Polyamine conjugates of stigmasterol

Steroids. 2012 Oct;77(12):1212-8. doi: 10.1016/j.steroids.2012.07.009. Epub 2012 Jul 28.

Abstract

Three new polyamine conjugates with stigmasterol [(3β,22E)-stigmasta-5,22-dien-3-ol] were synthesized and subjected to basic antimicrobial and cytotoxic tests. The conjugate derived from spermine, (3β,22E)-stigmasta-5,22-dien-3-yl 4(12-amino-4,9-diaza-dodecylamino)-4-oxobutanoate (5c), displayed considerable antimicrobial activity on Staphylococcus aureus at low concentration (50 μg mL(-1)). The cytotoxic activity was tested on cells of human T-lymfoblastic leukemia (IC(50)=35.8 ± 10.3 μM (5c) and IC(50)=35.9 ± 5.7 μM (5b)) and normal human fibroblasts (IC(50)=38.0 ± 2.8 μM (5c) and IC(50)=45.5 ± 1.9 μM (5b)). Conjugate 5a displayed no activity in both tests.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Carboxylic Acids / chemistry
  • Cell Line, Tumor
  • Chemical Phenomena
  • Dose-Response Relationship, Drug
  • Drug Design
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Polyamines / chemistry*
  • Staphylococcus aureus / drug effects
  • Stigmasterol / chemical synthesis
  • Stigmasterol / chemistry*
  • Stigmasterol / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Carboxylic Acids
  • Polyamines
  • Stigmasterol