Design, synthesis, and biological evaluation of efflux-resistant imatinib derivatives

Article

Chowdhury, M.M., Pretheshan, P., Chowdhury, N.S., Andriollo, P., Shah, A.J., Forbes, B., Pepper, C. and Rahman, K.M. 2025. Design, synthesis, and biological evaluation of efflux-resistant imatinib derivatives. Journal of Medicinal Chemistry. 68 (21), pp. 22619-22632. https://doi.org/10.1021/acs.jmedchem.5c01596
TypeArticle
TitleDesign, synthesis, and biological evaluation of efflux-resistant imatinib derivatives
AuthorsChowdhury, M.M., Pretheshan, P., Chowdhury, N.S., Andriollo, P., Shah, A.J., Forbes, B., Pepper, C. and Rahman, K.M.
Abstract

Resistance to imatinib, a first-line BCR-ABL1 tyrosine kinase inhibitor for chronic myeloid leukemia, is frequently mediated by drug efflux through P-glycoprotein (P-gp) overexpression. We report the design, synthesis, and evaluation of eight novel imatinib derivatives modified at the piperazine terminus with efflux resistance breaker (ERB) fragments to reduce P-gp-mediated efflux. In silico docking against cryo-EM P-gp structures predicted increased hydrophobic interactions and enhanced occupancy at the access tunnel, indicative of efflux inhibition. Compound 8 showed potency comparable to imatinib in BCR-ABL1+ K562 cells and a lower LC50 fold change in resistant K562/DOX cells, suggesting reduced efflux susceptibility. Accumulation assays confirmed the improved intracellular retention of compound 8. Compound 9 displayed increased potency in resistant cells, correlating with higher intracellular levels despite modest kinase inhibition. Verapamil assays confirmed reduced efflux liability for compounds 8 and 13. Compound 8 also showed a positive therapeutic index. These findings support rational design to mitigate efflux-mediated resistance.

KeywordsBCR-ABL1 tyrosine kinase inhibitor; myeloid leukaemia; imatinib derivatives
Sustainable Development Goals3 Good health and well-being
Middlesex University ThemeHealth & Wellbeing
PublisherAmerican Chemical Society
JournalJournal of Medicinal Chemistry
ISSN0022-2623
Electronic1520-4804
Publication dates
Online25 Oct 2025
Print13 Nov 2025
Publication process dates
Submitted10 Jun 2025
Accepted15 Oct 2025
Deposited28 Oct 2025
Output statusPublished
Publisher's version
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File Access Level
Open
Copyright Statement

© 2025 The Authors. Published by American Chemical Society. This publication is licensed under
CC-BY 4.0 .

Digital Object Identifier (DOI)https://doi.org/10.1021/acs.jmedchem.5c01596
PubMed ID41137772
Web of Science identifierWOS:001600342100001
LanguageEnglish
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