NMR studies on novel antitumor drug candidates, deoxoartemisinin and carboxypropyldeoxoartemisinin

Chang Hun Lee, Heedouk Hong, Joon Shin, Mankil Jung, Injae Shin, Jong-Bok Yoon, Weon Tae Lee

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Artemisinin and its derivatives, which have been known as antimalarial drugs, have also demonstrated their cytotoxicity against tumor cells. It has been proposed that antitumor activity depends on the lipophilicity of functional group on artemisinin derivatives. Solution structures of two artemisinin derivatives as antitumor drug candidates, deoxoartemisinin and carboxypropyldeoxoartemisinin, were determined by NMR spectroscopy to elucidate structure-activity relationship. According to biological assay, antitumor efficiencies are not dependent upon lipophilicity. Instead, these compounds demonstrated their distinctive structural features of boat/chair conformation and capability to interact with receptors, as they have different efficiencies on antitumor activity. Especially, carboxypropyl moiety or carbonyl moiety in artemisinin derivatives influences the conformation and stability of ring structure. Although the detailed mechanism of antitumor activity by artemisinin derivatives has not been addressed, we suggest that antitumor activity is not determined only with lipophilicity and that artemisinin derivatives have specific target proteins in each type of cancer. (C) 2000 Academic Press.

Original languageEnglish
Article number93086
Pages (from-to)359-369
Number of pages11
JournalBiochemical and Biophysical Research Communications
Volume274
Issue number2
DOIs
Publication statusPublished - 2000 Aug 2

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Antineoplastic Agents
Nuclear magnetic resonance
Derivatives
Conformations
Ships
Antimalarials
Boats
Structure-Activity Relationship
Cytotoxicity
Biological Assay
Functional groups
Nuclear magnetic resonance spectroscopy
artemisinine
carboxypropyldeoxoartemisinine
deoxoartemisinin
Tumors
Assays
Neoplasms
Magnetic Resonance Spectroscopy
Cells

All Science Journal Classification (ASJC) codes

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

Cite this

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abstract = "Artemisinin and its derivatives, which have been known as antimalarial drugs, have also demonstrated their cytotoxicity against tumor cells. It has been proposed that antitumor activity depends on the lipophilicity of functional group on artemisinin derivatives. Solution structures of two artemisinin derivatives as antitumor drug candidates, deoxoartemisinin and carboxypropyldeoxoartemisinin, were determined by NMR spectroscopy to elucidate structure-activity relationship. According to biological assay, antitumor efficiencies are not dependent upon lipophilicity. Instead, these compounds demonstrated their distinctive structural features of boat/chair conformation and capability to interact with receptors, as they have different efficiencies on antitumor activity. Especially, carboxypropyl moiety or carbonyl moiety in artemisinin derivatives influences the conformation and stability of ring structure. Although the detailed mechanism of antitumor activity by artemisinin derivatives has not been addressed, we suggest that antitumor activity is not determined only with lipophilicity and that artemisinin derivatives have specific target proteins in each type of cancer. (C) 2000 Academic Press.",
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NMR studies on novel antitumor drug candidates, deoxoartemisinin and carboxypropyldeoxoartemisinin. / Lee, Chang Hun; Hong, Heedouk; Shin, Joon; Jung, Mankil; Shin, Injae; Yoon, Jong-Bok; Lee, Weon Tae.

In: Biochemical and Biophysical Research Communications, Vol. 274, No. 2, 93086, 02.08.2000, p. 359-369.

Research output: Contribution to journalArticle

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AU - Yoon, Jong-Bok

AU - Lee, Weon Tae

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