Abstract
The naturally occurring (6Z)-(±)-2-methoxy-6-hexadecenoic acid (1) and (6Z)-(±)-2-methoxy-6-octadecenoic acid (2) were synthesized in 7-8 steps with 38 and 13% overall yields, respectively, by using an acetylide coupling approach, which made it possible to obtain a 100% cis-stereochemistry for the double bonds. In a similar fashion, the acetylenic analogs (±)-2-methoxy-6-hexadecynoic acid (3) and (±)-2-methoxy-6-octadecynoic acid (4) were also synthesized in 6-7 steps with 48 and 16% overall yields, respectively. The antibacterial activity of acids 1-4 was determined against clinical isolates of methicillin-resistant Staphylococcus aureus (ClMRSA) and Escherichia coli. Among the series of compounds, acid 4 was the most active bactericide towards CIMRSA displaying IC50s (half maximal inhibitory concentrations) between 17 and 37 μg/mL, in sharp contrast to the 6-octadecynoic acid, which was not bactericidal at all. On the other hand, acids 1 and 3 were the only acids that displayed antibacterial activity towards E. coli, but 1 stood out as the best candidate with an IC50 of 21 μg/mL. The critical micelle concentrations (CMCs) of acids 1-4 were also determined. The C18 acids 2 and 4 displayed a five-fold lower CMC (15-20 μg/mL) th...Continue Reading
References
Aug 28, 1990·Biochimica Et Biophysica Acta·P N Black
Jul 1, 1986·The Journal of Infectious Diseases·H R Knapp, M A Melly
Feb 1, 1986·Infection and Immunity·H S CourtneyE H Beachey
Apr 1, 1985·Lipids·A J ValicentiR T Holman
Dec 1, 1973·The Journal of Applied Bacteriology·H Galbraith, T B Miller
Aug 1, 1994·Molecular Microbiology·L FerreroF Blanche
Mar 27, 1998·FEBS Letters·M R Wieckowski, L Wojtczak
Dec 30, 1998·Journal of Natural Products·N M CarballeiraF A González
Jul 9, 1999·Progress in Lipid Research·C C DiRussoJ D Weimar
Apr 11, 2002·Lipids·Néstor M Carballeira, Johanna Alicea
Aug 10, 2002·Progress in Lipid Research·N M Carballeira
Nov 19, 2003·Chemistry and Physics of Lipids·Néstor M CarballeiraFernando A González
Mar 24, 2004·Archiv der Pharmazie·Néstor M CarballeiraSoroush Sardari
Dec 14, 2004·Lipids·Néstor M CarballeiraScott Franzblau
Jul 12, 2005·Current Opinion in Structural Biology·Bert van den Berg
Sep 9, 2005·FEBS Letters·Chang Ji ZhengWon-Gon Kim
Aug 22, 2007·Lipids·Néstor M CarballeiraAbimael D Rodriguez
Dec 4, 2009·Applied Microbiology and Biotechnology·Andrew P Desbois, Valerie J Smith
Feb 18, 2010·Tetrahedron Letters·Néstor M CarballeiraKeykavous Parang
Jul 31, 2012·Journal of Bacteriology·Joshua B ParsonsCharles O Rock
May 8, 2013·Chemistry and Physics of Lipids·Elsie A OrellanoNéstor M Carballeira
Dec 25, 2013·Chemistry and Physics of Lipids·David J Sanabria-RíosNéstor M Carballeira
Apr 9, 2014·Antimicrobial Agents and Chemotherapy·Michaël L CartronSimon J Foster
Oct 21, 2015·Bioorganic & Medicinal Chemistry Letters·David J Sanabria-RíosNéstor M Carballeira
Dec 24, 2015·Lipids·Néstor M CarballeiraRafael Balaña-Fouce
Citations
Jan 25, 2020·Lipids·David J Sanabria-RíosNéstor M Carballeira
Mar 13, 2019·Organic & Biomolecular Chemistry·Jogendra KumarSukalyan Bhadra
Feb 7, 2020·Chemistry, an Asian Journal·Jogendra KumarSukalyan Bhadra
Feb 13, 2021·Progress in Lipid Research·Giancarlo Casillas-VargasDavid J Sanabria-Ríos