Home LiteratureArticle Details
PMID: 15139849 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S.

Oxidative stress inhibits MEKK1 by site-specific glutathionylation in the ATP-binding domain.

The Biochemical journal ·Vol. 381 ·No. Pt 3 ·2004-08-01 ·Pages 675-83

Cross JV, Templeton DJ

Abstract

Many intracellular signalling events are accompanied by generation of reactive oxygen species in cells. Oxidation of protein thiol groups is an emerging theme in signal-transduction research. We have found that MEKK1 [MAPK (mitogen-activated protein kinase)/ERK (extracellular-signal-regulated kinase) kinase kinase 1], an upstream activator of the SAPK/JNK (stress-activated protein kinase/c-Jun N-terminal kinase) pathway, is directly inhibited by cysteine alkylation using NEM (N-ethylmaleimide). The related kinase, ASK1 (apoptosis signal-regulating kinase 1), was not inhibited, but was instead activated by NEM. Inhibition of MEKK1 requires a single unique cysteine residue (Cys1238) in the ATP-binding domain of MEKK1. Oxidative stress induced by menadione (2-methyl-1,4-naphthoquinone) also inhibited MEKK1, but activated ASK1, in cells. MEKK1 inhibition by menadione also required Cys1238. Oxidant-inhibited MEKK1 was re-activated by dithiothreitol and glutathione, supporting reversible cysteine oxidation as a mechanism. Using various chemical probes, we excluded modification by S-nitrosylation or oxidation of cysteine to sulphenic acid. Oxidant-inhibited MEKK1 migrated normally on non-reducing gels, excluding the possibility of intra- or inter-molecular disulphide bond formation. MEKK1 was inhibited by glutathionylation in vitro, and MEKK1 isolated from menadione-treated cells was shown by MS to be modified by glutathione on Cys1238. Our results support a model whereby the redox environment within the cell selectively regulates stress signalling through MEKK1 versus ASK1, and may thereby participate in the induction of apoptosis by oxidative stress.

MeSH Terms
Adenosine Triphosphate/metabolism Alkylation Amino Acid Sequence/genetics,physiology Amino Acid Substitution Binding Sites/physiology Catalytic Domain/drug effects Cell Line, Tumor Cysteine/metabolism Dithiothreitol/pharmacology Enzyme Inhibitors/pharmacology Ethylmaleimide/pharmacology Glutathione/metabolism Humans Lymph Nodes/enzymology,pathology MAP Kinase Kinase Kinase 1/antagonists & inhibitors,chemistry,metabolism,physiology Male Molecular Sequence Data Mutation/physiology Oxidants/antagonists & inhibitors,pharmacology Oxidation-Reduction Oxidative Stress/drug effects,physiology Peptides/chemistry,metabolism,physiology Prostatic Neoplasms/enzymology,pathology Protein Structure, Tertiary Valine/metabolism
Chemicals
Enzyme Inhibitors Oxidants Peptides Adenosine Triphosphate MAP Kinase Kinase Kinase 1 Glutathione Valine Cysteine Ethylmaleimide Dithiothreitol
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Cross Janet V
Department of Pathology, University of Virginia Medical School, PO Box 800214, Charlottesville, VA 22908-0214, U.S.A.
Templeton Dennis J
References (50)
50 references, click to expand
  1. Formation and reduction of glutathione-protein mixed disulfides during oxidative stress. A study with isolated hepatocytes and menadione (2-methyl-1,4-naphthoquinone).
    Biochem Pharmacol. 1987 Apr 15;36(8):1313-20 PMID: 3593416
  2. Redox cycling and sulphydryl arylation; their relative importance in the mechanism of quinone cytotoxicity to isolated hepatocytes.
    Chem Biol Interact. 1988;65(2):157-73 PMID: 2835188
  3. Human fibroblasts release reactive oxygen species in response to interleukin-1 or tumour necrosis factor-alpha.
    Biochem J. 1989 Oct 15;263(2):539-45 PMID: 2556998
  4. Mechanism of inhibition of aldose reductase by menadione (vitamin K3).
    Mol Pharmacol. 1992 Nov;42(5):917-21 PMID: 1435755
  5. Identification of an oncoprotein- and UV-responsive protein kinase that binds and potentiates the c-Jun activation domain.
    Genes Dev. 1993 Nov;7(11):2135-48 PMID: 8224842
  6. Free radicals in biology: oxidative stress and the effects of ionizing radiation.
    Int J Radiat Biol. 1994 Jan;65(1):27-33 PMID: 7905906
  7. Signal transduction by tumor necrosis factor mediated by JNK protein kinases.
    Mol Cell Biol. 1994 Dec;14(12):8376-84 PMID: 7969172
  8. Differential activation of ERK and JNK mitogen-activated protein kinases by Raf-1 and MEKK.
    Science. 1994 Dec 9;266(5191):1719-23 PMID: 7992057
  9. Activation of stress-activated protein kinase by MEKK1 phosphorylation of its activator SEK1.
    Nature. 1994 Dec 22-29;372(6508):798-800 PMID: 7997270
  10. Nitric oxide-stimulated guanine nucleotide exchange on p21ras.
    J Biol Chem. 1995 Mar 31;270(13):7017-20 PMID: 7706235
  11. Active oxygen mechanisms of UV inflammation.
    Adv Exp Med Biol. 1994;366:87-97 PMID: 7771293
  12. Persistent activation of c-Jun N-terminal kinase 1 (JNK1) in gamma radiation-induced apoptosis.
    J Biol Chem. 1996 Jan 12;271(2):631-4 PMID: 8557665
  13. Interaction between c-Rel and the mitogen-activated protein kinase kinase kinase 1 signaling cascade in mediating kappaB enhancer activation.
    J Biol Chem. 1996 Apr 12;271(15):8971-6 PMID: 8621542
  14. Cloning of rat MEK kinase 1 cDNA reveals an endogenous membrane-associated 195-kDa protein with a large regulatory domain.
    Proc Natl Acad Sci U S A. 1996 May 28;93(11):5291-5 PMID: 8643568
  15. Independent regulation of JNK/p38 mitogen-activated protein kinases by metabolic oxidative stress in the liver.
    Proc Natl Acad Sci U S A. 1996 Nov 12;93(23):12908-13 PMID: 8917518
  16. Induction of apoptosis by ASK1, a mammalian MAPKKK that activates SAPK/JNK and p38 signaling pathways.
    Science. 1997 Jan 3;275(5296):90-4 PMID: 8974401
  17. Regulation of the activity of MEK kinase 1 (MEKK1) by autophosphorylation within the kinase activation domain.
    Biochem J. 1997 Feb 15;322 ( Pt 1):185-92 PMID: 9078260
  18. The regulation of anoikis: MEKK-1 activation requires cleavage by caspases.
    Cell. 1997 Jul 25;90(2):315-23 PMID: 9244305
  19. Novel application of 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole to identify cysteine sulfenic acid in the AhpC component of alkyl hydroperoxide reductase.
    Biochemistry. 1997 Dec 2;36(48):15013-8 PMID: 9398227
  20. Activation of the OxyR transcription factor by reversible disulfide bond formation.
    Science. 1998 Mar 13;279(5357):1718-21 PMID: 9497290
  21. Stimulation of "stress-regulated" mitogen-activated protein kinases (stress-activated protein kinases/c-Jun N-terminal kinases and p38-mitogen-activated protein kinases) in perfused rat hearts by oxidative and other stresses.
    J Biol Chem. 1998 Mar 27;273(13):7228-34 PMID: 9516415
  22. MEK kinase 1, a substrate for DEVD-directed caspases, is involved in genotoxin-induced apoptosis.
    Mol Cell Biol. 1998 Apr;18(4):2416-29 PMID: 9528810
  23. Differential regulation of IkappaB kinase alpha and beta by two upstream kinases, NF-kappaB-inducing kinase and mitogen-activated protein kinase/ERK kinase kinase-1.
    Proc Natl Acad Sci U S A. 1998 Mar 31;95(7):3537-42 PMID: 9520401
  24. Mammalian thioredoxin is a direct inhibitor of apoptosis signal-regulating kinase (ASK) 1.
    EMBO J. 1998 May 1;17(9):2596-606 PMID: 9564042
  25. Fas-induced proteolytic activation and intracellular redistribution of the stress-signaling kinase MEKK1.
    Proc Natl Acad Sci U S A. 1998 May 12;95(10):5595-600 PMID: 9576928
  26. Reversible inactivation of protein-tyrosine phosphatase 1B in A431 cells stimulated with epidermal growth factor.
    J Biol Chem. 1998 Jun 19;273(25):15366-72 PMID: 9624118
  27. Stimulation of multiple mitogen-activated protein kinase sub-families by oxidative stress and phosphorylation of the small heat shock protein, HSP25/27, in neonatal ventricular myocytes.
    Biochem J. 1998 Aug 1;333 ( Pt 3):581-9 PMID: 9677316
  28. Coordinate regulation of IkappaB kinases by mitogen-activated protein kinase kinase kinase 1 and NF-kappaB-inducing kinase.
    Mol Cell Biol. 1998 Dec;18(12):7336-43 PMID: 9819420
  29. Regulation of JNK signaling by GSTp.
    EMBO J. 1999 Mar 1;18(5):1321-34 PMID: 10064598
  30. Regulation of PTP1B via glutathionylation of the active site cysteine 215.
    Biochemistry. 1999 May 18;38(20):6699-705 PMID: 10350489
  31. Oxidative stress differentially modulates phosphorylation of ERK, p38 and CREB induced by NGF or EGF in PC12 cells.
    Neurobiol Aging. 1999 May-Jun;20(3):271-8 PMID: 10588574
  32. MEK kinase 1 is critically required for c-Jun N-terminal kinase activation by proinflammatory stimuli and growth factor-induced cell migration.
    Proc Natl Acad Sci U S A. 2000 May 9;97(10):5243-8 PMID: 10805784
  33. MEK kinase 1 gene disruption alters cell migration and c-Jun NH2-terminal kinase regulation but does not cause a measurable defect in NF-kappa B activation.
    Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7272-7 PMID: 10852963
  34. Oxidant-induced S-glutathiolation inactivates protein kinase C-alpha (PKC-alpha): a potential mechanism of PKC isozyme regulation.
    Biochemistry. 2000 Aug 22;39(33):10319-29 PMID: 10956021
  35. Oxidative modification of H-ras: S-thiolation and S-nitrosylation of reactive cysteines.
    Biochem J. 2001 Apr 1;355(Pt 1):145-53 PMID: 11256959
  36. Oxidation of active center cysteine of bovine 1-Cys peroxiredoxin to the cysteine sulfenic acid form by peroxide and peroxynitrite.
    Free Radic Biol Med. 2001 Aug 1;31(3):292-303 PMID: 11461766
  37. Glutathionylation of the p50 subunit of NF-kappaB: a mechanism for redox-induced inhibition of DNA binding.
    Biochemistry. 2001 Nov 27;40(47):14134-42 PMID: 11714266
  38. Redox regulation of Cdc25C.
    J Biol Chem. 2002 Jun 7;277(23):20535-40 PMID: 11925443
  39. Regulation of cAMP-dependent protein kinase activity by glutathionylation.
    J Biol Chem. 2002 Nov 8;277(45):43505-11 PMID: 12189155
  40. An intramolecular disulfide bridge as a catalytic switch for serotonin N-acetyltransferase.
    J Biol Chem. 2002 Nov 15;277(46):44229-35 PMID: 12215431
  41. Redox regulation of protein tyrosine phosphatase 1B involves a sulphenyl-amide intermediate.
    Nature. 2003 Jun 12;423(6941):769-73 PMID: 12802338
  42. Oxidation state of the active-site cysteine in protein tyrosine phosphatase 1B.
    Nature. 2003 Jun 12;423(6941):773-7 PMID: 12802339
  43. Eukaryotic transient-expression system based on recombinant vaccinia virus that synthesizes bacteriophage T7 RNA polymerase.
    Proc Natl Acad Sci U S A. 1986 Nov;83(21):8122-6 PMID: 3095828
  44. Sulfenic acid formation in human serum albumin by hydrogen peroxide and peroxynitrite.
    Biochemistry. 2003 Aug 26;42(33):9906-14 PMID: 12924939
  45. Catalytic and chemical competence of regulation of cdc25 phosphatase by oxidation/reduction.
    Biochemistry. 2003 Sep 2;42(34):10060-70 PMID: 12939134
  46. The inactivation of the acyl phosphatase activity catalyzed by the sulfenic acid form of glyceraldehyde 3-phosphate dehydrogenase by dimedone and olefins.
    J Biol Chem. 1974 Oct 10;249(19):6234-43 PMID: 4371119
  47. The metabolism of menadione (2-methyl-1,4-naphthoquinone) by isolated hepatocytes. A study of the implications of oxidative stress in intact cells.
    J Biol Chem. 1982 Oct 25;257(20):12419-25 PMID: 6181068
  48. Alterations in intracellular thiol homeostasis during the metabolism of menadione by isolated rat hepatocytes.
    Arch Biochem Biophys. 1984 Dec;235(2):334-42 PMID: 6097182
  49. Menadione-induced cytotoxicity is associated with protein thiol oxidation and alteration in intracellular Ca2+ homeostasis.
    Arch Biochem Biophys. 1984 Dec;235(2):343-50 PMID: 6097183
  50. The role of oxidative processes in the cytotoxicity of substituted 1,4-naphthoquinones in isolated hepatocytes.
    Arch Biochem Biophys. 1986 Aug 1;248(2):460-6 PMID: 3017211
Article Info
Journal
The Biochemical journal
Abbr.
Biochem J
ISSN
1470-8728
Published
2004-08-01
Pages
675-83
Language
English
Region
England
NLM ID
2984726R
PMCID
PMC1133876
Subset
IM
Grants
NCI NIH HHS · R01 CA066134 · United States
NCI NIH HHS · CA66134 · United States
Corrections
CommentIn
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: product@genelibs.com