3smb › Citations

Structural interactions dictate the kinetics of macrophage migration inhibitory factor inhibition by different cancer-preventive isothiocyanates.

Crichlow GV, Fan C, Keeler C, Hodsdon M, Lolis EJ
Biochemistry 51 7506-14 (2012)
Cited: 20 times
EuropePMC logo PMID: 22931430

Abstract

Regulation of cellular processes by dietary nutrients is known to affect the likelihood of cancer development. One class of cancer-preventive nutrients, isothiocyanates (ITCs), derived from the consumption of cruciferous vegetables, is known to have various effects on cellular biochemistry. One target of ITCs is macrophage migration inhibitory factor (MIF), a widely expressed protein with known inflammatory, pro-tumorigenic, pro-angiogenic, and anti-apoptotic properties. MIF is covalently inhibited by a variety of ITCs, which in part may explain how they exert their cancer-preventive effects. We report the crystallographic structures of human MIF bound to phenethylisothiocyanate and to l-sulforaphane (dietary isothiocyanates derived from watercress and broccoli, respectively) and correlate structural features of these two isothiocyanates with their second-order rate constants for MIF inactivation. We also characterize changes in the MIF structure using nuclear magnetic resonance heteronuclear single-quantum coherence spectra of these complexes and observe many changes at the subunit interface. While a number of chemical shifts do not change, many of those that change do not have features similar in magnitude or direction for the two isothiocyanates. The difference in the binding modes of these two ITCs provides a means of using structure-activity relationships to reveal insights into MIF biological interactions. The results of this study provide a framework for the development of therapeutics that target MIF.

Reviews - 3smb mentioned but not cited (1)

  1. The Southern European Atlantic Diet and Its Supplements: The Chemical Bases of Its Anticancer Properties. Vivanco PG, Taboada P, Coelho A. Nutrients 15 4274 (2023)

Articles - 3smb mentioned but not cited (2)

  1. Structural interactions dictate the kinetics of macrophage migration inhibitory factor inhibition by different cancer-preventive isothiocyanates. Crichlow GV, Fan C, Keeler C, Hodsdon M, Lolis EJ. Biochemistry 51 7506-7514 (2012)
  2. Regulation of MIF Enzymatic Activity by an Allosteric Site at the Central Solvent Channel. Pantouris G, Khurana L, Ma A, Skeens E, Reiss K, Batista VS, Lisi GP, Lolis EJ. Cell Chem Biol 27 740-750.e5 (2020)


Reviews citing this publication (2)

  1. The Role of Isothiocyanates as Cancer Chemo-Preventive, Chemo-Therapeutic and Anti-Melanoma Agents. Mitsiogianni M, Koutsidis G, Mavroudis N, Trafalis DT, Botaitis S, Franco R, Zoumpourlis V, Amery T, Galanis A, Pappa A, Panayiotidis MI. Antioxidants (Basel) 8 E106 (2019)
  2. Isothiocyanates: a class of bioactive metabolites with chemopreventive potential. Kumar G, Tuli HS, Mittal S, Shandilya JK, Tiwari A, Sandhu SS. Tumour Biol 36 4005-4016 (2015)

Articles citing this publication (15)

  1. An Analysis of MIF Structural Features that Control Functional Activation of CD74. Pantouris G, Syed MA, Fan C, Rajasekaran D, Cho TY, Rosenberg EM, Bucala R, Bhandari V, Lolis EJ. Chem Biol 22 1197-1205 (2015)
  2. Targeting distinct tautomerase sites of D-DT and MIF with a single molecule for inhibition of neutrophil lung recruitment. Rajasekaran D, Zierow S, Syed M, Bucala R, Bhandari V, Lolis EJ. FASEB J 28 4961-4971 (2014)
  3. MIF intersubunit disulfide mutant antagonist supports activation of CD74 by endogenous MIF trimer at physiologic concentrations. Fan C, Rajasekaran D, Syed MA, Leng L, Loria JP, Bhandari V, Bucala R, Lolis EJ. Proc Natl Acad Sci U S A 110 10994-10999 (2013)
  4. Advances and Insights for Small Molecule Inhibition of Macrophage Migration Inhibitory Factor. Trivedi-Parmar V, Jorgensen WL. J Med Chem 61 8104-8119 (2018)
  5. Nanosecond Dynamics Regulate the MIF-Induced Activity of CD74. Pantouris G, Ho J, Shah D, Syed MA, Leng L, Bhandari V, Bucala R, Batista VS, Loria JP, Lolis EJ. Angew Chem Int Ed Engl 57 7116-7119 (2018)
  6. Obacunone causes sustained expression of MKP-1 thus inactivating p38 MAPK to suppress pro-inflammatory mediators through intracellular MIF. Gao Y, Hou R, Liu F, Liu H, Fei Q, Han Y, Cai R, Peng C, Qi Y. J Cell Biochem 119 837-849 (2018)
  7. Crystallographic and receptor binding characterization of Plasmodium falciparum macrophage migration inhibitory factor complexed to two potent inhibitors. Pantouris G, Rajasekaran D, Baeza Garcia A, Ruiz VG, Leng L, Jorgensen WL, Bucala R, Lolis EJ. J Med Chem 57 8652-8656 (2014)
  8. Multiple binding modes of isothiocyanates that inhibit macrophage migration inhibitory factor. Spencer ES, Dale EJ, Gommans AL, Rutledge MT, Vo CT, Nakatani Y, Gamble AB, Smith RA, Wilbanks SM, Hampton MB, Tyndall JD. Eur J Med Chem 93 501-510 (2015)
  9. Sulforaphane and iberin are potent epigenetic modulators of histone acetylation and methylation in malignant melanoma. Mitsiogianni M, Trafalis DT, Franco R, Zoumpourlis V, Pappa A, Panayiotidis MI. Eur J Nutr 60 147-158 (2021)
  10. Cross-Kingdom Analysis of Diversity, Evolutionary History, and Site Selection within the Eukaryotic Macrophage Migration Inhibitory Factor Superfamily. Michelet C, Danchin EGJ, Jaouannet M, Bernhagen J, Panstruga R, Kogel KH, Keller H, Coustau C. Genes (Basel) 10 E740 (2019)
  11. Macrophage migration inhibitory factor (MIF) is induced by cytotoxic drugs and is involved in immune escape and migration in childhood rhabdomyosarcoma. Johler SM, Fuchs J, Seitz G, Armeanu-Ebinger S. Cancer Immunol Immunother 65 1465-1476 (2016)
  12. Structural Plasticity in the C-Terminal Region of Macrophage Migration Inhibitory Factor-2 Is Associated with an Induced Fit Mechanism for a Selective Inhibitor. Pantouris G, Bucala R, Lolis EJ. Biochemistry 57 3599-3605 (2018)
  13. Structural basis for decreased induction of class IB PI3-kinases expression by MIF inhibitors. Singh AK, Pantouris G, Borosch S, Rojanasthien S, Cho TY. J Cell Mol Med 21 142-153 (2017)
  14. Discovery of novel MIF inhibitors that attenuate microglial inflammatory activation by structures-based virtual screening and in vitro bioassays. Zhang Y, Xu L, Zhang Y, Pan J, Wang PQ, Tian S, Li HT, Gao BW, Hou TJ, Zhen XC, Zheng LT. Acta Pharmacol Sin 43 1508-1520 (2022)
  15. A Cysteine Variant at an Allosteric Site Alters MIF Dynamics and Biological Function in Homo- and Heterotrimeric Assemblies. Skeens E, Pantouris G, Shah D, Manjula R, Ombrello MJ, Maluf NK, Bhandari V, Lisi GP, Lolis EJ. Front Mol Biosci 9 783669 (2022)


Quick links