Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study

Eur J Med Chem. 2020 Dec 15:208:112847. doi: 10.1016/j.ejmech.2020.112847. Epub 2020 Sep 18.

Abstract

Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over the normal human embryonic kidney HEK-293 cells (IC50 > 100 μM). Further mechanistic studies revealed that Iab significantly blocked tubulin polymerization and disrupted the intracellular microtubule network of A549 cells. Moreover, Iab induced G2/M cell cycle arrest by regulation of p-cdc2 and cyclin B1 expressions, and caused cell apoptosis through up-regulating cleaved PARP and cleaved caspase-3 expressions, and down-regulating of Bcl-2. Importantly, in vivo, Iab effectively suppressed tumor growth of A549 lung cancers in a xenograft mouse model without obvious signs of toxicity, confirming its potential as a promising candidate for cancer treatment.

Keywords: Antiproliferative activity; Structure-activity relationship; Triazolothiadiazine derivatives; Tubulin.

MeSH terms

  • A549 Cells
  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / therapeutic use*
  • Apoptosis / drug effects
  • Binding Sites
  • Cell Proliferation / drug effects
  • Female
  • G2 Phase Cell Cycle Checkpoints / drug effects
  • HEK293 Cells
  • Humans
  • Mice, Inbred BALB C
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Protein Binding
  • Structure-Activity Relationship
  • Thiadiazines / chemical synthesis
  • Thiadiazines / metabolism
  • Thiadiazines / therapeutic use*
  • Triazoles / chemical synthesis
  • Triazoles / metabolism
  • Triazoles / therapeutic use*
  • Tubulin / chemistry
  • Tubulin / metabolism*
  • Tubulin Modulators / chemical synthesis
  • Tubulin Modulators / metabolism
  • Tubulin Modulators / therapeutic use*
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Thiadiazines
  • Triazoles
  • Tubulin
  • Tubulin Modulators