In vitro and in vivo antineoplastic activity of a novel bromopyrrole and its potential mechanism of action

Br J Pharmacol. 2010 Feb;159(4):909-18. doi: 10.1111/j.1476-5381.2009.00573.x. Epub 2010 Jan 8.

Abstract

Background and purpose: Many bromopyrrole compounds have been reported to have in vitro antineoplastic activity. In a previous study, we isolated N-(4, 5-dibromo-pyrrole-2-carbonyl)-L-amino isovaleric acid methyl ester (B6) from marine sponges. Here, we investigated the in vitro and in vivo antineoplastic activity of B6 and its potential mechanism.

Experimental approach: The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay was used to determine the in vitro antineoplastic activity of B6. Flow cytometry, western blot analysis and morphological observations were used to investigate its mechanism of action. A mouse xenograft model was used to determine its in vivo activity.

Key results: B6 inhibited the proliferation of various human cancer cells in vitro, with highest activity on LOVO and HeLa cells. B6 also exhibited significant growth inhibitory effects in vivo in a xenograft mouse model. Acute toxicity analysis suggested that B6 has low toxicity. B6-treated cells arrested in the G1 phase of the cell cycle and had an increased fraction of sub-G1 cells. In addition, the population of Annexin V-positive/propidium iodide-negative cells increased, indicating the induction of early apoptosis. Indeed, B6-treated cells exhibited morphologies typical of cells undergoing apoptosis. Western blotting showed cleaved forms of caspase-9 and caspase-3 in cells exposed to B6. Moreover, B6-promoted Ca(2+) release and apoptosis was associated with elevated intracellular Ca(2+)concentration.

Conclusions and implications: B6 has significant antineoplastic activity in vitro as well as in vivo. It inhibits tumour cell proliferation by arresting the cell cycle and inducing apoptosis. With its low toxicity, B6 represents a promising antineoplastic, primary compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Antineoplastic Agents / toxicity
  • Apoptosis / drug effects
  • Blotting, Western
  • Calcium / metabolism
  • Caspase 3 / metabolism
  • Caspase 9 / metabolism
  • Cell Cycle / drug effects
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Female
  • Flow Cytometry
  • HeLa Cells
  • Hemiterpenes
  • Hep G2 Cells
  • Humans
  • Lethal Dose 50
  • Male
  • Mice
  • Neoplasms / drug therapy*
  • Neoplasms / pathology
  • Porifera* / chemistry
  • Pyrroles / isolation & purification
  • Pyrroles / pharmacology*
  • Pyrroles / toxicity
  • Time Factors
  • Tumor Burden
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Hemiterpenes
  • N-(4,5-dibromo-pyrrole-2-carbonyl)-L-amino isovaleric acid methyl ester
  • Pyrroles
  • CASP3 protein, human
  • CASP9 protein, human
  • Caspase 3
  • Caspase 9
  • Calcium