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Bioorg Med Chem. 2008 May 15;16(10):5536-46. doi: 10.1016/j.bmc.2008.04.006. Epub 2008 Apr 9.

Design, synthesis, and application of novel triclosan prodrugs as potential antimalarial and antibacterial agents.

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1
Molecular Biophysics Unit, Indian Institute of Science, Bangalore 560012, India.

Abstract

A number of new triclosan-conjugated analogs bearing biodegradable ester linkage have been synthesized, characterized and evaluated for their antimalarial and antibacterial activities. Many of these compounds exhibit good inhibition against Plasmodium falciparum and Escherichia coli. Among them tertiary amine containing triclosan-conjugated prodrug (5) inhibited both P. falciparum (IC(50); 0.62microM) and E. coli (IC(50); 0.26microM) at lower concentrations as compared to triclosan. Owing to the presence of a cleavable ester moiety, these new prodrugs are hydrolyzed under physiological conditions and parent molecule, triclosan, is released. Further, introduction of tertiary/quaternary functionality increases their cellular uptake. These properties impart them with higher potency to their antimalarial as well as antibacterial activities. The best compound among them 5 shows close to four-fold enhanced activities against P. falciparum and E. coli cultures as compared to triclosan.

PMID:
18434169
DOI:
10.1016/j.bmc.2008.04.006
[Indexed for MEDLINE]

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