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Literature DB >> 20830349

The natural product hybrid of Syringolin A and Glidobactin A synergizes proteasome inhibition potency with subsite selectivity.

Jérôme Clerc¹, Nan Li, Daniel Krahn, Michael Groll, André S Bachmann, Bogdan I Florea, Herman S Overkleeft, Markus Kaiser.

Abstract

The preparation of a Syringolin A/Glidobactin A hybrid (SylA-GlbA) consisting of a SylA macrocycle connected to the GlbA side chain and its potent proteasome targeting of all three proteasomal subsites is reported. The influence of the syrbactin macrocycle moiety on subsite selectivity is demonstrated.

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 20830349 DOI： 10.1039/c0cc02238a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

13 in total

1. Enzymatic timing and tailoring of macrolactamization in syringolin biosynthesis.

Authors: William M Wuest; Daniel Krahn; Markus Kaiser; Christopher T Walsh
Journal: Org Lett Date: 2011-08-03 Impact factor: 6.005

2. Proteasome activity imaging and profiling characterizes bacterial effector syringolin A.

Authors: Izabella Kolodziejek; Johana C Misas-Villamil; Farnusch Kaschani; Jérôme Clerc; Christian Gu; Daniel Krahn; Sherry Niessen; Martijn Verdoes; Lianne I Willems; Hermen S Overkleeft; Markus Kaiser; Renier A L van der Hoorn
Journal: Plant Physiol Date: 2010-11-02 Impact factor: 8.340

3. Syrbactin Structural Analog TIR-199 Blocks Proteasome Activity and Induces Tumor Cell Death.

Authors: André S Bachmann; John Opoku-Ansah; Tannya R Ibarra-Rivera; Lisette P Yco; Sudhakar Ambadi; Christopher C Roberts; Chia-En A Chang; Michael C Pirrung
Journal: J Biol Chem Date: 2016-02-23 Impact factor: 5.157

4. Substrate-guided optimization of the syringolins yields potent proteasome inhibitors with activity against leukemia cell lines.

Authors: Kyle A Totaro; Dominik Barthelme; Peter T Simpson; Robert T Sauer; Jason K Sello
Journal: Bioorg Med Chem Date: 2015-07-26 Impact factor: 3.641

5. Syrbactin proteasome inhibitor TIR-199 overcomes bortezomib chemoresistance and inhibits multiple myeloma tumor growth in vivo.

Authors: Marquicia R Pierce; Reeder M Robinson; Tannya R Ibarra-Rivera; Michael C Pirrung; Nathan G Dolloff; André S Bachmann
Journal: Leuk Res Date: 2019-11-12 Impact factor: 3.156

6. Discovery of a potent and highly β1 specific proteasome inhibitor from a focused library of urea-containing peptide vinyl sulfones and peptide epoxyketones.

Authors: Wouter A van der Linden; Lianne I Willems; Tamer B Shabaneh; Nan Li; Mark Ruben; Bogdan I Florea; Gijs A van der Marel; Markus Kaiser; Alexei F Kisselev; Herman S Overkleeft
Journal: Org Biomol Chem Date: 2011-11-22 Impact factor: 3.876

7. Syrbactin-class dual constitutive- and immuno-proteasome inhibitor TIR-199 impedes myeloma-mediated bone degeneration in vivo.

Authors: Vasudha Tandon; Ruturajsinh M Vala; Albert Chen; Robert L Sah; Hitendra M Patel; Michael C Pirrung; Sourav Banerjee
Journal: Biosci Rep Date: 2022-02-25 Impact factor: 3.840