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  • Title: Synthesis and antimicrobial evaluation of water-soluble, dendritic derivatives of epimeric 5alpha-cholestan-3-amines and 5alpha-cholestan-3-yl aminoethanoates.
    Author: Sugandhi EW, Slebodnick C, Falkinham JO, Gandour RD.
    Journal: Steroids; 2007 Jul; 72(8):615-26. PubMed ID: 17532019.
    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-(5alpha-cholestan-3-yl)ureido]heptanedioic acid (1) and 4-(2-carboxyethyl)-4-[3-(5alpha-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 microM, was found for the 3beta epimer of 1 against MRSA.
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