Novel synthetic oleanane triterpenoids: A series of highly active inhibitors of nitric oxide production in mouse macrophages

Tadashi Honda; Barbie Ann V. Rounds; Lothar Bore; Frank G. Favaloro; Gordon W. Gribble; Nanjoo Suh; Yongping Wang; Michael B. Sporn

doi:10.1016/S0960-894X(99)00623-X

Novel synthetic oleanane triterpenoids: A series of highly active inhibitors of nitric oxide production in mouse macrophages

Tadashi Honda, Barbie Ann V. Rounds, Lothar Bore, Frank G. Favaloro, Gordon W. Gribble, Nanjoo Suh, Yongping Wang, Michael B. Sporn

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

73 Scopus citations

Abstract

Novel oleanane triterpenoids with modified rings A and C were designed and synthesized. Among them, methyl 2-carboxy-3,12-dioxooleana-1,9-dien-28-oate showed similar high inhibitory activity (IC₅₀ = 0.8 nM) to 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), which we have synthesized previously, against production of nitric oxide induced by interferon-γ in mouse macrophages.

Original language	English (US)
Pages (from-to)	3429-3434
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	9
Issue number	24
DOIs	https://doi.org/10.1016/S0960-894X(99)00623-X
State	Published - Dec 20 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

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

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10.1016/S0960-894X(99)00623-X

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title = "Novel synthetic oleanane triterpenoids: A series of highly active inhibitors of nitric oxide production in mouse macrophages",

abstract = "Novel oleanane triterpenoids with modified rings A and C were designed and synthesized. Among them, methyl 2-carboxy-3,12-dioxooleana-1,9-dien-28-oate showed similar high inhibitory activity (IC50 = 0.8 nM) to 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), which we have synthesized previously, against production of nitric oxide induced by interferon-γ in mouse macrophages.",

author = "Tadashi Honda and Rounds, {Barbie Ann V.} and Lothar Bore and Favaloro, {Frank G.} and Gribble, {Gordon W.} and Nanjoo Suh and Yongping Wang and Sporn, {Michael B.}",

note = "Funding Information: Acknowledgments: We thank Drs. Carl Nathan and Qiao-wen Xie for expert advice on the preparation of macrophages and the nitric oxide assay. We also thank Dr. Steven Mullen (University of Illinois) for the mass spectra. This investigation was supported by funds from the NIH Grant 1 R01-CA78814, the Norris Cotton Cancer Center, U.S. Dept. of Defense Grants # DAMD17-96-1-6163, # DAMD17-98-1-8604, the Oliver and Jennie Donaldson Charitable Trust, the National Foundation for Cancer Research, and a Zenith Award from the Alzheimer's Association. M. B. S. is Oscar M. Cohn Professor, F. G. F., Jr. is Oscar M. Cohn Scholar, and Y. W. is a Howard Hughes Medical Institute Predoctoral Fellow.",

year = "1999",

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doi = "10.1016/S0960-894X(99)00623-X",

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volume = "9",

pages = "3429--3434",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Novel synthetic oleanane triterpenoids

T2 - A series of highly active inhibitors of nitric oxide production in mouse macrophages

AU - Honda, Tadashi

AU - Rounds, Barbie Ann V.

AU - Bore, Lothar

AU - Favaloro, Frank G.

AU - Gribble, Gordon W.

AU - Suh, Nanjoo

AU - Wang, Yongping

AU - Sporn, Michael B.

N1 - Funding Information: Acknowledgments: We thank Drs. Carl Nathan and Qiao-wen Xie for expert advice on the preparation of macrophages and the nitric oxide assay. We also thank Dr. Steven Mullen (University of Illinois) for the mass spectra. This investigation was supported by funds from the NIH Grant 1 R01-CA78814, the Norris Cotton Cancer Center, U.S. Dept. of Defense Grants # DAMD17-96-1-6163, # DAMD17-98-1-8604, the Oliver and Jennie Donaldson Charitable Trust, the National Foundation for Cancer Research, and a Zenith Award from the Alzheimer's Association. M. B. S. is Oscar M. Cohn Professor, F. G. F., Jr. is Oscar M. Cohn Scholar, and Y. W. is a Howard Hughes Medical Institute Predoctoral Fellow.

PY - 1999/12/20

Y1 - 1999/12/20

N2 - Novel oleanane triterpenoids with modified rings A and C were designed and synthesized. Among them, methyl 2-carboxy-3,12-dioxooleana-1,9-dien-28-oate showed similar high inhibitory activity (IC50 = 0.8 nM) to 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), which we have synthesized previously, against production of nitric oxide induced by interferon-γ in mouse macrophages.

AB - Novel oleanane triterpenoids with modified rings A and C were designed and synthesized. Among them, methyl 2-carboxy-3,12-dioxooleana-1,9-dien-28-oate showed similar high inhibitory activity (IC50 = 0.8 nM) to 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), which we have synthesized previously, against production of nitric oxide induced by interferon-γ in mouse macrophages.

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ER -

Novel synthetic oleanane triterpenoids: A series of highly active inhibitors of nitric oxide production in mouse macrophages

Abstract

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