7141-98-2Relevant academic research and scientific papers
BRARTEMICIN ANALOGUES
-
Page/Page column 50; 52; 65, (2019/05/22)
The invention relates to brartemicin analogues of Formula (IV) and their uses. These compounds are potent Mincle agonists and Th1-stimulating vaccine adjuvants.
Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants
Foster, Amy J.,Nagata, Masahiro,Lu, Xiuyuan,Lynch, Amy T.,Omahdi, Zakaria,Ishikawa, Eri,Yamasaki, Sho,Timmer, Mattie S. M.,Stocker, Bridget L.
, p. 1045 - 1060 (2018/02/17)
Effective Th1-stimulating vaccine adjuvants typically activate antigen presenting cells (APCs) through pattern recognition receptors (PRRs). Macrophage inducible C-type lectin (Mincle) is a PRR expressed on APCs and has been identified as a target for Th1-stimulating adjuvants. Herein, we report on the synthesis and adjuvanticity of rationally designed brartemicin analogues containing long-chain lipids and demonstrate that they are potent Mincle agonists that activate APCs to produce inflammatory cytokines in a Mincle-dependent fashion. Mincle binding, however, does not directly correlate to a functional immune response. Mutation studies indicated that the aromatic residue of lead compound 9a has an important interaction with Mincle Arg183. In vivo assessment of 9a highlighted the capability of this analogue to augment the Th1 response to a model vaccine antigen. Taken together, our results show that lipophilic brartemicin analogues are potent Mincle agonists and that 9a has superior in vivo adjuvant activity compared to TDB.
The natural product brartemicin is a high affinity ligand for the carbohydrate-recognition domain of the macrophage receptor mincle
Jacobsen, Kristian M.,Keiding, Ulrik B.,Clement, Lise L.,Schaffert, Eva S.,Rambaruth, Neela D. S.,Johannsen, Mogens,Drickamer, Kurt,Poulsen, Thomas B.
supporting information, p. 647 - 652 (2015/04/27)
We demonstrate that the natural product brartemicin, a newly discovered inhibitor of cancer cell invasion, is a high-affinity ligand of the carbohydrate-recognition domain (CRD) of the C-type lectin mincle. Recent studies have revealed that mincle is a ke
Facile syntheses of (-)-montagnetol and (-)-erythrin
Kumbaraci, Volkan,Gunduz, Hande,Karadeniz, Meric
, p. 6328 - 6330 (2013/11/06)
A novel synthetic method is introduced to prepare the biologically important montagnetol and erythrin compounds starting from a 1,3-benzodioxin-4-one, synthesized from commercially available orsellinic acid and erythritol.
Total synthesis of everninomicin 13,384-1 - Part 2: Synthesis of the FGHA2 fragment
Nicolaou,Mitchell, Helen J.,Fylaktakidou, Konstantina C.,Rodriguez, Rosa Maria,Suzuki, Hideo
, p. 3116 - 3148 (2007/10/03)
The stereoselective synthesis of everninomicin's 13,384-1 (1) FGHA2 fragment (2) in a suitable form for incorporation into the final target (1) is described. The construction of the FG 1,1′-disaccharide linkage relied on a new method based on tin-acetal chemistry, while for the GH orthoester bridge, a number of approaches were explored. Final success for the latter construction came when a novel 1,2-phenylseleno migration reaction was applied to couple rings G and H, followed by ketene acetal and orthoester formation.
Synthesis and absolute configuration of phomozin
Vicart, Nicolas,Ortholand, Jean-Yves,Emeric, Gilbert Y.,Greiner, Alfred
, p. 3917 - 3918 (2007/10/02)
The absolute configuration of the fungal phytotoxin phomozin has been unambiguously determined by the synthesis of its two enantiomers.
