Literature DB >> 18499453

Design, synthesis, and evaluation of inhibitors of cathepsin L: Exploiting a unique thiocarbazate chemotype.

Michael C Myers1, Parag P Shah, Mary Pat Beavers, Andrew D Napper, Scott L Diamond, Amos B Smith, Donna M Huryn.   

Abstract

Recently, we identified a thiocarbazate that exhibits potent inhibitory activity against human cathepsin L. Since this structure represents a novel chemotype with potential for activity against the entire cysteine protease family, we designed, synthesized, and assayed a series of analogs to probe the mechanism of action, as well as the structural requirements for cathepsin L activity. Molecular docking studies using coordinates of a papain-inhibitor complex as a model for cathepsin L provided useful insights.

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Year:  2008        PMID： 18499453      PMCID： PMC2494853          DOI： 10.1016/j.bmcl.2008.04.065

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


  29 in total

Review 1.  Human and parasitic papain-like cysteine proteases: their role in physiology and pathology and recent developments in inhibitor design.

Authors:  Fabien Lecaille; Jadwiga Kaleta; Dieter Brömme
Journal:  Chem Rev       Date:  2002-12       Impact factor: 60.622

Review 2.  Recent advances in the synthesis, design and selection of cysteine protease inhibitors.

Authors:  Alejandro Alvarez Hernandez; William R Roush
Journal:  Curr Opin Chem Biol       Date:  2002-08       Impact factor: 8.822

3.  Aza-amino acid scanning of secondary structure suited for solid-phase peptide synthesis with fmoc chemistry and aza-amino acids with heteroatomic side chains.

Authors:  Damien Boeglin; William D Lubell
Journal:  J Comb Chem       Date:  2005 Nov-Dec

4.  Kinetic characterization and molecular docking of a novel, potent, and selective slow-binding inhibitor of human cathepsin L.

Authors:  Parag P Shah; Michael C Myers; Mary Pat Beavers; Jeremy E Purvis; Huiyan Jing; Heather J Grieser; Elizabeth R Sharlow; Andrew D Napper; Donna M Huryn; Barry S Cooperman; Amos B Smith; Scott L Diamond
Journal:  Mol Pharmacol       Date:  2008-04-10       Impact factor: 4.436

5.  Inhibitors of cathepsin L prevent severe acute respiratory syndrome coronavirus entry.

Authors:  Graham Simmons; Dhaval N Gosalia; Andrew J Rennekamp; Jacqueline D Reeves; Scott L Diamond; Paul Bates
Journal:  Proc Natl Acad Sci U S A       Date:  2005-08-04       Impact factor: 11.205

6.  Purification of cathepsin B by a new form of affinity chromatography.

Authors:  D H Rich; M A Brown; A J Barrett
Journal:  Biochem J       Date:  1986-05-01       Impact factor: 3.857

7.  Endosomal proteolysis of the Ebola virus glycoprotein is necessary for infection.

Authors:  Kartik Chandran; Nancy J Sullivan; Ute Felbor; Sean P Whelan; James M Cunningham
Journal:  Science       Date:  2005-04-14       Impact factor: 47.728

8.  From good substrates to good inhibitors: design of inhibitors for serine and thiol proteases.

Authors:  R Baggio; Y Q Shi; Y Q Wu
Journal:  Biochemistry       Date:  1996-03-19       Impact factor: 3.162

9.  Cysteine protease inhibition by azapeptide esters.

Authors:  J Magrath; R H Abeles
Journal:  J Med Chem       Date:  1992-11-13       Impact factor: 7.446

10.  Targeting cathepsin L (CL) by specific ribozymes decreases CL protein synthesis and cartilage destruction in rheumatoid arthritis.

Authors:  J Schedel; C A Seemayer; T Pap; M Neidhart; S Kuchen; B A Michel; R E Gay; U Müller-Ladner; S Gay; W Zacharias
Journal:  Gene Ther       Date:  2004-07       Impact factor: 5.250
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  7 in total

1.  Design, synthesis and biological evaluation of a library of thiocarbazates and their activity as cysteine protease inhibitors.

Authors:  Zhuqing Liu; Michael C Myers; Parag P Shah; Mary Pat Beavers; Phillip A Benedetti; Scott L Diamond; Amos B Smith; Donna M Huryn
Journal:  Comb Chem High Throughput Screen       Date:  2010-05       Impact factor: 1.339

2.  A small-molecule oxocarbazate inhibitor of human cathepsin L blocks severe acute respiratory syndrome and ebola pseudotype virus infection into human embryonic kidney 293T cells.

Authors:  Parag P Shah; Tianhua Wang; Rachel L Kaletsky; Michael C Myers; Jeremy E Purvis; Huiyan Jing; Donna M Huryn; Doron C Greenbaum; Amos B Smith; Paul Bates; Scott L Diamond
Journal:  Mol Pharmacol       Date:  2010-05-13       Impact factor: 4.436

Review 3.  The identification, characterization and optimization of small molecule probes of cysteine proteases: experiences of the Penn Center for Molecular Discovery with cathepsin B and cathepsin L.

Authors:  Donna M Huryn; Amos B Smith
Journal:  Curr Top Med Chem       Date:  2009       Impact factor: 3.295

4.  Insights into the Interactions of Fasciola hepatica Cathepsin L3 with a Substrate and Potential Novel Inhibitors through In Silico Approaches.

Authors:  Lilian Hernández Alvarez; Dany Naranjo Feliciano; Jorge Enrique Hernández González; R O Soares; Rosemberg de Oliveira Soares; Diego Enry Barreto Gomes; Pedro Geraldo Pascutti
Journal:  PLoS Negl Trop Dis       Date:  2015-05-15

Review 5.  Cell entry of enveloped viruses.

Authors:  François-Loic Cosset; Dimitri Lavillette
Journal:  Adv Genet       Date:  2011       Impact factor: 1.944

6.  Design, synthesis, and biological evaluation of potent thiosemicarbazone based cathepsin L inhibitors.

Authors:  G D Kishore Kumar; Gustavo E Chavarria; Amanda K Charlton-Sevcik; Wara M Arispe; Matthew T Macdonough; Tracy E Strecker; Shen-En Chen; Bronwyn G Siim; David J Chaplin; Mary Lynn Trawick; Kevin G Pinney
Journal:  Bioorg Med Chem Lett       Date:  2010-01-06       Impact factor: 2.823

Review 7.  SARS-CoV-2 Entry Inhibitors: Small Molecules and Peptides Targeting Virus or Host Cells.

Authors:  Rolando Cannalire; Irina Stefanelli; Carmen Cerchia; Andrea R Beccari; Sveva Pelliccia; Vincenzo Summa
Journal:  Int J Mol Sci       Date:  2020-08-09       Impact factor: 5.923
  7 in total

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