Discovery of Novel Substrate-Competitive Lysine Methyltransferase G9a Inhibitors as Anticancer Agents

Journal of Medicinal Chemistry
2023.0

Abstract

Identification of structurally novel inhibitors of lysine methyltransferase G9a has been a subject of intense research in cancer epigenetics. Starting with the high-throughput screening (HTS) hit <i>rac</i>-<b>10a</b> obtained from the chemical library of the University of Tokyo Drug Discovery Initiative, the structure-activity relationship of the unique substrate-competitive inhibitors was established with the help of X-ray crystallography and fragment molecular orbital (FMO) calculations for the ligand-protein interaction. Further optimization of the <i>in vitro</i> characteristics and drug metabolism and pharmacokinetics (DMPK) properties led to the identification of <b>26j</b> (RK-701), which is a structurally distinct potent inhibitor of G9a/GLP (IC<sub>50</sub> = 27/53 nM). Compound <b>26j</b> exhibited remarkable selectivity against other related methyltransferases, dose-dependent attenuation of cellular H3K9me2 levels, and tumor growth inhibition in MOLT-4 cells <i>in vitro</i>. Moreover, compound <b>26j</b> showed inhibition of tumor initiation and growth in a carcinogen-induced hepatocellular carcinoma (HCC) <i>in vivo</i> mouse model without overt acute toxicity.

Knowledge Graph

Similar Paper

Discovery of Novel Substrate-Competitive Lysine Methyltransferase G9a Inhibitors as Anticancer Agents
Journal of Medicinal Chemistry 2023.0
Discovery of Reversible DNA Methyltransferase and Lysine Methyltransferase G9a Inhibitors with Antitumoral in Vivo Efficacy
Journal of Medicinal Chemistry 2018.0
Recent progress in histone methyltransferase (G9a) inhibitors as anticancer agents
European Journal of Medicinal Chemistry 2019.0
Identification of protoberberine alkaloids as novel histone methyltransferase G9a inhibitors by structure-based virtual screening
Journal of Computer-Aided Molecular Design 2018.0
Discovery of a Novel Chemotype of Histone Lysine Methyltransferase EHMT1/2 (GLP/G9a) Inhibitors: Rational Design, Synthesis, Biological Evaluation, and Co-crystal Structure
Journal of Medicinal Chemistry 2019.0
Epidithiodiketopiperazine as a pharmacophore for protein lysine methyltransferase G9a inhibitors: Reducing cytotoxicity by structural simplification
Bioorganic &amp; Medicinal Chemistry Letters 2013.0
Design and Synthesis of Novel Epigenetic Inhibitors Targeting Histone Deacetylases, DNA Methyltransferase 1, and Lysine Methyltransferase G9a with In Vivo Efficacy in Multiple Myeloma
Journal of Medicinal Chemistry 2021.0
Inhibition of histone lysine methyltransferases G9a and GLP by ejection of structural Zn(II)
Bioorganic &amp; Medicinal Chemistry Letters 2018.0
On the Histone Lysine Methyltransferase Activity of Fungal Metabolite Chaetocin
Journal of Medicinal Chemistry 2013.0
Histone lysine methyltransferase structure activity relationships that allow for segregation of G9a inhibition and anti-Plasmodium activity
MedChemComm 2017.0