Literature DB >> 19269184

Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform.

Konstantin V Kudryavtsev1, Matthew L Bentley, Dewey G McCafferty.   

Abstract

cis-5-Phenyl prolinates with electrophilic substituents at the fourth position of a pyrrolidine ring were synthesized by 1,3-dipolar cycloaddition of arylimino esters with divinyl sulfone and acrylonitrile. 4-Vinylsulfonyl 5-phenyl prolinates inhibit Staphylococcus aureus sortase SrtA irreversibly by modification of the enzyme Cys184 and could be used as hits for the development of antibacterials and antivirulence agents.

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Year:  2009        PMID： 19269184      PMCID： PMC2663005          DOI： 10.1016/j.bmc.2009.02.008

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  18 in total

1.  Structure, multiple site binding, and segmental accommodation in thymidylate synthase on binding dUMP and an anti-folate.

Authors:  W R Montfort; K M Perry; E B Fauman; J S Finer-Moore; G F Maley; L Hardy; F Maley; R M Stroud
Journal:  Biochemistry       Date:  1990-07-31       Impact factor: 3.162

Review 2.  Bad bugs need drugs: an update on the development pipeline from the Antimicrobial Availability Task Force of the Infectious Diseases Society of America.

Authors:  George H Talbot; John Bradley; John E Edwards; David Gilbert; Michael Scheld; John G Bartlett
Journal:  Clin Infect Dis       Date:  2005-01-25       Impact factor: 9.079

Review 3.  Sortases and the art of anchoring proteins to the envelopes of gram-positive bacteria.

Authors:  Luciano A Marraffini; Andrea C Dedent; Olaf Schneewind
Journal:  Microbiol Mol Biol Rev       Date:  2006-03       Impact factor: 11.056

4.  Inhibition of sortase-mediated Staphylococcus aureus adhesion to fibronectin via fibronectin-binding protein by sortase inhibitors.

Authors:  Ki-Bong Oh; Mi-Na Oh; Jae-Gyu Kim; Dong-Sun Shin; Jongheon Shin
Journal:  Appl Microbiol Biotechnol       Date:  2005-07-12       Impact factor: 4.813

5.  Curcuma longa L. constituents inhibit sortase A and Staphylococcus aureus cell adhesion to fibronectin.

Authors:  Byeoung-Soo Park; Jae-Gyu Kim; Mi-Ran Kim; Sung-Eun Lee; Gary R Takeoka; Ki-Bong Oh; Jeong-Han Kim
Journal:  J Agric Food Chem       Date:  2005-11-16       Impact factor: 5.279

6.  Flavonols inhibit sortases and sortase-mediated Staphylococcus aureus clumping to fibrinogen.

Authors:  Sam Sik Kang; Jae-Gyu Kim; Tae-Hoon Lee; Ki-Bong Oh
Journal:  Biol Pharm Bull       Date:  2006-08       Impact factor: 2.233

Review 7.  Vinyl sulfones: synthetic preparations and medicinal chemistry applications.

Authors:  D Christopher Meadows; Jacquelyn Gervay-Hague
Journal:  Med Res Rev       Date:  2006-11       Impact factor: 12.944

8.  A generally applicable method for assessing the electrophilicity and reactivity of diverse nitrile-containing compounds.

Authors:  Renata M Oballa; Jean-François Truchon; Christopher I Bayly; Nathalie Chauret; Stephen Day; Sheldon Crane; Carl Berthelette
Journal:  Bioorg Med Chem Lett       Date:  2006-11-17       Impact factor: 2.823

9.  Staphylococcus aureus sortase transpeptidase SrtA: insight into the kinetic mechanism and evidence for a reverse protonation catalytic mechanism.

Authors:  Brenda A Frankel; Ryan G Kruger; Dana E Robinson; Neil L Kelleher; Dewey G McCafferty
Journal:  Biochemistry       Date:  2005-08-23       Impact factor: 3.162

10.  Activation of inhibitors by sortase triggers irreversible modification of the active site.

Authors:  Anthony W Maresso; Ruiying Wu; Justin W Kern; Rongguang Zhang; Dorota Janik; Dominique M Missiakas; Mark-Eugene Duban; Andrzej Joachimiak; Olaf Schneewind
Journal:  J Biol Chem       Date:  2007-06-01       Impact factor: 5.157
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  11 in total

Review 1.  Sortase transpeptidases: insights into mechanism, substrate specificity, and inhibition.

Authors:  Kathleen W Clancy; Jeffrey A Melvin; Dewey G McCafferty
Journal:  Biopolymers       Date:  2010       Impact factor: 2.505

Review 2.  Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.

Authors:  Rubén Cebrián; Qian Li; Pablo Peñalver; Efres Belmonte-Reche; María Andrés-Bilbao; Ricardo Lucas; María Violante de Paz; Oscar P Kuipers; Juan Carlos Morales
Journal:  J Nat Prod       Date:  2022-05-27       Impact factor: 4.803

3.  Discovery and structure-activity relationship analysis of Staphylococcus aureus sortase A inhibitors.

Authors:  Nuttee Suree; Sung Wook Yi; William Thieu; Melanie Marohn; Robert Damoiseaux; Albert Chan; Michael E Jung; Robert T Clubb
Journal:  Bioorg Med Chem       Date:  2009-09-06       Impact factor: 3.641

4.  Discovery of Staphylococcus aureus sortase A inhibitors using virtual screening and the relaxed complex scheme.

Authors:  Albert H Chan; Jeff Wereszczynski; Brendan R Amer; Sung Wook Yi; Michael E Jung; J Andrew McCammon; Robert T Clubb
Journal:  Chem Biol Drug Des       Date:  2013-10       Impact factor: 2.817

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

Review 6.  Targeting Bacterial Sortases in Search of Anti-Virulence Therapies with Low Risk of Resistance Development.

Authors:  Georgiana Nitulescu; Denisa Margina; Anca Zanfirescu; Octavian Tudorel Olaru; George Mihai Nitulescu
Journal:  Pharmaceuticals (Basel)       Date:  2021-04-30

7.  Antimicrobial Effects of Sulfonyl Derivative of 2(5H)-Furanone against Planktonic and Biofilm Associated Methicillin-Resistant and -Susceptible Staphylococcus aureus.

Authors:  Irshad S Sharafutdinov; Elena Y Trizna; Diana R Baidamshina; Maria N Ryzhikova; Regina R Sibgatullina; Alsu M Khabibrakhmanova; Liliya Z Latypova; Almira R Kurbangalieva; Elvira V Rozhina; Mareike Klinger-Strobel; Rawil F Fakhrullin; Mathias W Pletz; Mikhail I Bogachev; Airat R Kayumov; Oliwia Makarewicz
Journal:  Front Microbiol       Date:  2017-11-20       Impact factor: 5.640

8.  Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C-H Borylation and Suzuki Coupling.

Authors:  Saba Kanwal; Noor-Ul- Ann; Saman Fatima; Abdul-Hamid Emwas; Meshari Alazmi; Xin Gao; Maha Ibrar; Rahman Shah Zaib Saleem; Ghayoor Abbas Chotana
Journal:  Molecules       Date:  2020-04-30       Impact factor: 4.411

9.  Exploration of multiple Sortase A protein conformations in virtual screening.

Authors:  Chunxia Gao; Ivana Uzelac; Johan Gottfries; Leif A Eriksson
Journal:  Sci Rep       Date:  2016-02-05       Impact factor: 4.379

10.  Selection of Promising Novel Fragment Sized S. aureus SrtA Noncovalent Inhibitors Based on QSAR and Docking Modeling Studies.

Authors:  Dmitry A Shulga; Konstantin V Kudryavtsev
Journal:  Molecules       Date:  2021-12-19       Impact factor: 4.411
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