Literature DB >> 22342144

Antidotes to anthrax lethal factor intoxication. Part 3: Evaluation of core structures and further modifications to the C2-side chain.

Guan-Sheng Jiao1, Seongjin Kim, Mahtab Moayeri, Devorah Crown, April Thai, Lynne Cregar-Hernandez, Linda McKasson, Banumathi Sankaran, Axel Lehrer, Teri Wong, Lisa Johns, Stephen A Margosiak, Stephen H Leppla, Alan T Johnson.   

Abstract

Four core structures capable of providing sub-nanomolar inhibitors of n class="Species">anthrax lethal factor (LF) were evaluated by comparing the potential for toxicity, physicochemical properties, in vitro ADME profiles, and relative efficacy in a rat lethal toxin (LT) model of LF intoxication. Poor efficacy in the rat LT model exhibited by the phenoxyacetic acid series (3) correlated with low rat microsome and plasma stability. Specific molecular interactions contributing to the high affinity of inhibitors with a secondary amine in the C2-side chain were revealed by X-ray crystallography. Copyright Â
© 2012 Elsevier Ltd. All rights reserved.

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Year:  2012        PMID: 22342144      PMCID: PMC3295836          DOI: 10.1016/j.bmcl.2012.01.095

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


  17 in total

1.  ElogD(oct): a tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds.

Authors:  F Lombardo; M Y Shalaeva; K A Tupper; F Gao
Journal:  J Med Chem       Date:  2001-07-19       Impact factor: 7.446

2.  Proteolytic inactivation of MAP-kinase-kinase by anthrax lethal factor.

Authors:  N S Duesbery; C P Webb; S H Leppla; V M Gordon; K R Klimpel; T D Copeland; N G Ahn; M K Oskarsson; K Fukasawa; K D Paull; G F Vande Woude
Journal:  Science       Date:  1998-05-01       Impact factor: 47.728

3.  High-throughput permeability pH profile and high-throughput alkane/water log P with artificial membranes.

Authors:  F Wohnsland; B Faller
Journal:  J Med Chem       Date:  2001-03-15       Impact factor: 7.446

4.  Susceptibility of mitogen-activated protein kinase kinase family members to proteolysis by anthrax lethal factor.

Authors:  G Vitale; L Bernardi; G Napolitani; M Mock; C Montecucco
Journal:  Biochem J       Date:  2000-12-15       Impact factor: 3.857

5.  Binding of hydroxamic acid inhibitors to crystalline thermolysin suggests a pentacoordinate zinc intermediate in catalysis.

Authors:  M A Holmes; B W Matthews
Journal:  Biochemistry       Date:  1981-11-24       Impact factor: 3.162

6.  Antidotes to anthrax lethal factor intoxication. Part 2: structural modifications leading to improved in vivo efficacy.

Authors:  Seongjin Kim; Guan-Sheng Jiao; Mahtab Moayeri; Devorah Crown; Lynne Cregar-Hernandez; Linda McKasson; Stephen A Margosiak; Stephen H Leppla; Alan T Johnson
Journal:  Bioorg Med Chem Lett       Date:  2011-02-18       Impact factor: 2.823

7.  Anthrax lethal factor inhibition.

Authors:  W L Shoop; Y Xiong; J Wiltsie; A Woods; J Guo; J V Pivnichny; T Felcetto; B F Michael; A Bansal; R T Cummings; B R Cunningham; A M Friedlander; C M Douglas; S B Patel; D Wisniewski; G Scapin; S P Salowe; D M Zaller; K T Chapman; E M Scolnick; D M Schmatz; K Bartizal; M MacCoss; J D Hermes
Journal:  Proc Natl Acad Sci U S A       Date:  2005-05-23       Impact factor: 11.205

Review 8.  Anthrax toxin.

Authors:  R John Collier; John A T Young
Journal:  Annu Rev Cell Dev Biol       Date:  2003       Impact factor: 13.827

9.  Anthrax toxin edema factor: a bacterial adenylate cyclase that increases cyclic AMP concentrations of eukaryotic cells.

Authors:  S H Leppla
Journal:  Proc Natl Acad Sci U S A       Date:  1982-05       Impact factor: 11.205

10.  Bioterrorism-related inhalational anthrax: the first 10 cases reported in the United States.

Authors:  J A Jernigan; D S Stephens; D A Ashford; C Omenaca; M S Topiel; M Galbraith; M Tapper; T L Fisk; S Zaki; T Popovic; R F Meyer; C P Quinn; S A Harper; S K Fridkin; J J Sejvar; C W Shepard; M McConnell; J Guarner; W J Shieh; J M Malecki; J L Gerberding; J M Hughes; B A Perkins
Journal:  Emerg Infect Dis       Date:  2001 Nov-Dec       Impact factor: 6.883

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  7 in total

Review 1.  Targeting Metalloenzymes for Therapeutic Intervention.

Authors:  Allie Y Chen; Rebecca N Adamek; Benjamin L Dick; Cy V Credille; Christine N Morrison; Seth M Cohen
Journal:  Chem Rev       Date:  2018-09-07       Impact factor: 60.622

Review 2.  Designing inhibitors of anthrax toxin.

Authors:  Ekaterina M Nestorovich; Sergey M Bezrukov
Journal:  Expert Opin Drug Discov       Date:  2014-01-22       Impact factor: 6.098

Review 3.  An overview of investigational toxin-directed therapies for the adjunctive management of Bacillus anthracis infection and sepsis.

Authors:  Lernik Ohanjanian; Kenneth E Remy; Yan Li; Xizhong Cui; Peter Q Eichacker
Journal:  Expert Opin Investig Drugs       Date:  2015-04-28       Impact factor: 6.206

4.  Anthrax toxin lethal factor domain 3 is highly mobile and responsive to ligand binding.

Authors:  Kimberly M Maize; Elbek K Kurbanov; Teresa De La Mora-Rey; Todd W Geders; Dong Jin Hwang; Michael A Walters; Rodney L Johnson; Elizabeth A Amin; Barry C Finzel
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2014-10-16

5.  Ligand-induced expansion of the S1' site in the anthrax toxin lethal factor.

Authors:  Kimberly M Maize; Elbek K Kurbanov; Rodney L Johnson; Elizabeth Ambrose Amin; Barry C Finzel
Journal:  FEBS Lett       Date:  2015-11-11       Impact factor: 4.124

6.  Small-molecule inhibitors of lethal factor protease activity protect against anthrax infection.

Authors:  Mahtab Moayeri; Devorah Crown; Guan-Sheng Jiao; Seongjin Kim; Alan Johnson; Clinton Leysath; Stephen H Leppla
Journal:  Antimicrob Agents Chemother       Date:  2013-06-17       Impact factor: 5.191

Review 7.  Inhibitors of the Metalloproteinase Anthrax Lethal Factor.

Authors:  Allison B Goldberg; Benjamin E Turk
Journal:  Curr Top Med Chem       Date:  2016       Impact factor: 3.295

  7 in total

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