Prostate-Specific Membrane Antigen-Specific Antitumor Activity of a Self-Immolative Tubulysin Conjugate

Bioconjug Chem. 2019 Jun 19;30(6):1805-1813. doi: 10.1021/acs.bioconjchem.9b00335. Epub 2019 May 22.

Abstract

Prostate-specific membrane antigen (PSMA) is a biomarker that is overexpressed on prostate cancer, and it is also present on the neovasculature within many non-prostate solid tumors. Herein, we report on the construction and biological testing of novel tubulysin B-containing therapeutic agents for the treatment of PSMA-expressing cancer. One of these compounds, EC1169, emerged as a lead candidate for preclinical development and phase 1 clinical testing. This water-soluble conjugate was shown to have high affinity for PSMA-positive cells. When tested in vitro, EC1169 was found to inhibit the growth of PSMA-positive cells, but it displayed no activity against PSMA-negative cells. Brief treatment of nude mice bearing PSMA-positive LNCaP human xenografts with EC1169 led to complete remissions and cures. Furthermore, this activity occurred in the absence of weight loss. In contrast, the nontargeted tubulysin B drug proved to be inactive against the LNCaP tumor model when administered at doses near to or greater than the maximum tolerated level. PSMA-negative KB tumors did not appreciably respond to EC1169 therapy, thereby confirming this compound's targeted specificity for PSMA-positive cells. Finally, treatment of LNCaP-bearing mice with docetaxel (the most active chemotherapeutic agent approved for late stage prostate cancer therapy) was found to produce only modest anti-tumor activity, and this outcome was also associated with severe weight loss. Taken together, these results strongly indicate that PSMA-positive tumors may be effectively treated using highly potent, PSMA-targeted small-molecule drug conjugates using regimens that do not cause undesirable side effects.

MeSH terms

  • Animals
  • Antigens, Surface / analysis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / therapeutic use*
  • Cell Line, Tumor
  • Glutamate Carboxypeptidase II / analysis*
  • Humans
  • Male
  • Mice, Nude
  • Oligopeptides / chemistry
  • Oligopeptides / therapeutic use*
  • Pipecolic Acids / chemistry
  • Pipecolic Acids / therapeutic use*
  • Prostatic Neoplasms / drug therapy*
  • Prostatic Neoplasms / pathology
  • Xenograft Model Antitumor Assays

Substances

  • Antigens, Surface
  • Antineoplastic Agents
  • Oligopeptides
  • Pipecolic Acids
  • tubulysin B
  • FOLH1 protein, human
  • Glutamate Carboxypeptidase II