3-Aroyl-1,4-diarylpyrroles Inhibit Chronic Myeloid Leukemia Cell Growth through an Interaction with Tubulin

ACS Medicinal Chemistry Letters
2017.0

Abstract

We designed 3-aroyl-1,4-diarylpyrrole (ARDAP) derivatives as potential anticancer agents having different substituents at the 1- or 4-phenyl ring. ARDAP compounds exhibited potent inhibition of tubulin polymerization, binding of colchicine to tubulin, and cancer cell growth. ARDAP derivative <b>10</b> inhibited the proliferation of BCR/ABL-expressing KU812 and LAMA84 cells from chronic myeloid leukemia (CML) patients in blast crisis and of hematopoietic cells ectopically expressing the imatinib mesylate (IM)-sensitive KBM5-WT or its IM-resistant KBM5-T315I mutation. Compound <b>10</b> minimally affected the proliferation of normal blood cells, indicating that it may be a promising agent to overcome broad tyrosine kinase inhibitor resistance in relapsed/refractory CML patients. Compound <b>10</b> significantly decreased CML proliferation by inducing G2/M phase arrest and apoptosis via a mitochondria-dependent pathway. ARDAP <b>10</b> augmented the cytotoxic effects of IM in human CML cells. Compound <b>10</b> represents a robust lead compound to develop tubulin inhibitors with potential as novel treatments for CML.

Knowledge Graph

Similar Paper

3-Aroyl-1,4-diarylpyrroles Inhibit Chronic Myeloid Leukemia Cell Growth through an Interaction with Tubulin
ACS Medicinal Chemistry Letters 2017.0
New Pyrrole Derivatives with Potent Tubulin Polymerization Inhibiting Activity As Anticancer Agents Including Hedgehog-Dependent Cancer
Journal of Medicinal Chemistry 2014.0
Structure-activity relationship studies and in vitro and in vivo anticancer activity of novel 3-aroyl-1,4-diarylpyrroles against solid tumors and hematological malignancies
European Journal of Medicinal Chemistry 2020.0
Synthesis of polyenylpyrrole derivatives with selective growth inhibitory activity against T-cell acute lymphoblastic leukemia cells
Bioorganic &amp; Medicinal Chemistry Letters 2021.0
Pyrrolo[1,2-b][1,2,5]benzothiadiazepines (PBTDs):  A New Class of Agents with High Apoptotic Activity in Chronic Myelogenous Leukemia K562 Cells and in Cells from Patients at Onset and Who Were Imatinib-Resistant
Journal of Medicinal Chemistry 2006.0
Synthesis and biological evaluation of novel aromatic amide derivatives as potential BCR-ABL inhibitors
Bioorganic &amp; Medicinal Chemistry Letters 2023.0
Toward Highly Potent Cancer Agents by Modulating the C-2 Group of the Arylthioindole Class of Tubulin Polymerization Inhibitors
Journal of Medicinal Chemistry 2013.0
Design, synthesis, and bioevaluation of pyrazolo[1,5-a]pyrimidine derivatives as tubulin polymerization inhibitors targeting the colchicine binding site with potent anticancer activities
European Journal of Medicinal Chemistry 2020.0
Discovery of (2-(pyrrolidin-1-yl)thieno[3,2-d]pyrimidin-4-yl)(3,4,5-trimethoxyphenyl)methanone as a novel potent tubulin depolymerizing and vascular disrupting agent
European Journal of Medicinal Chemistry 2022.0
Indirubin derivatives as potent FLT3 inhibitors with anti-proliferative activity of acute myeloid leukemic cells
Bioorganic &amp; Medicinal Chemistry Letters 2010.0