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Regioisomers of the Dinitroaniline Scaffold: Exploring Tubulin Assembly Inhibition through Novel Antikinetoplastid Agents

Latibeaudiere, Kirk D.
http://rave.ohiolink.edu/etdc/view?acc_num=osu1218135242

Abstract Details

2008, Master of Science, Ohio State University, Pharmacy.
Novel dinitroaniline regioisomers based on the herbicides trifluralin 1, oryzalin 4 and GB-II-5 5 were synthesized. These agents were evaluated for activity against the parasitic protozoans Trypanosoma brucei and Leishmania donovani as well as Leishmania tarentolae tubulin. Tubulin polymerization inhibition is the putative mechanism of antiparasitic action for trifluralin regioisomers; herein we report these compounds do not inhibit parasite growth through tubulin destabilization. We speculate that a separate mechanism of antiparasitic action is operative for trifluralin regioisomers, distinct from the destabilizing binding pocket proposed for other dinitroanilines. Regioisomers of oryzalin and GB-II-5 have weak antiparasitic activity and do not inhibit the assembly of tubulin. Regioisomers of the dinitroaniline sulfanilamide scaffold results in lowered affinity for the binding site; these compounds exhibit a several fold decrease in antikinetoplastid potency in comparison to GB-II-5.
Karl Werbovetz, PhD (Advisor)
Jim Fuchs, PhD (Committee Member)
108 p.
Organic Chemistry; Parasitology; Pharmacology
trifluralin; oryzalin; GB-II-5; regioisomer; Leishmaniasis; African trypanosomiasis

Recommended Citations

Citations

  • Latibeaudiere, K. D. (2008). Regioisomers of the Dinitroaniline Scaffold: Exploring Tubulin Assembly Inhibition through Novel Antikinetoplastid Agents [Master's thesis, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1218135242

    APA Style (7th edition)

  • Latibeaudiere, Kirk. Regioisomers of the Dinitroaniline Scaffold: Exploring Tubulin Assembly Inhibition through Novel Antikinetoplastid Agents. 2008. Ohio State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1218135242.

    MLA Style (8th edition)

  • Latibeaudiere, Kirk. "Regioisomers of the Dinitroaniline Scaffold: Exploring Tubulin Assembly Inhibition through Novel Antikinetoplastid Agents." Master's thesis, Ohio State University, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=osu1218135242

    Chicago Manual of Style (17th edition)

osu1218135242
1,067
© 2008, some rights reserved.Creative Commons License Regioisomers of the Dinitroaniline Scaffold: Exploring Tubulin Assembly Inhibition through Novel Antikinetoplastid Agents by Kirk D. Latibeaudiere is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. Based on a work at etd.ohiolink.edu.
This open access ETD is published by The Ohio State University and OhioLINK.