Literature DB >> 18499455

Carboxylic acid isosteres improve the activity of ring-fused 2-pyridones that inhibit pilus biogenesis in E. coli.

Veronica Berg1, Pralay Das, Erik Chorell, Mattias Hedenström, Jerome S Pinkner, Scott J Hultgren, Fredrik Almqvist.   

Abstract

Ring-fused 2-pyridones, termed pilicides, are small synthetic compounds that inhibit pilus assembly in uropathogenic Escherichia coli. Their biological activity is clearly dependent upon a carboxylic acid functionality. Here, we present the synthesis and biological evaluation of carboxylic acid isosteres, including, for example, tetrazoles, acyl sulfonamides, and hydroxamic acids of two lead 2-pyridones. Two independent biological evaluations show that acyl sulfonamides and tetrazoles significantly improve pilicide activity against uropathogenic E. coli.

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Year:  2008        PMID： 18499455      PMCID： PMC3665338          DOI： 10.1016/j.bmcl.2008.05.020

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


  29 in total

1.  Design and evaluation of pilicides: potential novel antibacterial agents directed against uropathogenic Escherichia coli.

Authors:  A Svensson; A Larsson; H Emtenäs; M Hedenström; T Fex; S J Hultgren; J S Pinkner; F Almqvist; J Kihlberg
Journal:  Chembiochem       Date:  2001-12-03       Impact factor: 3.164

Review 2.  Pilus biogenesis via the chaperone/usher pathway: an integration of structure and function.

Authors:  D L Hung; S J Hultgren
Journal:  J Struct Biol       Date:  1998-12-15       Impact factor: 2.867

3.  Catalysis of protein folding by chaperones in pathogenic bacteria.

Authors:  James G Bann; Jerome S Pinkner; Carl Frieden; Scott J Hultgren
Journal:  Proc Natl Acad Sci U S A       Date:  2004-12-06       Impact factor: 11.205

Review 4.  Physical properties of biopolymers assessed by optical tweezers: analysis of folding and refolding of bacterial pili.

Authors:  Magnus Andersson; Ove Axner; Fredrik Almqvist; Bernt Eric Uhlin; Erik Fällman
Journal:  Chemphyschem       Date:  2008-02-01       Impact factor: 3.102

5.  Induction and evasion of host defenses by type 1-piliated uropathogenic Escherichia coli.

Authors:  M A Mulvey; Y S Lopez-Boado; C L Wilson; R Roth; W C Parks; J Heuser; S J Hultgren
Journal:  Science       Date:  1998-11-20       Impact factor: 47.728

6.  Exploration of acyl sulfonamides as carboxylic acid replacements in protease inhibitors of the hepatitis C virus full-length NS3.

Authors:  Robert Rönn; Yogesh A Sabnis; Thomas Gossas; Eva Akerblom; U Helena Danielson; Anders Hallberg; Anja Johansson
Journal:  Bioorg Med Chem       Date:  2005-10-05       Impact factor: 3.641

7.  A highly potent, orally active imidazo[4,5-b]pyridine biphenylacylsulfonamide (MK-996; L-159,282): a new AT1-selective angiotensin II receptor antagonist.

Authors:  P K Chakravarty; E M Naylor; A Chen; R S Chang; T B Chen; K A Faust; V J Lotti; S D Kivlighn; R A Gable; G J Zingaro
Journal:  J Med Chem       Date:  1994-11-25       Impact factor: 7.446

8.  An enantioselective ketene-imine cycloaddition method for synthesis of substituted ring-fused 2-pyridinones.

Authors:  H Emtenäs; L Alderin; F Almqvist
Journal:  J Org Chem       Date:  2001-10-05       Impact factor: 4.354

9.  Acyl sulfonamides as potent protease inhibitors of the hepatitis C virus full-Length NS3 (protease-helicase/NTPase): a comparative study of different C-terminals.

Authors:  Anja Johansson; Anton Poliakov; Eva Akerblom; Karin Wiklund; Gunnar Lindeberg; Susanne Winiwarter; U Helena Danielson; Bertil Samuelsson; Anders Hallberg
Journal:  Bioorg Med Chem       Date:  2003-06-12       Impact factor: 3.641

10.  Efficient microwave assisted synthesis of optically active bicyclic 2-pyridinones via delta2-thiazolines.

Authors:  Hans Emtenäs; Camilla Taflin; Fredrik Almqvist
Journal:  Mol Divers       Date:  2003       Impact factor: 2.943
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  9 in total

1.  Design and synthesis of C-2 substituted thiazolo and dihydrothiazolo ring-fused 2-pyridones: pilicides with increased antivirulence activity.

Authors:  Erik Chorell; Jerome S Pinkner; Gilles Phan; Sofie Edvinsson; Floris Buelens; Han Remaut; Gabriel Waksman; Scott J Hultgren; Fredrik Almqvist
Journal:  J Med Chem       Date:  2010-08-12       Impact factor: 7.446

Review 2.  One hundred years of Meldrum's acid: advances in the synthesis of pyridine and pyrimidine derivatives.

Authors:  Victoria V Lipson; Nikolay Yu Gorobets
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

Review 3.  Bacterial biofilms: development, dispersal, and therapeutic strategies in the dawn of the postantibiotic era.

Authors:  Maria Kostakioti; Maria Hadjifrangiskou; Scott J Hultgren
Journal:  Cold Spring Harb Perspect Med       Date:  2013-04-01       Impact factor: 6.915

4.  Mapping pilicide anti-virulence effect in Escherichia coli, a comprehensive structure-activity study.

Authors:  Erik Chorell; Jerome S Pinkner; Christoffer Bengtsson; Thomas Sainte-Luce Banchelin; Sofie Edvinsson; Anna Linusson; Scott J Hultgren; Fredrik Almqvist
Journal:  Bioorg Med Chem       Date:  2012-02-04       Impact factor: 3.641

Review 5.  Productive steps toward an antimicrobial targeting virulence.

Authors:  Amy K Barczak; Deborah T Hung
Journal:  Curr Opin Microbiol       Date:  2009-07-22       Impact factor: 7.934

6.  A 2-pyridone-amide inhibitor targets the glucose metabolism pathway of Chlamydia trachomatis.

Authors:  Patrik Engström; K Syam Krishnan; Bidong D Ngyuen; Erik Chorell; Johan Normark; Jim Silver; Robert J Bastidas; Matthew D Welch; Scott J Hultgren; Hans Wolf-Watz; Raphael H Valdivia; Fredrik Almqvist; Sven Bergström
Journal:  MBio       Date:  2014-12-30       Impact factor: 7.867

Review 7.  Small Molecule Anti-biofilm Agents Developed on the Basis of Mechanistic Understanding of Biofilm Formation.

Authors:  Katrine Qvortrup; Louise Dahl Hultqvist; Martin Nilsson; Tim Holm Jakobsen; Charlotte Uldahl Jansen; Jesper Uhd; Jens Bo Andersen; Thomas E Nielsen; Michael Givskov; Tim Tolker-Nielsen
Journal:  Front Chem       Date:  2019-11-01       Impact factor: 5.221

Review 8.  The Association between Biofilm Formation and Antimicrobial Resistance with Possible Ingenious Bio-Remedial Approaches.

Authors:  Yogesh Dutt; Ruby Dhiman; Tanya Singh; Arpana Vibhuti; Archana Gupta; Ramendra Pati Pandey; V Samuel Raj; Chung-Ming Chang; Anjali Priyadarshini
Journal:  Antibiotics (Basel)       Date:  2022-07-11

9.  Pilicides inhibit the FGL chaperone/usher assisted biogenesis of the Dr fimbrial polyadhesin from uropathogenic Escherichia coli.

Authors:  Rafał Piatek; Beata Zalewska-Piatek; Krystyna Dzierzbicka; Sławomir Makowiec; Justyna Pilipczuk; Kasjan Szemiako; Anna Cyranka-Czaja; Marek Wojciechowski
Journal:  BMC Microbiol       Date:  2013-06-12       Impact factor: 3.605
  9 in total

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