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Current Medicinal Chemistry

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ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

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Research Article

Synthesis, In Silico Prediction, and In Vitro Evaluation of Anti-tumor Activities of Novel 4'-Hydroxybiphenyl-4-carboxylic Acid Derivatives as EGFR Allosteric Site Inhibitors

In Press, (this is not the final "Version of Record"). Available online 30 April, 2024
Author(s): Wurood A. Shihab, Ammar A. Razzak Kubba*, Lubna H. Tahtamouni*, Khaled M. Saleh, Mai F. AlSakhen, Sana I. Kanaan, Abdulrahman M. Saleh and Salem R. Yasin
Published on: 30 April, 2024

DOI: 10.2174/0109298673305163240427065543

Price: $95

Abstract

Introduction: Allosteric inhibition of EGFR Tyrosine Kinase (TK) is currently among the most attractive approaches for designing and developing anti-cancer drugs to avoid chemoresistance exhibited by clinically approved ATP-competitive inhibitors. The current work aimed to synthesize new biphenyl-containing derivatives that were predicted to act as EGFR TK allosteric site inhibitors based on molecular docking studies.

Method: A new series of 4'-hydroxybiphenyl-4-carboxylic acid derivatives, including hydrazine-1-carbothioamide (S3-S6) and 1,2,4-triazole (S7-S10) derivatives, were synthesized and characterized using IR, 1HNMR, 13CNMR, and HR-mass spectroscopy. Compound S4 had a relatively high pharmacophore-fit score, indicating that it may have biological activity similar to the EGFR allosteric inhibitor reference, and it scored a relatively low ΔG against EGFR TK allosteric site, indicating a high likelihood of drug-receptor complex formation. Compound S4 was cytotoxic to the three cancer cell lines tested, particularly HCT-116 colorectal cancer cells, with an IC50 value comparable to Erlotinib.

Compound S4 induced the intrinsic apoptotic pathway in HCT-116 cells by arresting them in the G2/M phase.

Result: All of the new derivatives, including S4, met the in silico requirements for EGFR allosteric inhibitory activity.

Conclusion: Compound S4 is a promising EGFR tyrosine kinase allosteric inhibitor that warrants further research.

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