balanced the inhibition of COX-1, COX-2, and lipoxygenase (LOX) [10][11][12]. As a part

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

• neurons and acetylcholine (ACh) levels, plaques caused by aggregation of the protein fragment amyloid-β (Aβ), tangles associated with irregular phosphorylation of tau protein, inflammation and increased oxidative stress from reactive oxygen species (ROS), as well as dyshomeostasis and

Synthesis and physicochemical characterization of novel phenotypic probes targeting the nuclear factor-kappa B signaling pathway

• Paul M. Hershberger,
• Satyamaheshwar Peddibhotla,
• E. Hampton Sessions,
• Daniela B. Divlianska,
• Ricardo G. Correa,
• Anthony B. Pinkerton,
• John C. Reed and
• Gregory P. Roth

Beilstein J. Org. Chem. 2013, 9, 900–907, doi:10.3762/bjoc.9.103

• center’s efforts. Within the realm of immunology and inflammation research, many cellular pathways leading to the activation of NF-κB family of transcription factors have been identified and several excellent reviews are available [2][3][4][5]. In general, these pathways have been shown to participate in

• host defense, immunity, and inflammation and even have implications in cancer. Thus, dysregulation of NF-κB activity contributes to numerous autoimmune and inflammatory disease states. With this, the availability of new chemical pathway probes will further enhance understanding of this complex network