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10.1021/cb501013w

http://scihub22266oqcxt.onion/10.1021/cb501013w
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suck abstract from ncbi


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pmid25588114      ACS+Chem+Biol 2015 ; 10 (4): 1099-109
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  • Synthesis, stereochemical analysis, and derivatization of myricanol provide new probes that promote autophagic tau clearance #MMPMID25588114
  • Martin MD; Calcul L; Smith C; Jinwal UK; Fontaine SN; Darling A; Seeley K; Wojtas L; Narayan M; Gestwicki JE; Smith GR; Reitz AB; Baker BJ; Dickey CA
  • ACS Chem Biol 2015[Apr]; 10 (4): 1099-109 PMID25588114show ga
  • We previously discovered that one specific scalemic preparation of myricanol (1), a constituent of Myrica cerifera (bayberry/southern wax myrtle) root bark, could lower the levels of the microtubule-associated protein tau (MAPT). The significance is that tau accumulates in a number of neurodegenerative diseases, the most common being Alzheimer's disease (AD). Herein, a new synthetic route to prepare myricanol using a suitable boronic acid pinacol ester intermediate is reported. An X-ray crystal structure of the isolated myricanol (1) was obtained and showed a co-crystal consisting of (+)-aR,11S-myricanol (2) and (-)-aS,11R-myricanol (3) coformers. Surprisingly, 3, obtained from chiral separation from 1, reduced tau levels in both cultured cells and ex vivo brain slices from a mouse model of tauopathy at reasonable mid-to-low micromolar potency, whereas 2 did not. SILAC proteomics and cell assays revealed that 3 promoted tau degradation through an autophagic mechanism, which was in contrast to that of other tau-lowering compounds previously identified by our group. During the course of structure-activity relationship (SAR) development, we prepared compound 13 by acid-catalyzed dehydration of 1. 13 had undergone an unexpected structural rearrangement through the isomyricanol substitution pattern (e.g., 16), as verified by X-ray structural analysis. Compound 13 displayed robust tau-lowering activity, and, importantly, its enantiomers reduced tau levels similarly. Therefore, the semisynthetic analogue 13 provides a foundation for further development as a tau-lowering agent without its SAR being based on chirality.
  • |Animals[MESH]
  • |Autophagy[MESH]
  • |Brain/drug effects/metabolism[MESH]
  • |Chemistry Techniques, Synthetic[MESH]
  • |Diarylheptanoids/*chemistry/isolation & purification/pharmacology[MESH]
  • |Epitopes/metabolism[MESH]
  • |HEK293 Cells/drug effects[MESH]
  • |Humans[MESH]
  • |Male[MESH]
  • |Mice, Transgenic[MESH]
  • |Molecular Structure[MESH]
  • |Molecular Targeted Therapy[MESH]
  • |Small Molecule Libraries/chemical synthesis/chemistry/*pharmacology[MESH]
  • |Stereoisomerism[MESH]
  • |Tauopathies/drug therapy/genetics/metabolism[MESH]


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