Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• human cancer cell lines and inhibition of the chemokine receptor CCR5, make them attractive synthetic targets. This review article highlights the recent synthetic methodologies and briefly summarizes their biological activities. Keywords: brevipolides; 5,6-dihydro-α-pyrone; Furukawa-modified Simmons

• the chemokine receptor 5 (CCR5), isolated from the Peruvian plant Lippia alva in 2004 [11]. Further, in 2017 Pereda-Miranda and co-workers isolated five more new 5,6-dihydro-α-pyrone derivatives, namely brevipolides K–O (11–15), from the same plant [1]. The structures have been determined by a

• ELISA NF-κB assay. Upon the mitochondrial transmembrane potential assay, three members demonstrated ED50 values in the nanomolar level [4]. Moreover, three of the members were identified as inhibitors of the chemokine receptor CCR5 [11]. Therefore, they are potential agents for treating human

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• structures, which makes them ideal molecules for novel ligand development [31]. Zhou et al. previously reported on an RNA aptamer specific for the HIV-1 entry coreceptor C-C chemokine receptor type 5 (CCR5) [34] and an RNA aptamer specific for the HIV-1 envelope protein gp160 [35]. The CCR5 RNA aptamer G-3

• complexation with cluster of differentiation 4 (CD4) and CCR5 or C-X-C motif chemokine receptor 4 (CXCR4) host cell surface receptors [35]. As such, gp160 expression on the host cell surface receptor may not be as adept at facilitating cell entry via receptor-mediated endocytosis. Although in 2009, Zhou et al

• LNPs that can cross the BBB, we developed and assessed two approaches. The first was centered on the BBB-penetrating trans-activator of transcription (Tat) peptide or the peptide T7, and the other on RNA aptamers targeted to glycoprotein gp160 from human immunodeficiency virus (HIV) or C-C chemokine

A toolbox of molecular photoswitches to modulate the CXCR3 chemokine receptor with light

• Xavier Gómez-Santacana,
• Sabrina M. de Munnik,
• Tamara A. M. Mocking,
• Niels J. Hauwert,
• Shanliang Sun,
• Prashanna Vijayachandran,
• Iwan J. P. de Esch,
• Henry F. Vischer,
• Maikel Wijtmans and
• Rob Leurs

Beilstein J. Org. Chem. 2019, 15, 2509–2523, doi:10.3762/bjoc.15.244

• full agonism. The compound class disclosed here can aid in new photopharmacology studies of CXCR3 signaling. Keywords: azo compounds; chemokine receptor; efficacy photoswitching; G protein-coupled receptors; photopharmacology; Introduction Photopharmacology is an emerging discipline at the interface

• . Results and Discussion Azologization design The chemokine receptor CXCR3 is endogenously activated by the chemotactic peptides CXCL11, CXCL10 and CXCL9. Synthetic small-molecule ligands can also bind to CXCR3 [25]. Multiple small-molecule CXCR3 antagonist scaffolds have been disclosed but small-molecule

• photopharmacological studies on the dynamic signaling of the chemokine receptor CXCR3. Design of the CXCR3 efficacy photowitchable ligands. A,B) Schematic representation of a GPCR photochromic ligand that photoisomerizes and thereby photoswitches (A) binding affinity and/or (B) functional efficacy. Red represents the

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

• Myriam Drouin and
• Jean-François Paquin

Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262

• isomerization or epimerization, cyclic pseudopeptides using Fmoc SPPS [48][50]. Biological studies were conducted on monofluoroalkene-containing analogues of FC131, which is a known antagonist of the chemokine receptor CXCR4. The latter has implications in cancer metastasis and HIV 1 infection. Anti-HIV 1

G-Protein coupled receptors: answers from simulations

• Timothy Clark

Beilstein J. Org. Chem. 2017, 13, 1071–1078, doi:10.3762/bjoc.13.106

• antagonists for both receptors would need to consider all three sites [41]. Multiple binding sites along the binding path are common in GPCRs. The human chemokine receptor CXCR3, for instance, exhibits distinct alternative binding sites that can be occupied simultaneously by competing ligands, which explains

Synthesis and in silico screening of a library of β-carboline-containing compounds

• Kay M. Brummond,
• John R. Goodell,
• Matthew G. LaPorte,
• Lirong Wang and
• Xiang-Qun Xie

Beilstein J. Org. Chem. 2012, 8, 1048–1058, doi:10.3762/bjoc.8.117

• structurally similar lead compounds in ChEMBL along with their reported potency and literature citations. Several interesting results emerge from the comparison study performed, including a number of targets that the compounds should be screened against, such as C–C chemokine receptor type 3, gamma