Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-α production is associated with a change of mechanism of action

Satomi Niwayama; Christine Loh; Benjamin E. Turk; Jun O. Liu; Hiroyuki Miyachi; Yuichi Hashimoto

doi:10.1016/S0960-894X(98)00171-1

Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-α production is associated with a change of mechanism of action

Satomi Niwayama, Christine Loh, Benjamin E. Turk, Jun O. Liu, Hiroyuki Miyachi, Yuichi Hashimoto

Faculty of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

Perfluorination of phthalimides leads to dramatically increased potency as inhibitors of TNF-α production. We examined the enantiodependence for several tetrafluorophthalimides and α-methylthalidomide, 3. Only 3 exhibited strikingly enantiodependent activity. The key structural determinant for the enhanced activity is the tetrafluorophthaloyl group, which confers enhanced potency and a change in the mechanism of inhibition.

Original language	English
Pages (from-to)	1071-1076
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	8
Issue number	9
DOIs	https://doi.org/10.1016/S0960-894X(98)00171-1
Publication status	Published - May 1998

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0960-894X(98)00171-1

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Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-α production is associated with a change of mechanism of action. / Niwayama, Satomi; Loh, Christine; Turk, Benjamin E. et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 8, No. 9, 05.1998, p. 1071-1076.

Research output: Contribution to journal › Article › peer-review

Niwayama, S, Loh, C, Turk, BE, Liu, JO, Miyachi, H & Hashimoto, Y 1998, 'Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-α production is associated with a change of mechanism of action', Bioorganic and Medicinal Chemistry Letters, vol. 8, no. 9, pp. 1071-1076. https://doi.org/10.1016/S0960-894X(98)00171-1

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Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-α production is associated with a change of mechanism of action

Abstract

ASJC Scopus subject areas

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