Synthesis and cytotoxicity studies of artemisinin derivatives containing lipophilic alkyl carbon chains

Yungen Liu; Vincent Kam-Wai Wong; Ben Chi-Bun Ko; Man-Kin Wong; Chi-Ming Che

doi:10.1021/ol050230o

Synthesis and cytotoxicity studies of artemisinin derivatives containing lipophilic alkyl carbon chains

Org Lett. 2005 Apr 14;7(8):1561-4. doi: 10.1021/ol050230o.

Authors

Yungen Liu¹, Vincent Kam-Wai Wong, Ben Chi-Bun Ko, Man-Kin Wong, Chi-Ming Che

Affiliation

¹ Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.

PMID: 15816752
DOI: 10.1021/ol050230o

Abstract

[reaction: see text] Cytotoxic artemisinin derivatives have been synthesized by a modular approach of "artemisinin + linker + lipophilic alkyl carbon chain". A strong correlation between the length of the carbon chains and the cytotoxicities against human hepatocellular carcinoma (HepG2) was revealed. Notably, compared with artemisinin (IC(50) = 97 microM), up to 200-fold more potent cytotoxicity (IC(50) = 0.46 microM) could be achieved by attachment of a C(14)H(29) carbon chain to artemisinin via an amide linker.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / toxicity*
Artemisinins / chemical synthesis*
Artemisinins / toxicity*
Carcinoma, Hepatocellular
Drug Screening Assays, Antitumor
Humans
Inhibitory Concentration 50
Lipids / chemistry
Molecular Structure
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / toxicity*
Structure-Activity Relationship
Tumor Cells, Cultured

Substances

Alkynes
Antineoplastic Agents
Artemisinins
Lipids
Sesquiterpenes
artemisinin