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102052-95-9,MFCD12545899
Catalog No.:AA0006ED

102052-95-9 | 3-Deazaneplanocin A

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  • Technical Information
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA0006ED
Chemical Name:
3-Deazaneplanocin A
CAS Number:
102052-95-9
Molecular Formula:
C12H14N4O3
Molecular Weight:
262.2646
MDL Number:
MFCD12545899
SMILES:
Nc1nccc2c1ncn2[C@@H]1C=C([C@H]([C@H]1O)O)CO
Properties
Computed Properties
 
Complexity:
378  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
2  
XLogP3:
-1.7  

Literature

Title: Upregulation of histone-lysine methyltransferases plays a causal role in hexavalent chromium-induced cancer stem cell-like property and cell transformation.

Journal: Toxicology and applied pharmacology 20180301

Title: Resveratrol suppresses myofibroblast activity of human buccal mucosal fibroblasts through the epigenetic inhibition of ZEB1 expression.

Journal: Oncotarget 20160315

Title: Epigenetic silencing of microRNA-218 via EZH2-mediated H3K27 trimethylation is involved in malignant transformation of HBE cells induced by cigarette smoke extract.

Journal: Archives of toxicology 20160201

Title: Disruption of the MYC-miRNA-EZH2 loop to suppress aggressive B-cell lymphoma survival and clonogenicity.

Journal: Leukemia 20131201

Title: Epigenetic therapy with 3-deazaneplanocin A, an inhibitor of the histone methyltransferase EZH2, inhibits growth of non-small cell lung cancer cells.

Journal: Lung cancer (Amsterdam, Netherlands) 20121101

Title: Targeting the enhancer of zeste homologue 2 in medulloblastoma.

Journal: International journal of cancer 20121015

Title: 3-Bromo-3-deazaneplanocin and 3-bromo-3-deazaaristeromycin: synthesis and antiviral activity.

Journal: Bioorganic & medicinal chemistry letters 20120815

Title: Molecular mechanisms involved in the synergistic interaction of the EZH2 inhibitor 3-deazaneplanocin A with gemcitabine in pancreatic cancer cells.

Journal: Molecular cancer therapeutics 20120801

Title: 3-Deazaneplanocin A is a promising therapeutic agent for the eradication of tumor-initiating hepatocellular carcinoma cells.

Journal: International journal of cancer 20120601

Title: Silencing of Kruppel-like factor 2 by the histone methyltransferase EZH2 in human cancer.

Journal: Oncogene 20120412

Title: The role of histone methyltransferase EZH2 in myelodysplastic syndromes.

Journal: Expert review of hematology 20120401

Title: Derivation of new human embryonic stem cell lines reveals rapid epigenetic progression in vitro that can be prevented by chemical modification of chromatin.

Journal: Human molecular genetics 20120215

Title: Inhibition of histone methylation arrests ongoing graft-versus-host disease in mice by selectively inducing apoptosis of alloreactive effector T cells.

Journal: Blood 20120202

Title: Loading 3-deazaneplanocin A into pegylated unilamellar liposomes by forming transient phenylboronic acid-drug complex and its pharmacokinetic features in Sprague-Dawley rats.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20120201

Title: Cloning and characterization of polyA- RNA transcripts encoded by activated B1-like retrotransposons in mouse erythroleukemia MEL cells exposed to methylation inhibitors.

Journal: BMB reports 20120201

Title: Polycomb repressor complex-2 is a novel target for mesothelioma therapy.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120101

Title: The role of EZH2 in the regulation of the activity of matrix metalloproteinases in prostate cancer cells.

Journal: PloS one 20120101

Title: Epigenetic regulation of endothelial lineage committed genes in pro-angiogenic hematopoietic and endothelial progenitor cells.

Journal: Circulation research 20111111

Title: (-)-Epigallocatechin-3-gallate and DZNep reduce polycomb protein level via a proteasome-dependent mechanism in skin cancer cells.

Journal: Carcinogenesis 20111001

Title: The histone methyltransferase inhibitor, DZNep, up-regulates TXNIP, increases ROS production, and targets leukemia cells in AML.

Journal: Blood 20110908

Title: PRAJA1 is a ubiquitin ligase for the polycomb repressive complex 2 proteins.

Journal: Biochemical and biophysical research communications 20110513

Title: S-adenosylhomocysteine hydrolase inhibition by 3-deazaneplanocin A analogues induces anti-cancer effects in breast cancer cell lines and synergy with both histone deacetylase and HER2 inhibition.

Journal: Breast cancer research and treatment 20110501

Title: Overexpression of Enhancer of zeste homolog 2 with trimethylation of lysine 27 on histone H3 in adult T-cell leukemia/lymphoma as a target for epigenetic therapy.

Journal: Haematologica 20110501

Title: Methotrexate induces apoptosis through p53/p21-dependent pathway and increases E-cadherin expression through downregulation of HDAC/EZH2.

Journal: Biochemical pharmacology 20110215

Title: Quantification of 3-deazaneplanocin A, a novel epigenetic anticancer agent, in rat biosamples by hydrophilic interaction liquid chromatography-tandem mass spectrometric detection.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110201

Title: Determinants of sensitivity to DZNep induced apoptosis in multiple myeloma cells.

Journal: PloS one 20110101

Title: Polycomb target genes are silenced in multiple myeloma.

Journal: PloS one 20100101

Title: Combinatorial pharmacologic approaches target EZH2-mediated gene repression in breast cancer cells.

Journal: Molecular cancer therapeutics 20091201

Title: Combined epigenetic therapy with the histone methyltransferase EZH2 inhibitor 3-deazaneplanocin A and the histone deacetylase inhibitor panobinostat against human AML cells.

Journal: Blood 20090924

Title: DZNep is a global histone methylation inhibitor that reactivates developmental genes not silenced by DNA methylation.

Journal: Molecular cancer therapeutics 20090601

Title: BRCA1-deficient mammary tumor cells are dependent on EZH2 expression and sensitive to Polycomb Repressive Complex 2-inhibitor 3-deazaneplanocin A.

Journal: Breast cancer research : BCR 20090101

Title: DACT3 is an epigenetic regulator of Wnt/beta-catenin signaling in colorectal cancer and is a therapeutic target of histone modifications.

Journal: Cancer cell 20080601

Title: Pharmacologic disruption of Polycomb-repressive complex 2-mediated gene repression selectively induces apoptosis in cancer cells.

Journal: Genes & development 20070501

Title: Blockade of murine erythroleukemia cell differentiation by hypomethylating agents causes accumulation of discrete small poly(A)- RNAs hybridized to 3'-end flanking sequences of beta(major) globin gene.

Journal: Biochimica et biophysica acta 20050322

Title: John Montgomery's legacy: carbocyclic adenosine analogues as SAH hydrolase inhibitors with broad-spectrum antiviral activity.

Journal: Nucleosides, nucleotides & nucleic acids 20050101

Title: Inhibition of severe acute respiratory syndrome-associated coronavirus (SARSCoV) by calpain inhibitors and beta-D-N4-hydroxycytidine.

Journal: Antiviral chemistry & chemotherapy 20040101

Title: Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners.

Journal: European journal of biochemistry 20030901

Title: Potential antiviral therapeutics for smallpox, monkeypox and other orthopoxvirus infections.

Journal: Antiviral research 20030101

Title: Identification of active antiviral compounds against a New York isolate of West Nile virus.

Journal: Antiviral research 20020701

Title: 3-deazaneplanocin A induces massively increased interferon-alpha production in Ebola virus-infected mice.

Journal: Antiviral research 20020701

Title: The role of the Type I interferon response in the resistance of mice to filovirus infection.

Journal: The Journal of general virology 20010601

Title: Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.

Journal: Clinical microbiology reviews 20010401

Title: Treatment of lethal Ebola virus infection in mice with a single dose of an S-adenosyl-L-homocysteine hydrolase inhibitor.

Journal: Antiviral research 20000201

Title: Carboxy terminal variants of Epstein-Barr virus-encoded latent membrane protein 1 during long-term human immunodeficiency virus infection: reliable markers for individual strain identification.

Journal: The Journal of infectious diseases 19990101

Title: Carbocyclic adenosine analogues as S-adenosylhomocysteine hydrolase inhibitors and antiviral agents: recent advances.

Journal: Nucleosides & nucleotides 19980101

Title: S-adenosylhomocysteine hydrolase inhibitors interfere with the replication of human immunodeficiency virus type 1 through inhibition of the LTR transactivation.

Journal: Molecular pharmacology 19971201

Title: Anti-human immunodeficiency virus 1 (HIV-1) activities of 3-deazaadenosine analogs: increased potency against 3'-azido-3'-deoxythymidine-resistant HIV-1 strains.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19950103

Title: Inhibitory activity of S-adenosylhomocysteine hydrolase inhibitors against human cytomegalovirus replication.

Journal: Antiviral research 19930701

Title: Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro.

Journal: Antiviral research 19900101

Title: Broad-spectrum antiviral activities of neplanocin A, 3-deazaneplanocin A, and their 5'-nor derivatives.

Journal: Antimicrobial agents and chemotherapy 19890801

Title: Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities.

Journal: Journal of medicinal chemistry 19890701

Title: 3-Deazaneplanocin: a new and potent inhibitor of S-adenosylhomocysteine hydrolase and its effects on human promyelocytic leukemia cell line HL-60.

Journal: Biochemical and biophysical research communications 19860313

Title: Fiskus W, et al. Combined epigenetic therapy with the histone methyltransferase EZH2 inhibitor 3-deazaneplanocin A and the histone deacetylase inhibitor panobinostat against human AML cells. Blood, 2009, 114(13), 2733-2743.

Title: Avan A, et al. Molecular mechanisms involved in the synergistic interaction of the EZH2 inhibitor 3-deazaneplanocin A with gemcitabine in pancreatic cancer cells. Mol Cancer Ther. 2012 Aug;11(8):1735-46.

Title: Kikuchi J, et al. Epigenetic therapy with 3-deazaneplanocin A, an inhibitor of the histone methyltransferase EZH2, inhibits growth of non-small cell lung cancer cells. Lung Cancer. 2012 Nov;78(2):138-43.

Title: Sun F, et al. Preclinical pharmacokinetic studies of 3-deazaneplanocin A, a potent epigenetic anticancer agent, and its human pharmacokinetic prediction using GastroPlus?. Eur J Pharm Sci. 2015 Sep 18;77:290-302.

Title: Siddiqi FS, et al. The Histone Methyltransferase Enzyme Enhancer of Zeste Homolog 2 Protects against Podocyte Oxidative Stress and Renal Injury in Diabetes. J Am Soc Nephrol. 2016 Jul;27(7):2021-34.

Title: Noriko Uchiyama, et al. Aristeromycin and DZNeP cause growth inhibition of prostate cancer via induction of mir-26a. Eur J Pharmacol. 2017 Oct 5;812:138-146.

Title: Smee DF, et al. A review of compounds exhibiting anti-orthopoxvirus activity in animal models. Antiviral Res. 2003 Jan;57(1-2):41-52.

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