Selected peptide-based fluorescent probes for biological applications

• Debabrata Maity

Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247

• diverse diseases, such as inflammation, tumor, silicosis, and various lysosomal storage diseases [61][62][63]. Therefore, closely monitoring/visualizing of the lysosomes acidic environment is required to study lysosome-related diseases. Spiropyran (SP) undergoes pH-induced interconversion among protonated

Synthesis of monophosphorylated lipid A precursors using 2-naphthylmethyl ether as a protecting group

• Jundi Xue,
• Ziyi Han,
• Gen Li,
• Khalisha A. Emmanuel,
• Cynthia L. McManus,
• Qiang Sui,
• Dongmian Ge,
• Qi Gao and
• Li Cai

Beilstein J. Org. Chem. 2020, 16, 1955–1962, doi:10.3762/bjoc.16.162

• localized infections, the occurrence of severe sepsis causes systemic release of inflammation mediators and stimulatory molecules, thus leading to various pathophysiological effects [6]. Accordingly, structure–activity relationship studies of lipid A which examine or facilitate the examination of how one

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors

• Abimelek Cortes-Pacheco,
• María Adelina Jiménez-Arellanes,
• Francisco José Palacios-Can,
• José Antonio Valcarcel-Gamiño,
• Rodrigo Said Razo-Hernández,
• María del Carmen Juárez-Vázquez,
• Adolfo López-Torres and
• Oscar Abelardo Ramírez-Marroquín

Beilstein J. Org. Chem. 2020, 16, 1277–1287, doi:10.3762/bjoc.16.108

• –activity relationship (SAR) and a molecular docking analysis of 3–6 helped us to explain the trend observed in biological tests. Considering all these aspects, we propose the inhibition of MMP-8 and MMP-9 as a possible action mechanism of the synthesized derivatives. Keywords: inflammation; molecular

• reported as inhibition and downregulation matrix metalloproteinase (MMP) agents [9][10][11]. In this regard, MMPs are a family of extracellular proteinases (24 isoenzymes in human) involved in tissue regeneration and are closely related to physiologic and physiopathological processes, such as inflammation

• , angiogenesis, and metastasis in cancer [12][13][14][15], pointing at bisphosphonates as potential treatments for cancer and other inflammation-related diseases. In this respect, MMP inhibition by phosphonates or bisphosphonates has been previously studied through computational or X-ray diffraction analyses to

Anthelmintic drug discovery: target identification, screening methods and the role of open science

• Frederick A. Partridge,
• Ruth Forman,
• Carole J. R. Bataille,
• Graham M. Wynne,
• Marina Nick,
• Angela J. Russell,
• Kathryn J. Else and
• David B. Sattelle

Beilstein J. Org. Chem. 2020, 16, 1203–1224, doi:10.3762/bjoc.16.105

• Institute for Immunology and Inflammation, Faculty of Biology, Medicine and Health, University of Manchester, Oxford Road, Manchester, M13 9PL, United Kingdom Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA United Kingdom Department of

A review of the total syntheses of triptolide

• Xiang Zhang,
• Zaozao Xiao and
• Hongtao Xu

Beilstein J. Org. Chem. 2019, 15, 1984–1995, doi:10.3762/bjoc.15.194

• cross-talk network amongst these targets and signaling pathways are considered to be responsible for the multiple anticancer activities of triptolide [18][19][20][21][22][23][24]. Triptolide could also suppress inflammation and stimulate cytoprotection by regulating pro-inflammatory cytokines and

One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion

• Christina Görgen,
• Katharina Boden,
• Guido J. Reiss,
• Walter Frank and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 1360–1370, doi:10.3762/bjoc.15.136

• , presumably by inhibition of microtubuli formation in cancer cells [22]. More specifically, a series of 60 1,3-diaryl-1-acylpyrazolines was tested as xanthine oxygenase inhibitors that can be efficacious against articular gout, cancer, and inflammation, with IC50 values of four derivatives in the range of 5.3

Stereo- and regioselective hydroboration of 1-exo-methylene pyranoses: discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors

• Alexander Dahlqvist,
• Axel Furevi,
• Niklas Warlin,
• Hakon Leffler and
• Ulf J. Nilsson

Beilstein J. Org. Chem. 2019, 15, 1046–1060, doi:10.3762/bjoc.15.102

• uptake and breakdown, respectively. The association of galectins to cell signaling and adhesion gives them roles in several different pathological processes, such as pulmonary fibrosis [6][10], pathological lymphangiogenesis [11], inflammation [12] and cancer [13], with galectin inhibitors demonstrated

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• polyanhydride microparticles do not cause significant levels of inflammation [55], as well as prior studies that the trimannose on a latex bead 1 is not inflammatory in the absence of an infection [40][42]. Fortunately, the newly designed probe with TAMRA did not elicit a large inflammatory response that would

• preclude its use as a biological probe. As shown by Akilov et al. [56] and Grinnage-Pulley et al. [42], mannose receptor deleted mice develop L. major infections similar to wild-type mice. L. major infected MR −/− mice developed progressive footpad inflammation as early as 21 days post-infection that

Synthesis and SAR of the antistaphylococcal natural product nematophin from Xenorhabdus nematophila

• Frank Wesche,
• Hélène Adihou,
• Thomas A. Wichelhaus and
• Helge B. Bode

Beilstein J. Org. Chem. 2019, 15, 535–541, doi:10.3762/bjoc.15.47

• Frank Wesche Helene Adihou Thomas A. Wichelhaus Helge B. Bode Molekulare Biotechnologie, Goethe University Frankfurt, Max-von-Laue-Str. 9, D-60438 Frankfurt am Main, Germany present address: Respiratory, Inflammation and Autoimmunity, Innovative Medicines and Early Development, Biotech Unit

Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents

• Mingjun Yuan,
• Song Lin Chua,
• Yang Liu,
• Daniela I. Drautz-Moses,
• Joey Kuok Hoong Yam,
• Thet Tun Aung,
• Roger W. Beuerman,
• May Margarette Santillan Salido,
• Stephan C. Schuster,
• Choon-Hong Tan,
• Michael Givskov,
• Liang Yang and
• Thomas E. Nielsen

Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284

• inflammation or adverse effects, when applied topically on scratched corneas with no bacterial infection (Supporting Information File 1, Figure S1). We then allowed P. aeruginosa PAO1 to colonize and establish infection in the scratched corneas of mice for 24 h. 10 µL of 1 × MIC (6.25 µM) of cisplatin and

Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer

• Sagnik Sengupta,
• Mena Asha Krishnan,
• Premansh Dudhe,
• Ramesh B. Reddy,
• Bishnubasu Giri,
• Sudeshna Chattopadhyay and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2018, 14, 2665–2679, doi:10.3762/bjoc.14.244

• the cell surface of prostate, brain, bladder and breast cancers. Whereas folate receptors are attached to the cell membrane by a glycophosphatidylinositol anchor and over-expressed on several cancers as well as activated macrophages during inflammation. Moreover, folate receptors were also discovered

The design and synthesis of an antibacterial phenothiazine–siderophore conjugate

• Abed Tarapdar,
• James K. S. Norris,
• Oliver Sampson,
• Galina Mukamolova and
• James T. Hodgkinson

Beilstein J. Org. Chem. 2018, 14, 2646–2650, doi:10.3762/bjoc.14.242

• , Department of Infection, Immunity and Inflammation, University of Leicester, Maurice Shock Medical Sciences Building, University Road, Leicester, LE1 9HN, UK 10.3762/bjoc.14.242 Abstract Siderophore–antibiotic conjugates consist of an antibiotic covalently linked by a tether to a siderophore. Such

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

• Matthew B. Calvert,
• Varsha R. Jumde and
• Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

• and invade bladder and kidney tissue, and to promote biofilm formation. Bladder-adhesive FimH is a mannose-specific lectin and the kidney-adhesive PapG binds galactosides. In a second indication, FimH also mediates the attachment of E. coli to the gut, inducing inflammation in Crohn’s disease [13

Impact of Pseudomonas aeruginosa quorum sensing signaling molecules on adhesion and inflammatory markers in endothelial cells

• Carmen Curutiu,
• Florin Iordache,
• Veronica Lazar,
• Aurelia Magdalena Pisoschi,
• Aneta Pop,
• Mariana Carmen Chifiriuc and
• Alina Maria Hoban

Beilstein J. Org. Chem. 2018, 14, 2580–2588, doi:10.3762/bjoc.14.235

• develop anti-QS therapeutic strategies to fight against P. aeruginosa infections. Keywords: adhesion; host–pathogen interaction; inflammation; Pseudomonas; quorum sensing; Introduction Pseudomonas (P.) aeruginosa is an opportunistic pathogen that causes severe and persistent infections in immune

• infection, inflammation and respiratory insufficiency [2]. P. aeruginosa pathogenesis is multifactorial, as suggested by the large number and wide spectrum of bacterial virulence factors present either attached to the cell wall or extracellular virulence factors capable of producing massive tissue damage

• in inflammation [11]. In order to avoid both chronic and acute inflammatory disease, e.g., atherosclerosis or loss of vascular volume, such as in septic shock, the soundness of the vascular permeability barrier is essential. The barrier function of the endothelium is strictly controlled by

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

• Femke Beiroth,
• Tomas Koudelka,
• Thorsten Overath,
• Stefan D. Knight,
• Andreas Tholey and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

• spectra of labeling experiments. Acknowledgements Financial support by the DFG-Cluster of Excellence “Inflammation at Interfaces” and by the DFG Collaborative Network SFB 677 is gratefully acknowledged.

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

• micro-heterogeneous structure distinguished by three regions: the lipid A [5], the core oligosaccharide [6] and the O-antigen [7] (Figure 1B). The TLR4·MD-2 receptor complex senses picomolar amounts of LPS and initiates the biosynthesis of diverse mediators of inflammation (such as tumor necrosis factor

• -TNF-α, interleukin 6 (IL-6) and IL-8) thereby triggering a downstream pro-inflammatory signaling cascade aimed at the clearance of infection [8]. Thus, LPS-induced TLR4·MD-2-mediated signaling largely contributes to the development of inflammation and initiation of the beneficial defensive host

• response which is essential for bacterial clearance and managing the Gram-negative bacterial disease. However, under circumstances of an upregulated inflammation, the TLR4 activation results in the excessive production of the pro-inflammatory mediators [9] leading to overstimulation of the innate immune

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

• Weizhun Yang,
• Bo Yang,
• Sherif Ramadan and
• Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

• ; Review Introduction Carbohydrates are widely present in nature and many of them are involved in important physiological and pathological events, such as anticoagulation, inflammation and pathogen infection [1][2]. In order to explore their biological functions, oligosaccharides with high purity are

Ni nanoparticles on RGO as reusable heterogeneous catalyst: effect of Ni particle size and intermediate composite structures in C–S cross-coupling reaction

• Debasish Sengupta,
• Koushik Bhowmik,
• Goutam De and
• Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 1796–1806, doi:10.3762/bjoc.13.174

• ; Introduction The formation of a carbon–sulfur bond is an imperative step for the synthesis of many biologically active chemical entities that have significant applications in different therapeutic areas such as HIV, cancer, diabetes, inflammation, Alzheimer’s and Parkinson’s diseases etc. [1][2][3][4]. The

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• defence mechanisms. This molecule is produced by macrophages and the antimicrobial and antiparasitic properties of NO have been well described [38]. Currently, the role of NO as a mediator between chronic inflammation and carcinogenesis is intensively studied [39]. The expression of inducible NO is under

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