Iguratimod, an allosteric inhibitor of macrophage migration inhibitory factor (MIF), prevents mortality and oxidative stress in a murine model of acetaminophen overdose

Aikawa Y, Yamamoto M, Yamamoto T, Morimoto K, Tanaka K. An anti-rheumatic agent T-614 inhibits NF-κB activation in LPS- and TNF-α-stimulated THP-1 cells without interfering with IκBα degradation. Inflamm Res. 2002;51:188–94.

Article  CAS  PubMed  Google Scholar 

Akakpo J, Ramachandran A, Kandel S, Ni H, Kumer S, Rumack B, et al. 4-Methylpyrazole protects against acetaminophen hepatotoxicity in mice and in primary human hepatocytes. Hum Exp Toxicol. 2018;37:1310–22.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Akakpo JY, Ramachandran A, Duan L, Schaich MA, Jaeschke MW, Freudenthal BD, et al. Delayed treatment with 4-Methylpyrazole protects against Acetaminophen Hepatotoxicity in mice by inhibition of c-Jun n-Terminal kinase. Toxicol Sci. 2019;170:57–68.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Al-Abed Y. 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;280:36541–4.

Article  CAS  PubMed  Google Scholar 

Bacher M, Meinhardt A, Lan HY, Mu W, Metz CN, Chesney JA, et al. Migration inhibitory factor expression in experimentally induced endotoxemia. Am J Pathol. 1997;150:235–46.

CAS  PubMed  PubMed Central  Google Scholar 

Barnes MA, McMullen MR, Roychowdhury S, Pisano SG, Liu X, Stavitsky AB, et al. Macrophage migration inhibitory factor contributes to ethanol-induced liver injury by mediating cell injury, steatohepatitis, and steatosis. Hepatology. 2013;57:1980–91.

Article  CAS  PubMed  Google Scholar 

Blair IA, Boobis AR, Davies DS, Cresp TM. Paracetamol oxidation: synthesis and reactivity of N-acetyl-p-benzoquinoneimine. Tetrahedron Lett. 1980;21:4947–50.

Article  CAS  Google Scholar 

Blocki FA, Schlievert PM, Wackett LP. Rat liver protein linking chemical and immunological detoxification systems. Nature. 1992;360:269–70.

Article  CAS  PubMed  Google Scholar 

Bloom J, Metz C, Nalawade S, Casabar J, Cheng KF, He M, et al. Identification of Iguratimod as an inhibitor of Macrophage Migration Inhibitory factor (MIF) with Steroid-Sparing Potential. J Biol Chem. 2016a;291:26502–514.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Bloom J, Sun S, Al-Abed Y. MIF, a controversial cytokine: a review of structural features, challenges, and opportunities for drug development. Expert Opin Ther Tar. 2016b;20:1463–75.

Article  CAS  Google Scholar 

Bloom J, Uzamere T, Hurd Y, Manini AF. Macrophage migration inhibitory factor as a potential biomarker in acetaminophen overdose: a pilot study. Toxicol Commun. 2022;6:1–5.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Bourdi M, Reilly TP, Elkahloun AG, George JW, Pohl LR. Macrophage migration inhibitory factor in drug-induced liver injury: a role in susceptibility and stress responsiveness. Biochem Biophys Res Commun. 2002;294:225–30.

Article  CAS  PubMed  Google Scholar 

Bozza M, Kolakowski LF, Jenkins NA, Gilbert DJ, Copeland NG, David JR, et al. Structural characterization and chromosomal location of the mouse macrophage migration inhibitory factor gene and pseudogenes. Genomics. 1995;27:412–9.

Article  CAS  PubMed  Google Scholar 

Bozza M, Satoskar AR, Lin G, Lu B, Humbles AA, Gerard C, et al. Targeted disruption of Migration Inhibitory factor gene reveals its critical role in Sepsis. J Exp Med. 1999;189:341–6.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Calandra T, Roger T. Macrophage migration inhibitory factor: a regulator of innate immunity. Nat Rev Immunol. 2003;3:791–800.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Careram® T. [package insert]. Tokyo, Japan: Eisai Co. Ltd; 2013.

Google Scholar 

Chen C, Krausz KW, Idle JR, Gonzalez FJ. Identification of novel toxicity-associated metabolites by metabolomics and mass isotopomer analysis of acetaminophen metabolism in wild-type and Cyp2e1-null mice. J Biol Chem. 2008;283:4543–59.

Article  CAS  PubMed  Google Scholar 

Cheng J, Ma X, Krausz KW, Idle JR, Gonzalez FJ. Rifampicin-activated human pregnane X receptor and CYP3A4 induction enhance Acetaminophen-Induced toxicity. Drug Metab Dispos. 2009;37:1611–21.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Crichlow GV, Lubetsky JB, Leng L, Bucala R, Lolis EJ. Structural and kinetic analyses of Macrophage Migration Inhibitory factor active site interactions. Biochemistry. 2009;48:132–9.

Article  CAS  PubMed  Google Scholar 

Cui N, Li H, Dun Y, Ripley-Gonzalez JW, You B, Li D, et al. Exercise inhibits JNK pathway activation and lipotoxicity via macrophage migration inhibitory factor in nonalcoholic fatty liver disease. Front Endocrinol. 2022;13:961231.

Article  Google Scholar 

Dahlin DC, Miwa GT, Lu AY, Nelson SD. N-acetyl-p-benzoquinone imine: a cytochrome P-450-mediated oxidation product of acetaminophen. Proc Natl Acad Sci USA. 1984;81:1327–31.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Davern TJ, James LP, Hinson JA, Polson J, Larson AM, Fontana RJ, et al. Measurement of serum acetaminophen–protein adducts in patients with Acute Liver failure. Gastroenterology. 2006;130:687–94.

Article  CAS  PubMed  Google Scholar 

de Jong YP, Abadia-Molina AC, Satoskar AR, Clarke K, Rietdijk ST, Faubion WA, et al. Development of chronic colitis is dependent on the cytokine MIF. Nat Immunol. 2001;2:1061–6.

Article  PubMed  Google Scholar 

Delano W. The PyMOL molecular graphics system. Palo Alto, CA: Delano Scientific; 2002.

Google Scholar 

Dios A, Mitchell RA, Aljabari B, Lubetsky J, O’Connor K, Liao H, et al. Inhibition of MIF Bioactivity by Rational Design of pharmacological inhibitors of MIF tautomerase activity. J Med Chem. 2002;45:2410–6.

Article  CAS  PubMed  Google Scholar 

Duan L, Davis JS, Woolbright BL, Du K, Cahkraborty M, Weemhoff J, et al. Differential susceptibility to acetaminophen-induced liver injury in sub-strains of C57BL/6 mice: 6 N versus 6J. Food Chem Toxicol. 2016;98:107–18.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Emsley P, Lohkamp B, Scott WG, Cowtan K. Features and development of Coot. Acta Crystallogr Sect D Biol Crystallogr. 2010;66:486–501.

Article  CAS  Google Scholar 

Gummin DD, Mowry JB, Beuhler MC, Spyker DA, Rivers LJ, Feldman R et al. 2021 Annual Report of the National Poison Data System© (NPDS) from America’s Poison Centers: 39th Annual Report. Clin Toxicol. 2022;60:1381–643.

Gunawan BK, Liu Z, Han D, Hanawa N, Gaarde WA. Kaplowitz N. c-Jun N-Terminal kinase plays a major role in Murine Acetaminophen Hepatotoxicity. Gastroenterology. 2006;131:165–78.

Article  CAS  PubMed  Google Scholar 

Jetten MJA, Ruiz-Aracama A, Coonen MLJ, Claessen SM, Herwijnen MHM, Lommen A, et al. Interindividual variation in gene expression responses and metabolite formation in acetaminophen-exposed primary human hepatocytes. Arch Toxicol. 2016;90:1103–15.

Article  CAS  PubMed  Google Scholar 

Kleemann R, Kapurniotu A, Frank RW, Gessner A, Mischke R, Flieger O, et al. Disulfide analysis reveals a role for macrophage migration inhibitory factor (MIF) as thiol-protein oxidoreductase. J Mol Biol. 1998;280:85–102.

Article  CAS  PubMed  Google Scholar 

Kudrin A, Scott M, Martin S, Chung CW, Donn R, McMaster A, et al. Human macrophage migration inhibitory factor: a proven immunomodulatory cytokine? J Biol Chem. 2006;28:29641–51.

Article  Google Scholar 

Kurien BT, Scofield RH. Mouse urine collection using clear plastic wrap. Lab Anim. 1999;33:83–6.

Article  CAS  PubMed  Google Scholar 

Leng L, Metz CN, Fang Y, Xu J, Donnelly S, Baugh J, et al. MIF Signal Transduction Initiated by binding to CD74. J Exp Med. 2003;197:1467–76.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Link SL, Rampon G, Osmon S, Scalzo AJ, Rumack BH. Fomepizole as an adjunct in acetylcysteine treated acetaminophen overdose patients: a case series. Clin Toxicol. 2022;60:472–7.

Article  CAS  Google Scholar 

Lubetsky JB. The tautomerase active site of Macrophage Migration Inhibitory factor is a potential target for Discovery of Novel anti-inflammatory agents. J Biol Chem. 2002;277:24976–82.

Article  CAS  PubMed  Google Scholar 

Lubetsky JB, Swope M, Dealwis C, Blake P, Lolis E. Pro-1 of Macrophage Migration Inhibitory factor functions as a Catalytic Base in the Phenylpyruvate tautomerase activity. Biochemistry. 1999;38:7346–54.

Article  CAS  PubMed  Google Scholar 

Lue H, Dewor M, Leng L, Bucala R, Bernhagen J. Activation of the JNK signalling pathway by macrophage migration inhibitory factor (MIF) and dependence on CXCR4 and CD74. Cell Signal. 2011;23:135–44.

Article  CAS  PubMed 

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