Chemical synthesis, cytotoxicity, selectivity and bioavailability of 5α-androstane-3α,17β-diol derivatives

Bioorg Med Chem. 2014 Nov 1;22(21):5847-59. doi: 10.1016/j.bmc.2014.09.026. Epub 2014 Sep 19.

Abstract

Aminosteroid derivatives represent a new family of compounds with promising antiproliferative activity over different cancer cell lines. Among all the aminosteroid derivatives synthesised in our laboratory, we have identified E-37P as one of the more potent when tested in vitro. Unfortunately, the pharmacokinetic properties of E-37P decrease its effectiveness when tested in vivo. To improve the bioavailability and increase the efficiency of aminosteroid E-37P, two series of analog compounds were synthesised by classic chemical synthesis, they were then characterized, and the concentration that inhibits 50% of cell proliferation (IC50) was determined on different cell lines. RM-133, a 5α-androstane-3α,17β-diol derivative with a quinoline nucleus at the end of the piperazine-proline side-chain at position 2β and an ethinyl at position 17α, showed very good antiproliferative activity among the five cancer cell lines studied (IC50=0.1, 0.1, 0.1, 2.0 and 1.1 μM for HL-60, MCF-7, T-47D, LNCaP and WEHI-3, respectively). Moreover, the plasmatic concentration of RM-133 at 3h, when injected subcutaneously in rats, was 2.3-fold higher than that of E-37P (151 vs 64.8 ng/mL). Furthermore, RM-133 weakly inhibited the two representative liver enzymes, CYP3A4 and CYP2D6, indicating a very low risk of drug-drug interactions. The cytotoxicity of RM-133 against normal cells was tested on peripheral blood lymphocytes (PBL) obtained from different donors and previously activated with phytohemagglutinin-L. PBL responded differently to treatment with RM-133, we observed a stimulation of cell proliferation and/or cytotoxicity in a dose-dependent manner. Based on these results, additional studies are currently underway to evaluate the selectivity of our lead compound against normal cell lines in a more detailed fashion.

Keywords: Aminosteroid; Cancer; Cytotoxicity; Lymphocytes; Selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androstenes / chemistry*
  • Androstenes / pharmacokinetics
  • Androstenes / toxicity
  • Animals
  • Biological Availability
  • Cell Survival / drug effects
  • Cells, Cultured
  • Cholestanols / chemical synthesis*
  • Cholestanols / pharmacokinetics
  • Cholestanols / toxicity
  • Cytochrome P-450 CYP2D6 / metabolism
  • Cytochrome P-450 CYP3A / metabolism
  • HL-60 Cells
  • Half-Life
  • Humans
  • Liver / drug effects
  • Liver / enzymology
  • Liver / metabolism
  • Lymphocytes / cytology
  • Lymphocytes / drug effects
  • Lymphocytes / metabolism
  • Mice
  • Piperazines / chemistry
  • Proline / chemistry
  • Quinolines / chemistry
  • Rats

Substances

  • Androstenes
  • Cholestanols
  • Piperazines
  • Quinolines
  • RM-133 aminosteroid
  • Proline
  • quinoline
  • Cytochrome P-450 CYP2D6
  • Cytochrome P-450 CYP3A