Literature DB >> 12798327

Acyloxyalkyl ester prodrugs of FR900098 with improved in vivo anti-malarial activity.

Regina Ortmann1, Jochen Wiesner, Armin Reichenberg, Dajana Henschker, Ewald Beck, Hassan Jomaa, Martin Schlitzer.   

Abstract

FR900098 represents an improved derivative of the new antimalarial drug fosmidomycin and acts through inhibition of the 1-deoxy-D-xylulose 5-phosphate (DOXP) reductoisomerase, an essential enzyme of the mevalonate independent pathway of isoprenoid biosynthesis. Prodrugs with increased activity after oral administration were obtained by chemical modification of the phosphonate moiety to yield acyloxyalkyl esters. The most successful compound demonstrated 2-fold increased activity in mice infected with the rodent malaria parasite Plasmodium vinckei.

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Year:  2003        PMID: 12798327     DOI: 10.1016/s0960-894x(03)00354-8

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


  13 in total

1.  Characterization and application of the Fe(II) and α-ketoglutarate dependent hydroxylase FrbJ.

Authors:  Matthew A DeSieno; Wilfred A van der Donk; Huimin Zhao
Journal:  Chem Commun (Camb)       Date:  2011-08-10       Impact factor: 6.222

Review 2.  Prodrugs of phosphonates and phosphates: crossing the membrane barrier.

Authors:  Andrew J Wiemer; David F Wiemer
Journal:  Top Curr Chem       Date:  2015

Review 3.  Phosphonate prodrugs: an overview and recent advances.

Authors:  Kenneth M Heidel; Cynthia S Dowd
Journal:  Future Med Chem       Date:  2019-07       Impact factor: 3.808

4.  Antibacterial and antitubercular activity of fosmidomycin, FR900098, and their lipophilic analogs.

Authors:  Eugene Uh; Emily R Jackson; Géraldine San Jose; Marcus Maddox; Robin E Lee; Richard E Lee; Helena I Boshoff; Cynthia S Dowd
Journal:  Bioorg Med Chem Lett       Date:  2011-10-05       Impact factor: 2.823

5.  Isoprenoid biosynthesis as a target for antibacterial and antiparasitic drugs: phosphonohydroxamic acids as inhibitors of deoxyxylulose phosphate reducto-isomerase.

Authors:  Lionel Kuntz; Denis Tritsch; Catherine Grosdemange-Billiard; Andréa Hemmerlin; Audrey Willem; Thomas J Bach; Michel Rohmer
Journal:  Biochem J       Date:  2005-02-15       Impact factor: 3.857

Review 6.  Microbial esterases and ester prodrugs: An unlikely marriage for combating antibiotic resistance.

Authors:  Erik M Larsen; R Jeremy Johnson
Journal:  Drug Dev Res       Date:  2018-10-10       Impact factor: 4.360

7.  Efficacy, pharmacokinetics, and metabolism of tetrahydroquinoline inhibitors of Plasmodium falciparum protein farnesyltransferase.

Authors:  Wesley C Van Voorhis; Kasey L Rivas; Pravin Bendale; Laxman Nallan; Carolyn Hornéy; Lynn K Barrett; Kevin D Bauer; Brian P Smart; Sudha Ankala; Oliver Hucke; Christophe L M J Verlinde; Debopam Chakrabarti; Corey Strickland; Kohei Yokoyama; Frederick S Buckner; Andrew D Hamilton; David K Williams; Louis J Lombardo; David Floyd; Michael H Gelb
Journal:  Antimicrob Agents Chemother       Date:  2007-07-02       Impact factor: 5.191

8.  Resistance of Francisella novicida to fosmidomycin associated with mutations in the glycerol-3-phosphate transporter.

Authors:  Ryan S Mackie; Elizabeth S McKenney; Monique L van Hoek
Journal:  Front Microbiol       Date:  2012-08-09       Impact factor: 5.640

9.  Apicoplast isoprenoid precursor synthesis and the molecular basis of fosmidomycin resistance in Toxoplasma gondii.

Authors:  Sethu C Nair; Carrie F Brooks; Christopher D Goodman; Angelika Sturm; Angelika Strurm; Geoffrey I McFadden; Sandeep Sundriyal; Justin L Anglin; Yongcheng Song; Silvia N J Moreno; Boris Striepen
Journal:  J Exp Med       Date:  2011-06-20       Impact factor: 14.307

10.  Lipophilic prodrugs of FR900098 are antimicrobial against Francisella novicida in vivo and in vitro and show GlpT independent efficacy.

Authors:  Elizabeth S McKenney; Michelle Sargent; Hameed Khan; Eugene Uh; Emily R Jackson; Géraldine San Jose; Robin D Couch; Cynthia S Dowd; Monique L van Hoek
Journal:  PLoS One       Date:  2012-10-15       Impact factor: 3.240

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