Literature DB >> 16996735

Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A.

Tadashi Honda1, Karen T Liby, Xiaobo Su, Chitra Sundararajan, Yukiko Honda, Nanjoo Suh, Renee Risingsong, Charlotte R Williams, Darlene B Royce, Michael B Sporn, Gordon W Gribble.   

Abstract

Fifteen new betulinic acid analogues were designed, synthesized, and tested for anti-inflammatory activity. Many of these analogues effectively suppress nitric oxide (NO) production in RAW cells stimulated with interferon-gamma. Analogue 10 is highly and orally active in vivo for induction of the anti-inflammatory and cytoprotective enzyme, heme oxygenase-1.

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Year:  2006        PMID： 16996735      PMCID： PMC1950140          DOI： 10.1016/j.bmcl.2006.09.012

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  10 in total

1.  Synthesis and cytotoxic activity of A-ring modified betulinic acid derivatives.

Authors:  Young-Jae You; Yong Kim; Nguyen-Hai Nam; Byung-Zun Ahn
Journal:  Bioorg Med Chem Lett       Date:  2003-10-06       Impact factor: 2.823

2.  A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production.

Authors:  Tadashi Honda; Yukiko Honda; Frank G Favaloro; Gordon W Gribble; Nanjoo Suh; Andrew E Place; Mara H Rendi; Michael B Sporn
Journal:  Bioorg Med Chem Lett       Date:  2002-04-08       Impact factor: 2.823

3.  Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells.

Authors:  Valentina Zuco; Rosanna Supino; Sabina C Righetti; Loredana Cleris; Edoardo Marchesi; Carlo Gambacorti-Passerini; Franca Formelli
Journal:  Cancer Lett       Date:  2002-01-10       Impact factor: 8.679

4.  The synthetic triterpenoids, CDDO and CDDO-imidazolide, are potent inducers of heme oxygenase-1 and Nrf2/ARE signaling.

Authors:  Karen Liby; Thomas Hock; Mark M Yore; Nanjoo Suh; Andrew E Place; Renee Risingsong; Charlotte R Williams; Darlene B Royce; Tadashi Honda; Yukiko Honda; Gordon W Gribble; Nathalie Hill-Kapturczak; Anupam Agarwal; Michael B Sporn
Journal:  Cancer Res       Date:  2005-06-01       Impact factor: 12.701

5.  Novel synthetic oleanane and ursane triterpenoids with various enone functionalities in ring A as inhibitors of nitric oxide production in mouse macrophages.

Authors:  T Honda; G W Gribble; N Suh; H J Finlay; B V Rounds; L Bore; F G Favaloro; Y Wang; M B Sporn
Journal:  J Med Chem       Date:  2000-05-04       Impact factor: 7.446

6.  Betulinic acid induces apoptosis in human neuroblastoma cell lines.

Authors:  M L Schmidt; K L Kuzmanoff; L Ling-Indeck; J M Pezzuto
Journal:  Eur J Cancer       Date:  1997-10       Impact factor: 9.162

Review 7.  Heme oxygenase-1/carbon monoxide: from basic science to therapeutic applications.

Authors:  Stefan W Ryter; Jawed Alam; Augustine M K Choi
Journal:  Physiol Rev       Date:  2006-04       Impact factor: 37.312

8.  Synthetic oleanane and ursane triterpenoids with modified rings A and C: a series of highly active inhibitors of nitric oxide production in mouse macrophages.

Authors:  T Honda; B V Rounds; L Bore; H J Finlay; F G Favaloro; N Suh; Y Wang; M B Sporn; G W Gribble
Journal:  J Med Chem       Date:  2000-11-02       Impact factor: 7.446

9.  Betulinic acid-induced apoptosis in leukemia cells.

Authors:  H Ehrhardt; S Fulda; M Führer; K M Debatin; I Jeremias
Journal:  Leukemia       Date:  2004-08       Impact factor: 11.528

10.  Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis.

Authors:  E Pisha; H Chai; I S Lee; T E Chagwedera; N R Farnsworth; G A Cordell; C W Beecher; H H Fong; A D Kinghorn; D M Brown
Journal:  Nat Med       Date:  1995-10       Impact factor: 53.440
  10 in total
  5 in total

1.  Betulinic acid suppresses constitutive and TNFalpha-induced NF-kappaB activation and induces apoptosis in human prostate carcinoma PC-3 cells.

Authors:  Thangaiyan Rabi; Sanjeev Shukla; Sanjay Gupta
Journal:  Mol Carcinog       Date:  2008-12       Impact factor: 4.784

2.  Chemical modifications of natural triterpenes - glycyrrhetinic and boswellic acids: evaluation of their biological activity.

Authors:  G S R Subba Rao; Paturu Kondaiah; Sanjay K Singh; Palaniyandi Ravanan; Michael B Sporn
Journal:  Tetrahedron       Date:  2008-12-15       Impact factor: 2.457

3.  2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent.

Authors:  Tadashi Honda; Eric M Padegimas; Emilie David; Chitra Sundararajan; Karen T Liby; Charlotte Williams; Michael B Sporn; Melean Visnick
Journal:  Bioorg Med Chem Lett       Date:  2010-02-06       Impact factor: 2.823

4.  Synthetic triterpenoid induces 15-PGDH expression and suppresses inflammation-driven colon carcinogenesis.

Authors:  Sung Hee Choi; Byung-Gyu Kim; Janet Robinson; Steve Fink; Min Yan; Michael B Sporn; Sanford D Markowitz; John J Letterio
Journal:  J Clin Invest       Date:  2014-05-16       Impact factor: 14.808

5.  Synthesis and pro-apoptotic activity of novel glycyrrhetinic acid derivatives.

Authors:  Evgeniya B Logashenko; Oksana V Salomatina; A V Markov; Dina V Korchagina; Nariman F Salakhutdinov; Genrikh A Tolstikov; Valentin V Vlassov; Marina A Zenkova
Journal:  Chembiochem       Date:  2011-02-15       Impact factor: 3.164
  5 in total

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