Literature DB >> 18420405

Discovery of trypanocidal thiosemicarbazone inhibitors of rhodesain and TbcatB.

Jeremy P Mallari1, Anang Shelat, Aaron Kosinski, Conor R Caffrey, Michele Connelly, Fangyi Zhu, James H McKerrow, R Kiplin Guy.   

Abstract

Human African trypanosomiasis (HAT) is caused by the protozoan parasite Trypanosoma brucei. The cysteine proteases of T. brucei have been shown to be crucial for parasite replication and represent an attractive point for therapeutic intervention. Herein we describe the synthesis of a series of thiosemicarbazones and their activity against the trypanosomal cathepsins TbcatB and rhodesain, as well as human cathepsins L and B. The activity of these compounds was determined against cultured T. brucei, and specificity was assessed with a panel of four mammalian cell lines.

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Year:  2008        PMID: 18420405      PMCID: PMC2435229          DOI: 10.1016/j.bmcl.2008.03.083

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


  16 in total

1.  Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi.

Authors:  Doron C Greenbaum; Zachary Mackey; Elizabeth Hansell; Patricia Doyle; Jiri Gut; Conor R Caffrey; Julia Lehrman; Philip J Rosenthal; James H McKerrow; Kelly Chibale
Journal:  J Med Chem       Date:  2004-06-03       Impact factor: 7.446

2.  Lysis of trypanosomes by peptidyl fluoromethyl ketones.

Authors:  F Ashall; H Angliker; E Shaw
Journal:  Biochem Biophys Res Commun       Date:  1990-07-31       Impact factor: 3.575

3.  Trypanosoma brucei: killing of bloodstream forms in vitro and in vivo by the cysteine proteinase inhibitor Z-phe-ala-CHN2.

Authors:  S Scory; C R Caffrey; Y D Stierhof; A Ruppel; D Steverding
Journal:  Exp Parasitol       Date:  1999-04       Impact factor: 2.011

4.  Cysteine proteinase inhibitors kill cultured bloodstream forms of Trypanosoma brucei brucei.

Authors:  L Troeberg; R E Morty; R N Pike; J D Lonsdale-Eccles; J T Palmer; J H McKerrow; T H Coetzer
Journal:  Exp Parasitol       Date:  1999-04       Impact factor: 2.011

5.  Risk factors for treatment failure after melarsoprol for Trypanosoma brucei gambiense trypanosomiasis in Uganda.

Authors:  D Legros; S Evans; F Maiso; J C Enyaru; D Mbulamberi
Journal:  Trans R Soc Trop Med Hyg       Date:  1999 Jul-Aug       Impact factor: 2.184

6.  Discovery of potent thiosemicarbazone inhibitors of rhodesain and cruzain.

Authors:  Naoaki Fujii; Jeremy P Mallari; Elizabeth J Hansell; Z Mackey; Patricia Doyle; Y M Zhou; Jiri Gut; Philip J Rosenthal; James H McKerrow; R Kiplin Guy
Journal:  Bioorg Med Chem Lett       Date:  2005-01-03       Impact factor: 2.823

7.  The phenomenon of treatment failures in Human African Trypanosomiasis.

Authors:  R Brun; R Schumacher; C Schmid; C Kunz; C Burri
Journal:  Trop Med Int Health       Date:  2001-11       Impact factor: 2.622

8.  A cathepsin B-like protease is required for host protein degradation in Trypanosoma brucei.

Authors:  Zachary B Mackey; Theresa C O'Brien; Doron C Greenbaum; Rebecca B Blank; James H McKerrow
Journal:  J Biol Chem       Date:  2004-08-23       Impact factor: 5.157

9.  2-Acetylpyridine thiosemicarbazones. 1. A new class of potential antimalarial agents.

Authors:  D L Klayman; J F Bartosevich; T S Griffin; C J Mason; J P Scovill
Journal:  J Med Chem       Date:  1979-07       Impact factor: 7.446

10.  Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain.

Authors:  Xiaohui Du; Chun Guo; Elizabeth Hansell; Patricia S Doyle; Conor R Caffrey; Tod P Holler; James H McKerrow; Fred E Cohen
Journal:  J Med Chem       Date:  2002-06-20       Impact factor: 7.446

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  16 in total

1.  Trypanocidal and cytotoxic evaluation of synthesized thiosemicarbazones as potential drug leads against sleeping sickness.

Authors:  Bienvenu Glinma; Sika D S Kpoviessi; Fernand A Gbaguidi; Coco N Kapanda; Joanne Bero; Joëlle Quetin-Leclercq; Mansourou Moudachirou; Jacques Poupaert; Georges C Accrombessi; Emma W Gachomo; Lamine Baba-Moussa; Simeon O Kotchoni
Journal:  Mol Biol Rep       Date:  2014-01-10       Impact factor: 2.316

2.  Synthesis and biochemical evaluation of benzoylbenzophenone thiosemicarbazone analogues as potent and selective inhibitors of cathepsin L.

Authors:  Erica N Parker; Jiangli Song; G D Kishore Kumar; Samuel O Odutola; Gustavo E Chavarria; Amanda K Charlton-Sevcik; Tracy E Strecker; Ashleigh L Barnes; Dhivya R Sudhan; Thomas R Wittenborn; Dietmar W Siemann; Michael R Horsman; David J Chaplin; Mary Lynn Trawick; Kevin G Pinney
Journal:  Bioorg Med Chem       Date:  2015-09-25       Impact factor: 3.641

3.  Synthesis and biochemical evaluation of thiochromanone thiosemicarbazone analogues as inhibitors of cathepsin L.

Authors:  Jiangli Song; Lindsay M Jones; G D Kishore Kumar; Elizabeth S Conner; Liela Bayeh; Gustavo E Chavarria; Amanda K Charlton-Sevcik; Shen-En Chen; David J Chaplin; Mary Lynn Trawick; Kevin G Pinney
Journal:  ACS Med Chem Lett       Date:  2012-04-18       Impact factor: 4.345

Review 4.  State of the art in African trypanosome drug discovery.

Authors:  Robert T Jacobs; Bakela Nare; Margaret A Phillips
Journal:  Curr Top Med Chem       Date:  2011       Impact factor: 3.295

5.  Assessing the trypanocidal potential of natural and semi-synthetic diketopiperazines from two deep water marine-derived fungi.

Authors:  Katharine R Watts; Joseline Ratnam; Kean-Hooi Ang; Karen Tenney; Jennifer E Compton; James McKerrow; Phillip Crews
Journal:  Bioorg Med Chem       Date:  2010-03-01       Impact factor: 3.641

6.  Synthesis of a sugar-based thiosemicarbazone series and structure-activity relationship versus the parasite cysteine proteases rhodesain, cruzain, and Schistosoma mansoni cathepsin B1.

Authors:  Nayara Cristina Fonseca; Luana Faria da Cruz; Filipe da Silva Villela; Glaécia Aparecida do Nascimento Pereira; Jair Lage de Siqueira-Neto; Danielle Kellar; Brian M Suzuki; Debalina Ray; Thiago Belarmino de Souza; Ricardo José Alves; Policarpo Ademar Sales Júnior; Alvaro José Romanha; Silvane Maria Fonseca Murta; James H McKerrow; Conor R Caffrey; Renata Barbosa de Oliveira; Rafaela Salgado Ferreira
Journal:  Antimicrob Agents Chemother       Date:  2015-02-23       Impact factor: 5.191

7.  Antimalarial activity of thiosemicarbazones and purine derived nitriles.

Authors:  Jeremy P Mallari; Wendyam A Guiguemde; R Kiplin Guy
Journal:  Bioorg Med Chem Lett       Date:  2009-05-05       Impact factor: 2.823

8.  Crystal Structures of TbCatB and rhodesain, potential chemotherapeutic targets and major cysteine proteases of Trypanosoma brucei.

Authors:  Iain D Kerr; Peng Wu; Rachael Marion-Tsukamaki; Zachary B Mackey; Linda S Brinen
Journal:  PLoS Negl Trop Dis       Date:  2010-06-08

9.  Structure-guided development of selective TbcatB inhibitors.

Authors:  Jeremy P Mallari; Anang A Shelat; Aaron Kosinski; Conor R Caffrey; Michele Connelly; Fangyi Zhu; James H McKerrow; R Kiplin Guy
Journal:  J Med Chem       Date:  2009-10-22       Impact factor: 7.446

10.  The marine sponge Diacarnus bismarckensis as a source of peroxiterpene inhibitors of Trypanosoma brucei, the causative agent of sleeping sickness.

Authors:  Brent K Rubio; Karen Tenney; Kean-Hooi Ang; Maha Abdulla; Michelle Arkin; James H McKerrow; Phillip Crews
Journal:  J Nat Prod       Date:  2009-02-27       Impact factor: 4.050

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