Literature DB >> 33751770

Scalable Total Synthesis, IP3R Inhibitory Activity of Desmethylxestospongin B, and Effect on Mitochondrial Function and Cancer Cell Survival.

Maša Podunavac1, Artur K Mailyan1, Jeffrey J Jackson1, Alenka Lovy2, Paula Farias2, Hernan Huerta2, Jordi Molgó3, Cesar Cardenas1,2,4, Armen Zakarian1.   

Abstract

The scalable synthesis of the oxaquinolizidine marine natural product desmethylxestospongin B is based on the early application of Ireland-Claisen rearrangement, macrolactamization, and a late-stage installation of the oxaquinolizidine units by lactam reduction. The synthesis serves as the source of material to investigate calcium signaling and its effect on mitochondrial metabolism in various cell types, including cancer cells.
© 2021 Wiley-VCH GmbH.

Entities:  

Keywords:  IP3R receptor; cancer; metabolism; total synthesis; xestospongins

Mesh：

Substances：

Year:  2021        PMID： 33751770      PMCID： PMC8174024          DOI： 10.1002/anie.202102259

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  16 in total

1.  Stereoselective synthesis of (.+-.)-cyanocycline.

Authors:  D A Evans; C R Illig; J C Saddler
Journal:  J Am Chem Soc       Date:  1986-04-01       Impact factor: 15.419

2.  A concise total synthesis of (-)-quinocarcin via aryne annulation.

Authors:  Kevin M Allan; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2008-12-24       Impact factor: 15.419

3.  (+)-7S-Hydroxyxestospongin A from the marine sponge Xestospongia sp. and absolute configuration of (+)-xestospongin D.

Authors:  Surk-Sik Moon; John B MacMillan; Marilyn M Olmstead; Tram Anh Ta; Isaac N Pessah; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2002-03       Impact factor: 4.050

4.  Araguspongines B, C, D, E, F, G, H, and J, new vasodilative bis-1-oxaquinolizidine alkaloids from an okinawan marine sponge, Xestospongia sp.

Authors:  M Kobayashi; K Kawazoe; I Kitagawa
Journal:  Chem Pharm Bull (Tokyo)       Date:  1989-06       Impact factor: 1.645

5.  Essential regulation of cell bioenergetics by constitutive InsP3 receptor Ca2+ transfer to mitochondria.

Authors:  César Cárdenas; Russell A Miller; Ian Smith; Thi Bui; Jordi Molgó; Marioly Müller; Horia Vais; King-Ho Cheung; Jun Yang; Ian Parker; Craig B Thompson; Morris J Birnbaum; Kenneth R Hallows; J Kevin Foskett
Journal:  Cell       Date:  2010-07-23       Impact factor: 41.582

6.  Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived delta-lactam.

Authors:  Mercedes Amat; Núria Llor; José Hidalgo; Carmen Escolano; Joan Bosch
Journal:  J Org Chem       Date:  2003-03-07       Impact factor: 4.354

7.  Expeditious and Divergent Total Syntheses of Aspidosperma Alkaloids Exploiting Iridium(I)-Catalyzed Generation of Reactive Enamine Intermediates.

Authors:  Peng Wen Tan; Jayasree Seayad; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-23       Impact factor: 15.336

8.  Selective Vulnerability of Cancer Cells by Inhibition of Ca(2+) Transfer from Endoplasmic Reticulum to Mitochondria.

Authors:  César Cárdenas; Marioly Müller; Andrew McNeal; Alenka Lovy; Fabian Jaňa; Galdo Bustos; Felix Urra; Natalia Smith; Jordi Molgó; J Alan Diehl; Todd W Ridky; J Kevin Foskett
Journal:  Cell Rep       Date:  2016-03-03       Impact factor: 9.423

9.  Cancer cells with defective oxidative phosphorylation require endoplasmic reticulum-to-mitochondria Ca2+ transfer for survival.

Authors:  Cesar Cardenas; Alenka Lovy; Eduardo Silva-Pavez; Felix Urra; Craig Mizzoni; Ulises Ahumada-Castro; Galdo Bustos; Fabian Jaňa; Pablo Cruz; Paula Farias; Elizabeth Mendoza; Hernan Huerta; Paola Murgas; Martin Hunter; Melany Rios; Oscar Cerda; Irene Georgakoudi; Armen Zakarian; Jordi Molgó; J Kevin Foskett
Journal:  Sci Signal       Date:  2020-07-14       Impact factor: 9.517

10.  Iridium-catalyzed reductive nitro-Mannich cyclization.

Authors:  Alex W Gregory; Alan Chambers; Alison Hawkins; Pavol Jakubec; Darren J Dixon
Journal:  Chemistry       Date:  2014-11-14       Impact factor: 5.236
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  2 in total

1.  A Ca2+-Dependent Mechanism Boosting Glycolysis and OXPHOS by Activating Aralar-Malate-Aspartate Shuttle, upon Neuronal Stimulation.

Authors:  Irene Pérez-Liébana; Inés Juaristi; Paloma González-Sánchez; Luis González-Moreno; Eduardo Rial; Maša Podunavac; Armen Zakarian; Jordi Molgó; Ainara Vallejo-Illarramendi; Laura Mosqueira-Martín; Adolfo Lopez de Munain; Beatriz Pardo; Jorgina Satrústegui; Araceli Del Arco
Journal:  J Neurosci       Date:  2022-04-06       Impact factor: 6.709

2.  One-Pot Synthesis of Strain-Release Reagents from Methyl Sulfones.

Authors:  Myunggi Jung; Vincent N G Lindsay
Journal:  J Am Chem Soc       Date:  2022-03-14       Impact factor: 16.383
  2 in total

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