Design, synthesis and biological evaluation of prostate-specific membrane antigen (PSMA)-targeted SIRT2 inhibitors

Bioorg Chem. 2024 Dec:153:107784. doi: 10.1016/j.bioorg.2024.107784. Epub 2024 Sep 16.

Abstract

Sirtuins belong to a specific class of enzymes called NAD+-dependent protein deacetylases. Among them, SIRT2 is predominantly localized in the cytoplasm and plays a vital role in tumor development and progression. As a result, it becomes an important target for the development of anticancer drugs. While SIRT2 inhibitors have shown broad-spectrum cytotoxicity against various cancer cells, their ability to inhibit the growth of certain cancers like prostate cancer has been limited, possibly due to insufficient targeting properties. To overcome this limitation, our goal was to target prostate-specific membrane antigen (PSMA), a valuable biomarker for prostate cancer, using lysine-urea-glutamic acid (KUE) as a PSMA ligand. This approach allowed us to systematically design new SIRT2 inhibitors. Evaluation showed that compound 17 exhibited superior inhibitory activity, improved targeting properties, and enhanced antiproliferative efficacy specifically in prostate cancer cells. These findings suggest a promising strategy for utilizing SIRT2 inhibitors in prostate cancer therapy.

Keywords: Anticancer; Inhibitor; PSMA; Prostate cancer; SIRT2.

MeSH terms

  • Antigens, Surface* / metabolism
  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation* / drug effects
  • Dose-Response Relationship, Drug*
  • Drug Design*
  • Drug Screening Assays, Antitumor*
  • Glutamate Carboxypeptidase II* / antagonists & inhibitors
  • Glutamate Carboxypeptidase II* / metabolism
  • Humans
  • Male
  • Molecular Structure
  • Prostatic Neoplasms* / drug therapy
  • Prostatic Neoplasms* / pathology
  • Sirtuin 2* / antagonists & inhibitors
  • Sirtuin 2* / metabolism
  • Structure-Activity Relationship

Substances

  • Sirtuin 2
  • SIRT2 protein, human
  • Antineoplastic Agents
  • Glutamate Carboxypeptidase II
  • Antigens, Surface
  • FOLH1 protein, human