Literature DB >> 19097779

Stereo-controlled synthesis of novel photoreactive gamma-secretase inhibitors.

Guangli Yang1, Ye Ingrid Yin, Jiong Chun, Christopher C Shelton, Ouathek Ouerfelli, Yue-Ming Li.   

Abstract

The stereoselective synthesis of novel photoreactive gamma-secretase inhibitors 2 and 3 has been achieved. Key steps of the strategy involve preparation of alpha-N-Boc-epoxide 8 and formation of lactone 14 in a practical and stereo-controlled fashion. Compounds 2 and 3 are potent gamma-secretase inhibitors and directly interact with presenilin-1, a catalytic subunit of gamma-secretase.

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Year:  2008        PMID： 19097779      PMCID： PMC3254698          DOI： 10.1016/j.bmcl.2008.11.117

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  11 in total

Review 1.  Regulated intramembrane proteolysis: a control mechanism conserved from bacteria to humans.

Authors:  M S Brown; J Ye; R B Rawson; J L Goldstein
Journal:  Cell       Date:  2000-02-18       Impact factor: 41.582

Review 2.  Aph-1, Pen-2, and Nicastrin with Presenilin generate an active gamma-Secretase complex.

Authors:  Bart De Strooper
Journal:  Neuron       Date:  2003-04-10       Impact factor: 17.173

Review 3.  Intramembrane proteolysis: theme and variations.

Authors:  Michael S Wolfe; Raphael Kopan
Journal:  Science       Date:  2004-08-20       Impact factor: 47.728

4.  Stereoselective synthesis of photoreactive peptidomimetic gamma-secretase inhibitors.

Authors:  Jiong Chun; Ye Ingrid Yin; Guangli Yang; Leonid Tarassishin; Yue-Ming Li
Journal:  J Org Chem       Date:  2004-10-15       Impact factor: 4.354

5.  Transition-state analogue inhibitors of gamma-secretase bind directly to presenilin-1.

Authors:  W P Esler; W T Kimberly; B L Ostaszewski; T S Diehl; C L Moore; J Y Tsai; T Rahmati; W Xia; D J Selkoe; M S Wolfe
Journal:  Nat Cell Biol       Date:  2000-07       Impact factor: 28.824

6.  Presenilin 1 is linked with gamma-secretase activity in the detergent solubilized state.

Authors:  Y M Li; M T Lai; M Xu; Q Huang; J DiMuzio-Mower; M K Sardana; X P Shi; K C Yin; J A Shafer; S J Gardell
Journal:  Proc Natl Acad Sci U S A       Date:  2000-05-23       Impact factor: 11.205

7.  L-685,458, an aspartyl protease transition state mimic, is a potent inhibitor of amyloid beta-protein precursor gamma-secretase activity.

Authors:  M S Shearman; D Beher; E E Clarke; H D Lewis; T Harrison; P Hunt; A Nadin; A L Smith; G Stevenson; J L Castro
Journal:  Biochemistry       Date:  2000-08-01       Impact factor: 3.162

8.  Photoactivated gamma-secretase inhibitors directed to the active site covalently label presenilin 1.

Authors:  Y M Li; M Xu; M T Lai; Q Huang; J L Castro; J DiMuzio-Mower; T Harrison; C Lellis; A Nadin; J G Neduvelil; R B Register; M K Sardana; M S Shearman; A L Smith; X P Shi; K C Yin; J A Shafer; S J Gardell
Journal:  Nature       Date:  2000-06-08       Impact factor: 49.962

Review 9.  Amyloid deposition as the central event in the aetiology of Alzheimer's disease.

Authors:  J Hardy; D Allsop
Journal:  Trends Pharmacol Sci       Date:  1991-10       Impact factor: 14.819

10.  Cloning of a gene bearing missense mutations in early-onset familial Alzheimer's disease.

Authors:  R Sherrington; E I Rogaev; Y Liang; E A Rogaeva; G Levesque; M Ikeda; H Chi; C Lin; G Li; K Holman; T Tsuda; L Mar; J F Foncin; A C Bruni; M P Montesi; S Sorbi; I Rainero; L Pinessi; L Nee; I Chumakov; D Pollen; A Brookes; P Sanseau; R J Polinsky; W Wasco; H A Da Silva; J L Haines; M A Perkicak-Vance; R E Tanzi; A D Roses; P E Fraser; J M Rommens; P H St George-Hyslop
Journal:  Nature       Date:  1995-06-29       Impact factor: 49.962
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  10 in total

1.  Modulation of gamma-secretase specificity using small molecule allosteric inhibitors.

Authors:  Christopher C Shelton; Lei Zhu; Deming Chau; Li Yang; Rong Wang; Hakim Djaballah; Hui Zheng; Yue-Ming Li
Journal:  Proc Natl Acad Sci U S A       Date:  2009-11-11       Impact factor: 11.205

2.  γ-Secretase Inhibitors and Modulators Induce Distinct Conformational Changes in the Active Sites of γ-Secretase and Signal Peptide Peptidase.

Authors:  Natalya Gertsik; De-Ming Chau; Yue-Ming Li
Journal:  ACS Chem Biol       Date:  2015-06-10       Impact factor: 5.100

3.  Nontranscriptional role of Hif-1α in activation of γ-secretase and notch signaling in breast cancer.

Authors:  Jennifer C Villa; Danica Chiu; Alissa H Brandes; Freddy E Escorcia; Carlos H Villa; William F Maguire; Cheng-Jun Hu; Elisa de Stanchina; M Celeste Simon; Sangram S Sisodia; David A Scheinberg; Yue-Ming Li
Journal:  Cell Rep       Date:  2014-08-14       Impact factor: 9.423

4.  Familial Alzheimer disease presenilin-1 mutations alter the active site conformation of γ-secretase.

Authors:  De-Ming Chau; Christina J Crump; Jennifer C Villa; David A Scheinberg; Yue-Ming Li
Journal:  J Biol Chem       Date:  2012-03-29       Impact factor: 5.157

5.  Piperidine acetic acid based γ-secretase modulators directly bind to Presenilin-1.

Authors:  Christina J Crump; Benjamin A Fish; Suita V Castro; De-Ming Chau; Natalya Gertsik; Kwangwook Ahn; Cory Stiff; Nikolay Pozdnyakov; Kelly R Bales; Douglas S Johnson; Yue-Ming Li
Journal:  ACS Chem Neurosci       Date:  2011-12-21       Impact factor: 4.418

Review 6.  Development and mechanism of γ-secretase modulators for Alzheimer's disease.

Authors:  Christina J Crump; Douglas S Johnson; Yue-Ming Li
Journal:  Biochemistry       Date:  2013-05-02       Impact factor: 3.162

7.  Pen2 and presenilin-1 modulate the dynamic equilibrium of presenilin-1 and presenilin-2 gamma-secretase complexes.

Authors:  Lisa Placanica; Leonid Tarassishin; Guangli Yang; Erica Peethumnongsin; Seong-Hun Kim; Hui Zheng; Sangram S Sisodia; Yue-Ming Li
Journal:  J Biol Chem       Date:  2008-11-25       Impact factor: 5.157

8.  An APP inhibitory domain containing the Flemish mutation residue modulates gamma-secretase activity for Abeta production.

Authors:  Yuan Tian; Bhramdeo Bassit; Deming Chau; Yue-Ming Li
Journal:  Nat Struct Mol Biol       Date:  2010-01-10       Impact factor: 15.369

Review 9.  Structural and Chemical Biology of Presenilin Complexes.

Authors:  Douglas S Johnson; Yue-Ming Li; Martin Pettersson; Peter H St George-Hyslop
Journal:  Cold Spring Harb Perspect Med       Date:  2017-12-01       Impact factor: 6.915

10.  The innate immunity protein IFITM3 modulates γ-secretase in Alzheimer's disease.

Authors:  Ji-Yeun Hur; Georgia R Frost; Xianzhong Wu; Christina Crump; Si Jia Pan; Eitan Wong; Marilia Barros; Thomas Li; Pengju Nie; Yujia Zhai; Jen Chyong Wang; Julia Tcw; Lei Guo; Andrew McKenzie; Chen Ming; Xianxiao Zhou; Minghui Wang; Yotam Sagi; Alan E Renton; Bianca T Esposito; Yong Kim; Katherine R Sadleir; Ivy Trinh; Robert A Rissman; Robert Vassar; Bin Zhang; Douglas S Johnson; Eliezer Masliah; Paul Greengard; Alison Goate; Yue-Ming Li
Journal:  Nature       Date:  2020-09-02       Impact factor: 49.962
  10 in total

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