title: Spirohexenolide A targets human macrophage migration inhibitory factor (hMIF).
abstract: Spirohexenolides A and B comprise a unique family of spirotetronate natural products. We report on the identification of their binding to and modulation of human macrophage migration inhibitor factor (hMIF). Using an immunoaffinity-fluorescent labeling method, the properties of this interaction are detailed and evidence is provided that hMIF plays a key role in the cytostatic activity of the spirohexenolides.
authors: Department of Chemistry and Biochemistry, University of California-San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, United States.
authors: Wei-Lun
authors: WL
authors: Yu
authors: Brian D
authors: BD
authors: Jones
authors: Minjin
authors: M
authors: Kang
authors: Justin C
authors: JC
authors: Hammons
authors: James J
authors: JJ
authors: La Clair
authors: Michael D
authors: MD
authors: Burkart
mesh_terms: D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D019746:Intramolecular Oxidoreductases; D008263:Macrophage Migration-Inhibitory Factors / Q000737:chemistry* / Q000378:metabolism; D008264:Macrophages / Q000378:metabolism
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D008263:Macrophage Migration-Inhibitory Factors; C547347:spirohexenolide A; D019746:Intramolecular Oxidoreductases; C022346:phenylpyruvate tautomerase
references: J Nat Prod. 2010 Oct 22;73(10):1659-66
references: 20836515
references: Chembiochem. 2006 Mar;7(3):409-16
references: 16432909
references: J Immunol Methods. 1983 Dec 16;65(1-2):55-63
references: 6606682
references: Oncogene. 2007 Aug 2;26(35):5046-59
references: 17310986
references: J Biol Chem. 2002 Jul 12;277(28):24976-82
references: 11997397
references: Proc Natl Acad Sci U S A. 1996 May 28;93(11):5191-6
references: 8643551
references: Med Res Rev. 2008 Mar;28(2):278-308
references: 17763363
references: J Am Chem Soc. 2009 Sep 2;131(34):12094-6
references: 19673475
references: J Immunol. 2011 Jan 1;186(1):527-38
references: 21106847
references: J Exp Med. 2003 Jun 2;197(11):1467-76
references: 12782713
references: QJM. 2010 Nov;103(11):831-6
references: 20805118
references: J Biochem Biophys Methods. 1990 Jun;21(1):35-46
references: 2120316
references: Cell Res. 2006 Feb;16(2):162-8
references: 16474429
references: J Interferon Cytokine Res. 2002 Mar;22(3):351-63
references: 12034043
references: Expert Opin Ther Targets. 2003 Apr;7(2):153-64
references: 12667094
references: EMBO J. 1998 Jul 1;17(13):3534-41
references: 9649424
references: J Biol Chem. 2010 Aug 20;285(34):26581-98
references: 20516071
references: Proc Natl Acad Sci U S A. 2002 Jan 8;99(1):144-9
references: 11773615
references: Angew Chem Int Ed Engl. 2009;48(4):728-32
references: 19097126
references: Nat Rev Immunol. 2003 Oct;3(10):791-800
references: 14502271
references: J Med Chem. 2012 Nov 26;55(22):10148-59
references: 23067344
references: J Biol Chem. 2009 Nov 20;284(47):32425-33
references: 19776019
references: Proc Natl Acad Sci U S A. 2010 Jun 22;107(25):11313-8
references: 20534506
references: Curr Top Med Chem. 2010;10(4):458-77
references: 20180757
references: Org Lett. 2010 Oct 15;12(20):4516-9
references: 20849075
references: Biofactors. 2009 Mar-Apr;35(2):165-8
references: 19322762
references: J Org Chem. 2009 Dec 4;74(23):9054-61
references: 19883063
references: Curr Pharm Des. 2008;14(36):3790-801
references: 19128232