Literature DB >> 11277531

Diaryl ester prodrugs of FR900098 with improved in vivo antimalarial activity.

A Reichenberg1, J Wiesner, C Weidemeyer, E Dreiseidler, S Sanderbrand, B Altincicek, E Beck, M Schlitzer, H Jomaa.   

Abstract

The fosmidomycin derivative FR900098 represents an inhibitor of the 1-deoxy-D-xylulose 5-phosphate (DOXP) reductoisomerase with potent antimalarial activity. Prodrugs of FR900098 with increased activity after oral administration were obtained by chemical modification of the phosphonate moiety to yield phosphodiaryl esters. One diaryl ester prodrug demonstrated efficacy in mice infected with the rodent malaria parasite Plasmodium vinckei comparable to i.p. drug administration.

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Year:  2001        PMID： 11277531     DOI： 10.1016/s0960-894x(01)00075-0

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


  21 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

3.  Structure-guided design and biosynthesis of a novel FR-900098 analogue as a potent Plasmodium falciparum 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr) inhibitor.

Authors:  Ryan E Cobb; Brian Bae; Zhi Li; Matthew A DeSieno; Satish K Nair; Huimin Zhao
Journal:  Chem Commun (Camb)       Date:  2015-02-14       Impact factor: 6.222

Review 4.  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

5.  New N-acetyltransferase fold in the structure and mechanism of the phosphonate biosynthetic enzyme FrbF.

Authors:  Brian Bae; Ryan E Cobb; Matthew A DeSieno; Huimin Zhao; Satish K Nair
Journal:  J Biol Chem       Date:  2011-08-24       Impact factor: 5.157

6.  Resistance to the antimicrobial agent fosmidomycin and an FR900098 prodrug through mutations in the deoxyxylulose phosphate reductoisomerase gene (dxr).

Authors:  Christopher M Armstrong; David J Meyers; Leah S Imlay; Caren Freel Meyers; Audrey R Odom
Journal:  Antimicrob Agents Chemother       Date:  2015-06-29       Impact factor: 5.191

Review 7.  Fosmidomycin for the treatment of malaria.

Authors:  Jochen Wiesner; Steffen Borrmann; Hassan Jomaa
Journal:  Parasitol Res       Date:  2002-11-30       Impact factor: 2.289

8.  The effect of chain length and unsaturation on Mtb Dxr inhibition and antitubercular killing activity of FR900098 analogs.

Authors:  Emily R Jackson; Géraldine San Jose; Robert C Brothers; Emma K Edelstein; Zachary Sheldon; Amanda Haymond; Chinchu Johny; Helena I Boshoff; Robin D Couch; Cynthia S Dowd
Journal:  Bioorg Med Chem Lett       Date:  2013-12-04       Impact factor: 2.823

9.  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

10.  Structure-Activity Relationships of the MEPicides: N-Acyl and O-Linked Analogs of FR900098 as Inhibitors of Dxr from Mycobacterium tuberculosis and Yersinia pestis.

Authors:  Géraldine San Jose; Emily R Jackson; Amanda Haymond; Chinchu Johny; Rachel L Edwards; Xu Wang; R Carl Brothers; Emma K Edelstein; Audrey R Odom; Helena I Boshoff; Robin D Couch; Cynthia S Dowd
Journal:  ACS Infect Dis       Date:  2016-10-12       Impact factor: 5.084
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