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Synthesis and antimicrobial evaluation of water-soluble, dendritic derivatives of epimeric 5α-cholestan-3-amines and 5α-cholestan-3-yl aminoethanoates

Authors
Journal
Steroids
0039-128X
Publisher
Elsevier
Publication Date
Volume
72
Issue
8
Identifiers
DOI: 10.1016/j.steroids.2007.04.001
Keywords
  • Cholestan-3-Amine
  • Dendritic Amphiphile
  • Antimicrobial
Disciplines
  • Philosophy

Abstract

Abstract To examine the effect of negatively charged steroidal amphiphiles on antimicrobial activity, two pairs of epimeric, dendritic tricarboxylato amphiphiles – 4-(2-carboxyethyl)-4-[3-(5α-cholestan-3-yl)ureido]heptanedioic acid ( 1) and 4-(2-carboxyethyl)-4-[3-(5α-cholestan-3-yloxycarbonylmethyl)ureido]heptanedioic acid ( 2) – were synthesized. A broad antimicrobial screen of 11 microbes revealed that these amphiphiles only showed good activity against a methicillin-resistant isolate of Staphylococcus aureus (MRSA) and modest activity against an unrelated strain of S. aureus. The best activity, a minimal inhibitory concentration (MIC) of 27 μM, was found for the 3β epimer of 1 against MRSA.

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