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

Mishra, Satyendra and Karmodiya, Krishanpal and Parasuraman, Prasanna and Surolia, Avadhesha and Surolia, Namita (2008) Design, synthesis, and application of novel triclosan prodrugs as potential antimalarial and antibacterial agents. In: Bioorganic & Medicinal Chemistry, 16 (10). pp. 5536-5546.

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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 (IC50; 0.62 μM) and E. coli (IC50; 0.26 μM) 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.

Item Type:	Journal Article
Publication:	Bioorganic & Medicinal Chemistry
Publisher:	Elsevier Science
Additional Information:	Copyright of this article belongs to Elsevier Science.
Keywords:	Prodrug;Triclosan;Antimalarial;Antibacterial;Plasmodium falciparum;Escherichia Coli.
Department/Centre:	Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited:	11 Mar 2010 06:46
Last Modified:	19 Sep 2010 05:56
URI:	http://eprints.iisc.ac.in/id/eprint/26100

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