Literature DB >> 24900710

Discovery of a New Class of Potent MMP Inhibitors by Structure-Based Optimization of the Arylsulfonamide Scaffold.

Mattia Mori1, Assunta Massaro2, Vito Calderone3, Marco Fragai4, Claudio Luchinat4, Alessandro Mordini5.   

Abstract

A new class of potent matrix metalloproteinase (MMP) inhibitors designed by structure-based optimization of the well-known arylsulfonamide scaffold is presented. Molecules show an ethylene linker connecting the sulfonamide group with the P1' aromatic portion and a d-proline residue bearing the zinc-binding group. The affinity improvement provided by these modifications led us to discover a nanomolar MMP inhibitor bearing a carboxylate moiety as zinc-binding group, which might be a promising lead molecule. Notably, a significant selectivity for MMP-8, MMP-12, and MMP-13 was observed with respect to MMP-1 and MMP-7.

Entities:  

Keywords:  MMP; X-ray; desolvation; docking; free energy; synthesis

Year:  2013        PMID： 24900710      PMCID： PMC4027459          DOI： 10.1021/ml300446a

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  28 in total

1.  A 'rule of three' for fragment-based lead discovery?

Authors:  Miles Congreve; Robin Carr; Chris Murray; Harren Jhoti
Journal:  Drug Discov Today       Date:  2003-10-01       Impact factor: 7.851

2.  Biphenyl sulfonylamino methyl bisphosphonic acids as inhibitors of matrix metalloproteinases and bone resorption.

Authors:  Maria Teresa Rubino; Mariangela Agamennone; Cristina Campestre; Pietro Campiglia; Viviana Cremasco; Roberta Faccio; Antonio Laghezza; Fulvio Loiodice; Dariana Maggi; Emilia Panza; Armando Rossello; Paolo Tortorella
Journal:  ChemMedChem       Date:  2011-03-15       Impact factor: 3.466

3.  Discovery of potent and selective matrix metalloprotease 12 inhibitors for the potential treatment of chronic obstructive pulmonary disease (COPD).

Authors:  Yuchuan Wu; Jianchang Li; Junjun Wu; Paul Morgan; Xin Xu; Fabio Rancati; Stefania Vallese; Luca Raveglia; Rajeev Hotchandani; Nathan Fuller; Joel Bard; Kristina Cunningham; Susan Fish; Rustem Krykbaev; Steve Tam; Samuel J Goldman; Cara Williams; Tarek S Mansour; Eddine Saiah; Joseph Sypek; Wei Li
Journal:  Bioorg Med Chem Lett       Date:  2011-11-20       Impact factor: 2.823

4.  Exploring the subtleties of drug-receptor interactions: the case of matrix metalloproteinases.

Authors:  Ivano Bertini; Vito Calderone; Marco Fragai; Andrea Giachetti; Mauro Loconte; Claudio Luchinat; Massimiliano Maletta; Cristina Nativi; Kwon Joo Yeo
Journal:  J Am Chem Soc       Date:  2007-02-02       Impact factor: 15.419

5.  A highly soluble matrix metalloproteinase-9 inhibitor for potential treatment of dry eye syndrome.

Authors:  Mattia Mori; Emanuele De Lorenzo; Eugenio Torre; Marco Fragai; Cristina Nativi; Claudio Luchinat; Annarosa Arcangeli
Journal:  Basic Clin Pharmacol Toxicol       Date:  2012-05-18       Impact factor: 4.080

Review 6.  Third generation of matrix metalloprotease inhibitors: Gain in selectivity by targeting the depth of the S1' cavity.

Authors:  Laurent Devel; Bertrand Czarny; Fabrice Beau; Dimitris Georgiadis; Enrico Stura; Vincent Dive
Journal:  Biochimie       Date:  2010-08-07       Impact factor: 4.079

7.  Comparison of the pharmacology of hydroxamate- and carboxylate-based matrix metalloproteinase inhibitors (MMPIs) for the treatment of osteoarthritis.

Authors:  M J Janusz; E B Hookfin; K K Brown; L C Hsieh; S A Heitmeyer; Y O Taiwo; M G Natchus; S Pikul; N G Almstead; B De; S X Peng; T R Baker; V Patel
Journal:  Inflamm Res       Date:  2006-02       Impact factor: 4.575

8.  A selective matrix metalloprotease 12 inhibitor for potential treatment of chronic obstructive pulmonary disease (COPD): discovery of (S)-2-(8-(methoxycarbonylamino)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoic acid (MMP408).

Authors:  Wei Li; Jianchang Li; Yuchuan Wu; Junjun Wu; Rajeev Hotchandani; Kristina Cunningham; Iain McFadyen; Joel Bard; Paul Morgan; Franklin Schlerman; Xin Xu; Steve Tam; Samuel J Goldman; Cara Williams; Joseph Sypek; Tarek S Mansour
Journal:  J Med Chem       Date:  2009-04-09       Impact factor: 7.446

9.  AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility.

Authors:  Garrett M Morris; Ruth Huey; William Lindstrom; Michel F Sanner; Richard K Belew; David S Goodsell; Arthur J Olson
Journal:  J Comput Chem       Date:  2009-12       Impact factor: 3.376

10.  Crystal structure of the catalytic domain of human matrix metalloproteinase 10.

Authors:  I Bertini; V Calderone; M Fragai; C Luchinat; S Mangani; B Terni
Journal:  J Mol Biol       Date:  2004-02-20       Impact factor: 5.469
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  4 in total

1.  An integrated structure- and pharmacophore-based MMP-12 virtual screening.

Authors:  Mohammad Ramezani; Jamal Shamsara
Journal:  Mol Divers       Date:  2018-02-08       Impact factor: 2.943

2.  Potent and Selective Carboxylic Acid Inhibitors of Tumor-Associated Carbonic Anhydrases IX and XII.

Authors:  Ylenia Cau; Daniela Vullo; Mattia Mori; Elena Dreassi; Claudiu T Supuran; Maurizio Botta
Journal:  Molecules       Date:  2017-12-22       Impact factor: 4.411

Review 3.  Regulation and involvement of matrix metalloproteinases in vascular diseases.

Authors:  Matthew Amin; Sathnur Pushpakumar; Nino Muradashvili; Sourav Kundu; Suresh C Tyagi; Utpal Sen
Journal:  Front Biosci (Landmark Ed)       Date:  2016-01-01

4.  Chemical, computational and functional insights into the chemical stability of the Hedgehog pathway inhibitor GANT61.

Authors:  Andrea Calcaterra; Valentina Iovine; Bruno Botta; Deborah Quaglio; Ilaria D'Acquarica; Alessia Ciogli; Antonia Iazzetti; Romina Alfonsi; Ludovica Lospinoso Severini; Paola Infante; Lucia Di Marcotullio; Mattia Mori; Francesca Ghirga
Journal:  J Enzyme Inhib Med Chem       Date:  2018-12       Impact factor: 5.051
  4 in total

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