Human CREBBP acetyltransferase is impaired by etoposide quinone, an oxidative and leukemogenic metabolite of the anticancer drug etoposide through modification of redox-sensitive zinc-finger cysteine residues.

[1]  Ximing Xu,et al.  T-Cell Protein Tyrosine Phosphatase Is Irreversibly Inhibited by Etoposide-Quinone, a Reactive Metabolite of the Chemotherapy Drug Etoposide , 2019, Molecular Pharmacology.

[2]  M. Davies,et al.  Reaction of quinones with proteins: Kinetics of adduct formation, effects on enzymatic activity and protein structure, and potential reversibility of modifications. , 2019, Free radical biology & medicine.

[3]  M. Dolenc,et al.  Chemicals and Drugs Forming Reactive Quinone and Quinone Imine Metabolites. , 2018, Chemical research in toxicology.

[4]  M. Dobbelstein,et al.  CDK4 inhibition diminishes p53 activation by MDM2 antagonists , 2018, Cell Death & Disease.

[5]  M. Manz,et al.  Inactivation of CREBBP expands the germinal center B cell compartment, down-regulates MHCII expression and promotes DLBCL growth , 2017, Proceedings of the National Academy of Sciences.

[6]  E. Laurenti,et al.  Early loss of Crebbp confers malignant stem cell properties on lymphoid progenitors , 2017, Nature Cell Biology.

[7]  H. Dyson,et al.  Role of the CBP catalytic core in intramolecular SUMOylation and control of histone H3 acetylation , 2017, Proceedings of the National Academy of Sciences.

[8]  K. Basso,et al.  The CREBBP Acetyltransferase Is a Haploinsufficient Tumor Suppressor in B-cell Lymphoma. , 2017, Cancer discovery.

[9]  C. Pui,et al.  Whole-transcriptome sequencing identifies a distinct subtype of acute lymphoblastic leukemia with predominant genomic abnormalities of EP300 and CREBBP , 2017, Genome research.

[10]  Emma Lishman,et al.  Myeloperoxidase Enhances Etoposide and Mitoxantrone-Mediated DNA Damage: A Target for Myeloprotection in Cancer Chemotherapy , 2017, Molecular Pharmacology.

[11]  Ash A. Alizadeh,et al.  Crebbp loss cooperates with Bcl2 overexpression to promote lymphoma in mice. , 2016, Blood.

[12]  J. Bolton,et al.  Formation and Biological Targets of Quinones: Cytotoxic versus Cytoprotective Effects , 2016, Chemical research in toxicology.

[13]  K. Sakamoto,et al.  CBP/p300 acetyltransferase activity in hematologic malignancies. , 2016, Molecular genetics and metabolism.

[14]  M. King,et al.  Two-Mechanism Model for the Interaction of Etoposide Quinone with Topoisomerase IIα. , 2016, Chemical research in toxicology.

[15]  B. Hales,et al.  The Effects of Chemotherapeutic Agents, Bleomycin, Etoposide, and Cisplatin, on Chromatin Remodeling in Male Rat Germ Cells , 2016, Biology of reproduction.

[16]  L. Fritsch,et al.  An acetyltransferase assay for CREB-binding protein based on reverse phase-ultra-fast liquid chromatography of fluorescent histone H3 peptides. , 2015, Analytical biochemistry.

[17]  N. Kishikawa,et al.  Characterization of quinone derived protein adducts and their selective identification using redox cycling based chemiluminescence assay. , 2015, Journal of chromatography. A.

[18]  M. Stiborová,et al.  The synergistic effects of DNA-damaging drugs cisplatin and etoposide with a histone deacetylase inhibitor valproate in high-risk neuroblastoma cells. , 2015, International journal of oncology.

[19]  H. Super A role for epigenetics in the formation of chromosome translocations in acute leukemia , 2015 .

[20]  Kristina M. Cook,et al.  Inhibition of the HIF1α-p300 interaction by quinone- and indandione-mediated ejection of structural Zn(II). , 2015, European journal of medicinal chemistry.

[21]  G. Biamonti,et al.  Molecular mechanisms of etoposide , 2015, EXCLI journal.

[22]  Philip A. Cole,et al.  Protein Lysine Acetylation by p300/CBP , 2015, Chemical reviews.

[23]  E. Verdin,et al.  50 years of protein acetylation: from gene regulation to epigenetics, metabolism and beyond , 2014, Nature Reviews Molecular Cell Biology.

[24]  Azra Rabbani-Chadegani,et al.  Spectroscopic detection of etoposide binding to chromatin components: the role of histone proteins. , 2014, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[25]  N. Osheroff,et al.  Etoposide Quinone Is a Covalent Poison of Human Topoisomerase IIβ , 2014, Biochemistry.

[26]  N. Osheroff,et al.  Topoisomerase II and leukemia , 2014, Annals of the New York Academy of Sciences.

[27]  T. Kundu,et al.  Naphthoquinone-mediated Inhibition of Lysine Acetyltransferase KAT3B/p300, Basis for Non-toxic Inhibitor Synthesis* , 2014, The Journal of Biological Chemistry.

[28]  E. Ortega,et al.  Structure of the p300 catalytic core and implications for chromatin targeting and HAT regulation , 2013, Nature Structural &Molecular Biology.

[29]  S. Akira,et al.  Zinc-finger antiviral protein mediates retinoic acid inducible gene I–like receptor-independent antiviral response to murine leukemia virus , 2013, Proceedings of the National Academy of Sciences.

[30]  Yan Liu,et al.  Akt kinase targets the association of CBP with histone H3 to regulate the acetylation of lysine K18 , 2013, FEBS letters.

[31]  Kevin Struhl,et al.  SIRT7 links H3K18 deacetylation to maintenance of oncogenic transformation , 2012, Nature.

[32]  E. Froňková,et al.  CREBBP HAT domain mutations prevail in relapse cases of high hyperdiploid childhood acute lymphoblastic leukemia , 2012, Leukemia.

[33]  B. Göttgens,et al.  The Transcriptional Coactivator Cbp Regulates Self-Renewal and Differentiation in Adult Hematopoietic Stem Cells , 2011, Molecular and Cellular Biology.

[34]  Raul Rabadan,et al.  Analysis of the Coding Genome of Diffuse Large B-Cell Lymphoma , 2011, Nature Genetics.

[35]  S. Armstrong,et al.  Crebbp haploinsufficiency in mice alters the bone marrow microenvironment, leading to loss of stem cells and excessive myelopoiesis. , 2011, Blood.

[36]  N. Osheroff,et al.  Etoposide quinone is a redox-dependent topoisomerase II poison. , 2011, Biochemistry.

[37]  Kenneth H. Buetow,et al.  CREBBP mutations in relapsed acute lymphoblastic leukaemia , 2011, Nature.

[38]  S. Gollin,et al.  Myeloperoxidase-Dependent Oxidation of Etoposide in Human Myeloid Progenitor CD34+ Cells , 2011, Molecular Pharmacology.

[39]  S. Quintal,et al.  Zinc finger proteins as templates for metal ion exchange and ligand reactivity. Chemical and biological consequences. , 2011, Metallomics : integrated biometal science.

[40]  C. Allis,et al.  Covalent histone modifications — miswritten, misinterpreted and mis-erased in human cancers , 2010, Nature Reviews Cancer.

[41]  K. Miyamoto,et al.  The creation of the artificial RING finger from the cross-brace zinc finger by alpha-helical region substitution. , 2010, Biochemical and biophysical research communications.

[42]  E. Rojas,et al.  DNA-AP sites generation by Etoposide in whole blood cells , 2009, BMC Cancer.

[43]  S. Agrawal,et al.  Inhibition of Lysine Acetyltransferase KAT3B/p300 Activity by a Naturally Occurring Hydroxynaphthoquinone, Plumbagin* , 2009, The Journal of Biological Chemistry.

[44]  B. Zayas,et al.  Thiols oxidation and covalent binding of BSA by cyclolignanic quinones are enhanced by the magnesium cation , 2008, Free radical research.

[45]  D. Peters,et al.  Rubinstein–Taybi syndrome: clinical and molecular overview , 2007, Expert Reviews in Molecular Medicine.

[46]  N. Osheroff,et al.  Quinone-induced enhancement of DNA cleavage by human topoisomerase IIalpha: adduction of cysteine residues 392 and 405. , 2007, Biochemistry.

[47]  B. Day,et al.  Myeloperoxidase-catalyzed metabolism of etoposide to its quinone and glutathione adduct forms in HL60 cells. , 2006, Chemical research in toxicology.

[48]  P. Hatcher,et al.  Mechanism of arylating quinone toxicity involving Michael adduct formation and induction of endoplasmic reticulum stress. , 2006, Proceedings of the National Academy of Sciences of the United States of America.

[49]  N. Osheroff,et al.  Etoposide, topoisomerase II and cancer. , 2005, Current medicinal chemistry. Anti-cancer agents.

[50]  M. Segal,et al.  DNA topoisomerase II in therapy-related acute promyelocytic leukemia. , 2005, The New England journal of medicine.

[51]  Robert A Copeland,et al.  Evaluation of enzyme inhibitors in drug discovery. A guide for medicinal chemists and pharmacologists. , 2005, Methods of biochemical analysis.

[52]  Xiang-Jiao Yang,et al.  Lysine acetylation and the bromodomain: a new partnership for signaling , 2004, BioEssays : news and reviews in molecular, cellular and developmental biology.

[53]  Ian A Blair,et al.  Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. , 2004, Drug metabolism and disposition: the biological fate of chemicals.

[54]  C. Felix,et al.  Plasma Etoposide Catechol Increases in Pediatric Patients Undergoing Multiple-Day Chemotherapy with Etoposide , 2004, Clinical Cancer Research.

[55]  R. Hennekam,et al.  Loss of CBP acetyltransferase activity by PHD finger mutations in Rubinstein-Taybi syndrome. , 2003, Human molecular genetics.

[56]  Andrew L. Kung,et al.  Distinct roles for CREB-binding protein and p300 in hematopoietic stem cell self-renewal , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[57]  E. Kalkhoven,et al.  The PHD Type Zinc Finger Is an Integral Part of the CBP Acetyltransferase Domain , 2002, Molecular and Cellular Biology.

[58]  Y. Tyurina,et al.  Pro-oxidant and antioxidant mechanisms of etoposide in HL-60 cells: role of myeloperoxidase. , 2001, Cancer research.

[59]  P. Nowell,et al.  Near-precise interchromosomal recombination and functional DNA topoisomerase II cleavage sites at MLL and AF-4 genomic breakpoints in treatment-related acute lymphoblastic leukemia with t(4;11) translocation , 2001, Proceedings of the National Academy of Sciences of the United States of America.

[60]  F. Marchetti,et al.  Etoposide induces heritable chromosomal aberrations and aneuploidy during male meiosis in the mouse , 2001, Proceedings of the National Academy of Sciences of the United States of America.

[61]  J. Bolton,et al.  Role of quinones in toxicology. , 2000, Chemical research in toxicology.

[62]  D. Livingston,et al.  Gene dose-dependent control of hematopoiesis and hematologic tumor suppression by CBP. , 2000, Genes & development.

[63]  Y. Tyurina,et al.  Mechanism-based chemopreventive strategies against etoposide-induced acute myeloid leukemia: free radical/antioxidant approach. , 1999, Molecular pharmacology.

[64]  B. Freidlin,et al.  Secondary leukemia or myelodysplastic syndrome after treatment with epipodophyllotoxins. , 1999, Journal of clinical oncology : official journal of the American Society of Clinical Oncology.

[65]  S. Rhee,et al.  Probing cellular protein targets of H2O2 with fluorescein‐conjugated iodoacetamide and antibodies to fluorescein , 1998, FEBS letters.

[66]  P. Nowell,et al.  Association of CYP3A4 genotype with treatment-related leukemia. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[67]  Wei Gu,et al.  Activation of p53 Sequence-Specific DNA Binding by Acetylation of the p53 C-Terminal Domain , 1997, Cell.

[68]  B. Howard,et al.  The Transcriptional Coactivators p300 and CBP Are Histone Acetyltransferases , 1996, Cell.

[69]  M. Relling,et al.  Etoposide pharmacokinetics and pharmacodynamics after acute and chronic exposure to cisplatin , 1994, Clinical pharmacology and therapeutics.

[70]  P. Gallop,et al.  Specific detection of quinoproteins by redox-cycling staining. , 1991, The Journal of biological chemistry.

[71]  N. Haim,et al.  Peroxidase-catalyzed metabolism of etoposide (VP-16-213) and covalent binding of reactive intermediates to cellular macromolecules. , 1987, Cancer research.

[72]  C. Myers,et al.  Irreversible binding of etoposide (VP-16-213) to deoxyribonucleic acid and proteins. , 1984, Biochemical pharmacology.

[73]  G. Campiani,et al.  Pyrrolo-1,5-benzoxazepines induce apoptosis in chronic myelogenous leukemia (CML) cells by bypassing the apoptotic suppressor bcr-abl. , 2001, The Journal of pharmacology and experimental therapeutics.