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Antimalarial activity of natural and synthetic prodiginines
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Papireddy, Kancharla, Smilkstein, Martin, Kelly, Jane Xu, Salem, Shaimaa M., Alhamadsheh, Mamoun, Haynes, Stuart W., Challis, Gregory L. and Reynolds, Kevin A. (2011) Antimalarial activity of natural and synthetic prodiginines. Journal of Medicinal Chemistry, Volume 54 (Number 15). pp. 5296-5306. doi:10.1021/jm200543y ISSN 0022-2623.
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Official URL: http://dx.doi.org/10.1021/jm200543y
Abstract
Prodiginines are a family of linear and cyclic oligopyrrole red-pigmented compounds. Herein we describe the in vitro antimalarial activity of four natural (IC(50) = 1.7-8.0 nM) and three sets of synthetic prodiginines against Plasmodium falciparum. Set 1 compounds replaced the terminal nonalkylated pyrrole ring of natural prodiginines and had diminished activity (IC(50) > 2920 nM). Set 2 and set 3 prodiginines were monosubstituted or disubstituted at either the 3 or 5 position of the right-hand terminal pyrrole, respectively. Potent in vitro activity (IC(50) = 09-16.0 nM) was observed using alkyl or aryl substituents. Metacycloprodiginine and more potent synthetic analogues were evaluated in a P. yoelii murine patent infection using oral administration. Each analogue reduced parasitemia by more than 90% after 2S (mg/kg)/day dosing and in some cases provided a cure. The most favorable profile was 92% parasite reduction at 5 (mg/kg)/day, and 100% reduction at 2S (mg/kg)/day without any evident weight loses or clinical overt toxicity.
| Item Type: | Journal Article | ||||||||
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| Subjects: | Q Science > QD Chemistry R Medicine > RC Internal medicine R Medicine > RM Therapeutics. Pharmacology |
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| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
| Library of Congress Subject Headings (LCSH): | Antimalarials, Malaria, Plasmodium falciparum, Streptomyces, Apoptosis, Antibiotics -- Synthesis | ||||||||
| Journal or Publication Title: | Journal of Medicinal Chemistry | ||||||||
| Publisher: | American Chemical Society | ||||||||
| ISSN: | 0022-2623 | ||||||||
| Official Date: | 11 August 2011 | ||||||||
| Dates: |
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| Volume: | Volume 54 | ||||||||
| Number: | Number 15 | ||||||||
| Page Range: | pp. 5296-5306 | ||||||||
| DOI: | 10.1021/jm200543y | ||||||||
| Status: | Peer Reviewed | ||||||||
| Publication Status: | Published | ||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||
| Description: | Author Manuscript available in PMC July 2015 |
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| Funder: | National Institutes of Health (U.S.) (NIH) | ||||||||
| Grant number: | GM077147 (NIH) | ||||||||
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