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

Journal of Medicinal Chemistry

Volumn 50, Issue 8, 2007, Pages 1993-1997

  Dabideen, Darrin R ^a   Kai, Fan Cheng ^a   Aljabari, Bayan ^a   Miller, Edmund J ^a   Pavlov, Valentin A ^a   Al Abed, Yousef ^a,b  

^a FEINSTEIN INSTITUTE FOR MEDICAL RESEARCH   (United States)

^b New York School of Medicine   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZONE DERIVATIVE; LIPOPOLYSACCHARIDE; MACROPHAGE MIGRATION INHIBITION FACTOR; PHENOL DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOKINE RELEASE; DOSE RESPONSE; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; HYDROGEN BOND; HYDROPHOBICITY; IC 50; INFLAMMATION; LETHALITY; MACROPHAGE ACTIVATION; MASS SPECTROMETRY; MOUSE; NONHUMAN; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; SEPSIS; SINGLE DRUG DOSE; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL LINE; HYDRAZONES; LIPOPOLYSACCHARIDES; MACROPHAGE ACTIVATION; MACROPHAGE MIGRATION-INHIBITORY FACTORS; MALE; MICE; MICE, INBRED BALB C; PHENOLS; SEPSIS; STRUCTURE-ACTIVITY RELATIONSHIP; SURVIVAL RATE; TUMOR NECROSIS FACTOR-ALPHA;

EID: 34247198421     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061477+     Document Type: Article

References (19)

1. Calandra, T.; Roger, T. Macrophage migration inhibitory factor: a regulator of innate immunity. Nat. Rev. Immunol. 2003, 3, 791-800.
2. Riedemann, N. C.; Guo, R. F.; Ward, P. A. Novel strategies for the treatment of sepsis. Nat. Med. 2003, 9, 517-524.
3. Calandra, T.; Echtenacher, B.; Roy, D. L.; Pugin, J.; Metz, C. N.; et al. Protection from septic shock by neutralization of macrophage migration inhibitory factor. Nat. Med. 2000, 6, 164-170.
4. Al-Abed, Y.; Dabideen, D.; Aljabari, B.; Valster, A.; Messmer, D.; et al. ISO-1 binding to the tautomerase active site of MIF inhibits its pro-inflammatory activity and increases survival in severe sepsis. J. Biol. Chem. 2005, 280, 36541-36544.
5. Sugimoto, H.; Suzuki, M.; Nakagawa, A.; Tanaka, I.; Fujinaga, M.; et al. Crystallization of rat liver macrophage migration inhibitory factor for MAD analysis. J. Struct. Biol. 1995, 115, 331-334.
6. Sun, H. W.; Bernhagen, J.; Bucala, R.; Lolis, E. Crystal structure at 2.6-Å resolution of human macrophage migration inhibitory factor. Proc Natl. Acad. Sci. U.S.A. 1996, 93, 5191-5196.
7. Suzuki, M.; Sugimoto, H.; Nakagawa, A.; Tanaka, I.; Nishihira, J.; et al. Crystal structure of the macrophage migration inhibitory factor from rat liver. Nat. Struct. Biol. 1996, 3, 259-266.
8. Taylor, A. B.; Johnson, W. H.; Czerwinski, R. M.; Li, H. S.; Hackert, M. L.; et al. Crystal structure of macrophage migration inhibitory factor-complexed with (E)-2-fluoro-p-hydroxycinnamate at 1.8 angstrom resolution: Implications for enzymatic catalysis and inhibition. Biochemistry 1999, 38, 7444-7452.
9. Rosengren, E.; Bucala, R.; Aman, P.; Jacobsson, L.; Odh, G.; et al. The immunoregulatory mediator macrophage migration inhibitory factor (MIF) catalyzes a tautomerization reaction. Mol. Med. 1996, 2, 143-149.
10. Dios, A.; Mitchell, R. A.; Aljabari, B.; Lubetsky, J.; O'Connor, K.; et al. Inhibition of MIF bioactivity by rational design of pharmacological inhibitors of MIF tautomerase activity. J. Med. Chem. 2002, 45, 2410-2416.
11. Cheng, K. F.; Al-Abed, Y. Critical modifications of the ISO-1 scaffold improve its potent inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity. Bioorg. Med. Chem. Lett. 2006, 16, 3376-3379.
12. Lubetsky, J. B.; Dios, A.; Han, J.; Aljabari, B.; Ruzsicska, B.; et al. The tautomerase active site of macrophage migration inhibitory factor is a potential target for discovery of novel anti-inflammatory agents. J. Biol. Chem. 2002, 277, 24976-24982.
13. Senter, P. D.; Al-Abed, Y.; Metz, C. N.; Benigni, F.; Mitchell, R. A.; et al. Inhibition of macrophage migration inhibitory factor (MIF) tautomerase and biological activities by acetaminophen metabolites. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 144-149.
14. Orita, M.; Yamamoto, S.; Katayama, N.; Aoki, M.; Takayama, K.; et al. Coumarin and chromen-4-one analogues as tautomerase inhibitors of macrophage migration inhibitory factor: Discovery and X-ray crystallography. J. Med. Chem. 2001, 44, 540-547.
15. Orita, M.; Yamamoto, S.; Katayama, N.; Fujita, S. Macrophage migration inhibitory factor and the discovery of tautomerase inhibitors. Curr. Pharm. Des. 2002, 8, 1297-1317.
16. Roger, T.; David, J.; Glauser, M. P.; Calandra, T. MIF regulates innate immune responses through modulation of Toll-like receptor 4. Nature 2001, 414, 920-924.
17. Bozza, M.; Satoskar, A. R.; Lin, G.; Lu, B.; Humbles, A. A.; et al. Targeted disruption of migration inhibitory factor gene reveals its critical role in sepsis. J. Exp. Med. 1999, 189, 341-346.
18. Mitchell, R. A.; Liao, H.; Chesney, J.; Fingerle-Rowson, G.; Baugh, J.; et al. Macrophage migration inhibitory factor (MIF) sustains macrophage proinflammatory function by inhibiting p53: regulatory role in the innate immune response. Proc Natl. Acad. Sci. U.S.A. 2002, 99, 345-350.
19. Wang, H.; Bloom, O.; Zhang, M.; Vishnubhakat, J. M.; Ombrellino, M.; et al. HMG-1 as a late mediator of endotoxin lethality in mice. Science 1999, 285, 248-251.