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Design, synthesis, and characterization of PROTACs targeting the androgen receptor in prostate and lung cancer models

Lukas Maria Gockel, Vladlena Pfeifer, Fabian Baltes, Rafael D. Bachmaier, Karl Wagner, Gerd Bendas, Michael Gütschow, Izidor Sosič, Christian Steinebach

2022Archiv der Pharmazie22 citationsDOIOpen Access PDF

Abstract

Abstract Although the androgen receptor (AR) is a validated target for the treatment of prostate cancer, resistance to antiandrogens necessitates the development of new therapeutic modalities. Exploiting the ubiquitin‐proteasome system with proteolysis‐targeting chimeras (PROTACs) has become a practical approach to degrade specific proteins and thus to extend the portfolio of small molecules used for the treatment of a broader spectrum of diseases. Herein, we present three subgroups of enzalutamide‐based PROTACs in which only the exit vector was modified. By recruiting cereblon, we were able to demonstrate the potent degradation of AR in lung cancer cells. Furthermore, the initial evaluation enabled the design of an optimized PROTAC with a rigid linker that degraded AR with a DC 50 value in the nanomolar range. These results provide novel AR‐directed PROTACs and a clear rationale for further investigating AR involvement in lung cancer models.

Topics & Concepts

EnzalutamideProstate cancerAndrogen receptorProteasomeAntiandrogensLung cancerCancer researchComputational biologyCancerMedicineChemistryPharmacologyBiologyInternal medicineBiochemistryProtein Degradation and InhibitorsPeptidase Inhibition and AnalysisUbiquitin and proteasome pathways
Design, synthesis, and characterization of PROTACs targeting the androgen receptor in prostate and lung cancer models | Litcius