Literature DB >> 22591513

Palau'amine and related oroidin alkaloids dibromophakellin and dibromophakellstatin inhibit the human 20S proteasome.

Theresa A Lansdell1, Nicole M Hewlett, Amanda P Skoumbourdis, Matthew D Fodor, Ian B Seiple, Shun Su, Phil S Baran, Ken S Feldman, Jetze J Tepe.   

Abstract

We report herein that the oroidin-derived alkaloids palau'amine (1), dibromophakellin (2), and dibromophakellstatin (3) inhibit the proteolytic activity of the human 20S proteasome as well as the (i)20S immunoproteasome catalytic core. Palau'amine is found to prevent the degradation of ubiquitinylated proteins, including IκBα, in cell culture, which may be indicative of the potential mechanism by which these agents exhibit their exciting cytotoxic and immunosuppressive properties.

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Year:  2012        PMID： 22591513      PMCID： PMC3367325          DOI： 10.1021/np300231f

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  45 in total

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Authors:  Mark Y Chiang; Edward A Stadtmauer
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5.  Extending Pummerer reaction chemistry. Synthesis of (+/-)-dibromophakellstatin by oxidative cyclization of an imidazole derivative.

Authors:  Ken S Feldman; Amanda P Skoumbourdis
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

6.  Total synthesis of the cytostatic marine natural product dibromophakellstatin via three-component imidazolidinone anellation.

Authors:  Michael Zöllinger; Peter Mayer; Thomas Lindel
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

7.  Bortezomib attenuates murine collagen-induced arthritis.

Authors:  S-W Lee; J-H Kim; Y-B Park; S-K Lee
Journal:  Ann Rheum Dis       Date:  2008-12-03       Impact factor: 19.103

8.  Enantioselective total synthesis of (+)-dibromophakellstatin.

Authors:  Karine G Poullennec; Daniel Romo
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419

9.  Extending Pummerer reaction chemistry. Synthesis studies in the phakellin alkaloid area.

Authors:  Ken S Feldman; Amanda P Skoumbourdis; Matthew D Fodor
Journal:  J Org Chem       Date:  2007-09-13       Impact factor: 4.354

10.  Design and synthesis of an orally bioavailable and selective peptide epoxyketone proteasome inhibitor (PR-047).

Authors:  Han-Jie Zhou; Monette A Aujay; Mark K Bennett; Maya Dajee; Susan D Demo; Ying Fang; Mark N Ho; Jing Jiang; Christopher J Kirk; Guy J Laidig; Evan R Lewis; Yan Lu; Tony Muchamuel; Francesco Parlati; Eileen Ring; Kevin D Shenk; Jamie Shields; Peter J Shwonek; Timothy Stanton; Congcong M Sun; Catherine Sylvain; Tina M Woo; Jinfu Yang
Journal:  J Med Chem       Date:  2009-05-14       Impact factor: 7.446
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  6 in total

1.  Small Molecule Enhancement of 20S Proteasome Activity Targets Intrinsically Disordered Proteins.

Authors:  Corey L Jones; Evert Njomen; Benita Sjögren; Thomas S Dexheimer; Jetze J Tepe
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2.  Structures and cytotoxic evaluation of new and known acyclic Ene-Ynes from an American Samoa Petrosia sp. Sponge.

Authors:  Eric J Mejia; Lindsay B Magranet; Nicole J De Voogd; Karen Tendyke; Dayong Qiu; Young Yongchun Shen; Zhongrui Zhou; Phillip Crews
Journal:  J Nat Prod       Date:  2013-01-31       Impact factor: 4.050

3.  Small Molecule Modulation of Proteasome Assembly.

Authors:  Evert Njomen; Pawel A Osmulski; Corey L Jones; Maria Gaczynska; Jetze J Tepe
Journal:  Biochemistry       Date:  2018-06-27       Impact factor: 3.162

Review 4.  Marine Pyrrole Alkaloids.

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Journal:  Mar Drugs       Date:  2021-09-10       Impact factor: 5.118

5.  Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors.

Authors:  Grace E Hubbell; Jetze J Tepe
Journal:  RSC Chem Biol       Date:  2020-09-16

6.  Total synthesis of palau'amine.

Authors:  Kosuke Namba; Kohei Takeuchi; Yukari Kaihara; Masataka Oda; Akira Nakayama; Atsushi Nakayama; Masahiro Yoshida; Keiji Tanino
Journal:  Nat Commun       Date:  2015-11-04       Impact factor: 14.919
  6 in total

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