Chemo-Enzymatic Synthesis and Antimicrobial Evaluation of Alkyloxy Propanol Amine-Based Cationic Ether Lipids
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ORIGINAL PAPER
Chemo-Enzymatic Synthesis and Antimicrobial Evaluation of Alkyloxy Propanol Amine-Based Cationic Ether Lipids J. R. C. Reddy • B. V. S. K. Rao • M. S. L. Karuna K. P. Kumar • U. S. N. Murthy • R. B. N. Prasad
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Received: 26 June 2012 / Revised: 27 August 2012 / Accepted: 25 October 2012 / Published online: 23 November 2012 Ó AOCS 2012
Abstract The present study involved the synthesis and antimicrobial evaluation of alkyloxy propanol amine-based cationic lipids N,N-dimethyl-1-octadecylamino-3-alkyloxy2-propanol (series A, 7a–e) and N-methyl-N,N-di-(2hydroxy-3-alkyloxy-2 propyl) octadecylamine (series B, 9a–e) and their acetylated derivatives (8a–e and 10a–e). A simple three-step chemo-enzymatic approach was employed for the synthesis of 7a–e and 9a–e in 71–80 and 67–88 % yields, respectively. The first step involved the synthesis of a series of glycidyl ethers from a series of alcohols (C4, C8, C10, C12, C14) which were opened in the second step with octadecylamine to obtain 1-octadecylamino-3-alkyloxy-2 propanol (5a–e) and N,N-di-(2-hydroxy-3-alkyloxypropyl) octadecylamine (6a–e). In the third step, alkyloxy propanolamines (5a–e, 6a–e) were quaternized using methyl iodide to yield quaternized ammonium salts. The quaternized ammonium salts were enzymatically acetylated using Candida antarctica lipase-B based immobilized enzyme Novozym 435 to obtain their acetylated derivatives. The quaternized salts as well as their acetylated derivatives were evaluated for antibacterial and antifungal properties. The title compounds were found to possess moderate to good antibacterial activities against all the studied bacterial strains namely, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Klebsiella aerogenes compared to streptomycin and cetyl trimethyl J. R. C. Reddy B. V. S. K. Rao M. S. L. Karuna R. B. N. Prasad (&) Centre for Lipid Research, Indian Institute of Chemical Technology, Hyderabad 500 007, India e-mail: [email protected] K. P. Kumar U. S. N. Murthy Biology Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India
ammonium bromide (CTAB). The title compounds exhibited relatively good antifungal activities against Candida albicans and no significant activities against other fungal strains namely, Saccharomyces cerevisiae, Rhizopus oryzae and Aspergillus niger when compared to amphotericin B and CTAB. Keywords Antimicrobial activity Cationic-ether lipids Chemo-enzymatic synthesis Quaternized salts Alkyloxy-propanolamine
Introduction Glycidyl derivatives namely acyloxy or alkyloxy propanol amines have been widely investigated for a variety of applications [1–8]. The presence of several key functional groups on the glycerol backbone makes them attractive chemical intermediates for several applications. Lipids with ether bonds to long chain alkyl moieties in addition to ester bonds to fatty acids are in general called as ether lipids and are common in nature especially as membrane constituents. In general, the ether bond is l
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