Literature DB >> 17385848

Phenolic hydrazones are potent inhibitors of macrophage migration inhibitory factor proinflammatory activity and survival improving agents in sepsis.

Darrin R Dabideen1, Kai Fan Cheng, Bayan Aljabari, Edmund J Miller, Valentin A Pavlov, Yousef Al-Abed.   

Abstract

A series of phenolic hydrazones were synthesized and evaluated for their inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity. Compound 7 emerged as a potent inhibitor of MIF with an IC50 of 130 nM. Compound 7 dose-dependently suppressed TNFalpha secretion from lipopolysaccharide stimulated macrophages. The therapeutic importance of the MIF inhibition by 7 is demonstrated by the significant protection from the lethality of sepsis when administration of the compound was initiated in a clinically relevant time frame.

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Year:  2007        PMID： 17385848      PMCID： PMC5710735          DOI： 10.1021/jm061477+

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  19 in total

1.  Protection from septic shock by neutralization of macrophage migration inhibitory factor.

Authors:  T Calandra; B Echtenacher; D L Roy; J Pugin; C N Metz; L Hültner; D Heumann; D Männel; R Bucala; M P Glauser
Journal:  Nat Med       Date:  2000-02       Impact factor: 53.440

2.  ISO-1 binding to the tautomerase active site of MIF inhibits its pro-inflammatory activity and increases survival in severe sepsis.

Authors:  Yousef Al-Abed; Darrin Dabideen; Bayan Aljabari; Aline Valster; Davorka Messmer; Mahendar Ochani; Mahira Tanovic; Kanta Ochani; Michael Bacher; Ferdinando Nicoletti; Christine Metz; Valentin A Pavlov; Edmund J Miller; Kevin J Tracey
Journal:  J Biol Chem       Date:  2005-08-22       Impact factor: 5.157

3.  Macrophage migration inhibitory factor (MIF) sustains macrophage proinflammatory function by inhibiting p53: regulatory role in the innate immune response.

Authors:  Robert A Mitchell; Hong Liao; Jason Chesney; Gunter Fingerle-Rowson; John Baugh; John David; Richard Bucala
Journal:  Proc Natl Acad Sci U S A       Date:  2001-12-26       Impact factor: 11.205

4.  Critical modifications of the ISO-1 scaffold improve its potent inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity.

Authors:  Kai Fan Cheng; Yousef Al-Abed
Journal:  Bioorg Med Chem Lett       Date:  2006-05-06       Impact factor: 2.823

5.  The immunoregulatory mediator macrophage migration inhibitory factor (MIF) catalyzes a tautomerization reaction.

Authors:  E Rosengren; R Bucala; P Aman; L Jacobsson; G Odh; C N Metz; H Rorsman
Journal:  Mol Med       Date:  1996-01       Impact factor: 6.354

6.  Inhibition of MIF bioactivity by rational design of pharmacological inhibitors of MIF tautomerase activity.

Authors:  Angeles Dios; Robert A Mitchell; Bayan Aljabari; Jodi Lubetsky; KerryAnn O'Connor; Hong Liao; Peter D Senter; Kirk R Manogue; Elias Lolis; Christine Metz; Richard Bucala; David J E Callaway; Yousef Al-Abed
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

7.  Crystal structure of macrophage migration inhibitory factor complexed with (E)-2-fluoro-p-hydroxycinnamate at 1.8 A resolution: implications for enzymatic catalysis and inhibition.

Authors:  A B Taylor; W H Johnson; R M Czerwinski; H S Li; M L Hackert; C P Whitman
Journal:  Biochemistry       Date:  1999-06-08       Impact factor: 3.162

8.  The tautomerase active site of macrophage migration inhibitory factor is a potential target for discovery of novel anti-inflammatory agents.

Authors:  Jodi B Lubetsky; Angeles Dios; Jialian Han; Bayan Aljabari; Bela Ruzsicska; Robert Mitchell; Elias Lolis; Yousef Al-Abed
Journal:  J Biol Chem       Date:  2002-05-07       Impact factor: 5.157

9.  Crystal structure at 2.6-A resolution of human macrophage migration inhibitory factor.

Authors:  H W Sun; J Bernhagen; R Bucala; E Lolis
Journal:  Proc Natl Acad Sci U S A       Date:  1996-05-28       Impact factor: 11.205

Review 10.  Macrophage migration inhibitory factor and the discovery of tautomerase inhibitors.

Authors:  Masaya Orita; Satoshi Yamamoto; Naoko Katayama; Shigeo Fujita
Journal:  Curr Pharm Des       Date:  2002       Impact factor: 3.116
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  21 in total

1.  Proteomic analysis of osteogenic sarcoma: association of tumour necrosis factor with poor prognosis.

Authors:  Justin M M Cates; David B Friedman; Erin H Seeley; William D Dupont; Herbert S Schwartz; Ginger E Holt; Richard M Caprioli; Pampee P Young
Journal:  Int J Exp Pathol       Date:  2010-03-26       Impact factor: 1.925

2.  Inactivation of tautomerase activity of macrophage migration inhibitory factor by sulforaphane: a potential biomarker for anti-inflammatory intervention.

Authors:  Zachary R Healy; Hua Liu; W David Holtzclaw; Paul Talalay
Journal:  Cancer Epidemiol Biomarkers Prev       Date:  2011-05-20       Impact factor: 4.254

3.  Drug repositioning and pharmacophore identification in the discovery of hookworm MIF inhibitors.

Authors:  Yoonsang Cho; Jon J Vermeire; Jane S Merkel; Lin Leng; Xin Du; Richard Bucala; Michael Cappello; Elias Lolis
Journal:  Chem Biol       Date:  2011-09-23

4.  Advances and Insights for Small Molecule Inhibition of Macrophage Migration Inhibitory Factor.

Authors:  Vinay Trivedi-Parmar; William L Jorgensen
Journal:  J Med Chem       Date:  2018-06-04       Impact factor: 7.446

5.  Aza-derivatives of resveratrol are potent macrophage migration inhibitory factor inhibitors.

Authors:  Yoshihiko Fujita; Rafiqul Islam; Kazuko Sakai; Hiroyasu Kaneda; Kanae Kudo; Daisuke Tamura; Keiichi Aomatsu; Tomoyuki Nagai; Hidekazu Kimura; Kazuko Matsumoto; Marco A de Velasco; Tokuzo Arao; Tadashi Okawara; Kazuto Nishio
Journal:  Invest New Drugs       Date:  2011-09-13       Impact factor: 3.850

6.  Molecular and functional characterization of macrophage migration inhibitory factor (MIF) homolog of human from lymphatic filarial parasite Wuchereria bancrofti.

Authors:  Rohit Sharma; S L Hoti; R L Meena; V Vasuki; T Sankari; P Kaliraj
Journal:  Parasitol Res       Date:  2012-08-09       Impact factor: 2.289

7.  Thyroxine is a potential endogenous antagonist of macrophage migration inhibitory factor (MIF) activity.

Authors:  Yousef Al-Abed; Christine N Metz; Kai Fan Cheng; Bayan Aljabari; Sonya VanPatten; Steven Blau; Hans Lee; Mahendar Ochani; Valentin A Pavlov; Thomas Coleman; Nathalie Meurice; Kevin J Tracey; Edmund J Miller
Journal:  Proc Natl Acad Sci U S A       Date:  2011-05-02       Impact factor: 11.205

8.  Synthesis of fluorinated δ-lactams via cycloisomerization of gem-difluoropropargyl amides.

Authors:  Satoru Arimitsu; Gerald B Hammond
Journal:  Beilstein J Org Chem       Date:  2010-05-14       Impact factor: 2.883

9.  A novel, macrophage migration inhibitory factor suicide substrate inhibits motility and growth of lung cancer cells.

Authors:  Millicent Winner; Jason Meier; Swen Zierow; Beatriz E Rendon; Gregg V Crichlow; Randall Riggs; Richard Bucala; Lin Leng; Ned Smith; Elias Lolis; John O Trent; Robert A Mitchell
Journal:  Cancer Res       Date:  2008-09-15       Impact factor: 12.701

10.  A new class of isothiocyanate-based irreversible inhibitors of macrophage migration inhibitory factor.

Authors:  Hajer Ouertatani-Sakouhi; Farah El-Turk; Bruno Fauvet; Thierry Roger; Didier Le Roy; Damla Pinar Karpinar; Lin Leng; Richard Bucala; Markus Zweckstetter; Thierry Calandra; Hilal A Lashuel
Journal:  Biochemistry       Date:  2009-10-20       Impact factor: 3.162
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