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Synthesis and activity of substituted anthraquinones against a human filarial parasite, Brugia malayi. J Med Chem 2005 Apr 21;48(8):2822-30

Date

04/15/2005

Pubmed ID

15828820

DOI

10.1021/jm0492655

Abstract

Lymphatic filariasis (elephantiasis) is a global public health problem caused by the parasitic nematodes Wuchereria bancrofti and Brugia malayi. We have previously reported anthraquinones from daylily roots with potent activity against pathogenic trematode Schistosoma mansoni. Here we report the synthesis of novel anthraquinones A-S and their antifilrarial activity. Anthraquinones A-S were synthesized by a single-step Friedel-Crafts acylation reaction between phthalic anhydrides and substituted benzenes. The antifilarial properties of these synthetic anthraquinones were tested against microfilaria as well as adult male and female worms of B. malayi. The most active anthraquinone was K, which showed 100% mortality within 1, 5, and 3 days, respectively, against microfilaria and adult male and female worms at 5 ppm concentration. Albendazole, an oral drug currently used to treat parasitic infections, was used as a positive control. Methylated products of anthraquinones did not affect the microfilaria. Histological examination of treated adult female parasites showed most of the anthraquinones caused marked effects on intrauterine embryos.

Author List

Dhananjeyan MR, Milev YP, Kron MA, Nair MG

Author

Michael Kron MD Director, Professor in the Medicine department at Medical College of Wisconsin




MESH terms used to index this publication - Major topics in bold

Animals
Anthraquinones
Brugia malayi
Embryo, Nonmammalian
Female
Filaricides
Humans
In Vitro Techniques
Larva
Male
Structure-Activity Relationship
jenkins-FCD Prod-410 e9586552fe7f53c71f7923aa6e27aeabbd3c2473